JP2014024839A - Pest-control composition and pest-control method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pest-control composition having excellent control efficacy on a pest.SOLUTION: A pest-control composition contains a compound represented by the formula (1) and an insecticidal compound such as fenitrothion, dichlorvos, propoxur, bistrifluron, diflubenzuron, hexaflumuron, amidoflumet, chlorfenapyr, cyromazine, hydroplane, methoprene, indoxacarb, metoxadiazone and etoxazole. [In the formula, Arepresents -NH-, an oxygen atom or a sulfur atom, Arepresents a nitrogen atom or =CH-, R, R, Rand Ridentically or differently represent a hydrogen atom, a halogen atom or the like, Rrepresents a perfluoroalkyl group, a trifluoromethylthio group or the like, and n represents 0, 1 or 2.]

Description

  The present invention relates to a pest control composition and a pest control method.

  Conventionally, many compounds are known as an active ingredient of a pest control composition (for example, refer nonpatent literature 1).

The Pesticide Manual-15th edition (BCPC) ISBN 978-1-901396-18-8

  This invention makes it a subject to provide the pest control composition which has the outstanding control effect with respect to a pest.

  As a result of studies to find a pest control composition having an excellent control effect against pests, the present inventors have found that the compound represented by the following formula (1) and one or more selected from the following group (A): It has been found that a composition containing an insecticidal compound has an excellent control effect against pests.

［式中、Ａ¹は−ＮＲ⁶−、酸素原子又は硫黄原子を表し、Ａ²は窒素原子又は＝ＣＨ−を表し、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴は同一又は相異なり、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基、群Ｚより選ばれる１個以上の原子もしくは基を有していてもよいフェニル基、群Ｚより選ばれる１個以上の原子もしくは基を有していてもよい６員複素環基、−ＯＲ⁷、−Ｓ（Ｏ）_mＲ⁷、ハロゲン原子、又は水素原子を表し（但し、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴のうち、少なくとも２つは水素原子を表す。）、Ｒ⁵は群Ｘより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ３鎖式炭化水素基、−ＯＲ⁷、−Ｓ（Ｏ）_mＲ⁷、又はハロゲン原子を表し、Ｒ⁶は群Ｗより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ３鎖式炭化水素基、群Wより選ばれる１個以上の原子もしくは基を有していてもよいＣ３−Ｃ６脂環式炭化水素基又は水素原子を表し、
Ｒ⁷は１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基又は水素原子を表し、ｍは０、１又は２を表し、ｎは０、１又は２を表す。
ここで、−Ｓ（Ｏ）_mＲ⁷において、ｍが１又は２の場合には、Ｒ⁷が水素原子を表すことはない。
群Ｘ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルケニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルキニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルファニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルホニル基、シアノ基、ヒドロキシ基およびハロゲン原子からなる群。
群Ｚ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルファニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルホニル基、シアノ基、ニトロ基およびハロゲン原子からなる群。
群Ｗ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルケニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルキニルオキシ基、ハロゲン原子およびヒドロキシ基からなる群。］
で示される化合物と、
化合物群（Ａ）より選ばれる１種以上の殺虫化合物とを含有する有害生物防除組成物。
化合物群（Ａ）
Ａ−１（ピレスロイド系化合物）：
ピレトリン、アレスリン、プラレトリン、イミプロトリン、レスメトリン、テトラメトリン、フェノトリン、シフェノトリン、フルメスリン、メトフルトリン、トランスフルトリン、プロフルトリン、ジメフルトリン、エンペントリン、フラメトリン、メパーフルトリン、２，３，５，６−テトラフルオロ−４−（メトキシメチル）ベンジル＝２，２−ジメチル−３−（２−シアノ−１−プロペニル）−シクロプロパンカルボキシレート、２，３，５，６−テトラフルオロ−４−（メトキシメチル）ベンジル＝２，２−ジメチル−３−（３，３，３−トリフルオロ−１−プロペニル）−シクロプロパンカルボキシレート、２，３，５，６−テトラフルオロ−４−プロパルギルベンジル＝２，２，３，３−テトラメチルシクロプロパンカルボキシレート；
Ａ−２（その他の系統の化合物）：
フェニトロチオン、ジクロルボス、プロポクスル、ビストリフルロン、ジフルベンズロン、ヘキサフルムロン、アミドフルメト、クロルフェナピル、シロマジン、ハイドロプレン、メトプレン、インドキサカルブ、メトキサジアゾン、エトキサゾール、ピペロニルブトキシド、Ｎ−（２−エチルヘキシル）−５−ノルボルネン−２，３−ジカルボキシイミド、下記式で示される化合物

〔式中、Ｃｙは群Ｅ１〜Ｅ２より選ばれる基で置換されていてもよいフェニル基、群Ｅ１〜Ｅ２より選ばれる基で置換されていてもよい５〜６員のヘテロアリール基、群Ｅ１〜Ｅ３より選ばれる基で置換されていてもよい３〜７員のシクロアルキル基又は群Ｅ１〜Ｅ３より選ばれる基で置換されていてもよい５〜７員のシクロアルケニル基を表し、Ｑ¹はハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、Ｑ²はハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、-Ｃ(=Ｇ)Ｑ⁴、シアノ基、ハロゲン原子又は水素原子を表し、Ｑ³は少なくとも１つのフッ素原子を含むＣ１〜Ｃ５ハロアルキル基又はフッ素原子を表し、Ｇは酸素原子又は硫黄原子を表し、Ｑ⁴はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ヒドロキシル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、ｋは０又は１を表し、ｈは０、１又は２を表し、群Ｅ１は、群Ｌから選ばれる基で置換されていてもよいＣ１〜Ｃ６鎖式炭化水素基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６シクロアルキル基、-ＯＱ⁵、-ＳＱ⁵、-Ｓ(=Ｏ)Ｑ⁵、-Ｓ(=Ｏ)₂Ｑ⁵、-Ｃ(=Ｏ)Ｑ⁶、-ＯＣ(=Ｏ)Ｑ⁷、シアノ基、ニトロ基、ヒドロキシル基およびハロゲン原子からなる一価基の群を表し、群Ｅ２は、群Ｌから選ばれる基で置換されていてもよいＣ２−Ｃ６アルカンジイル基、群Ｌから選ばれる基で置換されていてもよい１，３−ブタジエン−１，４−ジイル基、-Ｇ-Ｔ-Ｇ-および-Ｔ-Ｇ-Ｔ-からなる二価基の群を表し、群Ｅ３は、=Ｏ、=ＮＯ-Ｑ⁵、=Ｃ=ＣＨ₂および=Ｃ(Ｑ⁸)Ｑ⁹からなる二価基の群を表し、Ｔはメチレン基又はエチレン基を表し、Ｑ⁵は群Ｌから選ばれる基で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基又は群Ｌから選ばれる基で置換されていてもよいＣ３〜Ｃ６シクロアルキル基を表し、Ｑ⁶はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ヒドロキシル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、Ｑ⁷はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、Ｑ⁸およびＱ⁹は同一または相異なり、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、群Ｌは、ヒドロキシル基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、Ｃ２〜Ｃ５環状アミノ基、-Ｃ(=Ｏ)Ｑ⁶、-ＯＣ(=Ｏ)Ｑ⁷
およびハロゲン原子からなる群を表す。〕、下記式で示される化合物

〔式中、ｋ、ｈ、Ｑ¹、Ｑ²およびＱ³は前記と同じ意味を表し、Ｑ¹¹は少なくとも１個のフッ素原子を有するＣ１−Ｃ５ハロアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニル基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基を表し、Ｑ¹²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキルチオ基、ハロゲン原子又は水素原子を表し（但し、Ｑ¹¹がハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基である場合、Ｑ¹²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基又は水素原子である。）、Ｑ¹³はＣ１−Ｃ４アルキル基、ハロゲン原子又は水素原子を表す。〕、下記式で示される化合物

〔式中、Ｌ³はフッ素原子、塩素原子、臭素原子、メチル基、エチル基又は水素原子を表し、Ｌ⁴はＣ１−Ｃ６アルキル基、Ｃ１−Ｃ６ハロアルキル基、Ｃ３−Ｃ６シクロアルキル基又はＣ１−Ｃ６アルコキシ基で置換されたＣ１−Ｃ６アルキル基を表し、Ｌ⁵およびＬ⁶は同一又は相異なり、メチル基又は水素原子を表す。〕、
下記式で示される化合物

〔式中、Ｘ¹は２−メチルプロピル基または２−メチル−１−プロペニル基を表し、Ｘ²はメチル基を表し、Ｘ³は２−メチル−１−プロペニル基を表し、Ｘ⁴はメチル基を表す。〕
［２］ 式（１）で示される化合物と群（Ａ）より選ばれる１種以上の殺虫化合物との含有量の比が、重量比で１００：１〜１：１００である［１］に記載の有害生物防除組成物。
［３］ 式（１）で示される化合物と群（Ａ）より選ばれる１種以上の殺虫化合物との含有量の比が、重量比で１０：１〜１：１０である［１］に記載の有害生物防除組成物。
［４］ ［１］〜［３］のいずれかに記載の有害生物防除組成物の有効量を、有害生物又は有害生物の生息場所に施用する工程を有する有害生物の防除方法。 The present invention is as follows.
[1]
Formula (1)

[Wherein, A ¹ represents —NR ⁶ —, an oxygen atom or a sulfur atom, A ² represents a nitrogen atom or ═CH—, and R ¹ , R ² , R ³ and R ⁴ are the same or different; C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, phenyl group optionally having one or more atoms or groups selected from group Z, one selected from group Z It represents a 6-membered heterocyclic group optionally having the above atoms or groups, —OR ⁷ , —S (O) _m R ⁷ , a halogen atom, or a hydrogen atom (provided that R ¹ , R ² , R ³ And R ⁴ represents at least two hydrogen atoms.), R ⁵ is a C1-C3 chain hydrocarbon group optionally having one or more atoms or groups selected from group X, —OR ⁷ , —S (O) _m R ⁷ , or a halogen atom, R ⁶ has one or more atoms or groups selected from group W; A C1-C3 chain hydrocarbon group which may optionally be represented, a C3-C6 alicyclic hydrocarbon group which may have one or more atoms or groups selected from group W, or a hydrogen atom;
R ⁷ represents a C1-C3 chain hydrocarbon group or a hydrogen atom which may have one or more halogen atoms, m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, in —S (O) _m R ⁷ , when m is 1 or 2, R ⁷ does not represent a hydrogen atom.
Group X: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms An optionally substituted C2-C3 alkynyloxy group, a C1-C3 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C3 alkylsulfinyl optionally having one or more halogen atoms A group consisting of a group, a C1-C3 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group and a halogen atom;
Group Z: C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, C1-C3 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C3 alkylsulfanyl group optionally having one or more, a C1-C3 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C3 optionally having one or more halogen atoms A group consisting of an alkylsulfonyl group, a cyano group, a nitro group and a halogen atom.
Group W: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A group consisting of an optionally substituted C2-C3 alkynyloxy group, a halogen atom and a hydroxy group. ]
A compound represented by
A pest control composition comprising one or more insecticidal compounds selected from the compound group (A).
Compound group (A)
A-1 (Pyrethroid compound):
Pyrethrin, allethrin, plaretrin, imiprothrin, resmethrin, tetramethrin, phenothrin, ciphenothrin, flumethrin, metfurthrin, transfluthrin, profluthrin, dimefluthrin, empentrin, framethrin, meperfluthrin, 2,3,5,6-tetrafluoro-4- (methoxy Methyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2- Dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3-tetramethyl Cyclopropane carbox Rate;
A-2 (other series of compounds):
Fenitrothion, Dichlorvos, Propoxur, Bistrifluron, Diflubenzuron, Hexaflumuron, Amidoflumet, Chlorfenapyr, Cyromazine, Hydroprene, Metoprene, Indoxacarb, Metoxadiazone, Etoxazole, Piperonylbutoxide, N- (2-Ethylhexyl) -5-norbornene-2 , 3-Dicarboximide, a compound represented by the following formula

[Wherein Cy is a phenyl group optionally substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group optionally substituted with a group selected from groups E1 to E2, and group E1. Represents a 3- to 7-membered cycloalkyl group which may be substituted with a group selected from -E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3, and Q ¹ a halogen atom substituted by C1~C4 may chain hydrocarbon group, a halogen atom or a hydrogen atom, Q ² is optionally substituted C1~C4 chain hydrocarbon group with a halogen atom, -C (= G) Q ^{4 represents} a cyano group, a halogen atom or a hydrogen atom, Q ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom, G represents an oxygen atom or a sulfur atom, Q ⁴ is still at a halogen atom A C1-C4 alkyl group which may be substituted, a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, or a halogen atom Good C3-C6 alkynyloxy group, C1-C4 alkylamino group optionally substituted with a halogen atom, Di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, Hydroxyl group, Amino group, C2 -C5 represents a cyclic amino group or a hydrogen atom, k represents 0 or 1, h represents 0, 1 or 2, and group E1 is a C1-C6 chain optionally substituted with a group selected from group L wherein the hydrocarbon group, C3 -C6 cycloalkyl group which may be substituted with a halogen ^{atom, -OQ 5, -SQ 5, -S} (= O) Q 5, -S (= O) 2 Q 5, -C (= O) Q ^6, -O (= O) Q ^7, a cyano group, a nitro group, a group of monovalent radicals consisting of hydroxyl group and a halogen atom, the group E2 is a group optionally substituted by C2-C6 alkanediyl also selected from the group L A group of divalent groups consisting of a group, a 1,3-butadiene-1,4-diyl group, -GTG-G- and -TGGT- which may be substituted with a group selected from group L Group E3 represents a group of divalent groups consisting of ═O, ═NO—Q ⁵ , ═C═CH ₂ and ═C (Q ⁸ ) Q ⁹ , T represents a methylene group or an ethylene group, Q ⁵ represents a C1-C4 chain hydrocarbon group which may be substituted with a group selected from Group L or a C3-C6 cycloalkyl group which may be substituted with a group selected from Group L, Q ⁶ is C1-C4 alkoxy group optionally substituted with a halogen atom, C3-C6 alkyl optionally substituted with a halogen atom A kenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, a C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) optionally substituted with a halogen atom ) amino group, optionally substituted C1~C4 alkyl group with a halogen atom, a hydroxyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁷ is C1 which may optionally be substituted with a halogen atom -C4 alkoxy group, C3-C6 alkenyloxy group optionally substituted with a halogen atom, C3-C6 alkynyloxy group optionally substituted with a halogen atom, C1-C4 alkyl optionally substituted with a halogen atom Amino group, di (C1-C4 alkyl) amino group optionally substituted with halogen atom, halogen source In substituted C1~C4 may alkyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁸ and Q ⁹ are the same or different, C1 to which may be substituted with a halogen atom A C4 alkoxy group, a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom; Group L is a C1-C4 alkoxy optionally substituted with a hydroxyl group or a halogen atom A C3-C6 alkenyloxy group optionally substituted with a halogen atom, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, an amino group, a C1-C4 alkyl optionally substituted with a halogen atom amino groups, optionally substituted with a halogen atom di (C1 -C4 alkyl) amino group, C2-C5 cyclic amino group, -C (= O) Q ⁶ -OC (= O) Q ⁷
And a group consisting of halogen atoms. ], A compound represented by the following formula

[Wherein, k, h, Q ¹ , Q ² and Q ³ represent the same meaning as described above, and Q ¹¹ may be substituted with a C1-C5 haloalkyl group having at least one fluorine atom or a halogen atom. C3-C5 alkenyl group, C3-C5 alkenyloxy group optionally substituted with a halogen atom, C3-C5 alkynyl group optionally substituted with a halogen atom, or C3-C5 alkynyl optionally substituted with a halogen atom Represents an oxy group, and Q ¹² is a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, or a C1-C4 which may be substituted with a halogen atom. Represents an alkylthio group, a halogen atom or a hydrogen atom (provided that Q ¹¹ is a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or If substituted with a halogen atom may also be C3-C5 alkynyloxy group, Q ¹² is a is C1-C4 may be an alkyl group or a hydrogen atom substituted with a halogen atom.), Q ¹³ is C1-C4 Represents an alkyl group, a halogen atom or a hydrogen atom; ], A compound represented by the following formula

[Wherein L ³ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a hydrogen atom, and L ⁴ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or a C1 represents C1-C6 alkyl group substituted with -C6 alkoxy group, L ⁵ and L ⁶ are the same or different, represent a methyl group or a hydrogen atom. ],
Compound represented by the following formula

[Wherein, X ¹ represents a 2-methylpropyl group or a 2-methyl-1-propenyl group, X ² represents a methyl group, X ³ represents a 2-methyl-1-propenyl group, and X ⁴ represents methyl Represents a group. ]
[2] The ratio of the content of the compound represented by the formula (1) and one or more insecticidal compounds selected from the group (A) is 100: 1 to 1: 100 by weight ratio. Pest control composition.
[3] The ratio of the content of the compound represented by the formula (1) and one or more insecticidal compounds selected from the group (A) is 10: 1 to 1:10 by weight ratio. Pest control composition.
[4] A method for controlling pests comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [3] to a pest or a habitat of the pest.

According to the present invention, pests can be controlled.

［式中、Ａ¹は−ＮＲ⁶−、酸素原子又は硫黄原子を表し、Ａ²は窒素原子又は＝ＣＨ−を表し、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴は同一又は相異なり、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基、群Ｚより選ばれる１個以上の原子もしくは基を有していてもよいフェニル基、群Ｚより選ばれる１個以上の原子もしくは基を有していてもよい６員複素環基、−ＯＲ⁷、−Ｓ（Ｏ）_mＲ⁷、ハロゲン原子、又は水素原子を表し（但し、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴のうち、少なくとも２つは水素原子を表す。）、Ｒ⁵は、群Ｘより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ３鎖式炭化水素基、−ＯＲ⁷、−Ｓ（Ｏ）_mＲ⁷、又はハロゲン原子を表し、Ｒ⁶は群Ｗより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ３鎖式炭化水素基、群Wより選ばれる１個以上の原子もしくは基を有していてもよいＣ３−Ｃ６脂環式炭化水素基又は水素原子を表し、Ｒ⁷は、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基又は水素原子を表し、ｍは０、１又は２を表し、ｎは０、１又は２を表す。
ここで、−Ｓ（Ｏ）_mＲ⁷において、ｍが１又は２の場合には、Ｒ⁷が水素原子を表すことはない。
群Ｘ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルケニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルキニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルファニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルホニル基、シアノ基、ヒドロキシ基およびハロゲン原子からなる群。
群Ｚ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３鎖式炭化水素基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルファニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキルスルホニル基、シアノ基、ニトロ基およびハロゲン原子からなる群。
群Ｗ：１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルケニルオキシ基、１個以上のハロゲン原子を有していてもよいＣ２−Ｃ３アルキニルオキシ基、ハロゲン原子およびヒドロキシ基からなる群。］
で示される化合物（以下、本縮合複素環化合物と記す。）と、
（Ａ−１）ピレトリン（CAS登録番号 121-21-1）、アレスリン（CAS登録番号 584-79-2）、プラレトリン（CAS登録番号 23031-36-9）、イミプロトリン（CAS登録番号 72963-72-5）、レスメトリン（CAS登録番号 10453-86-8）、テトラメトリン（CAS登録番号 7696-12-0）、フェノトリン（CAS登録番号 26002-80-2）、シフェノトリン（CAS登録番号 39515-40-7）、フルメスリン（CAS登録番号 69770-45-2）、メトフルトリン（CAS登録番号 7696-12-0）、トランスフルトリン（CAS登録番号 118712-89-3）、プロフルトリン（CAS登録番号 223419-20-3）、ジメフルトリン（CAS登録番号 271241-14-6）、エンペントリン（CAS登録番号 54406-48-3）、フラメトリン（CAS登録番号 23031-38-1）、メパーフルトリン（CAS登録番号 915288-13-0）、２，３，５，６−テトラフルオロ−４−（メトキシメチル）ベンジル＝２，２−ジメチル−３−（２−シアノ−１−プロペニル）−シクロプロパンカルボキシレート、２，３，５，６−テトラフルオロ−４−（メトキシメチル）ベンジル＝２，２−ジメチル−３−（３，３，３−トリフルオロ−１−プロペニル）−シクロプロパンカルボキシレート（CAS登録番号 1130296-65-9）および２，３，５，６−テトラフルオロ−４−プロパルギルベンジル＝２，２，３，３−テトラメチルシクロプロパンカルボキシレート；並びに（Ａ−２）フェニトロチオン（CAS登録番号 122-14-5）、ジクロルボス（CAS登録番号 62-73-7）、プロポクスル（CAS登録番号 114-26-1）、ビストリフルロン（CAS登録番号 201593-84-2）、ジフルベンズロン（CAS登録番号 35367-38-5）、ヘキサフルムロン（CAS登録番号 86479-06-3）、アミドフルメト（CAS登録番号 84466-05-7）、クロルフェナピル（CAS登録番号 122453-73-0）、シロマジン（CAS登録番号 66215-27-8）、ハイドロプレン（CAS登録番号 41096-46-2）、メトプレン（CAS登録番号 40596-69-8）、インドキサカルブ（CAS登録番号 173584-44-6）、メトキサジアゾン（CAS登録番号 60589-06-2）、エトキサゾール（CAS登録番号 153233-91-1）、ピペロニルブトキシド（CAS登録番号 51-03-6）、Ｎ−（２−エチルヘキシル）−５−ノルボルネン−２，３−ジカルボキシイミド（CAS登録番号 113-48-4）、式（Ａ）で示される化合物

〔式中、Ｃｙは群Ｅ１〜Ｅ２より選ばれる基で置換されていてもよいフェニル基、群Ｅ１〜Ｅ２より選ばれる基で置換されていてもよい５〜６員のヘテロアリール基、群Ｅ１〜Ｅ３より選ばれる基で置換されていてもよい３〜７員のシクロアルキル基又は群Ｅ１〜Ｅ３より選ばれる基で置換されていてもよい５〜７員のシクロアルケニル基を表し、Ｑ¹はハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、Ｑ²はハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、-Ｃ(=Ｇ)Ｑ⁴、シアノ基、ハロゲン原子又は水素原子を表し、Ｑ³は少なくとも１つのフッ素原子を含むＣ１〜Ｃ５ハロアルキル基又はフッ素原子を表し、Ｇは酸素原子又は硫黄原子を表し、Ｑ⁴はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ヒドロキシル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、ｋは０又は１を表し、ｈは０、１又は２を表し、群Ｅ１は、群Ｌから選ばれる基で置換されていてもよいＣ１〜Ｃ６鎖式炭化水素基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６シクロアルキル基、-ＯＱ⁵、-ＳＱ⁵、-Ｓ(=Ｏ)Ｑ⁵、-Ｓ(=Ｏ)₂Ｑ⁵、-Ｃ(=Ｏ)Ｑ⁶、-ＯＣ(=Ｏ)Ｑ⁷、シアノ基、ニトロ基、ヒドロキシル基およびハロゲン原子からなる一価基の群を表し、群Ｅ２は、群Ｌから選ばれる基で置換されていてもよいＣ２−Ｃ６アルカンジイル基、群Ｌから選ばれる基で置換されていてもよい１，３−ブタジエン−１，４−ジイル基、-Ｇ-Ｔ-Ｇ-および-Ｔ-Ｇ-Ｔ-からなる二価基の群を表し、群Ｅ３は、=Ｏ、=ＮＯ-Ｑ⁵、=Ｃ=ＣＨ₂および=Ｃ(Ｑ⁸)Ｑ⁹からなる二価基の群を表し、Ｔはメチレン基又はエチレン基を表し、Ｑ⁵は群Ｌから選ばれる基で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基又は群Ｌから選ばれる基で置換されていてもよいＣ３〜Ｃ６シクロアルキル基を表し、Ｑ⁶はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、ヒドロキシル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、Ｑ⁷はハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキル基、アミノ基、Ｃ２〜Ｃ５環状アミノ基又は水素原子を表し、Ｑ⁸およびＱ⁹は同一または相異なり、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、群Ｌは、ヒドロキシル基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３〜Ｃ６アルキニルオキシ基、アミノ基、ハロゲン原子で置換されていてもよいＣ１〜Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１〜Ｃ４アルキル）アミノ基、Ｃ２〜Ｃ５環状アミノ基、-Ｃ(=Ｏ)Ｑ⁶、-ＯＣ(=Ｏ)Ｑ⁷
およびハロゲン原子からなる群を表す。〕、式（Ｂ）で示される化合物

〔式中、ｋ、ｈ、Ｑ¹、Ｑ²およびＱ³は前記と同じ意味を表し、Ｑ¹¹は少なくとも１個のフッ素原子を有するＣ１−Ｃ５ハロアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニル基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基を表し、Ｑ¹²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキルチオ基、ハロゲン原子又は水素原子を表し（但し、Ｑ¹¹がハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基である場合、Ｑ¹²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基又は水素原子である。）、Ｑ¹³はＣ１−Ｃ４アルキル基、ハロゲン原子又は水素原子を表す。〕、式（Ｃ）で示される化合物

〔式中、Ｌ³はフッ素原子、塩素原子、臭素原子、メチル基、エチル基又は水素原子を表し、Ｌ⁴はＣ１−Ｃ６アルキル基、Ｃ１−Ｃ６ハロアルキル基、Ｃ３−Ｃ６シクロアルキル基又はＣ１−Ｃ６アルコキシ基で置換されたＣ１−Ｃ６アルキル基を表し、Ｌ⁵およびＬ⁶は同一又は相異なり、メチル基又は水素原子を表す。〕、および式（Ｄ）で示される化合物

〔式中、Ｘ¹は２−メチルプロピル基または２−メチル−１−プロペニル基を表し、Ｘ²はメチル基を表し、Ｘ³は２−メチル−１−プロペニル基を表し、Ｘ⁴はメチル基を表す。〕からなる化合物群（Ａ）より選ばれる１種以上の殺虫化合物（以下、本殺虫化合物と記す。）とを含有する。 The pest control composition of the present invention has the formula (1)

[Wherein, A ¹ represents —NR ⁶ —, an oxygen atom or a sulfur atom, A ² represents a nitrogen atom or ═CH—, and R ¹ , R ² , R ³ and R ⁴ are the same or different; C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, phenyl group optionally having one or more atoms or groups selected from group Z, one selected from group Z It represents a 6-membered heterocyclic group optionally having the above atoms or groups, —OR ⁷ , —S (O) _m R ⁷ , a halogen atom, or a hydrogen atom (provided that R ¹ , R ² , R ³ And at least two of R ⁴ represent a hydrogen atom.), R ⁵ is a C1-C3 chain hydrocarbon group optionally having one or more atoms or groups selected from group X,- OR ⁷ , —S (O) _m R ⁷ , or a halogen atom, and R ⁶ represents one or more atoms or groups selected from the group W. Represents a C1-C3 chain hydrocarbon group which may have, a C3-C6 alicyclic hydrocarbon group which may have one or more atoms or groups selected from group W, or a hydrogen atom; ⁷ represents a C1-C3 chain hydrocarbon group or a hydrogen atom which may have one or more halogen atoms, m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, in —S (O) _m R ⁷ , when m is 1 or 2, R ⁷ does not represent a hydrogen atom.
Group X: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms An optionally substituted C2-C3 alkynyloxy group, a C1-C3 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C3 alkylsulfinyl optionally having one or more halogen atoms A group consisting of a group, a C1-C3 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group and a halogen atom;
Group Z: C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, C1-C3 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C3 alkylsulfanyl group optionally having one or more, a C1-C3 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C3 optionally having one or more halogen atoms A group consisting of an alkylsulfonyl group, a cyano group, a nitro group and a halogen atom.
Group W: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A group consisting of an optionally substituted C2-C3 alkynyloxy group, a halogen atom and a hydroxy group. ]
A compound represented by the following (hereinafter referred to as the present condensed heterocyclic compound);
(A-1) pyrethrin (CAS registration number 121-21-1), allethrin (CAS registration number 584-79-2), praretrin (CAS registration number 23031-36-9), imiproton (CAS registration number 72963-72- 5), Resmethrin (CAS registration number 10453-86-8), Tetramethrin (CAS registration number 7696-12-0), Phenothrin (CAS registration number 26002-80-2), Cifenotrin (CAS registration number 39515-40-7) ), Flumethrin (CAS registration number 69770-45-2), methfluthrin (CAS registration number 7696-12-0), transfluthrin (CAS registration number 118712-89-3), profluthrin (CAS registration number 223419-20-3) ), Dimefluthrin (CAS Registry Number 271241-14-6), Empentrin (CAS Registry Number 54406-48-3), Framethrin (CAS Registry Number 23031-38-1), Meperfluthrin (CAS Registry Number 915288-13-0), 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2- Methyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (3,3 , 3-trifluoro-1-propenyl) -cyclopropanecarboxylate (CAS Registry Number 1130296-65-9) and 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3- Tetramethylcyclopropanecarboxylate; and (A-2) fenitrothion (CAS registration number 122-14-5), dichlorvos (CAS registration number 62-73-7), propoxur (CAS registration number 114-26-1), bistri Fullon (CAS registration number 201593-84-2), Diflubenzuron (CAS registration number 35367-38-5), Hexaflumuron (CAS registration number 86479-06-3), Amidoflumet (CAS registration number 84466-05-7) , Ku Rufenapyr (CAS registration number 122453-73-0), Cyromazine (CAS registration number 66215-27-8), Hydroprene (CAS registration number 41096-46-2), Metoprene (CAS registration number 40596-69-8), India Oxacarb (CAS registration number 173584-44-6), methoxadiazone (CAS registration number 60589-06-2), etoxazole (CAS registration number 153233-91-1), piperonyl butoxide (CAS registration number 51-03-6), N -(2-Ethylhexyl) -5-norbornene-2,3-dicarboximide (CAS registration number 113-48-4), a compound represented by the formula (A)

[Wherein Cy is a phenyl group optionally substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group optionally substituted with a group selected from groups E1 to E2, and group E1. Represents a 3- to 7-membered cycloalkyl group which may be substituted with a group selected from -E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3, and Q ¹ a halogen atom substituted by C1~C4 may chain hydrocarbon group, a halogen atom or a hydrogen atom, Q ² is optionally substituted C1~C4 chain hydrocarbon group with a halogen atom, -C (= G) Q ^{4 represents} a cyano group, a halogen atom or a hydrogen atom, Q ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom, G represents an oxygen atom or a sulfur atom, Q ⁴ is still at a halogen atom A C1-C4 alkyl group which may be substituted, a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, or a halogen atom Good C3-C6 alkynyloxy group, C1-C4 alkylamino group optionally substituted with a halogen atom, Di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, Hydroxyl group, Amino group, C2 -C5 represents a cyclic amino group or a hydrogen atom, k represents 0 or 1, h represents 0, 1 or 2, and group E1 is a C1-C6 chain optionally substituted with a group selected from group L wherein the hydrocarbon group, C3 -C6 cycloalkyl group which may be substituted with a halogen ^{atom, -OQ 5, -SQ 5, -S} (= O) Q 5, -S (= O) 2 Q 5, -C (= O) Q ^6, -O (= O) Q ^7, a cyano group, a nitro group, a group of monovalent radicals consisting of hydroxyl group and a halogen atom, the group E2 is a group optionally substituted by C2-C6 alkanediyl also selected from the group L A group of divalent groups consisting of a group, a 1,3-butadiene-1,4-diyl group, -GTG-G- and -TGGT- which may be substituted with a group selected from group L Group E3 represents a group of divalent groups consisting of ═O, ═NO—Q ⁵ , ═C═CH ₂ and ═C (Q ⁸ ) Q ⁹ , T represents a methylene group or an ethylene group, Q ⁵ represents a C1-C4 chain hydrocarbon group which may be substituted with a group selected from Group L or a C3-C6 cycloalkyl group which may be substituted with a group selected from Group L, Q ⁶ is C1-C4 alkoxy group optionally substituted with a halogen atom, C3-C6 alkyl optionally substituted with a halogen atom A kenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, a C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) optionally substituted with a halogen atom ) amino group, optionally substituted C1~C4 alkyl group with a halogen atom, a hydroxyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁷ is C1 which may optionally be substituted with a halogen atom -C4 alkoxy group, C3-C6 alkenyloxy group optionally substituted with a halogen atom, C3-C6 alkynyloxy group optionally substituted with a halogen atom, C1-C4 alkyl optionally substituted with a halogen atom Amino group, di (C1-C4 alkyl) amino group optionally substituted with halogen atom, halogen source In substituted C1~C4 may alkyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁸ and Q ⁹ are the same or different, C1 to which may be substituted with a halogen atom A C4 alkoxy group, a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom; Group L is a C1-C4 alkoxy optionally substituted with a hydroxyl group or a halogen atom A C3-C6 alkenyloxy group optionally substituted with a halogen atom, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, an amino group, a C1-C4 alkyl optionally substituted with a halogen atom amino groups, optionally substituted with a halogen atom di (C1 -C4 alkyl) amino group, C2-C5 cyclic amino group, -C (= O) Q ⁶ -OC (= O) Q ⁷
And a group consisting of halogen atoms. ], Compound represented by formula (B)

[Wherein, k, h, Q ¹ , Q ² and Q ³ represent the same meaning as described above, and Q ¹¹ may be substituted with a C1-C5 haloalkyl group having at least one fluorine atom or a halogen atom. C3-C5 alkenyl group, C3-C5 alkenyloxy group optionally substituted with a halogen atom, C3-C5 alkynyl group optionally substituted with a halogen atom, or C3-C5 alkynyl optionally substituted with a halogen atom Represents an oxy group, and Q ¹² is a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, or a C1-C4 which may be substituted with a halogen atom. Represents an alkylthio group, a halogen atom or a hydrogen atom (provided that Q ¹¹ is a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or If substituted with a halogen atom may also be C3-C5 alkynyloxy group, Q ¹² is a is C1-C4 may be an alkyl group or a hydrogen atom substituted with a halogen atom.), Q ¹³ is C1-C4 Represents an alkyl group, a halogen atom or a hydrogen atom; ], Compound represented by formula (C)

[Wherein L ³ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a hydrogen atom, and L ⁴ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or a C1 represents C1-C6 alkyl group substituted with -C6 alkoxy group, L ⁵ and L ⁶ are the same or different, represent a methyl group or a hydrogen atom. And a compound represented by formula (D)

[Wherein, X ¹ represents a 2-methylpropyl group or a 2-methyl-1-propenyl group, X ² represents a methyl group, X ³ represents a 2-methyl-1-propenyl group, and X ⁴ represents methyl Represents a group. And one or more insecticidal compounds selected from the group of compounds (A) (hereinafter referred to as the present insecticidal compound).

Examples of substituents used in the description of the present specification will be described below.

  In this specification, the expression “C1-C3 chain hydrocarbon group” represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 3 carbon atoms, such as a methyl group. C1-C3 alkyl groups such as ethyl group, propyl group and isopropyl group; C2-C3 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group and 1-methylvinyl group; ethynyl group, propargyl group, 2 -C2-C3 alkynyl group such as butynyl group. The expression “C1-C2 chain hydrocarbon group” represents a methyl group, an ethyl group, a vinyl group, or an ethynyl group.

  In the present specification, the expression “C1-C3 alkyl group” represents a linear or branched hydrocarbon group having 1 to 3 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group. Groups. The expression “C1-C2 alkyl group” represents a methyl group or an ethyl group.

  In this specification, the expression “C2-C3 alkenyl group” is linear or branched having 2 to 3 carbon atoms, and has one or more double bonds in the molecule. Represents an unsaturated hydrocarbon group, and examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, and a 1-methylvinyl group.

  In this specification, the expression “C2-C3 alkynyl group” refers to a linear or branched chain having 2 to 3 carbon atoms and having one or more triple bonds in the molecule. A saturated hydrocarbon group is represented, and examples thereof include an ethynyl group and a propargyl group.

  In the present specification, the expression “C1-C3 alkoxy group” represents a group represented by linear or branched alkyl-O— having 1 to 3 carbon atoms, such as a methoxy group or an ethoxy group. , A propyloxy group, and an isopropyloxy group.

  In the present specification, the expression “C2-C3 alkenyloxy group” is a linear or branched chain having 2 to 3 carbon atoms, and has one or more double bonds in the molecule. Represents a group represented by alkenyl-O-, and examples thereof include a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, and a 1-methylvinyloxy group.

  In this specification, the expression “C2-C3 alkynyloxy group” is linear or branched having 2 to 3 carbon atoms, and has one or more triple bonds in the molecule. It represents a group represented by alkynyl-O—, and examples thereof include an ethynyloxy group and a propargyloxy group.

  In the present specification, the expression “C1-C3 alkylsulfanyl group” represents a group represented by linear or branched alkyl-S— having 1 to 3 carbon atoms, such as a methylsulfanyl group, Examples thereof include an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.

  In the present specification, the expression “C1-C3 alkylsulfinyl group” represents a group represented by linear or branched alkyl-S (O) — having 1 to 3 carbon atoms, such as methyl. Examples thereof include a sulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group.

In the present specification, the expression “C1-C3 alkylsulfonyl group” represents a group represented by linear or branched alkyl-S (O) ₂ — having 1 to 3 carbon atoms, for example, Examples include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

  In the present specification, the “C3-C6 alicyclic hydrocarbon group” represents a cyclic non-aromatic hydrocarbon group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, C3-C6 cycloalkyl group such as cyclohexyl group; C3-C6 cycloalkenyl group such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group and the like can be mentioned.

  In the present specification, the expression “C3-C6 cycloalkyl group” represents a cyclic alkyl group having 3 to 6 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

  In the present specification, the expression “may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, The atoms or groups selected from group X may be the same as or different from each other.

  In the present specification, the expression “may have one or more atoms or groups selected from group Z” means that when it has two or more atoms or groups selected from group Z, The atoms or groups selected from group Z may be the same as or different from each other.

  In the present specification, the expression “may have one or more atoms or groups selected from group W” means that when it has two or more atoms or groups selected from group W, The atoms or groups selected from group W may be the same as or different from each other.

  In the present specification, the expression “which may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other. May be.

In the present specification, the expression “6-membered heterocyclic group” is a 6-membered heterocyclic compound containing one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to the carbon atom in the ring structure. Represents a residue, and examples thereof include a 6-membered aromatic heterocyclic group and a 6-membered non-aromatic heterocyclic group.
Examples of the “6-membered aromatic heterocyclic group” include a pyrazinyl group, a pyrimidinyl group, a pyridyl group, and a pyridazinyl group.
Examples of the “6-membered non-aromatic heterocyclic group” include a piperidyl group, a morpholinyl group, a piperazinyl group, and a thiomorpholinyl group.

  In the present specification, the “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the present condensed heterocyclic compound, examples of the “C1-C3 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, difluoromethyl group, tri Fluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group , 2-chloro-1,1,1,3,3,3-hexafluoropropan-2-yl group (—C (Cl) (C _{3) 2),} heptafluoropropyl group, heptafluoroisopropyl group, methylsulfanyl ethyl group, ethylsulfanyl ethyl group, methylsulfinyl ethyl group, methylsulfonyl ethyl group, a methoxycarbonylmethyl group, 1 selected from the group X, such as a cyanomethyl group A C1-C3 alkyl group optionally having one or more atoms or groups;
Having one or more atoms or groups selected from group X such as vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1,1-difluoroallyl group, pentafluoroallyl group, etc. A good C2-C3 alkenyl group;
Examples include C2-C3 alkynyl group which may have one or more atoms or groups selected from group X such as ethynyl group, propargyl group and the like.

In the present condensed heterocyclic compound, examples of the “C1-C3 chain hydrocarbon group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, It has one or more halogen atoms such as trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoroisopropyl group, etc. An optionally substituted C1-C3 alkyl group;
C2-C3 alkenyl optionally having one or more halogen atoms such as vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1,1-difluoroallyl group and pentafluoroallyl group Group;
Examples include C2-C3 alkynyl groups which may have one or more halogen atoms of ethynyl group and propargyl group.

In the present condensed heterocyclic compound, examples of the “phenyl group optionally having one or more atoms or groups selected from group Z” include a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, 4- Fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl Group, 2,3,4,5,6-pentafluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-trifluoromethylphenyl group, 3-trifluoro Oromethylphenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-trifluoromethylsulfanylphenyl group, 3-trifluoro Methylsulfanylphenyl group, 4-trifluoromethylsulfanylphenyl group, 4-methoxycarbonylphenyl group, 4-nitrophenyl group, 4-cyanophenyl group, 4-methylaminophenyl group, 4-dimethylaminophenyl group, 4-methyl Examples thereof include a sulfinylphenyl group and a 4-methylsulfonylphenyl group.

Examples of the “6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” in the present condensed heterocyclic compound include group Z such as piperidyl group, morpholyl group, and thiomorpholyl group. A 6-membered non-aromatic heterocyclic group optionally having one or more atoms or groups selected from;
Pyrazinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group , 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group, 2-pyrimidinyl group, 4-trifluoromethylpyridin-2-yl group, 5-trifluoromethylpyridin-2-yl group, etc. Examples thereof include a 6-membered aromatic heterocyclic group which may have one or more atoms or groups selected from Z.

In the present condensed heterocyclic compound, examples of the “C1-C3 chain hydrocarbon group optionally having one or more atoms or groups selected from group W” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. , Trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, methoxymethyl group, ethoxymethyl group, propyloxy Group W such as methyl group, isopropyloxymethyl group, methoxyethyl group, ethoxyethyl group, propyloxyethyl group, isopropyloxyethyl group, methylsulfanylethyl group, ethylsulfanylethyl group, methylsulfinylethyl group, and methylsulfonylethyl group Having one or more atoms or groups selected from There may be C1-C3 alkyl group;
C2-C3 alkenyl optionally having one or more atoms or groups selected from group W such as vinyl group, 1-propenyl group, 2-propenyl group, 1,1-difluoroallyl group, pentafluoroallyl group, etc. Group;
C2-C3 alkynyl group which may have one or more atoms or groups selected from group W such as ethynyl group and propargyl group.

In the present condensed heterocyclic compound, “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group W” includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl Group, cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group and 3-cyclohexenyl group.

Examples of the “C1-C3 alkylsulfanyl group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, and trifluoromethyl. A sulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, and a pentafluoroethylsulfanyl group are mentioned.

Examples of the “C1-C3 alkylsulfinyl group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, and trifluoromethyl. Examples thereof include a sulfinyl group, a 2,2,2-trifluoroethylsulfinyl group and a pentafluoroethylsulfinyl group.

Examples of the “C1-C3 alkylsulfonyl group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, and trifluoromethyl. Examples include a sulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, and a pentafluoroethylsulfonyl group.

Examples of the “C1-C3 alkoxy group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a methoxy group, a trifluoromethoxy group, an ethoxy group, and 2,2,2-trifluoroethoxy. Group, propyloxy group and isopropyloxy group.

In the present condensed heterocyclic compound, examples of the “C2-C3 alkenyloxy group optionally having one or more halogen atoms” include 2-propenyloxy group, 2-methyl-2-propenyloxy group, 3, 3 -A difluoroallyloxy group and a 3, 3- dichloroallyloxy group are mentioned.

Examples of the “C2-C3 alkynyloxy group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a propargyloxy group.

In the present condensed heterocyclic compound, “one or more” means one or more and the maximum number to which atoms or groups can be bonded, unless otherwise specified.

［式中、
Ａ^1Ａは−ＮＲ^6Ａ−、酸素原子又は硫黄原子を表し、
Ａ^2Ａは窒素原子又は＝ＣＨ−を表し、
Ｒ^1Ａ、Ｒ^3ＡおよびＲ^4Ａは同一又は相異なり、ハロゲン原子又は水素原子を表し（但し、Ｒ^1Ａ、Ｒ^3ＡおよびＲ^4Ａのうち、少なくとも２つは水素原子を表す）、
Ｒ^2Ａは１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキル基、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルコキシ基、１個以上のハロゲン原子を有するＣ１−Ｃ３アルキル基を有していてもよい６員芳香族複素環基、ハロゲン原子又は水素原子を表し、
Ｒ^5Ａは１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキル基、又は−Ｓ（Ｏ）_ｍＲ^7Ａを表し、
Ｒ^6ＡはＣ１−Ｃ３アルキル基又はＣ３−Ｃ６シクロアルキル基を表し、
Ｒ^7Ａは１個以上のハロゲン原子を有していてもよいＣ１−Ｃ３アルキル基を表し、
ｍは０、１又は２を表し、ｎは０、１又は２を表す。］
で示される化合物；
式（１Ａ）において、Ａ^1Ａが−ＮＲ^6A−である化合物；
式（１Ａ）において、Ａ^1Ａが酸素原子である化合物；
式（１Ａ）において、Ａ^1Ａが硫黄原子である化合物；
式（１Ａ）において、Ａ^2Ａが窒素原子である化合物；
式（１Ａ）において、Ａ^2Ａが＝ＣＨ−である化合物；
式（１Ｂ）

［式中、
Ａ^1Ｂは−ＮＲ^6Ｂ−、酸素原子又は硫黄原子を表し、
Ａ^2Ｂは窒素原子又は＝ＣＨ−を表し、
Ｒ^1Ｂ、Ｒ^3ＢおよびＲ^4Ｂは同一又は相異なり、フッ素原子、塩素原子又は水素原子を表し（但し、Ｒ^1Ｂ、Ｒ^3ＢおよびＲ^4Ｂのうち、少なくとも２つは水素原子を表す）、
Ｒ^2ＢはＣ１−Ｃ３アルキル基（特に、メチル基、エチル基又はイソプロピル基）、１個以上のハロゲン原子を有するＣ１−Ｃ３アルキル基（特に、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、ヘプタフルオロプロピル基等）、１個以上のハロゲン原子を有するＣ１−Ｃ３アルコキシ基（特に、トリフルオロメトキシ基等）、含窒素６員芳香族複素環基（特に、２−、３−又は４−ピリジル基、２−ピリミジニル基等）、ハロゲン原子（特に、フッ素原子、塩素原子、臭素原子等）又は水素原子を表し、
Ｒ^5Ｂは１個以上のハロゲン原子を有するＣ１−Ｃ３アルキル基（特に、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、２−クロロ−１，１，１，３，３，３−ヘキサフルオロプロパン−２−イル基（−Ｃ（Ｃｌ）（ＣＦ_３）_２）、ヘプタフルオロイソプロピル基等）、又は−Ｓ（Ｏ）_ｍＲ^7Ｂを表し、
Ｒ^6ＢはＣ１−Ｃ３アルキル基（メチル基、エチル基、プロピル基又はイソプロピル基、特にメチル基）を表し、
Ｒ^7Ｂは１個以上のハロゲン原子を有するＣ１−Ｃ３アルキル（トリフルオロメチル基、ペンタフルオロエチル基等、特にトリフルオロメチル基）を表し、
ｍは０、１又は２を表し、ｎは０、１又は２を表す。］
で示される化合物；
式（１Ｂ）において、Ａ^1Ｂが−ＮＲ^6Ｂ−である化合物；
式（１Ｂ）において、Ａ^1Ｂが酸素原子である化合物；
式（１Ｂ）において、Ａ^1Ｂが硫黄原子である化合物；
式（１Ｂ）において、Ａ^2Ｂが窒素原子である化合物；
式（１Ｂ）において、Ａ^2Ｂが＝ＣＨ−である化合物。
上記一般式（１Ａ）および（１Ｂ）で示される化合物は、一般式（１）で示される化合物に包含される。 Examples of the present condensed heterocyclic compound include the following compounds.
In the formula (1), A ¹ is —NR ⁶ —, an oxygen atom or a sulfur atom, and R ⁵ has one C1-C3 alkoxy group which may have one or more halogen atoms. A C1-C3 chain hydrocarbon group, a compound which is a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms;
In formula (1), a compound wherein A ¹ is —NR ⁶ — or a sulfur atom, and R ⁵ is a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms;
In formula (1), A ¹ is —NR ⁶ —, an oxygen atom or a sulfur atom, A ² is N, and R ⁵ may have one or more halogen atoms. A compound having a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms;
In formula (1), A ¹ is —NR ⁶ — or a sulfur atom, A ² is N, and R ⁵ may have one or more halogen atoms. A compound which is
In the formula (1), A ¹ is —NR ⁶ —, an oxygen atom or a sulfur atom, and R ⁵ has one C1-C3 alkoxy group which may have one or more halogen atoms. A C1-C3-chain hydrocarbon group, a C1-C3-chain hydrocarbon group optionally having one or more halogen atoms, and a compound wherein R ⁶ is a methyl group;
In formula (1), A ¹ is —NR ⁶ — or a sulfur atom, R ⁵ is a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, and R ⁶ is methyl. A compound which is a group;
In formula (1), A ¹ is —NR ⁶ —, an oxygen atom or a sulfur atom, A ² is N, and R ⁵ may have one or more halogen atoms. A C1-C3 chain hydrocarbon group having 1, a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, and R ⁶ is a methyl group;
In formula (1), A ¹ is —NR ⁶ — or a sulfur atom, A ² is N, and R ⁵ may have one or more halogen atoms. And R ⁶ is a methyl group;
In formula (1), A ¹ is —NR ⁶ —, A ² is N, and R ⁵ is a C1-C2 chain hydrocarbon group optionally having one or more halogen atoms, A compound wherein R ⁶ is a methyl group;
In the formula (1), A ¹ is —NR ⁶ — or a sulfur atom, R ⁵ is —S (O) _m R ⁷ , and R ⁷ may have a halogen atom. A compound which is a hydrocarbon group;
In the formula (1), A ¹ is —NR ⁶ — or a sulfur atom, A ² is N, R ⁵ is —S (O) _m R ⁷ , and R ⁷ represents one or more halogen atoms. A compound which is a C1-C3 chain hydrocarbon group optionally having;
In Formula (1), A ¹ is —NR ⁶ — or a sulfur atom, R ⁵ is —S (O) _m R ⁷ , R ⁶ is a methyl group, and R ⁷ is one or more halogen atoms. A compound which is a C1-C3 chain hydrocarbon group optionally having:
In Formula (1), A ¹ is —NR ⁶ — or a sulfur atom, A ² is N, R ⁵ is —S (O) _m R ⁷ , R ⁶ is a methyl group, and R ⁷ Is a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms;
In Formula (1), A ¹ is a sulfur atom, A ² is N, R ⁵ is —S (O) _m R ⁷ , R ⁶ is a methyl group, and R ⁷ is one or more. A compound which is a C1-C2 chain hydrocarbon group optionally having a halogen atom;
In the formula (1), R ² , R ³ and R ⁴ are the same or different, and a C1-C3 chain hydrocarbon group which may have one or more halogen atoms, —OR ⁷ , halogen atom or hydrogen A compound which is an atom and R ⁵ is a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, —OR ⁷ , or a halogen atom;
In the formula (1), R ² , R ³ and R ⁴ are the same or different and each have a C1-C2 alkyl group which may have one or more halogen atoms or one or more halogen atoms. A 6-membered heterocyclic group or a hydrogen atom, and R ⁵ may have a C1-C2 alkyl group which may have one or more halogen atoms or one or more halogen atoms. A compound which is a heterocyclic group;
In the formula (1), R ² , R ³ and R ⁴ are the same or different and are a methyl group, an ethyl group, a trifluoromethyl group, a trifluoromethoxy group or a hydrogen atom, and R ⁵ is a methyl group, an ethyl group, A compound which is a trifluoromethyl group or a trifluoromethoxy group;
In the formula (1), R ² , R ³ and R ⁴ are the same or different and are a fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom, and R ⁵ is a fluorine atom, chlorine atom, bromine atom or iodine. A compound that is an atom;
In the formula (1), R ² , R ³ and R ⁴ are the same or different, and are fluorine atom, chlorine atom, bromine atom, methyl group, trifluoromethyl group, trifluoromethoxy group, pentafluoroethyl group or hydrogen atom. A compound in which R ⁵ is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a trifluoromethoxy group or a pentafluoroethyl group;
In the formula (1), compounds wherein A ¹ is —NR ⁶ —;
In the formula (1), compounds wherein A ¹ is an oxygen atom;
In the formula (1), compounds wherein A ¹ is a sulfur atom;
In the formula (1), compounds wherein A ² is a nitrogen atom;
In the formula (1), compounds wherein A ² is ═CH—;
In the formula (1), compounds wherein R ¹ , R ³ and R ⁴ are the same or different and are a halogen atom or a hydrogen atom;
In formula (1), R ² may have one or more halogen atoms, a C1-C3 alkyl group, one or more halogen atoms, a C1-C3 alkoxy group, one or more. A compound which is a 6-membered aromatic heterocyclic group, a halogen atom or a hydrogen atom which may have a C1-C3 alkyl group having a halogen atom of
In formula (1), R ¹ , R ³ and R ⁴ are the same or different and are a halogen atom or a hydrogen atom, and R ² may be a C1-C3 alkyl group optionally having one or more halogen atoms, A C1-C3 alkoxy group optionally having one or more halogen atoms, a 6-membered aromatic heterocyclic group optionally having a C1-C3 alkyl group having one or more halogen atoms, a halogen atom or A compound that is a hydrogen atom;
Formula (1A)

[Where:
A ^1A represents —NR ^6A —, an oxygen atom or a sulfur atom,
A ^2A represents a nitrogen atom or = CH-,
R ^1A , R ^3A and R ^4A are the same or different and represent a halogen atom or a hydrogen atom (provided that at least two of R ^1A , R ^3A and R ^4A represent a hydrogen atom),
R ^2A is a C1-C3 alkyl group which may have one or more halogen atoms, a C1-C3 alkoxy group which may have one or more halogen atoms, or a C1 which has one or more halogen atoms. -Represents a 6-membered aromatic heterocyclic group optionally having a -C3 alkyl group, a halogen atom or a hydrogen atom,
R ^5A represents a C1-C3 alkyl group optionally having one or more halogen atoms, or —S (O) _m R ^7A ;
R ^6A represents a C1-C3 alkyl group or a C3-C6 cycloalkyl group,
R ^7A represents a C1-C3 alkyl group optionally having one or more halogen atoms,
m represents 0, 1 or 2, and n represents 0, 1 or 2. ]
A compound represented by:
In the formula (1A), compounds wherein A ^1A is —NR ^6A —;
In the formula (1A), compounds wherein A ^1A is an oxygen atom;
In the formula (1A), compounds wherein A ^1A is a sulfur atom;
In the formula (1A), compounds wherein A ^2A is a nitrogen atom;
In the formula (1A), compounds wherein A ^2A is ═CH—;
Formula (1B)

[Where:
A ^1B represents —NR ^6B —, an oxygen atom or a sulfur atom,
A ^2B represents a nitrogen atom or ═CH—,
R ^1B , R ^3B and R ^4B are the same or different and represent a fluorine atom, a chlorine atom or a hydrogen atom (provided that at least two of R ^1B , R ^3B and R ^4B represent a hydrogen atom),
R ^2B is a C1-C3 alkyl group (particularly a methyl group, an ethyl group or an isopropyl group), and a C1-C3 alkyl group having one or more halogen atoms (particularly a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group). A C1-C3 alkoxy group having 1 or more halogen atoms (especially a trifluoromethoxy group), a nitrogen-containing 6-membered aromatic heterocyclic group (especially 2-, 3- or 4). -Pyridyl group, 2-pyrimidinyl group, etc.), a halogen atom (especially a fluorine atom, a chlorine atom, a bromine atom, etc.) or a hydrogen atom,
R ^5B represents a C1-C3 alkyl group having one or more halogen atoms (in particular, difluoromethyl group, trifluoromethyl group, pentafluoroethyl group, 2-chloro-1,1,1,3,3,3-hexa). A fluoropropan-2-yl group (—C (Cl) (CF ₃ ) ₂ ), a heptafluoroisopropyl group, or the like), or —S (O) _m R ^7B ;
R ^6B represents a C1-C3 alkyl group (methyl group, ethyl group, propyl group or isopropyl group, particularly methyl group),
R ^7B represents C1-C3 alkyl having one or more halogen atoms (trifluoromethyl group, pentafluoroethyl group, etc., particularly trifluoromethyl group),
m represents 0, 1 or 2, and n represents 0, 1 or 2. ]
A compound represented by:
In the formula (1B), compounds wherein A ^1B is —NR ^6B —;
In the formula (1B), compounds wherein A ^1B is an oxygen atom;
In the formula (1B), compounds wherein A ^1B is a sulfur atom;
In the formula (1B), compounds wherein A ^2B is a nitrogen atom;
In the formula (1B), compounds wherein A ^2B is ═CH—.
The compounds represented by the general formulas (1A) and (1B) are included in the compound represented by the general formula (1).

  Next, the manufacturing method of this condensed heterocyclic compound is demonstrated.

  The present condensed heterocyclic compound can be produced, for example, by the following (Production Method A) to (Production Method F).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびｎは前記と同じ意味を表す。］
（製造法Ｂ）
本縮合複素環化合物（１）は、化合物（Ｍ１）と化合物（Ｍ４）とを反応させることにより製造できる。または化合物（Ｍ１）と化合物（Ｍ４）とを反応させることにより化合物（Ｍ３）を製造し、化合物（Ｍ３）を環化させることにより製造できる。

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびｎは前記と同じ意味を表す。］
（製造法Ｃ）
本縮合複素環化合物（１）は、化合物（Ｍ１）と化合物（Ｍ５）とを反応させることにより製造できる。または化合物（Ｍ１）と化合物（Ｍ５）とを反応させることにより化合物（Ｍ６）を製造し、化合物（Ｍ６）を環化させることにより製造できる。

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびｎは前記と同じ意味を表す。］
（製造法Ｄ）
式（１）においてＡ¹が硫黄原子である化合物（２）は、化合物（Ｍ７）と硫化剤とを反応させることにより製造することができる。

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
（製造法Ｅ）
式（１）においてｎが０である化合物（３）は、例えば以下の方法により製造することができる。

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹およびＡ²は前記と同じ意味を表し、Ｖ²はフッ素原子又は塩素原子を表す。］
（製造法Ｆ）
式（１）においてｎが０である化合物（３）は、例えば以下の方法により製造することができる。

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびＶ²は前記と同じ意味を表す。］ (Production method A)
This condensed heterocyclic compound (1) can be produced by reacting the compound (M1) with the compound (M2). Alternatively, it can be produced by reacting the compound (M1) and the compound (M2) to produce the compound (M3) and cyclizing the compound (M3).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and n represent the same meaning as described above. ]
(Production method B)
This condensed heterocyclic compound (1) can be produced by reacting the compound (M1) with the compound (M4). Alternatively, it can be produced by reacting the compound (M1) and the compound (M4) to produce the compound (M3) and cyclizing the compound (M3).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and n represent the same meaning as described above. ]
(Production method C)
This fused heterocyclic compound (1) can be produced by reacting compound (M1) with compound (M5). Alternatively, it can be produced by reacting the compound (M1) and the compound (M5) to produce the compound (M6) and cyclizing the compound (M6).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and n represent the same meaning as described above. ]
(Production Method D)
Compound (2) in which A ¹ is a sulfur atom in formula (1) can be produced by reacting compound (M7) with a sulfurizing agent.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
(Production method E)
Compound (3) in which n is 0 in formula (1) can be produced, for example, by the following method.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ and A ² represent the same meaning as described above, and V ² represents a fluorine atom or a chlorine atom. ]
(Production Method F)
Compound (3) in which n is 0 in formula (1) can be produced, for example, by the following method.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and V ² represent the same meaning as described above. ]

  The production methods (Production Method A) to (Production Method F) of the present condensed heterocyclic compound will be described in more detail below. In addition, a production method from the present condensed heterocyclic compound to another condensed heterocyclic compound will be described. The present condensed heterocyclic compound can be produced, for example, by the following (Production Method 1) to (Production Method 23).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常塩基、酸、亜硫酸塩あるいは二亜硫酸塩の存在下で行われる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる塩基としては、炭酸水素ナトリウム、炭酸水素カリウム等の炭酸水素塩類、炭酸ナトリウム、炭酸カリウム等の炭酸塩類およびこれらの混合物が挙げられる。
反応に用いられる酸としては、ｐ−トルエンスルホン酸等のスルホン酸類、酢酸等のカルボン酸類が挙げられる。
反応に用いられる亜硫酸塩としては、亜硫酸ナトリウム、亜硫酸カリウム等が挙げられる。
反応に用いられる二亜硫酸塩としては、二亜硫酸ナトリウム、二亜硫酸カリウム等が挙げられる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す。）、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す。）、Ｎ−メチルピロリドン（以下、ＮＭＰと記す。）等の酸アミド類、ジメチルスルホキシド（以下、ＤＭＳＯと記す。）等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
該反応は、必要に応じて酸化剤を加えて行うこともできる。
反応に用いられる酸化剤としては、例えば酸素、塩化銅（ＩＩ）、２，３−ジクロロ−５，６−ジシアノ−ｐ−ベンゾキノン等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ５）が通常１〜３モルの割合、塩基が通常１〜５モルの割合、酸が通常１〜５モルの割合、亜硫酸塩が通常１〜５モルの割合、二亜硫酸塩が通常１〜５モルの割合、酸化剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（４）を単離することができる。単離された化合物（４）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 1) (Step (C-1))
Compound (4) in which A ¹ is —NR ⁶ — in formula (1) can be produced by reacting compound (M12) with compound (M5) according to step (C-1).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually carried out in the presence of a base, acid, sulfite or disulfite.
The reaction is usually performed in the presence of a solvent.
Examples of the base used in the reaction include hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, carbonates such as sodium carbonate and potassium carbonate, and mixtures thereof.
Examples of the acid used for the reaction include sulfonic acids such as p-toluenesulfonic acid and carboxylic acids such as acetic acid.
Examples of the sulfite used in the reaction include sodium sulfite and potassium sulfite.
Examples of the disulfite used in the reaction include sodium disulfite and potassium disulfite.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether, 1,4-dioxane, and aliphatic hydrocarbons such as hexane, heptane, and octane. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide (hereinafter referred to as DMF) ), Acid amides such as N-methylpyrrolidone (hereinafter referred to as NMP), sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO), nitrogen-containing aromatic compounds such as pyridine and quinoline, and the like. A mixture is mentioned.
The reaction can be carried out by adding an oxidizing agent as necessary.
Examples of the oxidizing agent used in the reaction include oxygen, copper (II) chloride, 2,3-dichloro-5,6-dicyano-p-benzoquinone, and the like.
For this reaction, the compound (M5) is usually in a proportion of 1 to 3 mol, the base is usually in a proportion of 1 to 5 mol, the acid is usually in a proportion of 1 to 5 mol, and the sulfite with respect to 1 mol of the compound (M12). Is usually used in a proportion of 1 to 5 mol, disulfite is usually used in a proportion of 1 to 5 mol, and oxidizing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The isolated compound (4) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す。）、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、（ベンゾトリアゾール−１−イルオキシ）トリス（ジメチルアミノ）ホスホニウムヘキサフルオロリン酸塩（以下、ＢＯＰ試薬と記す。）等が挙げられる。
該反応は、必要に応じて触媒を加えて行うこともできる。
反応に用いられる触媒としては、１−ヒドロキシベンゾトリアゾール（以下、ＨＯＢｔと記す。）等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合、触媒が通常０．０１〜０．１モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（４）を単離することができる。単離された化合物（４）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。
また、工程（Ｂ−１）に従い、化合物（Ｍ２）に代えて化合物（M４）を用い、上記方法に準じて化合物（４）を製造することもできる。
化合物（M４）を用いる場合は、通常脱水縮合剤を加えずに行われる。必要に応じて塩基を加えて行うこともできる。
塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（M４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。 (Production Method 2) (Step A-1)
Compound (4) in which A ¹ is —NR ⁶ — in formula (1) is obtained by reacting compound (M12) and compound (M2) in the presence of a dehydration condensing agent according to step (A-1). Can be manufactured.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC), carbodiimides such as 1,3-dicyclohexylcarbodiimide, (benzotriazole- 1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter referred to as BOP reagent) and the like.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).
In the reaction, with respect to 1 mole of the compound (M12), the ratio of the compound (M2) is usually 1 to 3 moles, the dehydration condensing agent is usually 1 to 5 moles, and the catalyst is usually 0.01 to 0.1. Used in molar proportions.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The isolated compound (4) can be further purified by chromatography, recrystallization and the like.
Moreover, according to the step (B-1), the compound (M4) can be used instead of the compound (M2), and the compound (4) can be produced according to the above method.
When the compound (M4) is used, it is usually carried out without adding a dehydrating condensing agent. A base can be added as necessary.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、メタノール、エタノール、プロパノール、ブタノール、ペンタノール等のアルコール類およびこれらの混合物が挙げられる。
該反応は必要に応じて、酸又は脱水剤を用いることができる。反応に用いられる酸としては、ｐ−トルエンスルホン酸等のスルホン酸類、酢酸等のカルボン酸類が挙げられ、反応に用いられる脱水剤としては、オキシ塩化リン、無水酢酸、トリフルオロ酢酸無水物等が挙げられる。
該反応には、化合物（Ｍ１３）１モルに対して、酸又は脱水剤が通常１モル〜１０モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（４）を単離することができる。単離された化合物（４）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 3) (Step (A-3), Step (B-3))
Compound (4) in which A ¹ is —NR ⁶ — in formula (1) can be produced by dehydrating condensation of compound (M13) according to step (A-3) or step (B-3). .

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, methanol, ethanol, propanol , Alcohols such as butanol and pentanol, and mixtures thereof.
In the reaction, an acid or a dehydrating agent can be used as necessary. Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, and carboxylic acids such as acetic acid. Examples of the dehydrating agent used in the reaction include phosphorus oxychloride, acetic anhydride, trifluoroacetic anhydride, and the like. Can be mentioned.
In the reaction, with respect to 1 mol of the compound (M13), an acid or a dehydrating agent is generally used in a proportion of 1 mol to 10 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (4) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、メタノール、エタノール、プロパノール、ブタノール、ｔｅｒｔ−ブタノール、ペンタノール等のアルコール類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、リン酸三カリウム等が挙げられる。
該反応には、化合物（Ｍ１３）１モルに対して、塩基が通常１モル〜１０モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（４）を単離することができる。単離された化合物（４）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 4) (Step (A-3), Step (B-3))
Compound (4) in which A ¹ is —NR ⁶ — in formula (1) is produced by reacting compound (M13) in the presence of a base according to step (A-3) or step (B-3). can do.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, methanol, ethanol, propanol , Butanol, tert-butanol, pentanol and the like, and mixtures thereof.
Examples of the base used for the reaction include tripotassium phosphate.
In the reaction, with respect to 1 mol of the compound (M13), the base is generally used at a ratio of 1 mol to 10 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (4) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表し、Ｌは塩素原子、臭素原子、ヨウ素原子、トリフルオロメチルスルホニルオキシ基およびメチルスルホニルオキシ基等の脱離基を表し、ここでＲ⁶は群Ｗより選ばれる１個以上の原子もしくは基を有していてもよいＣ１−Ｃ３鎖式炭化水素基を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム、水素化カルシウム等のアルカリ金属もしくはアルカリ土類金属の水素化物、炭酸ナトリウム、炭酸カリウム等の無機塩基、又はトリエチルアミン等の有機塩基等が挙げられる。
該反応には、化合物（５）１モルに対して、化合物（Ｍ１４）が通常１〜５モルの割合で用いられる。
該反応には、化合物（５）１モルに対して、塩基が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（４）を単離することができる。単離された化合物（４）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 5)
Compound (4) in which A ¹ is —NR ⁶ — in formula (1) can be produced by reacting compound (5) with compound (M14) in the presence of a base.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above, and L represents a chlorine atom, a bromine atom, an iodine atom, a trifluoromethylsulfonyloxy group and methyl. Represents a leaving group such as a sulfonyloxy group, wherein R ⁶ represents a C1-C3 chain hydrocarbon group which may have one or more atoms or groups selected from group W; ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Is mentioned.
In the reaction, compound (M14) is usually used at a ratio of 1 to 5 mol with respect to 1 mol of compound (5).
In the reaction, the base is generally used at a ratio of 1 to 3 moles relative to 1 mole of the compound (5).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (4) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下または非存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水素類およびこれらの混合物が挙げられる。
反応に用いられる酸としては、ポリリン酸やトリメチルシリルポリホスフェート等が挙げられる。
該反応は、酸としてポリリン酸を用いる場合は通常無溶媒で行うが、溶媒中で行ってもよい。
該反応には、化合物（Ｍ１５）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、酸が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（６）を単離することができる。単離された化合物（６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。
また、化合物（Ｍ２）に代えて化合物（M４）を用い、工程（Ｂ−１）に従い、上記方法に準じて化合物（６）を製造することもできる。
化合物（M４）を用いる場合は、通常脱水縮合剤を加えずに行われる。必要に応じて塩基を加えて行うこともできる。
塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１５）１モルに対して、化合物（M４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。 (Manufacturing method 6) (Process (A-1))
Compound (6) in which A ¹ is an oxygen atom in formula (1) is produced by reacting compound (M15) and compound (M2) in the presence of an acid according to step (A-1). Can do.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, and mixtures thereof.
Examples of the acid used for the reaction include polyphosphoric acid and trimethylsilyl polyphosphate.
The reaction is usually carried out without a solvent when polyphosphoric acid is used as the acid, but it may be carried out in a solvent.
In the reaction, with respect to 1 mol of the compound (M15), the compound (M2) is usually used in a proportion of 1 to 3 mol, and the acid is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (6) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (6) can be further purified by chromatography, recrystallization and the like.
Moreover, it can replace with a compound (M2) and can use a compound (M4) and can manufacture a compound (6) according to the said method according to a process (B-1).
When the compound (M4) is used, it is usually carried out without adding a dehydrating condensing agent. A base can be added as necessary.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M15), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、メタノール、エタノール等のアルコール類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、酢酸およびこれらの混合物が挙げられる。
反応に用いられる酸化剤としては、酢酸鉛（ＩＶ）、酸化鉛（ＩＶ）等の金属酸化剤、ヨードベンゼンジアセタート等の超原子価ヨウ素化合物等が挙げられる。
該反応には、化合物（Ｍ１６）１モルに対して、酸化剤が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（６）を単離することができる。単離された化合物（６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Manufacturing method 7) (Process (C-3))
Compound (6) in which A ¹ is an oxygen atom in formula (1) can be produced by subjecting compound (M16) to an oxidation reaction according to step (C-3).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, nitriles such as acetonitrile, and acid amides such as DMF and NMP , Sulfoxides such as DMSO, acetic acid and mixtures thereof.
Examples of the oxidizing agent used in the reaction include metal oxidizing agents such as lead (IV) acetate and lead (IV) oxide, hypervalent iodine compounds such as iodobenzene diacetate, and the like.
In the reaction, with respect to 1 mol of the compound (M16), the oxidizing agent is usually used at a ratio of 1 to 3 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (6) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (6) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、四塩化炭素、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類およびこれらの混合物が挙げられる。このうち、四塩化炭素は、脱水縮合剤としても用いることができる。
反応に用いられる脱水縮合剤としては、トリフェニルホスフィンと塩基と四塩化炭素もしくは四臭化炭素との混合物、トリフェニルホスフィンとアゾジカルボン酸ジエチルエステル等のアゾジエステル類との混合物等が挙げられる。
反応に用いられる塩基としては、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類等が挙げられる。
該反応には、化合物（Ｍ１７）１モルに対して、脱水縮合剤が通常１〜３モルの割合で用いられる。塩基を用いる場合は、化合物（Ｍ１７）１モルに対して、塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常−３０〜１００℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（６）を単離することができる。単離された化合物（６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 8) (Step (A-3), Step (B-3))
Compound (6) in which A ¹ is an oxygen atom in formula (1) is produced by reacting compound (M17) in the presence of a dehydration condensing agent according to step (A-3) or step (B-3). can do.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, dichloromethane, chloroform, carbon tetrachloride, Examples thereof include halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, and mixtures thereof. Of these, carbon tetrachloride can also be used as a dehydrating condensing agent.
Examples of the dehydrating condensing agent used in the reaction include a mixture of triphenylphosphine, a base, and carbon tetrachloride or carbon tetrabromide, a mixture of triphenylphosphine and an azodiester such as azodicarboxylic acid diethyl ester, and the like.
Examples of the base used in the reaction include tertiary amines such as triethylamine and diisopropylethylamine.
In the reaction, the dehydrating condensing agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the compound (M17). When using a base, a base is normally used in the ratio of 1-5 mol with respect to 1 mol of compounds (M17).
The reaction temperature of the reaction is usually in the range of -30 to 100 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (6) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (6) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、クロロベンゼン等のハロゲン化炭化水素類およびこれらの混合物が挙げられる。
上記酸としては、ｐ−トルエンスルホン酸等のスルホン酸類、ポリリン酸等が挙げられる。
該反応には、化合物（Ｍ１７）１モルに対して、酸が通常０．１〜３モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（６）を単離することができる。単離された化合物（６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 9) (Step (A-3), Step (B-3))
Compound (6) in which A ¹ is an oxygen atom in formula (1) is produced by reacting compound (M17) in the presence of an acid according to step (A-3) or step (B-3). Can do.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and halogens such as dichloromethane, chloroform, and chlorobenzene. Hydrocarbons and mixtures thereof.
Examples of the acid include sulfonic acids such as p-toluenesulfonic acid, polyphosphoric acid, and the like.
In the reaction, an acid is usually used at a ratio of 0.1 to 3 mol with respect to 1 mol of the compound (M17).
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (6) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (6) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常塩基、酸、亜硫酸塩あるいは二亜硫酸塩の存在下で行われる。
反応に用いられる塩基としては、炭酸水素ナトリウム、炭酸水素カリウム等の炭酸水素塩類、炭酸ナトリウム、炭酸カリウム等の炭酸塩類およびこれらの混合物が挙げられる。
反応に用いられる酸としては、ｐ−トルエンスルホン酸等のスルホン酸類、酢酸等のカルボン酸類が挙げられる。
反応に用いられる亜硫酸塩としては、亜硫酸ナトリウム、亜硫酸カリウム等が挙げられる。
反応に用いられる二亜硫酸塩としては、二亜硫酸ナトリウム、二亜硫酸カリウム等が挙げられる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えば、ＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、Ｎ−、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、トルエン、キシレン、ニトロベンゼン等の芳香族炭化水素類およびこれらの混合物が挙げられる。
該反応は、必要に応じて酸化剤を加えて行うこともできる。
反応に用いられる酸化剤としては、例えば酸素、塩化銅（ＩＩ）、２，３−ジクロロ−５，６−ジシアノ−ｐ−ベンゾキノン等が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（Ｍ５）が通常１〜３モルの割合、塩基が１〜５モルの割合、酸が通常１〜５モルの割合、亜硫酸塩が通常１〜５モルの割合、二亜硫酸塩が通常１〜５モルの割合、酸化剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に加えた後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（２）を単離することができる。単離された化合物（２）は、クロマトグラフィー、再結晶等により精製することもできる。 (Manufacturing method 10) (Process (C-1))
Compound (2) in which A ¹ is a sulfur atom in formula (1) can be produced by reacting compound (M18) and compound (M5) according to step (C-1).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually carried out in the presence of a base, acid, sulfite or disulfite.
Examples of the base used in the reaction include hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, carbonates such as sodium carbonate and potassium carbonate, and mixtures thereof.
Examples of the acid used for the reaction include sulfonic acids such as p-toluenesulfonic acid and carboxylic acids such as acetic acid.
Examples of the sulfite used in the reaction include sodium sulfite and potassium sulfite.
Examples of the disulfite used in the reaction include sodium disulfite and potassium disulfite.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and halogenation such as chlorobenzene. Hydrocarbons, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF, N- and NMP, sulfoxides such as DMSO, and aromatic hydrocarbons such as toluene, xylene and nitrobenzene And mixtures thereof.
The reaction can be carried out by adding an oxidizing agent as necessary.
Examples of the oxidizing agent used in the reaction include oxygen, copper (II) chloride, 2,3-dichloro-5,6-dicyano-p-benzoquinone, and the like.
In the reaction, with respect to 1 mole of the compound (M18), the ratio of the compound (M5) is usually 1 to 3 moles, the base is 1 to 5 moles, the acid is usually 1 to 5 moles, and the sulfite is Usually, 1 to 5 mole ratio, disulfite is usually used in 1 to 5 mole ratio, and oxidizing agent is usually used in 1 to 5 mole ratio.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (2) can be isolated by performing post-treatment operations such as addition of the reaction mixture to water, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (2) can also be purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、塩基の存在下、通常溶媒の存在下で行われる。
反応に用いられる塩基としては、例えばジイソプロピルエチルアミン、トリエチルアミン等の第三級アミンが挙げられる。
反応に用いられる溶媒としては、例えばＤＭＳＯ等のスルホキシド類、ニトロベンゼン等の芳香族炭化水素類およびこれらの混合物が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（Ｍ５）が通常０．５〜３モルの割合で用いられ、塩基が通常１〜２モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に加えた後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（２）を単離することができる。単離された化合物（２）は、クロマトグラフィー、再結晶等により精製することもできる。 (Manufacturing method 11) (Process (C-1))
Compound (2) in which A ¹ is a sulfur atom in formula (1) can be produced by reacting hydrochloride of compound (M18) with compound (M5) according to step (C-1).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is carried out in the presence of a base and usually in the presence of a solvent.
Examples of the base used in the reaction include tertiary amines such as diisopropylethylamine and triethylamine.
Examples of the solvent used in the reaction include sulfoxides such as DMSO, aromatic hydrocarbons such as nitrobenzene, and mixtures thereof.
In the reaction, the compound (M5) is usually used at a ratio of 0.5 to 3 moles and the base is usually used at a ratio of 1 to 2 moles relative to 1 mole of the compound (M18).
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (2) can be isolated by performing post-treatment operations such as addition of the reaction mixture to water, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (2) can also be purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ａ¹、Ａ²およびｎは前記と同じ意味を表し、Ｖ¹は臭素原子又はヨウ素原子等の脱離基を表し、Ｒ^5ｚはシアノ基又はＣ１−Ｃ３アルキル基を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、メタノール、エタノール等のアルコール類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられるシアノ化剤としては、例えばシアン化亜鉛が挙げられ、ジ（Ｃ１−Ｃ３アルキル）亜鉛としては、例えば、ジメチル亜鉛、ジエチル亜鉛、ジイソプロピル亜鉛が挙げられる。
反応に用いられるパラジウム化合物としては、テトラキス（トリフェニルフォスフィン）パラジウム等が挙げられる。
該反応には、化合物（７）１モルに対して、シアノ化剤又はジ（Ｃ１−Ｃ３アルキル）亜鉛が通常１〜５モルの割合、パラジウム化合物が通常０．０１〜０．５モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（８）を単離することができる。単離された化合物（８）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 12)
In the compound (8) in which R ⁵ is a cyano group or a C1-C3 alkyl group in the formula (1), the compound (7) is combined with a cyanating agent or di (C1-C3 alkyl) zinc in the presence of a palladium compound. It can be produced by reacting.

[Wherein R ¹ , R ² , R ³ , R ⁴ , A ¹ , A ² and n represent the same meaning as described above, V ¹ represents a leaving group such as a bromine atom or an iodine atom, and R ^5z represents Represents a cyano group or a C1-C3 alkyl group. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, alcohols such as methanol and ethanol, acid amides such as DMF and NMP, sulfoxides such as DMSO and mixtures thereof.
Examples of the cyanating agent used in the reaction include zinc cyanide, and examples of the di (C1-C3 alkyl) zinc include dimethyl zinc, diethyl zinc, and diisopropyl zinc.
Examples of the palladium compound used for the reaction include tetrakis (triphenylphosphine) palladium.
In the reaction, with respect to 1 mol of the compound (7), the cyanating agent or di (C1-C3 alkyl) zinc is usually in a proportion of 1 to 5 mol, and the palladium compound is usually in a proportion of 0.01 to 0.5 mol. Used in
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (8) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (8) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ａ¹、Ａ²、ｎおよびＶ¹は前記と同じ意味を表し、Ｒ^ｆはＣ１−Ｃ３パーフルオロアルキル基を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばトルエン、キシレン等の芳香族炭化水素類、ＤＭＦ、ＮＭＰ等の酸アミド類およびこれらの混合物が挙げられる。
該反応には、化合物（７）１モルに対して、化合物（Ｍ１９）が通常１〜１０モルの割合、ヨウ化銅が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（９）を単離することができる。単離された化合物（９）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 13)
Compound (9) in which R ⁵ is a C1-C3 perfluoroalkyl group in formula (1) can be produced by reacting compound (7) and compound (M19) in the presence of copper iodide. it can.

[Wherein R ¹ , R ² , R ³ , R ⁴ , A ¹ , A ² , n and V ¹ represent the same meaning as described above, and R ^f represents a C1-C3 perfluoroalkyl group. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, and mixtures thereof.
In the reaction, with respect to 1 mol of the compound (7), the compound (M19) is usually used in a proportion of 1 to 10 mol, and the copper iodide is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (9) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えば水、ＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、メタノール、エタノール等のアルコール類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類が挙げられる。
該反応には、化合物（Ｍ１０）１モルに対して、化合物（Ｍ２０）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０〜１５０℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（３）を単離することができる。単離された化合物（３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Manufacturing method 14) (Process (E-4))
Compound (3) in which n is 0 in formula (1) can be produced by reacting compound (M10) and compound (M20) in the presence of a base according to step (E-4). .

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol and ethanol. Nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydrides such as sodium hydride.
In the reaction, with respect to 1 mol of the compound (M10), the compound (M20) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (3) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびＬは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム、水素化カルシウム等のアルカリ金属もしくはアルカリ土類金属の水素化物、炭酸ナトリウム、炭酸カリウム等の無機塩基、又はトリエチルアミン等の有機塩基が挙げられる。
該反応には、化合物（Ｍ１１）１モルに対して、塩基が通常１〜３モルの割合、化合物（Ｍ２１）が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（３）を単離することができる。単離された化合物（３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Manufacturing method 15) (Process (F-2))
Compound (3) in which n is 0 in formula (1) can be produced by reacting compound (M11) and compound (M21) in the presence of a base according to step (F-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and L represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
In the reaction, with respect to 1 mol of the compound (M11), the base is usually used at a ratio of 1 to 3 mol, and the compound (M21) is usually used at a ratio of 1 to 3 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (3) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹およびＡ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等のハロゲン化炭化水素類、メタノール、エタノール等のアルコール類、酢酸、水およびこれらの混合物が挙げられる。
反応に用いられる酸化剤としては、例えば過ヨウ素酸ナトリウム又はｍ−クロロ過安息香酸が挙げられる。
該反応には、化合物（３）１モルに対して、酸化剤が通常１〜３モルの割合で用いられる。好ましくは、化合物（３）１モルに対して、酸化剤が１〜１．２モルの割合で用いられる。
該反応の反応温度は、通常−２０〜８０℃の範囲である。該反応の反応時間は通常０．１〜１２時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、乾燥、濃縮する等の後処理操作を行うことにより、化合物（１０）を単離することができる。単離された化合物（１０）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 16)
Compound (10) in which n is 1 in formula (1) can be produced by subjecting compound (3) to an oxidation reaction.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ and A ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used for the reaction include sodium periodate or m-chloroperbenzoic acid.
In the reaction, the oxidizing agent is usually used in a ratio of 1 to 3 moles relative to 1 mole of the compound (3). Preferably, the oxidizing agent is used in a proportion of 1 to 1.2 mol per 1 mol of compound (3).
The reaction temperature of the reaction is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (10) can be isolated by performing post-treatment operations such as concentration. The isolated compound (10) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹およびＡ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等のハロゲン化炭化水素類、メタノール、エタノール等のアルコール類、酢酸、水およびこれらの混合物が挙げられる。
反応に用いられる酸化剤としては、例えばｍ−クロロ過安息香酸又は過酸化水素水が挙げられる。
該反応には、化合物（３）１モルに対して、酸化剤が通常２〜５モルの割合で用いられる。好ましくは、化合物（３）１モルに対して、酸化剤が２〜３モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１２０℃の範囲である。該反応の反応時間は通常０．１〜１２時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、乾燥、濃縮する等の後処理操作を行うことにより、化合物（１１）を単離することができる。単離された化合物（１１）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 17)
Compound (11) in which n is 2 in formula (1) can be produced by reacting compound (3) in the presence of an oxidizing agent.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ and A ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
In the reaction, the oxidizing agent is usually used at a ratio of 2 to 5 mol with respect to 1 mol of the compound (3). Preferably, the oxidizing agent is used in a ratio of 2 to 3 moles relative to 1 mole of the compound (3).
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, Compound (11) can be isolated by performing post-treatment operations such as concentration. The isolated compound (11) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹およびＡ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等のハロゲン化炭化水素類、メタノール、エタノール等のアルコール類、酢酸、水およびこれらの混合物が挙げられる。
反応に用いられる酸化剤としては、例えばｍ−クロロ過安息香酸又は過酸化水素水が挙げられる。
該反応には、化合物（１０）１モルに対して、酸化剤が通常１〜４モルの割合で用いられる。好ましくは、化合物（１０）１モルに対して、酸化剤が１〜２モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１２０℃の範囲である。該反応の反応時間は通常０．１〜１２時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、乾燥、濃縮する等の後処理操作を行うことにより、化合物（１１）を単離することができる。単離された化合物（１１）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 18)
Compound (11) wherein n is 2 in formula (1) can be produced by reacting compound (10) in the presence of an oxidizing agent.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ and A ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
In the reaction, with respect to 1 mol of the compound (10), the oxidizing agent is usually used at a ratio of 1 to 4 mol. Preferably, the oxidizing agent is used in a ratio of 1 to 2 moles relative to 1 mole of the compound (10).
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, Compound (11) can be isolated by performing post-treatment operations such as concentration. The isolated compound (11) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、クロロベンゼン等のハロゲン化炭化水素類およびこれらの混合物が挙げられる。
反応に用いられる酸としては、例えばｐ−トルエンスルホン酸等のスルホン酸類、ポリリン酸が挙げられる。
該反応には、化合物（Ｍ２２）１モルに対して、酸が通常０．１〜３モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（２）を単離することができる。単離された化合物（２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 19) (Step (A-3), Step (B-3))
Compound (2) in which A ¹ is a sulfur atom in formula (1) is produced by reacting compound (M22) in the presence of an acid according to step (A-3) or step (B-3). Can do.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and halogens such as dichloromethane, chloroform, and chlorobenzene. Hydrocarbons and mixtures thereof.
Examples of the acid used for the reaction include sulfonic acids such as p-toluenesulfonic acid and polyphosphoric acid.
In the reaction, an acid is usually used at a ratio of 0.1 to 3 mol with respect to 1 mol of the compound (M22).
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (2) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁷、Ａ¹、Ａ²、ｎ、ｍ、Ｖ¹およびＬは前記と同じ意味を表す。］
工程（２２−１）
化合物（１２−ａ）および／又は化合物（１２−ｂ）は、化合物（７）とチオール化剤とを、触媒の存在下反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばトルエン、キシレン等の芳香族炭化水素類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、およびこれらの混合物が挙げられる。
反応に用いられるチオール化剤としては、例えば硫化ナトリウム、硫化ナトリウム９水和物、チオウレアが挙げられる。
反応に用いられる触媒としては、例えば塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）が挙げられる。
該反応は必要に応じて塩基の存在下で行うこともできる。
反応に用いられる塩基としては、例えば炭酸カリウム、炭酸セシウム、リン酸三カリウム、トリエチルアミンが挙げられる。
該反応には、化合物（７）１モルに対して、チオール化剤が通常１〜１０モルの割合、触媒が通常０．１〜５モルの割合で用いられる。
該反応の反応温度は、通常５０〜２００℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（１２−ａ）および／又は化合物（１２−ｂ）を単離することができる。単離された化合物（１２−ａ）および／又は化合物（１２−ｂ）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 20)
In the formula (1), a compound (12-a) in which R ⁵ is represented by —SH, a compound (12-b) which is a disulfide compound of the compound (12-a), a compound in which R ⁵ is represented by —SR ⁷ (13) The compound (14) in which R ⁵ is represented by —S (O) mR ⁷ can be produced, for example, by the following method.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , A ¹ , A ² , n, m, V ¹ and L represent the same meaning as described above. ]
Step (22-1)
Compound (12-a) and / or compound (12-b) can be produced by reacting compound (7) with a thiolating agent in the presence of a catalyst.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the thiolating agent used in the reaction include sodium sulfide, sodium sulfide nonahydrate, and thiourea.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed in presence of a base as needed.
Examples of the base used in the reaction include potassium carbonate, cesium carbonate, tripotassium phosphate, and triethylamine.
In the reaction, with respect to 1 mol of the compound (7), the thiolating agent is usually used in a proportion of 1 to 10 mol, and the catalyst is usually used in a proportion of 0.1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (12-a) and / or the compound (12-b) is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. be able to. The isolated compound (12-a) and / or compound (12-b) can be further purified by chromatography, recrystallization and the like.

Step (22-2)
Compound (13) can be produced by reacting compound (12-a) and / or compound (12-b) with compound (M23) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether, THF and tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, and 1,2. -Halogenated hydrocarbons such as dichloroethane and chlorobenzene, aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl Examples thereof include aprotic polar solvents such as 2-imidazolidinone and dimethyl sulfoxide, nitrogen-containing aromatic compounds such as pyridine and quinoline, water, and mixtures thereof.
Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, diazabicycloundecene (hereinafter referred to as DBU), 1,5-diazabicyclo [4.3.0] -5-nonene, and the like. And nitrogen-containing heterocyclic compounds, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as tripotassium phosphate, potassium carbonate, sodium hydride, sodium hydroxide and potassium hydroxide.
In the reaction, with respect to 1 mol of the compound (12-a) and / or the compound (12-b), the compound (M23) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 5 mol. It is done.
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (13) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (13) can be further purified by chromatography, recrystallization and the like.

Step (22-3)
In compound (14), a compound wherein m is 1 or 2 can be produced by subjecting compound (13) to an oxidation reaction.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In the reaction, with respect to 1 mol of the compound (13), the oxidizing agent is usually used at a ratio of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, Compound (14) can be isolated by post-treatment such as concentration. The isolated compound (14) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁷、Ａ¹、Ａ²、Ｖ¹およびｎは前記と同じ意味を表す。］
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム、水素化カルシウム等のアルカリ金属もしくはアルカリ土類金属の水素化物、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等の無機塩基、又はトリエチルアミン等の有機塩基が挙げられる。
該反応は、必要に応じて銅化合物を加えて行うこともできる。
反応に用いられる銅化合物としては、例えば銅、ヨウ化銅（Ｉ）、臭化銅（Ｉ）、塩化銅（Ｉ）が挙げられる。
該反応には、化合物（７）１モルに対して、化合物（Ｍ２４）が通常１〜５モルの割合で用いられ、塩基が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常２０〜２５０℃の範囲である。該反応の反応時間は通常０．１〜４８時間の範囲である。
反応終了後は、反応混合物を水に注加してから有機溶媒抽出し、有機層を濃縮する；反応混合物を水に注加して生じた固体を濾過により集める；または、反応混合物中に生成した固体を濾過により集めることにより化合物（１５）を単離することができる。単離された化合物（１５）は、再結晶、クロマトグラフィ−等により更に精製することもできる。 (Production method 21)
In the formula (1), the compound (15) in which R ⁵ is —OR ⁷ can be produced, for example, by the following method.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , A ¹ , A ² , V ¹ and n represent the same meaning as described above. ]
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate, or triethylamine. An organic base is mentioned.
This reaction can also be performed by adding a copper compound as necessary.
Examples of the copper compound used for the reaction include copper, copper (I) iodide, copper (I) bromide, and copper (I) chloride.
In the reaction, with respect to 1 mol of the compound (7), the compound (M24) is usually used in a proportion of 1 to 5 mol, and the base is usually used in a proportion of 1 to 3 mol.
The reaction temperature of the reaction is usually in the range of 20 to 250 ° C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (15). The isolated compound (15) can be further purified by recrystallization, chromatography or the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、ＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬等が挙げられる。
該反応は、必要に応じて触媒を加えて行うこともできる。
反応に用いられる触媒としては、ＨＯＢｔ等が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合、触媒が通常０．０１〜０．１モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（２）を単離することができる。単離された化合物（２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。
また、化合物（Ｍ２）に代えて化合物（M４）を用い、工程（Ｂ−１）に従い、上記方法に準じて化合物（２）を製造することもできる。
化合物（M４）を用いる場合は、通常脱水縮合剤を加えずに行われる。必要に応じて塩基を加えて行うこともできる。
塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（M４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。 (Manufacturing method 22) (Process (A-1))
Compound (2) in which A ¹ is a sulfur atom in formula (1) can be produced by reacting compound (M18) and compound (M2) according to step (A-1).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, BOP reagent and the like.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used for the reaction include HOBt.
In the reaction, with respect to 1 mol of the compound (M18), the compound (M2) is usually in a proportion of 1 to 3 mol, the dehydration condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually in a range of 0.01 to 0.1. Used in molar proportions.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (2) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The isolated compound (2) can be further purified by chromatography, recrystallization and the like.
Moreover, it can replace with a compound (M2), a compound (M4) can be used, and a compound (2) can also be manufactured according to the said method according to a process (B-1).
When the compound (M4) is used, it is usually carried out without adding a dehydrating condensing agent. A base can be added as necessary.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M18), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、溶媒の存在下または非存在下で行われる。
反応に用いられる溶媒としては、例えば１，４−ジオキサン、ジエチルエーテル、テトラヒドロフラン、ｔｅｒｔ−ブチルメチルエーテル、ジグライム等のエーテル、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、ベンゼン、キシレン等の炭化水素、アセトニトリル等のニトリル、ピリジン、ピコリン、ルチジン等のピリジンおよびこれらの混合物が挙げられる。
該反応に用いられる硫化剤としては、五硫化ニリン、ローソン試薬（２，４−ビス−（４−メトキシフェニル）−１，３−ジチア−２，４−ジホスフェタン−２，４−ジスルフィド）等が挙げられる。
該反応に用いられる硫化剤の量は、化合物（Ｍ７）1モルに対して、通常１モル以上である。
該反応の反応温度は、通常、０℃〜２００℃の範囲であり、反応時間は、通常、１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加してから有機溶媒抽出し、有機層を濃縮する；反応混合物を水に注加して生じた固体を濾過により集める；または、反応混合物中に生成した固体を濾過により集めることにより化合物（２）を単離することができる。単離された化合物（２）は、再結晶、クロマトグラフィ−等により更に精製することもできる。 (Production Method 23) (Production Method D)
Compound (2) in which A ¹ is a sulfur atom in formula (1) can be produced by reacting compound (M7) with a sulfurizing agent according to (Production Method D).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent used for the reaction include 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, diglyme and other ethers, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples thereof include hydrocarbons, hydrocarbons such as toluene, benzene and xylene, nitriles such as acetonitrile, pyridines such as pyridine, picoline and lutidine, and mixtures thereof.
Examples of the sulfurizing agent used in the reaction include niline pentasulfide, Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide), and the like. Can be mentioned.
The amount of the sulfurizing agent used in the reaction is usually 1 mol or more per 1 mol of the compound (M7).
The reaction temperature of the reaction is usually in the range of 0 ° C. to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (2). The isolated compound (2) can be further purified by recrystallization, chromatography or the like.

［式中、Ｒ⁵、Ｒ⁶およびＡ²は前記と同じ意味を表す。］
（工程１）
化合物（Ｍ２６）は、化合物（Ｍ２５）をニトロ化剤の存在下で反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等のハロゲン化炭化水素類、酢酸、濃硫酸、濃硝酸、水およびこれらの混合物が挙げられる。
反応に用いられるニトロ化剤としては、例えば濃硝酸が挙げられる。
該反応には、化合物（Ｍ２５）１モルに対して、ニトロ化剤が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常−１０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ２６）を単離することができる。単離された化合物（Ｍ２６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 The intermediate of the present invention can be produced, for example, by the following method.
(Intermediate production method 1)
Compound (M12) can be produced by the following method.

[Wherein, R ⁵ , R ⁶ and A ² represent the same meaning as described above. ]
(Process 1)
Compound (M26) can be produced by reacting compound (M25) in the presence of a nitrating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
An example of the nitrating agent used in the reaction is concentrated nitric acid.
In the reaction, the nitrating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the compound (M25).
The reaction temperature of the reaction is usually in the range of -10 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M26) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M26) can be further purified by chromatography, recrystallization and the like.

(Process 2)
Compound (M12) can be produced by reacting compound (M26) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in the presence of a solvent under a hydrogen atmosphere of 1 to 100 atm.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, with respect to 1 mol of the compound (M26), hydrogen is usually used in a proportion of 3 mol, and a hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol.
This reaction can also be carried out by adding an acid (such as a base) as necessary.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M12) can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent, if necessary, and drying and concentration of the organic layer. The isolated compound (M12) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、例えばＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ１３）を単離することができる。単離された化合物（Ｍ１３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 2) (Step (A-2))
Compound (M13) can be produced by reacting compound (M12) and compound (M2) in the presence of a dehydration condensing agent according to step (A-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M2) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M13) can be isolated by performing post-treatment operations such as water addition to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M13) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
上記塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ１３）を単離することができる。単離された化合物（Ｍ１３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 3) (Step (B-2))
Compound (M13) can be produced by reacting compound (M12) and compound (M4) in the presence of a base according to step (B-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M13) can be isolated by performing post-treatment operations such as water addition to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M13) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ⁵およびＡ²は前記と同じ意味を表す。］
（工程１）
化合物（Ｍ２８）は、化合物（Ｍ２７）をニトロ化剤の存在下で反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばクロロホルム等の脂肪族ハロゲン化炭化水素類、酢酸、濃硫酸、濃硝酸、水およびこれらの混合物が挙げられる。
反応に用いられるニトロ化剤としては、例えば濃硝酸が挙げられる。
該反応には、化合物（Ｍ２７）１モルに対して、ニトロ化剤が通常１〜３モルの割合で用いられる。
該反応の反応温度は、通常−１０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ２８）を単離することができる。単離された化合物（Ｍ２８）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate production method 4)
Compound (M15) can be produced by the following method.

[Wherein, R ⁵ and A ² represent the same meaning as described above. ]
(Process 1)
Compound (M28) can be produced by reacting compound (M27) in the presence of a nitrating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
An example of the nitrating agent used in the reaction is concentrated nitric acid.
In the reaction, the nitrating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the compound (M27).
The reaction temperature of the reaction is usually in the range of -10 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M28) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M28) can be further purified by chromatography, recrystallization and the like.

(Process 2)
Compound (M15) can be produced by reacting compound (M28) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in the presence of a solvent under a hydrogen atmosphere of 1 to 100 atm.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, with respect to 1 mol of the compound (M28), hydrogen is usually used in a proportion of 3 mol, and the hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol.
This reaction can also be carried out by adding an acid (such as a base) as necessary.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M15) can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent, if necessary, and drying and concentration of the organic layer. The isolated compound (M15) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばメタノール、エタノール等のアルコール類、ＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類およびこれらの混合物が挙げられる。
該反応には、化合物（Ｍ１５）１モルに対して、化合物（Ｍ５）が通常１〜３モルの割合で用いられる。
該反応は、必要に応じて酸や塩基等を加えて行うこともできる。
該反応の反応温度は、通常０〜１５０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ１６）を単離することができる。単離された化合物（Ｍ１６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 5) (Step (C-2))
Compound (M16) can be produced by reacting compound (M15) with compound (M5) according to step (C-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used for the reaction include alcohols such as methanol and ethanol, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and the like. These mixtures are mentioned.
In the reaction, compound (M5) is generally used at a ratio of 1 to 3 mol with respect to 1 mol of compound (M15).
This reaction can also be performed by adding an acid, a base, or the like, if necessary.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M16) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound (M16) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、例えばＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬が挙げられる。
該反応には、化合物（Ｍ１５）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ１７）を単離することができる。単離された化合物（Ｍ１７）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 6) (Step (A-2))
Compound (M17) can be produced by reacting compound (M15) and compound (M2) in the presence of a dehydration condensing agent according to step (A-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, with respect to 1 mol of the compound (M15), the compound (M2) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M17) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M17) can be further purified by chromatography, recrystallization, and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１５）１モルに対して、化合物（Ｍ４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ１７）を単離することができる。単離された化合物（Ｍ１７）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 7) (Step (B-2))
Compound (M17) can be produced by reacting compound (M15) and compound (M4) in the presence of a base according to step (B-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
In the reaction, with respect to 1 mol of the compound (M15), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M17) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M17) can be further purified by chromatography, recrystallization, and the like.

［式中、Ｒ⁵およびＡ²は前記と同じ意味を表す。］
（工程１）
化合物（Ｍ３０）は、化合物（Ｍ２９）とチオウレアとを塩基の存在下で反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばメタノール、エタノール等のアルコール類、水およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物が挙げられる。
該反応には、化合物（Ｍ２９）１モルに対して、チオウレアが通常０．５〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に酸を加えた後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３０）を単離することができる。単離された化合物（Ｍ３０）は、クロマトグラフィー、再結晶等により精製することもできる。 (Intermediate production method 8)
Compound (M18) can be produced by the following method.

[Wherein, R ⁵ and A ² represent the same meaning as described above. ]
(Process 1)
Compound (M30) can be produced by reacting compound (M29) with thiourea in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, with respect to 1 mol of the compound (M29), thiourea is usually used in a proportion of 0.5 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M30) can be isolated by post-treatment such as addition of an acid to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M30) can also be purified by chromatography, recrystallization and the like.

(Process 2)
Compound (M18) can be produced by subjecting compound (M30) to a reduction reaction.
The reduction reaction can be performed in the presence of a reducing agent such as iron powder or zinc powder; an acid such as hydrochloric acid or acetic acid; and water.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, Examples thereof include acid amides such as DMF and NMP, and mixtures thereof.
.
In the reaction, a reducing agent is usually used in a proportion of 3 to 10 mol with respect to 1 mol of the compound (M30).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M18) can be isolated by performing post-treatment operations such as addition of water to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M18) can also be purified by chromatography, recrystallization, and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる塩基としては、炭酸水素ナトリウム、炭酸水素カリウム等の炭酸水素塩類、炭酸ナトリウム、炭酸カリウム等の炭酸塩類、亜硫酸ナトリウム、亜硫酸カリウム等の亜硫酸塩類およびこれらの混合物が挙げられる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ３１）が通常１〜３モルの割合、塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３３）を単離することができる。単離された化合物（Ｍ３３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate production method 9)
In compound (M10), compound (M33) in which A ¹ is —NR ⁶ — can be produced by reacting compound (M12) and compound (M31) in the presence of a base.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the base used in the reaction include hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, carbonates such as sodium carbonate and potassium carbonate, sulfites such as sodium sulfite and potassium sulfite, and mixtures thereof.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M31) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M33) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M33) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、ＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬等が挙げられる。
該反応は、必要に応じて触媒を加えて行うこともできる。
反応に用いられる触媒としては、ＨＯＢｔ等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ８）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合、触媒が通常０．０１〜０．１モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３３）を単離することができる。単離された化合物（Ｍ３３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 10) (Step (E-1))
In compound (M10), compound (M33) in which A ¹ is —NR ⁶ — reacts compound (M12) and compound (M8) in the presence of a dehydration condensing agent according to step (E-1). Can be manufactured.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, BOP reagent and the like.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used for the reaction include HOBt.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M8) is usually in a proportion of 1 to 3 mol, the dehydration condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually in a range of 0.01 to 0.1. Used in molar proportions.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M33) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M33) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、メタノール、エタノール、プロパノール、ブタノール、ペンタノール等のアルコール類およびこれらの混合物が挙げられる。
該反応は必要に応じて、酸又は脱水剤を用いることができる。反応に用いられる酸としては、ｐ−トルエンスルホン酸等のスルホン酸類、酢酸等のカルボン酸類が挙げられ、反応に用いられる脱水剤としては、オキシ塩化リン、無水酢酸、トリフルオロ酢酸無水物等が挙げられる。
該反応には、化合物（Ｍ３２）１モルに対して、酸又は脱水剤が通常１モル〜１０モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３３）を単離することができる。単離された化合物（Ｍ３３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 11) (Step (E-3))
In compound (M10), compound (M33) wherein A ¹ is —NR ⁶ — can be produced by subjecting compound (M32) to dehydration condensation according to step (E-3).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, methanol, ethanol, propanol , Alcohols such as butanol and pentanol, and mixtures thereof.
In the reaction, an acid or a dehydrating agent can be used as necessary. Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, and carboxylic acids such as acetic acid. Examples of the dehydrating agent used in the reaction include phosphorus oxychloride, acetic anhydride, trifluoroacetic anhydride, and the like. Can be mentioned.
In the reaction, with respect to 1 mol of the compound (M32), an acid or a dehydrating agent is usually used at a ratio of 1 mol to 10 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M33) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M33) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、メタノール、エタノール、プロパノール、ブタノール、ｔｅｒｔ−ブタノール、ペンタノール等のアルコール類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、リン酸三カリウム等が挙げられる。
該反応には、化合物（Ｍ３２）１モルに対して、塩基が通常１モル〜１０モルの割合で用いられる。
該反応の反応温度は、通常３０〜２００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３３）を単離することができる。単離された化合物（Ｍ３３）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate production method 12) (Step (E-3))
In compound (M10), compound (M33) wherein A ¹ is —NR ⁶ — can be produced by reacting compound (M32) in the presence of a base according to step (E-3).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, methanol, ethanol, propanol , Butanol, tert-butanol, pentanol and the like, and mixtures thereof.
Examples of the base used for the reaction include tripotassium phosphate.
In the reaction, with respect to 1 mol of the compound (M32), the base is generally used at a ratio of 1 mol to 10 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M33) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M33) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、例えばＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ８）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３２）を単離することができる。単離された化合物（Ｍ３２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate production method 13) (Step (E-2))
Compound (M32) can be produced by reacting compound (M12) and compound (M8) in the presence of a dehydration condensing agent according to step (E-2).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M8) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M32) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M32) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ａ²およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
上記塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１２）１モルに対して、化合物（Ｍ３４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３２）を単離することができる。単離された化合物（Ｍ３２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate production method 14)
Compound (M32) can be produced by reacting compound (M12) with compound (M34) in the presence of a base.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ² and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M12), the compound (M34) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M32) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M32) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴およびＶ²は前記と同じ意味を表す。］
（工程Ｉ１５−１）
化合物（Ｍ３６）は、化合物（Ｍ３５）と化合物（Ｍ２０）とを、塩基の存在下に反応させることにより製造することができる。
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類が挙げられる。
該反応には、化合物（Ｍ３５）１モルに対して、化合物（Ｍ２０）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０〜１５０℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３６）を単離することができる。単離された化合物（Ｍ３６）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 15)
Among compounds (M5), compound (M37) in which n is 0 can be produced by the following method.

[Wherein R ¹ , R ² , R ³ , R ⁴ and V ² represent the same meaning as described above. ]
(Step I15-1)
Compound (M36) can be produced by reacting compound (M35) with compound (M20) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydrides such as sodium hydride.
In the reaction, with respect to 1 mol of the compound (M35), the compound (M20) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M36) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M36) can be further purified by chromatography, recrystallization and the like.

(Step I15-2)
Compound (M37) can be produced by subjecting compound (M36) to a reduction reaction.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and halogenated carbonization such as dichloromethane and chloroform. Examples include hydrogens and mixtures thereof.
Examples of the reducing agent used in the reaction include diisobutylaluminum hydride.
In the reaction, the reducing agent is usually used at a ratio of 1 to 2 mol with respect to 1 mol of the compound (M36).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M37) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M37) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴およびＶ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類等が挙げられる。
該反応には、化合物（Ｍ３８）１モルに対して、化合物（Ｍ２０）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０〜１５０℃の範囲である。該反応の反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３７）を単離することができる。単離された化合物（Ｍ３７）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 16)
Among compounds (M5), compound (M37) in which n is 0 can be produced by reacting compound (M38) and compound (M20) in the presence of a base.

[Wherein R ¹ , R ² , R ³ , R ⁴ and V ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include acid amides such as NMP, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydrides such as sodium hydride.
In the reaction, with respect to 1 mol of the compound (M38), the compound (M20) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M37) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M37) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴は前記と同じ意味を表し、ｒは１又は２を表す。］
（工程Ｉ１７−１）
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、メタノール、エタノール等のアルコール類、水およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物が挙げられる。
該反応には、化合物（Ｍ３６）１モルに対して、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常０〜１２０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応液を酸性にした後、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３９）を単離することができる。単離された化合物（Ｍ３９）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 17)
Among the compounds (M2), the compound (M39) in which n is 0 can be produced by hydrolyzing the compound (M36) in the presence of a base, and the compound (M41) in which n is 1 or 2. ) Can be produced by the following method.

[Wherein, R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above, and r represents 1 or 2. ]
(Step I17-1)
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used for the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is generally used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (M36).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M39) can be isolated by performing post-treatment operations such as acidification of the reaction mixture, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. . The isolated compound (M39) can be further purified by chromatography, recrystallization and the like.

(Step I17-2)
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In the reaction, with respect to 1 mole of the compound (M36), the oxidizing agent is usually used at a ratio of 1 to 5 moles.
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (M40) can be isolated by performing post-treatment operations such as concentration. The isolated compound (M40) can be further purified by chromatography, recrystallization and the like.

(Step I17-3)
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used for the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is generally used at a ratio of 1 to 10 mol per 1 mol of the compound (M40).
The reaction temperature of the reaction is usually in the range of 0 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 acidified, and then the compound (M41) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. . The isolated compound (M41) can be further purified by chromatography, recrystallization and the like.

(Process I17-4)
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In the reaction, with respect to 1 mol of the compound (M39), the oxidizing agent is usually used at a ratio of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, The compound (M41) can be isolated by performing post-treatment operations such as concentration. The isolated compound (M41) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³およびＲ⁴は前記と同じ意味を表す。］
該反応は、通常酸の水溶液を溶媒として行われる。
反応に用いられる酸としては、例えば塩酸、硝酸、リン酸、硫酸等の鉱酸類、酢酸、トリフルオロ酢酸等のカルボン酸類が挙げられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ３９）を単離することができる。単離された化合物（Ｍ３９）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 18)
Among compounds (M2), compound (M39) in which n is 0 can be produced by subjecting compound (M36) to a hydrolysis reaction in the presence of an acid.

[Wherein, R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above. ]
The reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used for 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 of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M39) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M39) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム等のハロゲン化炭化水素類およびこれらの混合物が挙げられる。
反応に用いられる塩素化剤としては、塩化チオニル、二塩化オキサリル等が挙げられる。
該反応には、化合物（Ｍ２）１モルに対して、塩素化剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、溶媒を留去することにより、化合物（Ｍ４）を単離することができる。 (Intermediate Production Method 19)
Compound (M4) can be produced by chlorinating compound (M2) in the presence of a chlorinating agent.

[Wherein, R ¹ , R ² , R ³ , R ⁴ and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and halogenated carbonization such as dichloromethane and chloroform. Examples include hydrogens and mixtures thereof.
Examples of the chlorinating agent used in the reaction include thionyl chloride and oxalyl dichloride.
In the reaction, a chlorinating agent is usually used at a ratio of 1 to 5 mol with respect to 1 mol of the compound (M2).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M4) can be isolated by removing the solvent.

［式中、Ｒ⁵およびＲ⁶は前記と同じ意味を表し、X^ｇは塩素原子、臭素原子又はヨウ素原子等のハロゲン原子を表す。］
（工程Ｉ２０−１）
化合物（Ｍ４３）は、化合物（Ｍ４２）と化合物（Ｍ４６）とを反応させることにより製造することができる。
該反応は、通常溶媒の存在下あるいは非存在下で行われる。
反応に用いられる溶媒としては、例えば水、メタノール、エタノール等のアルコール類、１，４−ジオキサン、ジエチルエーテル、ＴＨＦ等のエーテル類、酢酸エチル、酢酸ブチル等のエステル類、ジクロロメタン、クロロホルム、四塩化炭素、１，２−ジクロロエタン等のハロゲン化炭化水素、アセトニトリル等のニトリル、ＤＭＦ、ＮＭＰ、ジメチルスルホキシド等の非プロトン性極性溶媒、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
該反応は、必要に応じて塩基を加えて行うこともできる。
反応に用いられる塩基としては、例えばピリジン、ピコリン、２，６−ルチジン、ＤＢＵ、１，５−ジアザビシクロ〔４．３．０〕−５−ノネン等の含窒素複素環化合物、トリエチルアミン、Ｎ−エチルジイソプロピルアミン等の第３級アミン、炭酸カリウム、炭酸セシウム、水酸化ナトリウム等の無機塩基が挙げられる。
化合物（Ｍ４２）１モルに対して、化合物（Ｍ４６）が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜２００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加してから有機溶媒抽出し、有機層を濃縮する；反応混合物を水に注加して生じた固体を濾過により集める；または、反応混合物中に生成した固体を濾過により集めることにより化合物（Ｍ４３）を単離することができる。単離された化合物（Ｍ４３）は、再結晶、クロマトグラフィ−等により更に精製することもできる。 (Intermediate production method 20)
Among the compounds (M12), the compound (M45) in which A ² is a nitrogen atom can be produced, for example, by the following method.

[Wherein, R ⁵ and R ⁶ represent the same meaning as described above, and X ^g represents a halogen atom such as a chlorine atom, a bromine atom or an iodine atom. ]
(Process I20-1)
Compound (M43) can be produced by reacting compound (M42) with compound (M46).
The reaction is usually performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform and tetrachloride. Examples include carbon, halogenated hydrocarbons such as 1,2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, and dimethyl sulfoxide, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof. It is done.
This reaction can also be performed by adding a base as necessary.
Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, and N-ethyl. Tertiary amines such as diisopropylamine, and inorganic bases such as potassium carbonate, cesium carbonate, sodium hydroxide and the like.
The compound (M46) is usually used at a ratio of 1 to 5 mol with respect to 1 mol of the compound (M42).
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (M43). The isolated compound (M43) can be further purified by recrystallization, chromatography or the like.

(Process I20-2)
Compound (M44) can be produced by reacting compound (M43) with a halogenating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, acetic acid, 1,4-dioxane, diethyl ether, THF and other ethers, ethyl acetate, butyl acetate and other esters, dichloromethane, chloroform, carbon tetrachloride, 1,2- Examples thereof include halogenated hydrocarbons such as dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF and NMP, and mixtures thereof.
Examples of the halogenating agent used in the reaction include chlorinating agents such as N-chlorosuccinimide and chlorine, brominating agents such as N-bromosuccinimide and bromine, and chlorinating agents such as N-iodosuccinimide and iodine.
The halogenating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the compound (M43).
The reaction temperature of the reaction is usually in the range of −10 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate the compound (M44). The isolated compound (M44) can be further purified by recrystallization, chromatography or the like.

(Process I20-3)
Compound (M45) can be produced by reacting compound (M44) with an aminating agent in the presence of a copper compound.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform and tetrachloride. Carbon, halogenated hydrocarbons such as 1,2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, and dimethyl sulfoxide, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof Can be mentioned.
Examples of the aminating agent used in the reaction include ammonia, aqueous ammonia, and lithium amide.
Examples of the copper compound used in the reaction include copper, copper (I) iodide, copper (I) oxide, copper (II) oxide, acetylacetone copper (II), copper acetate (II), and copper (II) sulfate. It is done.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, and phenanthroline.
This reaction can also be performed by adding a base as necessary.
Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, and N-ethyl. Tertiary amines such as diisopropylamine, and inorganic bases such as tripotassium phosphate, potassium carbonate, cesium carbonate, and sodium hydroxide.
The aminating agent is usually used in a proportion of 1 to 5 mol, and the copper compound is usually used in a proportion of 0.02 to 0.5 mol per 1 mol of the compound (M44). Is used in a proportion of 0.02 to 2 mol, and a base is used in a proportion of 1 to 5 mol if necessary.
The reaction temperature is usually in the range of 30 to 200 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (M45). The isolated compound (M45) can be further purified by recrystallization, chromatography or the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、例えばＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ２２）を単離することができる。単離された化合物（Ｍ２２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 21) (Step (A-2))
Compound (M22) can be produced by reacting compound (M18) and compound (M2) in the presence of a dehydration condensing agent according to step (A-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, with respect to 1 mol of the compound (M18), the compound (M2) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M22) can be isolated by performing post-treatment operations such as water addition to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M22) can be further purified by chromatography, recrystallization, and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類およびこれらの混合物が挙げられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ１８）１モルに対して、化合物（Ｍ４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は、通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ２２）を単離することができる。単離された化合物（Ｍ２２）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Intermediate Production Method 22) (Step (B-2))
Compound (M22) can be produced by reacting compound (M18) and compound (M4) in the presence of a base according to step (B-2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, and mixtures thereof It is done.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
In the reaction, with respect to 1 mol of the compound (M18), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M22) can be isolated by performing post-treatment operations such as water addition to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M22) can be further purified by chromatography, recrystallization, and the like.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²、ｎおよびＶ²は前記と同じ意味を表す。］
化合物（Ｍ２）に代えて化合物（Ｍ８）を用い、（製造法６）記載の方法に準じて、化合物（Ｍ４７）を製造することができる。 (Intermediate Production Example 23) (Step (E-1))
Compound (M47) in which A ¹ is an oxygen atom in compound (M10) can be produced by reacting compound (M15) with compound (M8) according to step (E-1).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² , n and V ² represent the same meaning as described above. ]
Compound (M47) can be produced according to the method described in (Production Method 6) using compound (M8) in place of compound (M2).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびＶ²は前記と同じ意味を表す。］
化合物（Ｍ２）に代えて化合物（Ｍ８）を用い、（中間体製造法６）記載の方法に準じて、化合物（Ｍ４８）を製造することができる。
化合物（Ｍ２）に代えて化合物（Ｍ８）を用い、（中間体製造法２１）記載の方法に準じて、化合物（Ｍ４９）を製造することができる。 (Intermediate Production Example 24) (Step (E-2))
Compound (M48) in which A ¹ is an oxygen atom in compound (M9) can be produced by reacting compound (M15) with compound (M8) according to step (E-2). In the compound (M9), the compound (M49) in which A ¹ is a sulfur atom can be produced by reacting the compound (M18) with the compound (M8).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and V ² represent the same meaning as described above. ]
Compound (M48) can be produced according to the method described in (Intermediate Production Method 6) using Compound (M8) instead of Compound (M2).
Compound (M49) can be produced according to the method described in (Intermediate Production Method 21) using Compound (M8) instead of Compound (M2).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびＶ²は前記と同じ意味を表す。］
化合物（Ｍ１７）に代えて化合物（Ｍ４８）を用い、（製造法８）あるいは（製造法９）記載の方法に準じて、化合物（Ｍ４７）を製造することができる。
化合物（Ｍ２２）に代えて化合物（Ｍ４９）を用い、（製造法２１）記載の方法に準じて、化合物（Ｍ５０）を製造することができる。 (Intermediate Production Example 25) (Step (E-3))
Compound (M47) wherein A ¹ is an oxygen atom in compound (M10) can be produced by cyclizing compound (M48) according to step (E-3). In compound (M10), compound (M50) wherein A ¹ is a sulfur atom can be produced by cyclizing compound (M49) according to step (E-3).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and V ² represent the same meaning as described above. ]
Using compound (M48) instead of compound (M17), compound (M47) can be produced according to the method described in (Production Method 8) or (Production Method 9).
The compound (M50) can be produced according to the method described in (Production Method 21) using the compound (M49) instead of the compound (M22).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ¹、Ａ²およびＶ²は前記と同じ意味を表す。］
化合物（Ｍ２０）に代えて硫化ナトリウム、硫化水素ナトリウム又は硫化水素を用い、（製造法１６）記載の方法に準じて、化合物（Ｍ１１）を製造することができる。
硫化ナトリウム、硫化水素ナトリウムを用いる場合は、通常塩基を加えずに行われる。 (Intermediate Production Method 26) (Step (F-1))
Compound (M11) can be produced by reacting compound (M10) with sodium sulfide, sodium hydrogen sulfide or hydrogen sulfide according to step (F-1).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ¹ , A ² and V ² represent the same meaning as described above. ]
Compound (M11) can be produced according to the method described in (Production Process 16) using sodium sulfide, sodium hydrogen sulfide or hydrogen sulfide instead of compound (M20).
When sodium sulfide or sodium hydrogen sulfide is used, it is usually carried out without adding a base.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ａ²およびｎは前記と同じ意味を表す。］
（工程Ｉ２７−１）
化合物（Ｍ５１）は、化合物（Ｍ２９）を還元反応に付すことにより製造することができる。
該還元反応は、例えば鉄粉、亜鉛粉等の還元剤；塩酸、酢酸等の酸；および水の存在下で行うことができる。
該反応は通常溶媒の存在下で行われる。
該反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、酢酸エチル、酢酸ブチル等のエステル類、メタノール、エタノール等のアルコール類、ＤＭＦ、ＮＭＰ等の酸アミド類およびこれらの混合物が挙げられる。
。
該反応には、化合物（Ｍ２９）１モルに対して、還元剤が通常３〜１０モルの割合で用いられる。
該反応の反応温度は通常０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ５１）を単離することができる。単離された化合物（Ｍ５１）は、クロマトグラフィー、再結晶等により精製することもできる。
（工程Ｉ２７−２）
該反応は、通常溶媒の存在下あるいは非存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、１，４−ジオキサン等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル等のニトリル類、ＤＭＦ、ＮＭＰ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、ピリジン、キノリン等の含窒素芳香族化合物類およびこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、例えばＷＳＣ、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、ＢＯＰ試薬が挙げられる。
該反応には、化合物（Ｍ５１）１モルに対して、化合物（Ｍ２）が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を注加した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ７）を単離することができる。単離された化合物（Ｍ７）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。
また、化合物（Ｍ２）に代えて化合物（Ｍ４）を用い、上記方法に準じて化合物（Ｍ７）を製造することもできる。
化合物（Ｍ４）を用いる場合は、通常脱水縮合剤を加えずに行われる。必要に応じて塩基を加えて行うこともできる。
塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類およびピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
該反応には、化合物（Ｍ５１）１モルに対して、化合物（Ｍ４）が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。 (Intermediate Production Method 27) (Production Method D)
Compound (M7) can be produced by reacting compound (M51) with compound (M2).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ² and n represent the same meaning as described above. ]
(Process I27-1)
Compound (M51) can be produced by subjecting compound (M29) to a reduction reaction.
The reduction reaction can be performed in the presence of a reducing agent such as iron powder or zinc powder; an acid such as hydrochloric acid or acetic acid; and water.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, Examples thereof include acid amides such as DMF and NMP, and mixtures thereof.
.
In the reaction, a reducing agent is usually used in a proportion of 3 to 10 mol per 1 mol of the compound (M29).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M51) can be isolated by post-treatment such as addition of water to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M51) can also be purified by chromatography, recrystallization, and the like.
(Process I27-2)
The reaction is usually performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, acid amides such as DMF and NMP, sulfoxides such as DMSO, pyridine and quinoline Nitrogen-containing aromatic compounds and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, with respect to 1 mol of the compound (M51), the compound (M2) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M7) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. The isolated compound (M7) can be further purified by chromatography, recrystallization and the like.
Moreover, it can replace with a compound (M2) and a compound (M4) can be used, and a compound (M7) can also be manufactured according to the said method.
When the compound (M4) is used, it is usually carried out without adding a dehydrating condensing agent. A base can be added as necessary.
Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the compound (M51), the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.

［式中、X^ｇ、Ｒ⁵、Ａ¹およびＡ²は前記と同じ意味を表す。］
化合物（Ｍ４４）に代えて化合物（Ｍ５２）を用い、（中間体製造法２０）の工程（Ｉ２０−３）記載の方法に準じて、化合物（Ｍ１）を製造することができる。 (Intermediate Production Method 28)
Compound (M1) can be produced by reacting compound (M52) with an aminating agent.

[Wherein, X ^g , R ⁵ , A ¹ and A ² represent the same meaning as described above. ]
Compound (M1) can be produced according to the method described in Step (I20-3) of (Intermediate Production Method 20) using Compound (M52) instead of Compound (M44).

Next, specific examples of the present condensed heterocyclic compound are shown below. In the table, R ^{1 to} R ⁵ , A ¹ , A ² and n represent symbols in the compound represented by the formula (1).

[Table 1]

[Continuation of Table 1]

[Continuation of Table 1]

[Continuation of Table 1]

(In [Table 1] above, Me represents a methyl group, Et represents an ethyl group, iPr represents an isopropyl group, and CycPr represents a cyclopropyl group.)

  Among the insecticidal compounds, pyrethrin, allethrin, praretrin, imiprothrin, resmethrin, tetramethrin, phenothrin, ciphenothrin, flumethrin, methfluthrin, transfluthrin, profluthrin, dimeflutrin, empentrin, framethrin, meperfluthrin, fenitrothion profluxuron, dichlorvos, dichlorvos , Diflubenzuron, hexaflumuron, amidoflumet, chlorfenapyr, cyromazine, hydroprene, metoprene, indoxacarb, methoxadiazone, etoxazole, piperonylbutoxide and N- (2-ethylhexyl) -5-norbornene-2,3-dicarboximide are known A compound such as “THE PESTICIDE MANUAL-15t Has been described in EDITION (BCPC published) ISBN 978-1-901396-18-8 ". These compounds can be obtained from commercially available preparations or produced by known methods.

  Among the insecticidal compounds, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate is This is a compound described in Japanese Utility Model Publication No. 2004-2363, and can be produced by the method described in the publication. 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate is a Chinese patent The compound described in Japanese Patent Publication No. 101367722, and can be produced by the method described in the publication. 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3-tetramethylcyclopropanecarboxylate is a compound described in JP 2001-302591 A, It can be produced by the method described in 1.

  Among the insecticidal compounds, the compound represented by the formula (A) is a compound described in JP 2010-150157 A, and can be produced by the method described in the publication. The compound represented by the formula (B) is a compound described in JP 2010-116346 A, and can be produced by the method described in the publication. The compound represented by the formula (C) is a compound described in JP 2012-36098 A, and can be produced by the method described in the publication. The compound represented by the formula (D) is a compound described in an international publication number WO2012 / 066690 publication pamphlet, and can be produced by a method described in the pamphlet.

The pest control composition of the present invention may be a mixture of the condensed heterocyclic compound and the insecticidal compound, but usually the mixed heterocyclic compound, the insecticidal compound and an inert carrier are mixed, Add emulsions, oils, powders, granules, wettable powders, flowables, microbes by adding surfactants and other formulation adjuvants as necessary, or impregnating with an inert base as necessary. A capsule, aerosol, smoke, poison bait, resin preparation, shampoo, paste preparation, foam, carbon dioxide preparation, tablet, etc. are used. Furthermore, those processed into mosquito-repellent incense sticks, electric mosquito-repellent mats, liquid mosquito-repellent preparations, fumigants, fumigants, sheet preparations, spot-on agents, oral treatment agents and the like are used.
The total amount of the present condensed heterocyclic compound and the present insecticidal compound in the pest control composition of the present invention is usually 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80%. It is in the range of wt%.

  Examples of the inert carrier used for formulation include a solid carrier and a liquid carrier. Examples of the solid support include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate). , Hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphoric acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Polyester resin, nylon resin such as nylon-6, nylon-11, nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer).

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonates, alkyl benzene sulfonates, alkyl sulfates, and the like. An ionic surfactant is mentioned.

  Examples of other formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.

  The content ratio of the present condensed heterocyclic compound and the present insecticidal compound in the pesticidal composition of the present invention is not particularly limited, but the present insecticidal compound is contained with respect to 1000 parts by weight of the present condensed heterocyclic compound. The amount is usually 10 to 100,000 parts by weight, preferably 100 to 10,000 parts by weight. That is, the ratio of the content of the present condensed heterocyclic compound and the present insecticidal compound is usually 100: 1 to 1: 100 by weight, and particularly 10: 1 to 1:10.

  Controlling pests by applying an effective amount of the pest control composition of the present invention directly to the pests and / or to pest habitats (plants, soil, households, animal bodies, etc.) Can do.

Examples of pests for which the composition of the present invention is effective include harmful insects, harmful mites, plant parasitic nematodes, pathogenic endoparasites, and the like. Specific examples of such pests include the following.

Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids rosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), barley aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles, Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorina chinensis), bark beetle bugs (Eysarcoris parvus), stag beetle (Haryomorpha mista) whiteflies (Remiorum), whiteflies (Bemisia tabaci), whiteflies (Dialeurodes citri), whiteflies (Aleurocanthus spiniferus) and other whiteflies, .

Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibatatsuga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia septata), Atoga larvae such as ra brassae, Agrotis ipsilon, Tamanaginoria or Pseudomonas, Pseudomonas virgoe, L. ), Azuki beetle (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyes orana fasciata), Chinese wolfberry (Adoxophyces honamii), Chamonaki (Homomonaki) genus s fuscocupreanus, Cydia pomonella, etc., genus genus, genus moss, genus moss, etc. Species of the genus Proctis, Suga such as Plutella xylostella, Pterophora gossypiella potato moth, such as Phthorimaea operculella, and Athyri Tinea translucens), Hirozukoga such as webbing clothes moth (Tineola bisselliella).

Thrips pests: Frankliniella occidentalis, Thrips palmi et al.

Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans) and other species of houseflies, fly flies, sphagnum flies, fly flies, leaf fly (Delia platura), leaf flies D (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, flea flies, Megasaria sp. Abu acids, and stable flies such as gadfly (Tabanus trigonus).

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohopoptrus oryzophilus), Bone weevil (Echinocnemus squameus), Butterfly weevil (Anthonomus grandis) s venatus) weevil such as, Chai loco Meno mealworm (Tenebrio molitor), mealworm such as red flour beetle (Tribolium castaneum),
Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), beetles such as Colorado potato beetle (Leptinotarsa decemlineata), varied carpet beetle (Anthrenus verbasci), carpet beetle such as Hara Giro beetle (Dermestes maculates), cigarette beetle (Lasiderma serricorne) and the like, Epilachna vigintioctopuncta and other epilacunas, Lyctus brunneus and pine beetle (Pompicus) erda), bark beetles, leopard hornworms, longhorn beetles (Anoprophora malasiaca), longhorn beetles (Agriotes spp.), and red-footed beetle es p.
Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), beetles such as Colorado potato beetle (Leptinotarsa decemlineata), varied carpet beetle (Anthrenus verbasci), carpet beetle such as Hara Giro beetle (Dermestes maculates), cigarette beetle (Lasiderma serricorne) and the like, Epilachna vigintioctopuncta and other epilacunas, Lyctus brunneus and pine beetle (Pompicus) erda), bark beetles, leopard hornworms, longhorn beetles (Anoprophora malasiaca), longhorn beetles (Agriotes spp.), and red-footed beetle es p.

Hymenoptera: Monomorium phalaosis, Formica fusca japonica, Ochellelus glove, pistomrme puns, pol. Spr. Ants such as Argentine ants (Linepithema humile), wasps such as wasps, scallops, and wasps such as Athalia rosae and Japanese bee (Athalia japonica).

Cockroach insects: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroaches (Periplaneta brunet)

Mite order pests: Taninychus urticae, Kantawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), mite spider mite (Pananycos ulmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi); Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese prickly ticks (Acaphylla theavagrans), Green rust mites (Eriophyes chibaensis), Apple rust ticles li) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), Yamato tick (Ixodes ovatus), Schulz tick (Ixodes persulcatus), Black legged tick (Ixodes scapularis), Boobius microplus, Rhipice tick (Rhipicph) Ticks such as anguineus), Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), house dust mite such as pteronyssinus (Dermatophagoides ptrenyssnus), Hosotsumedani (Cheyletus eruditus), Stag Tsumedani (Cheyletus malaccensis), claw mites such as Cheyletus moorei, house dust mite (Ornithonyssus bacoti), bird mite (Ornithonysus sylvairum), duck (Derman) Wasps such as Yssus gallinae, Tsutsugamushi such as Leptotrombidium akamushi, and Chiracanthium japonicum, Latrodectus spiders, etc.

Plant parasitic nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines ), Potato cyst nematode (Globodera rostochiensis), southern nematode crest nematode (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus).

Pathogenic endoparasites: Diphyllobothrium spp., Spirometra spp., Sistocefalus spp., Ligula Pseudophyllidea parasites such as Ligula spp., Bothridium spp., Diphlogonoporus spp., Etc.
Mesocestoides subgenus (Mesocestoides spp.), Anoprocephala subgenus (Lepidoptera) (Anoblockephala spp.), Paranoprocephala spp. Sub-genus (Thysanosomsa spp.), Sub-genus Thysnesia spp., Sub-genus Abitellina spp., Subgenus Stilesia spp., Sub-genus Sittenia sp. Andyra spp.), Bertieella spp., Tenia spp., Echinococcus subgenus (Echi ococcus spp.), Hydatigera spp., Davinea spp., Raileitina spp., Hymenolepsis spp. (Hymenolepis sp.), Hymenolepis sp. (Echinolepis spp.), Echinocotiple spp., Diorchis spp., Dipyridium spp., Joyeuxella. Cyclophilidea parasites such as Dipropyridium spp.,
Monogenea subclass parasites such as Gyrodactyllus spp., Dactyrogyrus spp., Polystoma spp.
Diprostom spp., Postdiprostom spp., Sistosoma spp., Trichobilharzia sp., Trichobilharzia sp. Sub-genus (Ornithobilharzia spp.), Sub-genus (Austrobiharharzia spp.), Sub-genus (Gigantobilharzia spp.), Subgenus Leucochloridium (Subgenus Leucochloridium spp.) Brachylama spp.), Echinostoma spp. (Echinostoma spp.), Echinopa L. subtilis (Echinoparyphium spp.), Echinocasmus spp., Hypoderaum spp., Fasciola spp., Fasciides ol. Subspecies of Lopsis (hypertrophic flukes) (Fasciolopsis spp.), Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp. (Paramphistomum spp.), Subgenus (Calicophoron spp.), Cotylophoron spp., Gigantocotile subgenus Gigantotile spp.), Fischeredelius spp., Gastrothylracus spp., Notococtylus spp., Catatropis spp. Spg. ), Prosthogonimus spp., Diclochelium spp. (Dicocoelium spp.), Eurytrema spp., Troglotrema spp., Troglotrema spp. Genus (Pulmonary flukes) (Paragonimus spp. ), Coryricrum spp., Nanophyetas spp., Opistorchis spp., Clonorchis spp., Metorkis Digenea parasites, such as the subclasses of Methorchis spp., Heterophyces spp., Metagonimus spp.

When the pest control agent of the present invention is used, the application amount is usually 1 to 10,000 g in terms of the amount of the present condensed heterocyclic compound per 10,000 m ² . When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are.

When the pest control composition of the present invention is used for controlling pests living in a house, the amount applied is that of the condensed heterocyclic compound and the insecticidal compound per 1 m ² of treatment area when treated on the surface. The total amount is usually 0.01 to 1000 mg, and when processing in a space, the total amount of the present condensed heterocyclic compound and the present insecticidal compound per 1 m ³ of the processing space is usually 0.01 to 500 mg. When the pest control composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. Apply aerosols, smoke agents, poison baits, etc. as they are.

  These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil. You may process to soil.

When the pest control agent of the present invention is used for controlling ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., a method known in veterinary medicine Can be used on animals. As a specific method of use, for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression. In this case, for example, an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
In addition, when used for endoparasite control, for example, enteral, parenteral, skin, nasal cavity, by treating the environment where the animal is present, or a molded article containing the compound of the present invention (for example, It is administered using strips, tablets, tapes, collars, ear tags, limb bands, marking devices, etc.
Enteral administration is carried out orally, for example, in the form of powders, suppositories, tablets, capsules, pastes, beverages, granules, liquid medicines, bolus, feeds with drugs or drinking water. Specifically, it is applied to the skin in the form of, for example, dipping, spraying, bathing, washing, pouring-on and spotting-on and spraying. Alternatively, it is administered parenterally, for example, in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or by implant.

The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.);
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), foliage plants, etc.
“Crop” also includes genetically modified crops.

Hereinafter, the present invention will be described in more detail with reference to production examples, reference production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.
First, a manufacture example is shown about manufacture of this condensed heterocyclic compound. The present fused heterocyclic compound is not limited to these examples.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７２−８．７０（１Ｈ，ｍ），８．３３−８．３１（１Ｈ，ｍ），７．５６−７．４９（２Ｈ，ｍ），７．４７−７．４３（１Ｈ，ｍ），７．３９−７．３４（１Ｈ，ｍ），３．７７（３Ｈ，ｓ），２．８７（２Ｈ，ｑ），１．２４（３Ｈ，ｔ） Production Example 1
A mixture of 1.0 g of N ² -methyl-5-trifluoromethylpyridine-2,3-diamine, 0.96 g of 2-ethylsulfanylbenzaldehyde, 1.80 g of sodium hydrogen sulfite and 10 ml of DMF was heated and stirred at 160 ° C. for 5 hours. . The reaction mixture was ice-cooled, water was added, and the precipitated crystals were collected by filtration, washed with water and then hexane. The obtained crystals were dried under reduced pressure to give 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound). 1)) 1.09 g was obtained.
This condensed heterocyclic compound 1

¹ H-NMR (CDCl ₃ ) δ: 8.72-8.70 (1H, m), 8.33-8.31 (1H, m), 7.56-7.49 (2H, m), 7 .47-7.43 (1H, m), 7.39-7.34 (1H, m), 3.77 (3H, s), 2.87 (2H, q), 1.24 (3H, t )

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７６−８．７４（１Ｈ，ｍ），８．３２−８．３０（１Ｈ，ｍ），８．２７−８．２４（１Ｈ，ｍ），７．８６−７．８１（１Ｈ，ｍ），７．７２−７．６８（１Ｈ，ｍ），７．６２−７．５９（１Ｈ，ｍ），３．８９（３Ｈ，ｓ），３．４２−３．３１（１Ｈ，ｍ），３．０２−２．９２（１Ｈ，ｍ），１．３１（３Ｈ，ｔ） Production Example 2
2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 0.25 g, sodium periodate 0.24 g, methanol 6 ml, water 2 ml and THF0 .8 ml of the mixture was stirred at room temperature for 20 minutes, heated to 50 ° C., and further heated and stirred for 1.5 hours. Water was added to the ice-cooled reaction mixture, and the precipitated crystals were collected by filtration. The crystals collected by filtration were dissolved in ethyl acetate, washed successively with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was washed with hexane, and 2- (2-ethylsulfinylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 2). 0.20 g was obtained.
This condensed heterocyclic compound 2

¹ H-NMR (CDCl ₃ ) δ: 8.76-8.74 (1H, m), 8.32-8.30 (1H, m), 8.27-8.24 (1H, m), 7 .86-7.81 (1H, m), 7.72-7.68 (1H, m), 7.62-7.59 (1H, m), 3.89 (3H, s), 3.42 -3.31 (1H, m), 3.02-2.92 (1H, m), 1.31 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７５−８．７３（１Ｈ，ｍ），８．２９−８．２７（１Ｈ，ｍ），８．２５−８．２１（１Ｈ，ｍ），７．８７−７．７９（２Ｈ，ｍ），７．５８−７．５５（１Ｈ，ｍ），３．７２（３Ｈ，ｓ），３．４２（２Ｈ，ｑ），１．２６（３Ｈ，ｔ） Production Example 3
2-Chloroperbenzoic acid was added to a mixture of 0.25 g of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 3 ml of chloroform under ice cooling. After adding 0.43 g (purity 65% or more), the mixture was warmed to room temperature and stirred for 1 hour. Chloroform was added to the reaction mixture under ice-cooling, saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then with a saturated saline solution, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with hexane and then with methyl-tert-butyl ether to give 2- (2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2-ethylsulfonylphenyl) -3-methyl-tert-butyl ether)”. And referred to as the present condensed heterocyclic compound 3.) 0.27 g was obtained.
This condensed heterocyclic compound 3

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.73 (1H, m), 8.29-8.27 (1H, m), 8.25-8.21 (1H, m), 7 .87-7.79 (2H, m), 7.58-7.55 (1H, m), 3.72 (3H, s), 3.42 (2H, q), 1.26 (3H, t )

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７０（１Ｈ，ｓ），８．３２（１Ｈ，ｓ），７．６０−７．３０（４Ｈ，ｍ），４．２５（２Ｈ，ｑ），２．８９（２Ｈ，ｑ），１．３５−１．３０（３Ｈ，ｍ），１．２７−１．２１（３Ｈ，ｍ） Production Example 4
To a mixture of 700 mg of N ² -ethyl-5-trifluoromethylpyridine-2,3-diamine, 690 mg of 2-ethylsulfanylbenzoic acid and 20 ml of pyridine, 720 mg of WSC was added at room temperature, heated to 95 ° C. and heated for 10 hours. Stir. To the reaction mixture cooled to room temperature, a saturated aqueous sodium carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure.
The obtained residue was dissolved in 20 ml of xylene, and 1.6 g of p-toluenesulfonic acid monohydrate was added. The mixture was heated to 170 ° C. and stirred with heating for 9.5 hours. To the reaction mixture cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was poured, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 3-ethyl-2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed complex). This is referred to as ring compound 4.) 295 mg was obtained.
This condensed heterocyclic compound 4

¹ H-NMR (CDCl ₃ ) δ: 8.70 (1H, s), 8.32 (1H, s), 7.60-7.30 (4H, m), 4.25 (2H, q), 2.89 (2H, q), 1.35-1.30 (3H, m), 1.27-1.21 (3H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７５（１Ｈ，ｄ），８．３１（１Ｈ，ｄ），８．２４（１Ｈ，ｄｄ），７．８４（１Ｈ，ｄｔ），７．７０（１Ｈ，ｄｔ），７．５８（１Ｈ，ｄｄ），４．３５（２Ｈ，ｑ），３．４３−３．３０（１Ｈ，ｍ），３．０６−２．９４（１Ｈ，ｍ），１．４１（３Ｈ，ｔ），１．３０（３Ｈ，ｔ）
本縮合複素環化合物６

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７１（１Ｈ，ｄ），８．３２（１Ｈ，ｄ），７．５６−７．４７（２Ｈ，ｍ），７．４３（１Ｈ，ｄｄ），７．３９−７．３１（１Ｈ，ｍ），４．２５（２Ｈ，ｑ），２．８９（２Ｈ，ｑ），１．３２（３Ｈ，ｔ），１．２５（３Ｈ，ｔ） Production Examples 5 and 6
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 3-ethyl-2- (2-ethylsulfanylphenyl) ) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 2- (2-ethylsulfinylphenyl) -3-ethyl-6 according to the methods described in Preparation Examples 32 and 33 -Trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 5) 140 mg, and 2- (2-ethylsulfonylphenyl) -3-ethyl-6-trifluoro 60 mg of methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 6) was obtained.
This condensed heterocyclic compound 5

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, d), 8.31 (1H, d), 8.24 (1H, dd), 7.84 (1H, dt), 7.70 ( 1H, dt), 7.58 (1H, dd), 4.35 (2H, q), 3.43-3.30 (1H, m), 3.06-2.94 (1H, m), 1 .41 (3H, t), 1.30 (3H, t)
This condensed heterocyclic compound 6

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.32 (1H, d), 7.56-7.47 (2H, m), 7.43 (1H, dd), 7.39-7.31 (1H, m), 4.25 (2H, q), 2.89 (2H, q), 1.32 (3H, t), 1.25 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６８（１Ｈ，ｄ），８．２８（１Ｈ，ｄ），７．５５−７．４７（２Ｈ，ｍ），７．３９−７．３１（２Ｈ，ｍ），４．４０−４．３３（１Ｈ，ｍ），２．９１（２Ｈ，ｑ），１．７７−１．６６（６Ｈ，ｍ），１．２５（３Ｈ，ｔ） Production Example 7
In accordance with the method described in Preparation Example 4, using N ² -isopropyl-5-trifluoromethyl-pyridine-2,3-diamine instead of N ² -ethyl-5-trifluoromethyl-pyridine-2,3-diamine. Thus, 130 mg of 2- (2-ethylsulfanylphenyl) -3-isopropyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 7) was obtained. .
This condensed heterocyclic compound 7

¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.28 (1H, d), 7.55-7.47 (2H, m), 7.39-7.31 (2H M), 4.40-4.33 (1H, m), 2.91 (2H, q), 1.77-1.66 (6H, m), 1.25 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７３（１Ｈ，ｄ），８．２８（１Ｈ，ｄ），８．２２（１Ｈ，ｄｄ），７．８３（１Ｈ，ｔｄ），７．６９（１Ｈ，ｔｄ），７．５０（１Ｈ，ｄｄ），４．６０−４．４８（１Ｈ，ｍ），３．３８−３．２６（１Ｈ，ｍ），３．０５−２．９５（１Ｈ，ｍ），１．７７−１．７１（６Ｈ，ｍ），１．２７（３Ｈ，ｔ）
本縮合複素環化合物９

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７１（１Ｈ，ｄ），８．２４−８．２２（２Ｈ，ｍ），７．８５−７．７８（２Ｈ，ｍ），７．５５−７．５２（１Ｈ，ｍ），４．３３−４．２６（１Ｈ，ｍ），３．７２−３．６２（１Ｈ，ｍ），３．４４−３．３４（１Ｈ，ｍ），１．７７−１．６９（６Ｈ，ｍ），１．２８（３Ｈ，ｔ） Production Examples 8 and 9
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -3- 2- (2-Ethylsulfinylphenyl) -3-isopropyl-6-, using isopropyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, according to the methods described in Preparation Examples 32 and 33 60 mg of trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 8), and 2- (2-ethylsulfonylphenyl) -3-isopropyl-6-trifluoromethyl 55 mg of -3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 9) was obtained.
This condensed heterocyclic compound 8

¹ H-NMR (CDCl ₃ ) δ: 8.73 (1H, d), 8.28 (1H, d), 8.22 (1H, dd), 7.83 (1H, td), 7.69 ( 1H, td), 7.50 (1H, dd), 4.60-4.48 (1H, m), 3.38-3.26 (1H, m), 3.05-2.95 (1H, m), 1.77-1.71 (6H, m), 1.27 (3H, t)
This condensed heterocyclic compound 9

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.24-8.22 (2H, m), 7.85-7.78 (2H, m), 7.55-7 .52 (1H, m), 4.33-4.26 (1H, m), 3.72-3.62 (1H, m), 3.44-3.34 (1H, m), 1.77 -1.69 (6H, m), 1.28 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７４（１Ｈ，ｓ），８．３１（１Ｈ，ｓ），７．５３−７．４７（３Ｈ，ｍ），７．３９−７．３１（１Ｈ，ｍ），３．５５−３．４９（１Ｈ，ｍ），２．９０（２Ｈ，ｑ），１．２５（３Ｈ，ｔ），１．０１−０．９４（２Ｈ，ｍ），０．９３−０．８６（２Ｈ，ｍ） Production Example 10
N ² - ethyl-5-trifluoromethyl - instead of pyridine-2,3-diamine N ² - cyclopropyl-5- trifluoromethyl - using pyridine-2,3-diamine, the method of Production Example 4 according Accordingly, 280 mg of 3-cyclopropyl-2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 10) is added. Obtained.
The present condensed heterocyclic compound 10

¹ H-NMR (CDCl ₃ ) δ: 8.74 (1H, s), 8.31 (1H, s), 7.53-7.47 (3H, m), 7.39-7.31 (1H M), 3.55-3.49 (1H, m), 2.90 (2H, q), 1.25 (3H, t), 1.01-0.94 (2H, m),. 93-0.86 (2H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７７（１Ｈ，ｄ），８．２９−８．２６（２Ｈ，ｍ），７．８５−７．７９（２Ｈ，ｍ），７．７２−７．６７（１Ｈ，ｍ），３．５７−３．５１（１Ｈ，ｍ），３．４９−３．３９（１Ｈ，ｍ），３．０９−２．９５（１Ｈ，ｍ），１．３４（３Ｈ，ｔ），１．２９−１．１６（１Ｈ，ｍ），１．０９−０．９２（２Ｈ，ｍ），０．８０−０．６５（１Ｈ，ｍ）
本縮合複素環化合物１２

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７６（１Ｈ，ｓ），８．２７−８．２２（２Ｈ，ｍ），７．８７−７．７８（２Ｈ，ｍ），７．６５（１Ｈ，ｄｄ），３．６０（２Ｈ，ｂｒｓ），３．３９−３．３３（１Ｈ，ｍ），１．２９（３Ｈ，ｔ），１．１１−１．１１（２Ｈ，ｍ），０．９３（２Ｈ，ｂｒｓ）． Production Examples 11 and 12
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 3-cyclopropyl-2- (2-ethylsulfanyl) 3-cyclopropyl-2- (2-ethylsulfinylphenyl)-using phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine according to the methods described in Preparation Examples 32 and 33 114 mg of 6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 11), and 3-cyclopropyl-2- (2-ethylsulfonylphenyl) -6- 109 mg of trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 12) was obtained.
This condensed heterocyclic compound 11

¹ H-NMR (CDCl ₃ ) δ: 8.77 (1H, d), 8.29-8.26 (2H, m), 7.85-7.79 (2H, m), 7.72-7 .67 (1H, m), 3.57-3.51 (1H, m), 3.49-3.39 (1H, m), 3.09-2.95 (1H, m), 1.34 (3H, t), 1.29-1.16 (1H, m), 1.09-0.92 (2H, m), 0.80-0.65 (1H, m)
This condensed heterocyclic compound 12

¹ H-NMR (CDCl ₃ ) δ: 8.76 (1H, s), 8.27-8.22 (2H, m), 7.87-7.78 (2H, m), 7.65 (1H , Dd), 3.60 (2H, brs), 3.39-3.33 (1H, m), 1.29 (3H, t), 1.11-1.11 (2H, m), 0. 93 (2H, brs).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．５９（１Ｈ，ｓ），８．２３（１Ｈ，ｓ），７．５６−７．４３（３Ｈ，ｍ），７．３８−７．３３（１Ｈ，ｍ），６．８８（１Ｈ，ｔ），３．７７（３Ｈ，ｓ），２．８７（２Ｈ，ｑ），１．２３（３Ｈ，ｔ） Production Example 13
To a mixture of 2- (2-ethylsulfanylphenyl) -3-methyl-3H-imidazo [4,5-b] pyridine-6-carbaldehyde 122 mg and chloroform 3 ml was added bis (2-methoxyethyl) amino under ice cooling. 700 μl of sulfatrifluoride was added. The mixture was warmed to room temperature and stirred for 3 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted successively with chloroform and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 6-difluoromethyl-2- (2-ethylsulfanylphenyl) -3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic ring). It is described as Compound 13.) 49 mg was obtained.
This condensed heterocyclic compound 13

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, s), 8.23 (1H, s), 7.56-7.43 (3H, m), 7.38-7.33 (1H M), 6.88 (1H, t), 3.77 (3H, s), 2.87 (2H, q), 1.23 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６２（１Ｈ，ｓ），８．２６−８．２３（２Ｈ，ｍ），７．８３（１Ｈ，ｔｄ），７．７０（１Ｈ，ｔｄ），７．６２（１Ｈ，ｄｄ），６．９０（１Ｈ，ｔ），３．８９（３Ｈ，ｓ），３．４２−３．３２（１Ｈ，ｍ），３．０２−２．９２（１Ｈ，ｍ），１．３０（３Ｈ，ｔ）
本縮合複素環化合物１５

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６１（１Ｈ，ｓ），８．２４−８．１９（２Ｈ，ｍ），７．８７−７．７８（２Ｈ，ｍ），７．５８（１Ｈ，ｄｄ），６．８９（１Ｈ，ｔ），３．７１（３Ｈ，ｓ），３．４３（２Ｈ，ｑ），１．２５（３Ｈ，ｔ） Production Examples 14 and 15
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 6-difluoromethyl-2- (2-ethylsulfanyl) Using phenyl) -3-methyl-3H-imidazo [4,5-b] pyridine, according to the methods described in Preparation Examples 32 and 33, 6-difluoromethyl-2- (2-ethylsulfinylphenyl) -3- 110 mg of methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 14) and 6-difluoromethyl-2- (2-ethylsulfonylphenyl) -3-methyl-3H-imidazo 101 mg of [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 15) was obtained.
The present condensed heterocyclic compound 14

¹ H-NMR (CDCl ₃ ) δ: 8.62 (1H, s), 8.26-8.23 (2H, m), 7.83 (1H, td), 7.70 (1H, td), 7.62 (1H, dd), 6.90 (1H, t), 3.89 (3H, s), 3.42-3.32 (1H, m), 3.02-2.92 (1H, m), 1.30 (3H, t)
This condensed heterocyclic compound 15

¹ H-NMR (CDCl ₃ ) δ: 8.61 (1H, s), 8.24-8.19 (2H, m), 7.87-7.78 (2H, m), 7.58 (1H , Dd), 6.89 (1H, t), 3.71 (3H, s), 3.43 (2H, q), 1.25 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６６（１Ｈ，ｄ），８．３０（１Ｈ，ｄ），７．５６−７．４９（２Ｈ，ｍ），７．４７−７．４３（１Ｈ，ｍ），７．３８−７．３４（１Ｈ，ｍ），３．７８（３Ｈ，ｓ），２．８８（２Ｈ，ｑ），１．２４（３Ｈ，ｔ） Production Example 16
500 mg of 6-bromo-2- (2-ethylsulfanylphenyl) -3-methyl-3H-imidazo [4,5-b] pyridine, 24 ml of NMP, 10 ml of xylene, 1.1 g of copper iodide and sodium pentafluoropropionate 1 g of the mixture was heated to 170 ° C. and stirred for 3 days. A saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanylphenyl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed complex). It is described as ring compound 16.) 43 mg was obtained.
The present condensed heterocyclic compound 16

¹ H-NMR (CDCl ₃ ) δ: 8.66 (1H, d), 8.30 (1H, d), 7.56-7.49 (2H, m), 7.47-7.43 (1H M), 7.38-7.34 (1H, m), 3.78 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．１２−８．１０（１Ｈ，ｍ），７．６１−７．５８（１Ｈ，ｍ），７．５３−７．４４（４Ｈ，ｍ），７．３８−７．３２（１Ｈ，ｍ），３．６９（３Ｈ，ｓ），２．８４（２Ｈ，ｑ），１．２２（３Ｈ，ｔ） Production Example 17
A mixture of 1.64 g of 2-ethylsulfanyl-N- (2-methylamino-5-trifluoromethylphenyl) -benzamide, 1.76 g of p-toluenesulfonic acid monohydrate and 50 ml of xylene at 150 ° C. for 1 hour, Stir with heating to reflux. To the reaction mixture cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanylphenyl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as the present condensed heterocyclic compound 17). 1.40 g was obtained.
The present condensed heterocyclic compound 17

¹ H-NMR (CDCl ₃ ) δ: 8.12-8.10 (1H, m), 7.61-7.58 (1H, m), 7.53-7.44 (4H, m), 7 .38-7.32 (1H, m), 3.69 (3H, s), 2.84 (2H, q), 1.22 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．２４−８．２０（１Ｈ，ｍ），８．１０−８．０７（１Ｈ，ｍ），７．８３−７．７８（１Ｈ，ｍ），７．７０−７．６２（２Ｈ，ｍ），７．５７−７．５１（２Ｈ，ｍ），３．７９（３Ｈ，ｓ），３．３６−３．２６（１Ｈ，ｍ），２．９８−２．８８（１Ｈ，ｍ），１．２６（３Ｈ，ｔ） Production Example 18
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -1-methyl-5 Using trifluoromethyl-1H-benzimidazole, 2- (2-ethylsulfinylphenyl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, this condensation) according to the method described in Production Example 2 This is referred to as heterocyclic compound 18.) 0.30 g was obtained.
The present condensed heterocyclic compound 18

¹ H-NMR (CDCl ₃ ) δ: 8.24-8.20 (1H, m), 8.10-8.07 (1H, m), 7.83-7.78 (1H, m), 7 .70-7.62 (2H, m), 7.57-7.51 (2H, m), 3.79 (3H, s), 3.36-3.26 (1H, m), 2.98 -2.88 (1H, m), 1.26 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．２４−８．２０（１Ｈ，ｍ），８．０７−８．０５（１Ｈ，ｍ），７．８４−７．７７（２Ｈ，ｍ），７．６４−７．６１（１Ｈ，ｍ），７．５７−７．５４（１Ｈ，ｍ），７．５３−７．４９（１Ｈ，ｍ），３．６３（３Ｈ，ｓ），３．４６−３．３４（２Ｈ，ｍ），１．２３（３Ｈ，ｔ） Production Example 19
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -1-methyl-5 Using trifluoromethyl-1H-benzimidazole, 2- (2-ethylsulfonylphenyl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, this condensation) according to the method described in Production Example 3 This is referred to as heterocyclic compound 19.) 0.24 g was obtained.
The present condensed heterocyclic compound 19

¹ H-NMR (CDCl ₃ ) δ: 8.24-8.20 (1H, m), 8.07-8.05 (1H, m), 7.84-7.77 (2H, m), 7 .64-7.61 (1H, m), 7.57-7.54 (1H, m), 7.53-7.49 (1H, m), 3.63 (3H, s), 3.46 -3.34 (2H, m), 1.23 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．１９−８．１５（２Ｈ，ｍ），７．７１−７．６７（１Ｈ，ｍ），７．６６−７．６３（１Ｈ，ｍ），７．５２−７．４７（１Ｈ，ｍ），７．４５−７．４２（１Ｈ，ｍ），７．３１−７．２７（１Ｈ，ｍ），３．０６（２Ｈ，ｑ），１．４４（３Ｈ，ｔ） Production Example 20
A mixture of 0.97 g of 2-amino-4-trifluoromethyl-phenol, 1.10 g of 2-ethylsulfanylbenzoic acid, 1.27 g of WSC, 37 mg of HOBt and 5 ml of pyridine was stirred at 115 ° C. for 2.5 hours with heating under reflux. After leaving still overnight, the mixture was again stirred at 115 ° C. for 6 hours with heating under reflux. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.
A mixture of the obtained residue, 2.09 g of p-toluenesulfonic acid monohydrate and 50 ml of xylene was stirred at 153 ° C. for 2 hours with heating under reflux. To the reaction mixture cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution, water, 10% citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.98 g of 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenzoxazole (hereinafter referred to as the present condensed heterocyclic compound 20).
The present condensed heterocyclic compound 20

¹ H-NMR (CDCl ₃ ) δ: 8.19-8.15 (2H, m), 7.71-7.67 (1H, m), 7.66-7.63 (1H, m), 7 .52-7.47 (1H, m), 7.45-7.42 (1H, m), 7.31-7.27 (1H, m), 3.06 (2H, q), 1.44 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．３５−８．３０（２Ｈ，ｍ），８．１２−８．１０（１Ｈ，ｍ），７．８５−７．７９（１Ｈ，ｍ），７．７５−７．６６（３Ｈ，ｍ），３．４８−３．３８（１Ｈ，ｍ），３．００−２．９０（１Ｈ，ｍ），１．４１（３Ｈ，ｔ） Production Example 21
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenz Using oxazole, 0.27 g of 2- (2-ethylsulfinylphenyl) -5-trifluoromethylbenzoxazole (hereinafter referred to as the present condensed heterocyclic compound 21) was obtained according to the method described in Production Example 2. .
The present condensed heterocyclic compound 21

¹ H-NMR (CDCl ₃ ) δ: 8.35-8.30 (2H, m), 8.12-8.10 (1H, m), 7.85-7.79 (1H, m), 7 .75-7.66 (3H, m), 3.48-3.38 (1H, m), 3.00-2.90 (1H, m), 1.41 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．２８−８．２４（１Ｈ，ｍ），８．１１−８．０９（１Ｈ，ｍ），７．９９−７．９５（１Ｈ，ｍ），７．８５−７．７７（２Ｈ，ｍ），７．７２−７．７０（２Ｈ，ｍ），３．８２（２Ｈ，ｑ），１．４０（３Ｈ，ｔ） Production Example 22
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenz Using oxazole, 0.24 g of 2- (2-ethylsulfonylphenyl) -5-trifluoromethylbenzoxazole (hereinafter referred to as the present condensed heterocyclic compound 22) was obtained according to the method described in Production Example 3. .
The present condensed heterocyclic compound 22

¹ H-NMR (CDCl ₃ ) δ: 8.28-8.24 (1H, m), 8.11-8.09 (1H, m), 7.9-7.95 (1H, m), 7 .85-7.77 (2H, m), 7.72-7.70 (2H, m), 3.82 (2H, q), 1.40 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６７（１Ｈ，ｓ），８．４０（１Ｈ，ｓ），８．２５（１Ｈ，ｄ），７．５３（１Ｈ，ｔ），７．４５（１Ｈ，ｄ），７．３２（１Ｈ，ｔ），３．０８（２Ｈ，ｑ），１．４５（３Ｈ，ｔ） Production Example 23
A mixture of 0.92 g of 2-ethylsulfanylphenyl-N- (2-hydroxy-5-trifluoromethylpyridin-3-yl) -benzamide and 5 ml of phosphorus oxychloride was heated to 120 ° C. and stirred with heating under reflux. The reaction mixture cooled to room temperature was left overnight. The temperature was raised again to 120 ° C., and the mixture was stirred for 2 hours under reflux. Water was poured into the reaction mixture cooled to room temperature, and the precipitated solid was collected by filtration, washed with water and hexane, dried, and 2- (2-ethylsulfanylphenyl) -6-trifluoromethyloxazolo. 0.53 g of [5,4-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 23) was obtained.
The present condensed heterocyclic compound 23

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, s), 8.40 (1H, s), 8.25 (1H, d), 7.53 (1H, t), 7.45 ( 1H, d), 7.32 (1H, t), 3.08 (2H, q), 1.45 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７３−８．７２（１Ｈ，ｍ），８．４１−８．３８（２Ｈ，ｍ），８．３６−８．３３（１Ｈ，ｍ），７．９０−７．８４（１Ｈ，ｍ），７．７４−７．６９（１Ｈ，ｍ），３．４５−３．３５（１Ｈ，ｍ），３．００−２．９０（１Ｈ，ｍ），１．４０（３Ｈ，ｔ） Production Example 24
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -6-trifluoromethyloxa 2- (2-ethylsulfinylphenyl) -6-trifluoromethyloxazolo [5,4-b] pyridine (hereinafter, referred to as “Production Example 2”) using zolo [5,4-b] pyridine. This is referred to as the present condensed heterocyclic compound 24.) 0.17 g was obtained.
The present condensed heterocyclic compound 24

¹ H-NMR (CDCl ₃ ) δ: 8.73-8.72 (1H, m), 8.41-8.38 (2H, m), 8.36-8.33 (1H, m), 7 .90-7.84 (1H, m), 7.74-7.69 (1H, m), 3.45-3.35 (1H, m), 3.00-2.90 (1H, m) , 1.40 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７５−８．７３（１Ｈ，ｍ），８．４０−８．３７（１Ｈ，ｍ），８．２９−８．２６（１Ｈ，ｍ），８．０５−８．０２（１Ｈ，ｍ），７．８９−７．８１（２Ｈ，ｍ），３．８１（２Ｈ，ｑ），１．４３（３Ｈ，ｔ） Production Example 25
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -6-trifluoromethyloxa 2- (2-ethylsulfonylphenyl) -6-trifluoromethyloxazolo [5,4-b] pyridine (hereinafter, referred to as “Production Example 3”) using zolo [5,4-b] pyridine. This is referred to as the present condensed heterocyclic compound 25.) 0.19 g was obtained.
This condensed heterocyclic compound 25

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.73 (1H, m), 8.40-8.37 (1H, m), 8.29-8.26 (1H, m), 8 .05-8.02 (1H, m), 7.89-7.81 (2H, m), 3.81 (2H, q), 1.43 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．４１−８．３９（１Ｈ，ｍ），８．０６−８．００（２Ｈ，ｍ），７．６６−７．６２（１Ｈ，ｍ），７．５５−７．５１（１Ｈ，ｍ），７．４８−７．４２（１Ｈ，ｍ），７．３７−７．３２（１Ｈ，ｍ），２．９６（２Ｈ，ｑ），１．３３（３Ｈ，ｔ） Production Example 26
A mixture of 1.08 g of 2-amino-4-trifluoromethylbenzenethiol hydrochloride, 1.04 g of 2-ethylsulfanylbenzoic acid chloride and 10 mL of THF was stirred at room temperature for 3 hours. To the reaction mixture, 0.43 g of sodium hydrogen carbonate was added and stirred at room temperature for 8 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.50 g of 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenzothiazole (hereinafter referred to as the present condensed heterocyclic compound 26).
The present condensed heterocyclic compound 26

¹ H-NMR (CDCl ₃ ) δ: 8.41-8.39 (1H, m), 8.06-8.00 (2H, m), 7.66-7.62 (1H, m), 7 .55-7.51 (1H, m), 7.48-7.42 (1H, m), 7.37-7.32 (1H, m), 2.96 (2H, q), 1.33 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．３６−８．３２（１Ｈ，ｍ），８．３２−８．３０（１Ｈ，ｍ），８．０８−８．０５（１Ｈ，ｍ），７．９７−７．９４（１Ｈ，ｍ），７．８０−７．７５（１Ｈ，ｍ），７．７１−７．６８（１Ｈ，ｍ），７．６６−７．６１（１Ｈ，ｍ），３．５６−３．４５（１Ｈ，ｍ），３．０２−２．９３（１Ｈ，ｍ），１．４６（３Ｈ，ｔ） Production Example 27
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenzo Using thiazole, 0.25 g of 2- (2-ethylsulfinylphenyl) -5-trifluoromethylbenzothiazole (hereinafter referred to as the present condensed heterocyclic compound 27) was obtained according to the method described in Production Example 2. .
This condensed heterocyclic compound 27

¹ H-NMR (CDCl ₃ ) δ: 8.36-8.32 (1H, m), 8.32-8.30 (1H, m), 8.08-8.05 (1H, m), 7 97-7.94 (1H, m), 7.80-7.75 (1H, m), 7.71-7.68 (1H, m), 7.66-7.61 (1H, m) 3.56-3.45 (1H, m), 3.02-2.93 (1H, m), 1.46 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．３３−８．３１（１Ｈ，ｍ），８．２６−８．２３（１Ｈ，ｍ），８．１０−８．０６（１Ｈ，ｍ），７．８１−７．６９（４Ｈ，ｍ），３．７５（２Ｈ，ｑ），１．３６（３Ｈ，ｔ） Production Example 28
Instead of 2- (2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -5-trifluoromethylbenzo Using thiazole, 0.30 g of 2- (2-ethylsulfonylphenyl) -5-trifluoromethylbenzothiazole (hereinafter referred to as the present condensed heterocyclic compound 28) was obtained according to the method described in Production Example 3. .
The present condensed heterocyclic compound 28

¹ H-NMR (CDCl ₃ ) δ: 8.33-8.31 (1H, m), 8.26-8.23 (1H, m), 8.10-8.06 (1H, m), 7 .81-7.69 (4H, m), 3.75 (2H, q), 1.36 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７０（１Ｈ，ｄ），８．２９（１Ｈ，ｄ），８．２７（１Ｈ，ｄ），７．８４（１Ｈ，ｔ），７．７１（１Ｈ，ｔ），７．６０（１Ｈ，ｄ），３．９０（３Ｈ，ｓ），３．４３−３．３３（１Ｈ，ｍ），３．０４−２．９４（１Ｈ，ｍ），１．３１（３Ｈ，ｔ）
本縮合複素環化合物３０

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６９（１Ｈ，ｓ），８．２５（１Ｈ，ｓ），８．２３−８．２２（１Ｈ，ｍ），７．８８−７．７９（２Ｈ，ｍ），７．５９−７．５２（１Ｈ，ｍ），３．７２（３Ｈ，ｓ），３．４３（２Ｈ，ｑ），１．２６（３Ｈ，ｔ） Production Examples 29 and 30
2- (2-ethylsulfanyl-4-phenyl) -3 instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine Using 2-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, according to the method described in Preparation Examples 32 and 33, 2- (2-ethylsulfinyl-phenyl) -3-methyl- 27 mg of 6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 29) and 2- (2-ethylsulfonylphenyl) -3-methyl-6-pentafluoro 31 mg of ethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 30) was obtained.
This condensed heterocyclic compound 29

¹ H-NMR (CDCl ₃ ) δ: 8.70 (1H, d), 8.29 (1H, d), 8.27 (1H, d), 7.84 (1H, t), 7.71 ( 1H, t), 7.60 (1H, d), 3.90 (3H, s), 3.43-3.33 (1H, m), 3.04-2.94 (1H, m), 1 .31 (3H, t)
This condensed heterocyclic compound 30

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, s), 8.25 (1H, s), 8.23-8.22 (1H, m), 7.88-7.79 (2H , M), 7.59-7.52 (1H, m), 3.72 (3H, s), 3.43 (2H, q), 1.26 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７０−８．６８（１Ｈ，ｍ），８．３１−８．２８（１Ｈ，ｍ），７．４３−７．３８（１Ｈ，ｍ），７．１７−７．１３（１Ｈ，ｍ），７．０４−６．９８（１Ｈ，ｍ），３．７５（３Ｈ，ｓ），２．８９（２Ｈ，ｑ），１．２６（３Ｈ，ｔ） Production Example 31
A mixture of 1.14 g of N ² -methyl-5-trifluoromethylpyridine-2,3-diamine, 1.44 g of 2-ethylsulfanyl-4-fluorobenzoic acid, 1.02 g of WSC and 12 ml of pyridine at 120 ° C. The mixture was heated and stirred for 5 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure.
To the obtained residue, 3.42 g of p-toluenesulfonic acid, 10 ml of xylene and 2 ml of NMP were added, and the mixture was stirred while heating under reflux at 150 ° C. for 4.5 hours while removing water using a Dean-Stark apparatus. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine”). This is referred to as the present condensed heterocyclic compound 31.) 1.05 g was obtained.
This condensed heterocyclic compound 31

¹ H-NMR (CDCl ₃ ) δ: 8.70-8.68 (1H, m), 8.31-8.28 (1H, m), 7.43-7.38 (1H, m), 7 .17-7.13 (1H, m), 7.04-6.98 (1H, m), 3.75 (3H, s), 2.89 (2H, q), 1.26 (3H, t )

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７６−８．７５（１Ｈ，ｍ），８．３１−８．３０（１Ｈ，ｍ），８．０１−７．９８（１Ｈ，ｍ），７．６５−７．６１（１Ｈ，ｍ），７．４１−７．３６（１Ｈ，ｍ），３．９０（３Ｈ，ｓ），３．４７−３．３７（１Ｈ，ｍ），３．０４−２．９４（１Ｈ，ｍ），１．３３（３Ｈ，ｔ）
本縮合複素環化合物３３

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７６−８．７４（１Ｈ，ｍ），８．２９−８．２７（１Ｈ，ｍ），７．９７−７．９４（１Ｈ，ｍ），７．６０−７．５１（２Ｈ，ｍ），３．７２（３Ｈ，ｓ），３．４４（２Ｈ，ｑ），１．２８（３Ｈ，ｔ） Production Examples 32 and 33
To a mixture of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (0.85 g) and chloroform (12 ml) was added 3- After adding 0.81 g of chloroperbenzoic acid (purity 65% or more), the temperature was raised to room temperature and stirred for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfinyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2-ethylsulfinyl-4-fluorophenyl) -3-methyl-6H-imidazo [4,5-b] pyridine”). This is referred to as the present condensed heterocyclic compound 32.) 0.33 g, and 2- (2-ethylsulfonyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (Hereinafter referred to as the present condensed heterocyclic compound 33.) 0.52 g was obtained.
The present condensed heterocyclic compound 32

¹ H-NMR (CDCl ₃ ) δ: 8.76-8.75 (1H, m), 8.31-8.30 (1H, m), 8.01-7.98 (1H, m), 7 .65-7.61 (1H, m), 7.41-7.36 (1H, m), 3.90 (3H, s), 3.47-3.37 (1H, m), 3.04 -2.94 (1H, m), 1.33 (3H, t)
This condensed heterocyclic compound 33

¹ H-NMR (CDCl ₃ ) δ: 8.76-8.74 (1H, m), 8.29-8.27 (1H, m), 7.97-7.94 (1H, m), 7 .60-7.51 (2H, m), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７５−８．７３（１Ｈ，ｍ），８．３５−８．３３（１Ｈ，ｍ），７．７０−７．６８（１Ｈ，ｍ），７．６２−７．５６（２Ｈ，ｍ），３．７９（３Ｈ，ｓ），２．９５（２Ｈ，ｑ），１．２８（３Ｈ，ｔ） Production Example 34
To a mixture of 0.35 g of ethyl mercaptan sodium salt (80%) and 9 ml of DMF was added ice-cooled 2- (2-fluoro-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [ 4,5-b] pyridine (1.0 g) in DMF was added dropwise, and the mixture was warmed to room temperature and stirred at room temperature for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. (Hereinafter referred to as the present condensed heterocyclic compound 34) 1.10 g was obtained.
The present condensed heterocyclic compound 34

¹ H-NMR (CDCl ₃ ) δ: 8.75-8.73 (1H, m), 8.35-8.33 (1H, m), 7.70-7.68 (1H, m), 7 .62-7.56 (2H, m), 3.79 (3H, s), 2.95 (2H, q), 1.28 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６５（１Ｈ，ｄ），８．２９（１Ｈ，ｄ），７．５６−７．５１（２Ｈ，ｍ），７．４８−７．４３（１Ｈ，ｍ），７．３８−７．３４（１Ｈ，ｍ），３．７８（３Ｈ，ｓ），２．８９（２Ｈ，ｑ），１．２５（３Ｈ，ｔ） Production Example 35
2- (2-ethylsulfanyl-phenyl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine 311 mg, copper iodide 1.5 g, sodium heptafluorobutyrate 1.8 N, NMP 5 mL and xylene 25 mL of the mixture was heated and stirred at 150 ° C. for 12 hours. To the reaction mixture cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution and 28% aqueous ammonia were added, and the mixture was extracted with tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (2-ethylsulfanyl-phenyl) -6-heptafluoropropyl-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound). 35.) 118 mg was obtained.
This condensed heterocyclic compound 35

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, d), 8.29 (1H, d), 7.56-7.51 (2H, m), 7.48-7.43 (1H M), 7.38-7.34 (1H, m), 3.78 (3H, s), 2.89 (2H, q), 1.25 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６８（１Ｈ，ｄ），８．２９−８．２４（２Ｈ，ｍ），７．８７−７．８１（１Ｈ，ｍ），７．７４−７．６８（１Ｈ，ｍ），７．６１（１Ｈ，ｄｄ），３．９１（３Ｈ，ｓ），３．４３−３．３２（１Ｈ，ｍ），３．０５−２．９４（１Ｈ，ｍ），１．３１（３Ｈ，ｔ）
本縮合複素環化合物３７

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６７（１Ｈ，ｄ），８．２６−８．２２（２Ｈ，ｍ），７．８７−７．８１（２Ｈ，ｍ），７．５９−７．５５（１Ｈ，ｍ），３．７３（３Ｈ，ｓ），３．４３（２Ｈ，ｑ），１．２６（３Ｈ，ｔ）． Production Examples 36 and 37
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanyl-phenyl) -6 2- (2-Ethylsulfinyl-phenyl) -6-heptafluoro using -heptafluoropropyl-3-methyl-3H-imidazo [4,5-b] pyridine according to the methods described in Preparation Examples 32 and 33 Propyl-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 36) and 2- (2-ethylsulfonylphenyl) -6-heptafluoropropyl-3-methyl -3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 37) was obtained.
The present condensed heterocyclic compound 36

¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.29-8.24 (2H, m), 7.87-7.81 (1H, m), 7.74-7 .68 (1H, m), 7.61 (1H, dd), 3.91 (3H, s), 3.43-3.32 (1H, m), 3.05-2.94 (1H, m ), 1.31 (3H, t)
The present condensed heterocyclic compound 37

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.26-8.22 (2H, m), 7.87-7.81 (2H, m), 7.59-7 .55 (1H, m), 3.73 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７９−８．７８（１Ｈ，ｍ），８．５７−８．５５（１Ｈ，ｍ），８．３５−８．３４（１Ｈ，ｍ），７．９７−７．９４（１Ｈ，ｍ），７．７７（１Ｈ，ｄ），３．９４（３Ｈ，ｓ），３．５３−３．４３（１Ｈ，ｍ），３．０７−２．９８（１Ｈ，ｍ），１．３６（３Ｈ，ｔ）
本縮合複素環化合物３９

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７８−８．７６（１Ｈ，ｍ），８．５１−８．４９（１Ｈ，ｍ），８．３１−８．３０（１Ｈ，ｍ），８．１２−８．０９（１Ｈ，ｍ），７．７４（１Ｈ，ｄ），３．７４（３Ｈ，ｓ），３．４８（２Ｈ，ｑ），１．２９（３Ｈ，ｔ） Production Examples 38 and 39
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanyl-4-trifluoro 2- (2-Ethylsulfinyl-4-methyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine was used according to the methods described in Preparation Examples 32 and 33. Trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 38) 0.51 g, and 2- (2- Ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as this condensed heterocyclic ring) Referred to as compound 39.) Was obtained 0.26g.
The present condensed heterocyclic compound 38

¹ H-NMR (CDCl ₃ ) δ: 8.79-8.78 (1H, m), 8.57-8.55 (1H, m), 8.35-8.34 (1H, m), 7 .97-7.94 (1H, m), 7.77 (1H, d), 3.94 (3H, s), 3.53-3.43 (1H, m), 3.07-2.98 (1H, m), 1.36 (3H, t)
The present condensed heterocyclic compound 39

¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.51-8.49 (1H, m), 8.31-8.30 (1H, m), 8 .12-8.09 (1H, m), 7.74 (1H, d), 3.74 (3H, s), 3.48 (2H, q), 1.29 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．８６（１Ｈ，ｄ），８．５７（１Ｈ，ｄ），８．０３（１Ｈ，ｄｄ），７．５５（１Ｈ，ｄｄ），７．４８（１Ｈ，ｔｄ），７．３６（１Ｈ，ｔｄ），２．９８（２Ｈ，ｑ），１．３４（３Ｈ，ｔ）． Production Example 40
A mixture of 0.56 g of 3-amino-5- (trifluoromethyl) pyridine-2-thiol, 0.52 g of 2-ethylsulfanylbenzoic acid, 0.80 g of WSC, 39 mg of HOBt and 6 ml of pyridine was stirred at 60 ° C. for 2 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
A mixture of the obtained residue, p-toluenesulfonic acid monohydrate 0.65 g and N-methylpyrrolidinone 5 mL was stirred with heating at 150 ° C. for 2 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanylphenyl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 40). .) 0.38 g was obtained.
The present condensed heterocyclic compound 40

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, d), 8.57 (1H, d), 8.03 (1H, dd), 7.55 (1H, dd), 7.48 ( 1H, td), 7.36 (1H, td), 2.98 (2H, q), 1.34 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．９０（１Ｈ，ｄ），８．４９（１Ｈ，ｄ），８．３７（１Ｈ，ｄｄ），７．９９（１Ｈ，ｄｄ），７．８１（１Ｈ，ｔｄ），７．６７（１Ｈ，ｔｄ），３．５２−３．４２（１Ｈ，ｍ），３．０１−２．９２（１Ｈ，ｍ），１．４５（３Ｈ，ｔ）．
本縮合複素環化合物４２

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．９２（１Ｈ，ｄ），８．５２（１Ｈ，ｄ），８．２５（１Ｈ，ｄｄ），７．８４−７．７１（３Ｈ，ｍ），３．７３（２Ｈ，ｑ），１．３７（３Ｈ，ｔ）． Production Examples 41 and 42
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfanylphenyl) -6- 2- (2-Ethylsulfinylphenyl) -6- (trifluoromethyl) thiazolo [5, using (trifluoromethyl) thiazolo [5,4-b] pyridine according to the method described in Production Examples 32 and 33 4-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 41) 0.13 g, and 2- (2-ethylsulfonylphenyl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine ( Hereinafter, this is referred to as the present condensed heterocyclic compound 42.) 0.14 g was obtained.
The present condensed heterocyclic compound 41

¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, d), 8.49 (1H, d), 8.37 (1H, dd), 7.99 (1H, dd), 7.81 ( 1H, td), 7.67 (1H, td), 3.52-3.42 (1H, m), 3.01-2.92 (1H, m), 1.45 (3H, t).
The present condensed heterocyclic compound 42

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, d), 8.52 (1H, d), 8.25 (1H, dd), 7.84-7.71 (3H, m), 3.73 (2H, q), 1.37 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６８（１Ｈ，ｄ），８．３６（１Ｈ，ｄ），８．２１（１Ｈ，ｄｄ），７．８７−７．７７（２Ｈ，ｍ），７．５９（１Ｈ，ｄｄ），３．７１（３Ｈ，ｓ），３．４４（２Ｈ，ｑ），１．２４（３Ｈ，ｔ）
本縮合複素環化合物４４

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．６９（１Ｈ，ｄ），８．３８（１Ｈ，ｄ），８．２５（１Ｈ，ｄｄ），７．８６−７．８０（１Ｈ，ｍ），７．７２−７．６７（１Ｈ，ｍ），７．６０（１Ｈ，ｄｄ），３．８８（３Ｈ，ｓ），３．４３−３．３１（１Ｈ，ｍ），３．０３−２．９２（１Ｈ，ｍ），１．３１（３Ｈ，ｔ） Production Examples 43 and 44
2- (2-ethylsulfanyl-4-phenyl) -3 instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 2- (2-ethylsulfonylphenyl) -6-trifluoro-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine was used according to the methods described in Preparation Examples 32 and 33. Methylsulfanyl-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 43) and 2- (2-ethylsulfinyl-phenyl) -6-trifluoromethylsulfanyl- 3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 44) was obtained.
The present condensed heterocyclic compound 43

¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.36 (1H, d), 8.21 (1H, dd), 7.87-7.77 (2H, m), 7.59 (1H, dd), 3.71 (3H, s), 3.44 (2H, q), 1.24 (3H, t)
The present condensed heterocyclic compound 44

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.38 (1H, d), 8.25 (1H, dd), 7.86-7.80 (1H, m), 7.72-7.67 (1H, m), 7.60 (1H, dd), 3.88 (3H, s), 3.43-3.31 (1H, m), 3.03-2. 92 (1H, m), 1.31 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７７（１Ｈ，ｄ），８．５５（１Ｈ，ｄ），８．２４（１Ｈ，ｄｄ），７．９０−７．８３（２Ｈ，ｍ），７．６１（１Ｈ，ｄｄ），３．７５（３Ｈ，ｓ），３．４３（２Ｈ，ｑ），１．２６（３Ｈ，ｔ）
本縮合複素環化合物４６

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：９．０５（１Ｈ，ｄ），８．６５（１Ｈ，ｄ），８．２６−８．２３（１Ｈ，ｍ），７．９０−７．８５（２Ｈ，ｍ），７．６１−７．５７（１Ｈ，ｍ），３．７７（３Ｈ，ｓ），３．４１（２Ｈ，ｑ），１．２７（３Ｈ，ｔ） Production Examples 45 and 46
Instead of 2- (2-ethylsulfanyl-4-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (2-ethylsulfonylphenyl) -6- 2- (2-Ethylsulfonylphenyl) -6-trifluoromethyl using trifluoromethylsulfanyl-3-methyl-3H-imidazo [4,5-b] pyridine according to the methods described in Preparation Examples 32 and 33 Sulfinyl-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 45) and 2- (2-ethylsulfonylphenyl) -6-trifluoromethylsulfonyl 3-methyl -3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 46) was obtained.
The present condensed heterocyclic compound 45

¹ H-NMR (CDCl ₃ ) δ: 8.77 (1H, d), 8.55 (1H, d), 8.24 (1H, dd), 7.90-7.83 (2H, m), 7.61 (1H, dd), 3.75 (3H, s), 3.43 (2H, q), 1.26 (3H, t)
The present condensed heterocyclic compound 46

¹ H-NMR (CDCl ₃ ) δ: 9.05 (1H, d), 8.65 (1H, d), 8.26-8.23 (1H, m), 7.90-7.85 (2H M), 7.61-7.57 (1H, m), 3.77 (3H, s), 3.41 (2H, q), 1.27 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．９０（１Ｈ，ｄ），８．６１（１Ｈ，ｄ），８．１４（１Ｈ，ｄ），７．７５（１Ｈ，ｓ），７．５８（１Ｈ，ｄ），３．０４（２Ｈ，ｑ），１．３８（３Ｈ，ｔ）． Production Example 47
2- [2-Fluoro-4- (trifluoromethyl) phenyl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (0.18 g) and DMF (2 ml) were mixed with sodium thiomethoxide under ice-cooling. 63 mg was added and stirred at room temperature for 4 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- [2-ethylsulfanyl-4- (trifluoromethyl) phenyl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter, This is referred to as the present condensed heterocyclic compound 47.) 0.11 g was obtained.
The present condensed heterocyclic compound 47

¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, d), 8.61 (1H, d), 8.14 (1H, d), 7.75 (1H, s), 7.58 ( 1H, d), 3.04 (2H, q), 1.38 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．９５（１Ｈ，ｓ），８．５５（１Ｈ，ｓ），８．５２（１Ｈ，ｓ），８．０７（１Ｈ，ｄ），７．８８（１Ｈ，ｄ），３．７７（２Ｈ，ｑ），１．４０（３Ｈ，ｔ）． Production Example 48
3-Chloroperbenzoic acid was added to a mixture of 0.11 g of 2- [2-ethylsulfanyl-4- (trifluoromethyl) phenyl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine and 3 ml of chloroform. After adding 0.13 g (purity 65% or more), the mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with chloroform, washed successively with 10% aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2- [2-ethylsulfonyl 4- (trifluoromethyl) phenyl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as the present). This is referred to as a condensed heterocyclic compound 48.) 0.11 g was obtained.
The present condensed heterocyclic compound 48

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, s), 8.55 (1H, s), 8.52 (1H, s), 8.07 (1H, d), 7.88 ( 1H, d), 3.77 (2H, q), 1.40 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．４６（１Ｈ，ｄ），８．１０（１Ｈ，ｄ），７．５２−７．４２（３Ｈ，ｍ），７．３７−７．２６（１Ｈ，ｍ），３．７３（３Ｈ，ｓ），２．８６（２Ｈ，ｑ），２．５４（３Ｈ，ｓ），１．２２（３Ｈ，ｔ） Production Example 49
To a mixture of 535 mg of 2- (2-ethylsulfanyl-phenyl) -3-methyl-3H-imidazo [4,5-b] pyridine-6-thiol, 166 μL of iodomethane and 5 mL of ethanol, 200 mg of potassium hydroxide was added at room temperature for 5 hours. Stir. To this reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-phenyl) -3-methyl-6-methylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 49). 515 mg was obtained.
This condensed heterocyclic compound 49

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, d), 8.10 (1H, d), 7.52-7.42 (3H, m), 7.37-7.26 (1H M), 3.73 (3H, s), 2.86 (2H, q), 2.54 (3H, s), 1.22 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：９．０２（１Ｈ，ｄ），８．５８（１Ｈ，ｄ），８．２３（１Ｈ，ｄｄ），７．９０−７．８１（２Ｈ，ｍ），７．５９（１Ｈ，ｄｄ），３．７４（３Ｈ，ｓ），３．４２（２Ｈ，ｑ），３．１９（３Ｈ，ｓ），１．２６（３Ｈ，ｔ）． Production Example 50
To a mixture of 363 mg of 2- (2-ethylsulfanyl-phenyl) -3-methyl-6-methylsulfanyl-3H-imidazo [4,5-b] pyridine and 5 mL of chloroform was added 69-75% 3-chloroperoxide under ice-cooling. 1.13 g of benzoic acid was added. The mixture was warmed to room temperature and stirred for 5 hours, and then a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added thereto, and the mixture was extracted with chloroform. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonylphenyl) -6-methylsulfonyl-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 50). ) 356 mg was obtained.
This condensed heterocyclic compound 50

¹ H-NMR (CDCl ₃ ) δ: 9.02 (1H, d), 8.58 (1H, d), 8.23 (1H, dd), 7.90-7.81 (2H, m), 7.59 (1H, dd), 3.74 (3H, s), 3.42 (2H, q), 3.19 (3H, s), 1.26 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．６６（１Ｈ，ｄ）８．３９（１Ｈ，ｄ），７．６７−７．６４（１Ｈ，ｍ），７．５９−７．５２（２Ｈ，ｍ），３．７５（３Ｈ，ｓ），２．９４（２Ｈ，ｑ），１．２７（３Ｈ，ｔ）． Production Example 51
2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -6 instead of 2- (2-ethylsulfanyl-phenyl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine Compound 301A was obtained according to the method described in Production Example 103 using iodo-3-methyl-3H-imidazo [4,5-b] pyridine.
A mixture of 0.94 g of Compound 301A and 13 ml of DMF was cooled to −50 ° C., an excess amount of CF ₃ I gas was bubbled and dissolved in DMF. 1.2 ml of tetrakisdimethylaminoethylenediamine was added dropwise at a rate such that the internal temperature did not exceed -40 ° C. Then, it heated up to -10 degreeC over 1 hour, and also stirred at -10 degreeC for 1 hour. Water was poured into the reaction mixture, and the mixture was warmed to room temperature and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b]. 0.68 g of pyridine (hereinafter referred to as the present condensed heterocyclic compound 51) was obtained.
This condensed heterocyclic compound 51

¹ H-NMR (CDCl ₃ ) δ: 8.66 (1H, d) 8.39 (1H, d), 7.67-7.64 (1H, m), 7.59-7.52 (2H, m), 3.75 (3H, s), 2.94 (2H, q), 1.27 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．７１−８．７０（１Ｈ，ｍ），８．５０−８．４９（１Ｈ，ｍ），８．３８−８．３６（１Ｈ，ｍ），８．１２−８．０８（１Ｈ，ｍ），７．７４−７．７１（１Ｈ，ｍ），３．７２（３Ｈ，ｓ），３．４９（２Ｈ，ｑ），１．２９（３Ｈ，ｔ）． Production Example 52
To a mixture of 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine and 5 ml of chloroform was added 69. After adding 1.05 g of% 3-chloroperbenzoic acid, the mixture was warmed to room temperature and stirred for 1.5 hours. Thereafter, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b]. 0.20 g of pyridine (hereinafter referred to as the present condensed heterocyclic compound 52) was obtained.
The present condensed heterocyclic compound 52

¹ H-NMR (CDCl ₃ ) δ: 8.71-8.70 (1H, m), 8.50-8.49 (1H, m), 8.38-8.36 (1H, m), 8 .12-8.08 (1H, m), 7.74-7.71 (1H, m), 3.72 (3H, s), 3.49 (2H, q), 1.29 (3H, t ).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：９．０８−９．０７（１Ｈ，ｍ），８．６８−８．６６（１Ｈ，ｍ），８．５２−８．５０（１Ｈ，ｍ），８．１６−８．１２（１Ｈ，ｍ），７．７６−７．７３（１Ｈ，ｍ），３．７８（３Ｈ，ｓ），３．４６（２Ｈ，ｑ），１．３０（３Ｈ，ｔ） Production Example 53
2- (2-Ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethylsulfinyl-3H-imidazo [4,5-b] pyridine 0.26 g, sodium tungstate dihydrate 36 mg Then, a mixture of 1 ml of 30% hydrogen peroxide and 5 ml of acetonitrile was stirred for 4.5 hours with heating under reflux. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -3-methyl-6-trifluoromethylsulfonyl-3H-imidazo [4,5-b]. 0.24 g of pyridine (hereinafter referred to as the present condensed heterocyclic compound 53) was obtained.
This condensed heterocyclic compound 53

¹ H-NMR (CDCl ₃ ) δ: 9.08-9.07 (1H, m), 8.68-8.66 (1H, m), 8.52-8.50 (1H, m), 8 .16-8.12 (1H, m), 7.76-7.73 (1H, m), 3.78 (3H, s), 3.46 (2H, q), 1.30 (3H, t )

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：１２．０８−１１．８７（１Ｈ，ｍ），８．３１（１Ｈ，ｓ），８．１２−７．４４（４Ｈ，ｍ），７．４２−７．３０（２Ｈ，ｍ），２．８６（２Ｈ，ｑ），１．２２（３Ｈ，ｔ）． Production Example 54
4- (1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl) -benzene-1,2-diamine (552 mg), 2-ethylsulfanylbenzoic acid (401 mg) and pyridine (27 mL) 422 mg of ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 27 mg of 1-hydroxybenzotriazole were added. After 5 hours at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in a mixed solution of 7.5 mL of DMF and 30 mL of toluene, and 837 mg of p-toluenesulfonic acid was added at room temperature. The mixture was heated and stirred at 130 ° C. for 8 hours, and then allowed to cool to room temperature. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. This is referred to as the present condensed heterocyclic compound 54.) 97 mg was obtained.
The present condensed heterocyclic compound 54

¹ H-NMR (CDCl ₃ ) δ: 12.08-11.87 (1H, m), 8.31 (1H, s), 8.12-7.44 (4H, m), 7.42-7 .30 (2H, m), 2.86 (2H, q), 1.22 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７３−８．７１（１Ｈ，ｍ），８．３３−８．３２（１Ｈ，ｍ），７．５９（１Ｈ，ｄ），７．５０−７．４７（１Ｈ，ｍ），７．３０（１Ｈ，ｄ），３．７７（３Ｈ，ｓ），２．９１（２Ｈ，ｑ），１．２７（３Ｈ，ｔ）． Production Example 55
To a mixture of 0.63 g of ethyl mercaptan sodium salt (80%) and 10 ml of DMF was added 2- (4-bromo-2-fluorophenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4, under ice cooling. 5-b] 2.08 g of pyridine in DMF was added dropwise, and the mixture was warmed to room temperature and stirred for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-bromo-2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2-bromo-4-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine”). This is referred to as the present condensed heterocyclic compound 55.) 1.57 g was obtained.
The present condensed heterocyclic compound 55

¹ H-NMR (CDCl ₃ ) δ: 8.73-8.71 (1H, m), 8.33-8.32 (1H, m), 7.59 (1H, d), 7.50-7 .47 (1H, m), 7.30 (1H, d), 3.77 (3H, s), 2.91 (2H, q), 1.27 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７７−８．７５（１Ｈ，ｍ），８．３９（１Ｈ，ｄ），８．３２−８．３１（１Ｈ，ｍ），７．８４−７．８１（１Ｈ，ｍ），７．４９（１Ｈ，ｄ），３．９１（３Ｈ，ｓ），３．５０−３．４０（１Ｈ，ｍ），３．０６−２．９６（１Ｈ，ｍ），１．３５（３Ｈ，ｔ）．
本縮合複素環化合物５７

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７７−８．７５（１Ｈ，ｍ），８．３７（１Ｈ，ｄ），８．３１−８．２９（１Ｈ，ｍ），７．９９−７．９６（１Ｈ，ｍ），７．４４（１Ｈ，ｄ），３．７２（３Ｈ，ｓ），３．４４（２Ｈ，ｑ），１．２８（３Ｈ，ｔ）． Production Examples 56 and 57
To a mixture of 2- (4-bromo-2-ethylsulfanylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (0.40 g) and chloroform (5 ml) was added 3- After adding 0.29 g of chloroperbenzoic acid (purity 65% or more), the mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2- (4-bromo-2-ethylsulfinylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2-bromo-4-ethylsulfinylphenyl) -3-methyl)” was obtained. And this condensed heterocyclic compound 56.) 0.26 g, and 2- (4-bromo-2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] 0.17 g of pyridine (hereinafter referred to as the present condensed heterocyclic compound 57) was obtained.
The present condensed heterocyclic compound 56

¹ H-NMR (CDCl ₃ ) δ: 8.77-8.75 (1H, m), 8.39 (1H, d), 8.32-8.31 (1H, m), 7.84-7 .81 (1H, m), 7.49 (1H, d), 3.91 (3H, s), 3.50-3.40 (1H, m), 3.06-2.96 (1H, m ), 1.35 (3H, t).
The present condensed heterocyclic compound 57

¹ H-NMR (CDCl ₃ ) δ: 8.77-8.75 (1H, m), 8.37 (1H, d), 8.31-8.29 (1H, m), 7.9-7 .96 (1H, m), 7.44 (1H, d), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．７７−８．７４（１Ｈ，ｍ），８．３８−８．３６（１Ｈ，ｍ），８．３０−８．２７（１Ｈ，ｍ），８．００−７．９５（１Ｈ，ｍ），７．６３−７．５５（１Ｈ，ｍ），７．４３（１Ｈ，ｄ），７．４１−７．３０（２Ｈ，ｍ），３．７２（３Ｈ，ｓ），３．４４（２Ｈ，ｑ），１．２８（３Ｈ，ｔ）． Production Example 58
2- (4-Bromo-2-ethylsulfonylphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 0.20 g, 2-tributylstannylpyrimidine 0.17 g, tetrakis A mixture of 27 mg of triphenylphosphine palladium and 5 ml of toluene was heated to reflux under a nitrogen atmosphere for 5.5 hours. After cooling to room temperature, 0.17 g of 2-tributylstannylpyrimidine and 27 mg of tetrakistriphenylphosphine palladium were added, and the mixture was further stirred for 8 hours with heating under reflux. After cooling to room temperature, water was added and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2- [2-ethylsulfonyl-4- (pyrimidin-2-yl) -phenyl] -3-methyl-6-trifluoromethyl-3H-imidazo [4, 5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 58) 0.20 g was obtained.
The present condensed heterocyclic compound 58

¹ H-NMR (CDCl ₃ ) δ: 8.77-8.74 (1H, m), 8.38-8.36 (1H, m), 8.30-8.27 (1H, m), 8 .00-7.95 (1H, m), 7.63-7.55 (1H, m), 7.43 (1H, d), 7.41-7.30 (2H, m), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．２７（１Ｈ，ｄ），７．８６（１Ｈ，ｄ），５．３８（２Ｈ，ｂｒｓ）．
製造例５９−２
３−ブロモ−５−トリフルオロメチル−ピリジン−２−イルアミン４０ｇ、アセチルアセトン銅（ＩＩ）２．２ｇ、アセチルアセトン６．６ｇ、炭酸セシウム５９ｇ、ＮＭＰ１０５ｍＬをオートクレーブ反応装置に加え、氷冷下２８％アンモニア水溶液２５ｍＬを加えた。密封後、１１０℃まで昇温し、１２時間加熱撹拌した。室温まで氷冷後、反応混合物を水で希釈し、酢酸エチルで抽出した。合わせた有機層を硫酸ナトリウムで乾燥させた後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、５−トリフルオロメチル−ピリジン−２，３−ジアミン１５ｇを得た。
５−トリフルオロメチル−ピリジン−２，３−ジアミン

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：７．９３（１Ｈ，ｄ），７．０４（１Ｈ，ｄ），４．７１（２Ｈ，ｂｒｓ），３．４６（２Ｈ，ｂｒｓ）．
製造例５９−３
２−フルオロー４−トリフルオロメチルベンズアルデヒド１５．１ｇおよびDMF６１ｍｌの混合物に、氷冷下ナトリウムエタンチオラート（９０％）７．３５ｇを加え、室温で６時間攪拌した。反応混合物を水に注加し、酢酸エチルで抽出した。合わせた有機層を硫酸マグネシウムで乾燥させた後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、２−ホルミル−５−トリフルオロメチルフェニルエチルスルフィド１１．８ｇを得た。
２−ホルミル−５−トリフルオロメチルフェニルエチルスルフィド

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：１０．４１（１Ｈ，ｓ），７．９４（１Ｈ，ｄ），７．６３（１Ｈ，ｓ），７．５３（１Ｈ，ｄ），３．０４（２Ｈ，ｑ），１．４１（３Ｈ，ｔ）．
製造例５９−４
５−トリフルオロメチル−ピリジン−２，３−ジアミン８．６ｇ、２−ホルミル−５−トリフルオロメチルフェニルエチルスルフィド１１ｇ、およびＤＭＦ６７ｍＬの混合物に、室温下にて亜硫酸水素ナトリウム６．１ｇを加えた。１００℃にて３時間加熱撹拌した後、塩化銅（ＩＩ）二水和物１ｇを加え、さらに１００℃にて１時間加熱攪拌した。室温まで放冷後、この反応混合物を水に加え、酢酸エチル抽出した。合わせた有機層を硫酸ナトリウムで乾燥し、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、黄色い粉末固体を得た。これを熱ヘキサンで洗浄することで２−（２−エチルスルファニル−４−トリフルオロメチル−フェニル）−６−トリフルオロメチル−３Ｈ−イミダゾ［４，５−ｂ］ピリジン（以下、本縮合複素環化合物５９と記す。）１２ｇを得た。
本縮合複素環化合物５９

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：１２．７９（１Ｈ，ｂｒｓ），８．７２（１Ｈ，ｂｒｓ），８．４９−８．３４（２Ｈ，ｍ），７．７９（１Ｈ，ｓ），７．６４（１Ｈ，ｄ），３．００（２Ｈ，ｑ），１．３１（３Ｈ，ｔ）． Production Example 59-1
To a mixture of 65 g of 5-trifluoromethyl-pyridin-2-ylamine and 100 mL of chloroform, 71 g of N-bromosuccinimide was added in 5 portions under cooling with ice water. After heating up to room temperature and stirring for 1 hour, it heated to 80 degreeC and heated and stirred for 30 minutes. After allowing to cool to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium bicarbonate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine.
3-Bromo-5-trifluoromethyl-pyridin-2-ylamine

¹ H-NMR (CDCl ₃ ) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).
Production Example 59-2
3-Bromo-5-trifluoromethyl-pyridin-2-ylamine 40 g, acetylacetone copper (II) 2.2 g, acetylacetone 6.6 g, cesium carbonate 59 g, and NMP 105 mL were added to an autoclave reactor, and 28% aqueous ammonia solution was cooled with ice. 25 mL was added. After sealing, the temperature was raised to 110 ° C. and heated and stirred for 12 hours. After cooling to room temperature with ice, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 15 g of 5-trifluoromethyl-pyridine-2,3-diamine.
5-Trifluoromethyl-pyridine-2,3-diamine

¹ H-NMR (CDCl ₃ ) δ: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs).
Production Example 59-3
7.35 g of sodium ethanethiolate (90%) was added to a mixture of 15.1 g of 2-fluoro-4-trifluoromethylbenzaldehyde and 61 ml of DMF, and the mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 11.8 g of 2-formyl-5-trifluoromethylphenylethyl sulfide.
2-Formyl-5-trifluoromethylphenyl ethyl sulfide

¹ H-NMR (CDCl ₃ ) δ: 10.41 (1H, s), 7.94 (1H, d), 7.63 (1H, s), 7.53 (1H, d), 3.04 ( 2H, q), 1.41 (3H, t).
Production Example 59-4
To a mixture of 8.6 g of 5-trifluoromethyl-pyridine-2,3-diamine, 11 g of 2-formyl-5-trifluoromethylphenylethyl sulfide, and 67 mL of DMF, 6.1 g of sodium bisulfite was added at room temperature. . After heating and stirring at 100 ° C. for 3 hours, 1 g of copper (II) chloride dihydrate was added, and the mixture was further heated and stirred at 100 ° C. for 1 hour. After cooling to room temperature, the reaction mixture was added to water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain a yellow powdered solid. This was washed with hot hexane to give 2- (2-ethylsulfanyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic ring). This is referred to as compound 59.) 12 g were obtained.
This condensed heterocyclic compound 59

¹ H-NMR (CDCl ₃ ) δ: 12.79 (1H, brs), 8.72 (1H, brs), 8.49-8.34 (2H, m), 7.79 (1H, s), 7.64 (1H, d), 3.00 (2H, q), 1.31 (3H, t).

¹Ｈ−ＮＭＲ（ＤＭＳＯ−Ｄ_６）δ：１４．１５（１Ｈ，ｂｒｓ），８．８３（１Ｈ，ｓ），８．５８（１Ｈ，ｓ），８．４１（１Ｈ，ｄ），８．３７（１Ｈ，ｓ），８．１９（１Ｈ，ｄ），３．９７（２Ｈ，ｑ），１．２３（３Ｈ，ｔ）． Production Example 60
To a mixture of 12 g of 2- (2-ethylsulfanyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 111 mL of chloroform was added 69 to 75% 3 under ice cooling. -8.0 g of chloroperbenzoic acid was added. The mixture was warmed to room temperature and stirred for 0.5 hour, and then a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (2-ethylsulfonyl-4-trifluoromethyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed complex). 9.1 g was obtained.
The present condensed heterocyclic compound 60

¹ H-NMR (DMSO-D ₆ ) δ: 14.15 (1H, brs), 8.83 (1H, s), 8.58 (1H, s), 8.41 (1H, d), 8. 37 (1H, s), 8.19 (1H, d), 3.97 (2H, q), 1.23 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．６７（１Ｈ，ｄ），８．５１−８．４８（１Ｈ，ｍ），８．３３（１Ｈ，ｄ），７．６６−７．６１（１Ｈ，ｍ），７．５１−７．４６（２Ｈ，ｍ），２．９３（２Ｈ，ｑ），１．２７（３Ｈ，ｔ） Production Example 61
A mixture of 200 mg of N- (2-amino-5-trifluoromethylpyridin-3-yl) -2-ethylsulfanyl-benzamide, 1 ml of tert-butyl alcohol and 9 ml of THF was heated and stirred at 80 ° C., and 60% 56 mg of sodium hydride (oily) was added. The mixture was heated and stirred at 80 ° C. for 2 hours, and 56 mg of 60% sodium hydride (oily) was added. Furthermore, after stirring with heating at the same temperature for 2 hours, 56 mg of 60% sodium hydride (oily) was added, and the mixture was heated with stirring at the same temperature for 2 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 61 and 132 mg was obtained.
The present condensed heterocyclic compound 61

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.51-8.48 (1H, m), 8.33 (1H, d), 7.66-7.61 (1H M), 7.51-7.46 (2H, m), 2.93 (2H, q), 1.27 (3H, t)

¹Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．６３（１Ｈ，ｓ），８．３５（１Ｈ，ｓ），８．２４（１Ｈ，ｄ），８．０９（１Ｈ，ｄ），７．８３（１Ｈ，ｔ），７．７６（１Ｈ，ｔ），３．３３（２Ｈ，ｑ），０．８８（３Ｈ，ｔ）． Production Example 62
To a mixture of 2.28 g of 2- (2-ethylsulfanylphenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 20 ml of chloroform was added 69-75% 3-chloroperbenzoic acid under ice cooling. 8.0 g of acid was added. The mixture was warmed to room temperature and stirred for 0.5 hour, and then a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resulting crystals were washed with hexane to give 2- (2-ethylsulfonyl-phenyl) -6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. (Hereinafter referred to as the present condensed heterocyclic compound 62.) 2.5 g was obtained.
The present condensed heterocyclic compound 62

¹ H-NMR (CDCl ₃ ) δ: 8.63 (1H, s), 8.35 (1H, s), 8.24 (1H, d), 8.09 (1H, d), 7.83 ( 1H, t), 7.76 (1H, t), 3.33 (2H, q), 0.88 (3H, t).

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７８−８．７６（１Ｈ，ｍ），８．３３−８．３１（１Ｈ，ｍ），８．１４−８．１２（１Ｈ，ｍ），７．６８（１Ｈ，ｄ），７．５４−７．５０（１Ｈ，ｍ），３．９３（３Ｈ，ｓ），３．４９−３．３９（１Ｈ，ｍ），３．０６−２．９６（１Ｈ，ｍ），１．３３（３Ｈ，ｔ）．
本縮合複素環化合物６４

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７７−８．７５（１Ｈ，ｍ），８．３０−８．２８（１Ｈ，ｍ），８．０９−８．０７（１Ｈ，ｍ），７．７０−７．６６（１Ｈ，ｍ），７．６３（１Ｈ，ｄ），３．７４（３Ｈ，ｓ），３．４６（２Ｈ，ｑ），１．２８（３Ｈ，ｔ）．
製造例６５
２−（２−エチルスルフィニル−４−トリフルオロメトキシフェニル）−３−メチル−６−トリフルオロメチル−３Ｈ−イミダゾ［４，５−ｂ］ピリジン０．３４ｇ、塩化ジルコニウム０．３６ｇ、ヨウ化ナトリウム０．４７ｇおよびアセトニトリル８ｍｌの混合物を２時間、加熱還流下撹拌した。室温まで冷却した後、反応混合物に、飽和炭酸水素ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を硫酸マグネシウムで乾燥させた後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、２−（２−エチルスルファニル−４−トリフルオロメトキシフェニル）−３−メチル−６−トリフルオロメチル−３Ｈ−イミダゾ［４，５−ｂ］ピリジン（以下、本縮合複素環化合物６５と記す。）０．２９ｇを得た。
本縮合複素環化合物６５

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃）δ：８．７４−８．７２（１Ｈ，ｍ），８．３３−８．３２（１Ｈ，ｍ），７．４８（１Ｈ，ｄ），７．２９−７．２７（１Ｈ， ｍ），７．２１−７．１７（１Ｈ，ｍ），３．７９（３Ｈ，ｓ），２．９２（２Ｈ，ｑ），１．２９（３Ｈ，ｔ）． Production Examples 63 and 64
To a mixture of 0.31 g of ethyl mercaptan sodium salt (80%) and 9 ml of DMF was added ice-cooled 2- (2-fluoro-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [ After adding 1.05 g of 4,5-b] pyridine, the mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. And 0.82 g of a mixture (approximately 3: 1) of 2- (2-fluoro-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine It was.
After adding 0.45 g of 3-chloroperbenzoic acid (purity 65% or more) to the mixture obtained and 4 ml of chloroform under ice cooling, the mixture was warmed to room temperature and stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfinyl-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. (Hereinafter referred to as the present condensed heterocyclic compound 63.) 0.47 g, 2- (2-ethanesulfonyl-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5 -B] 0.14 g of pyridine (hereinafter referred to as the present condensed heterocyclic compound 64) was obtained.
The present condensed heterocyclic compound 63

¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.33-8.31 (1H, m), 8.14-8.12 (1H, m), 7 .68 (1H, d), 7.54-7.50 (1H, m), 3.93 (3H, s), 3.49-3.39 (1H, m), 3.06-2.96 (1H, m), 1.33 (3H, t).
The present condensed heterocyclic compound 64

¹ H-NMR (CDCl ₃ ) δ: 8.77-8.75 (1H, m), 8.30-8.28 (1H, m), 8.09-8.07 (1H, m), 7 .70-7.66 (1H, m), 7.63 (1H, d), 3.74 (3H, s), 3.46 (2H, q), 1.28 (3H, t).
Production Example 65
2- (2-Ethylsulfinyl-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine 0.34 g, zirconium chloride 0.36 g, sodium iodide A mixture of 0.47 g and 8 ml of acetonitrile was stirred with heating under reflux for 2 hours. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfanyl-4-trifluoromethoxyphenyl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. (Hereinafter referred to as the present condensed heterocyclic compound 65.) 0.29 g was obtained.
This condensed heterocyclic compound 65

¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.33-8.32 (1H, m), 7.48 (1H, d), 7.29-7 .27 (1H, m), 7.21-7.17 (1H, m), 3.79 (3H, s), 2.92 (2H, q), 1.29 (3H, t).

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：９．３３（１Ｈ，ｂｒｓ），８．８７（１Ｈ，ｓ），８．０３（１Ｈ，ｄ），７．７５（１Ｈ，ｓ），７．６２（１Ｈ，ｄ），７．５７（１Ｈ，ｓ），７．４４（１Ｈ，ｄ），７．１４（１Ｈ，ｄ），３．０５（２Ｈ，ｑ），１．３６（３Ｈ，ｔ）
製造例６６−２
２−エチルスルファニル−４−トリフルオロメチル−Ｎ−［２−ヒドロキシ−５−トリフルオロメチルフェニル］ベンズアミド０．５６ｇ、ジ−２−メトキシエチルアゾジカルボキシレート（以下、ＤＭＥＡＤと記す）０．４０ｇ、トリフェニルホスフィン０．３９ｇ及びＴＨＦ１５ｍｌの混合物を、室温で３０分間及び５０℃で１時間攪拌した。室温まで放冷した反応混合物を減圧下濃縮した後に水を注加し、酢酸エチルで抽出した。有機層を飽和塩水で水洗した後、無水硫酸ナトリウムで乾燥し、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、２−（２−エチルスルファニル−４−トリフルオロメチルフェニル）−５−トリフルオロメチルベンズオキサゾール０．５２ｇを得た。
２−（２−エチルスルファニル−４−トリフルオロメチルフェニル）−５−トリフルオロメチルベンズオキサゾール

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．２９（１Ｈ，ｄ），８．１９（１Ｈ，ｄ），７．７５−７．６６（２Ｈ，ｍ），７．６３（１Ｈ，ｓ），７．５１（１Ｈ，ｄｄ），３．１０（２Ｈ，ｑ），１．４７（３Ｈ，ｔ）．
製造例６６−３
２−（２−エチルスルファニル−４−トリフルオロメチルフェニル）−５−トリフルオロメチルベンズオキサゾール０．３５ｇ及びクロロホルム１０ｍｌの混合物に、氷冷下、ｍ−クロロ過安息香酸（純度６５％以上）０．４６ｇを添加した後、室温で１時間半撹拌した。反応混合物に１０％亜硫酸ナトリウム水溶液を加え、クロロホルムで抽出した。有機層を飽和炭酸水素ナトリウム水溶液で洗浄した後、無水硫酸ナトリウムで乾燥し、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、２−（２−エチルスルホニル−４−トリフルオロメチルフェニル）−５−トリフルオロメチルベンズオキサゾール（以下、本縮合複素環化合物１３０と記す。）０．３４ｇを得た。
本縮合複素環化合物１３０

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．５４（１Ｈ，ｓ），８．１８−８．１２（２Ｈ，ｍ），８．０８（１Ｈ，ｄｄ），７．７７−７．７４（２Ｈ，ｍ），３．９０（２Ｈ，ｑ），１．４４（３Ｈ，ｔ）． Production Example 66-1
A mixture of 0.50 g of 2-amino-4-trifluoromethylphenol, 0.71 g of 2-ethylsulfanyl-4-trifluoromethylbenzoic acid, 0.65 g of WSC and 6 ml of chloroform was stirred at room temperature for 3.5 hours. Saturated aqueous ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.57 g of 2-ethylsulfanyl-4-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylphenyl] benzamide.
2-Ethylsulfanyl-4-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylphenyl] benzamide

¹ H-NMR (CDCl ₃ ) δ: 9.33 (1H, brs), 8.87 (1H, s), 8.03 (1H, d), 7.75 (1H, s), 7.62 ( 1H, d), 7.57 (1H, s), 7.44 (1H, d), 7.14 (1H, d), 3.05 (2H, q), 1.36 (3H, t)
Production Example 66-2
2-ethylsulfanyl-4-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylphenyl] benzamide 0.56 g, di-2-methoxyethyl azodicarboxylate (hereinafter referred to as DMEAD) 0.40 g A mixture of 0.39 g of triphenylphosphine and 15 ml of THF was stirred at room temperature for 30 minutes and at 50 ° C. for 1 hour. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.52 g of 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -5-trifluoromethylbenzoxazole.
2- (2-Ethylsulfanyl-4-trifluoromethylphenyl) -5-trifluoromethylbenzoxazole

¹ H-NMR (CDCl ₃ ) δ: 8.29 (1H, d), 8.19 (1H, d), 7.75-7.66 (2H, m), 7.63 (1H, s), 7.51 (1H, dd), 3.10 (2H, q), 1.47 (3H, t).
Production Example 66-3
To a mixture of 2- (2-ethylsulfanyl-4-trifluoromethylphenyl) -5-trifluoromethylbenzoxazole 0.35 g and chloroform 10 ml, m-chloroperbenzoic acid (purity 65% or more) 0 After adding .46 g, the mixture was stirred at room temperature for 1.5 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (2-ethylsulfonyl-4-trifluoromethylphenyl) -5-trifluoromethylbenzoxazole (hereinafter referred to as the present condensed heterocyclic compound 130). .34 g was obtained.
The present condensed heterocyclic compound 130

¹ H-NMR (CDCl ₃ ) δ: 8.54 (1H, s), 8.18-8.12 (2H, m), 8.08 (1H, dd), 7.77-7.74 (2H M), 3.90 (2H, q), 1.44 (3H, t).

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：９．８９（１Ｈ，ｓ），９．７１（１Ｈ，ｓ），８．０５（１Ｈ，ｄｄ），７．５８（１Ｈ，ｄｄ），７．５１（１Ｈ，ｄｄｄ），７．４８−７．４１（３Ｈ，ｍ），７．１２（１Ｈ，ｄ），２．９９（２Ｈ，ｑ），１．３１（３Ｈ，ｔ）．
製造例６７−２
２−エチルスルファニル−Ｎ−［２−ヒドロキシ−５−（トリフルオロメチルスルファニル）フェニル］ベンズアミド１．７８ｇ、ＤＭＥＡＤ１．７９ｇ、トリフェニルホスフィン１．８８ｇ及びＴＨＦ２０ｍｌの混合物を、室温で３０分間及び５０℃で１時間攪拌した。室温まで放冷した反応混合物を減圧下濃縮した後に水を注加し、酢酸エチルで抽出した。有機層を飽和塩水で水洗した後、無水硫酸ナトリウムで乾燥し、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、２−（２−エチルスルファニルフェニル）−５−（トリフルオロメチルスルファニル）ベンズオキサゾール１．３３ｇを得た。
２−（２−エチルスルファニルフェニル）−５−（トリフルオロメチルスルファニル）ベンズオキサゾール

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．２１（１Ｈ，ｄ），８．１７（１Ｈ，ｄｄ），７．６７（１Ｈ，ｄｄ），７．６４（１Ｈ，ｄ），７．５２−７．４６（１Ｈ，ｍ），７．４３（１Ｈ，ｄｄ），７．３１−７．２７（１Ｈ，ｍ），３．０７（２Ｈ，ｑ），１．４５（３Ｈ，ｔ）．
製造例６７−３
２−（２−エチルスルファニルフェニル）−５−（トリフルオロメチルスルファニル）ベンズオキサゾール１．１５ｇ及びクロロホルム２５ｍｌの混合物に、氷冷下、ｍ−クロロ過安息香酸（純度６５％以上）２．０４ｇを添加した後、室温で１日間半撹拌した。反応混合物に１０％亜硫酸ナトリウム水溶液を加え、クロロホルムで抽出した。有機層を飽和炭酸水素ナトリウム水溶液で洗浄した後、無水硫酸ナトリウムで乾燥し、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、２−（２−エチルスルホニルフェニル）−５−（トリフルオロメチルスルファニル）ベンズオキサゾール０．３８ｇ及び２−（２−エチルスルホニルフェニル）−５−（トリフルオロメチルスルフィニル）ベンズオキサゾール（以下、本縮合複素環化合物１３１と記す。）０．５５ｇを得た。
２−（２−エチルスルホニルフェニル）−５−（トリフルオロメチルスルファニル）ベンズオキサゾール

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．２８−８．２４（１Ｈ，ｍ），８．１６−８．１３（１Ｈ，ｍ），７．９９−７．９５（１Ｈ，ｍ），７．８５−７．７６（２Ｈ，ｍ），７．７３（１Ｈ，ｄｄ），７．６６（１Ｈ，ｄ），３．８３（２Ｈ，ｑ），１．４０（３Ｈ，ｔ）．
本縮合複素環化合物１３１

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：８．３０−８．２５（２Ｈ，ｍ），８．０１−７．９７（１Ｈ，ｍ），７．８７−７．７９（４Ｈ，ｍ），３．８２（２Ｈ，ｑ），１．４１（３Ｈ，ｔ）． Production Example 67-1
To a mixture of 1.2 g of 2-ethylsulfanylbenzoic acid, 10 ml of chloroform and 0.1 ml of DMF, 1.1 ml of oxalyl chloride was added and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and 10 ml of THF was added to the reaction mixture. This was added to a mixture of 1.38 g of 2-amino-4- (trifluoromethylsulfanyl) phenol and 15 ml of THF under ice cooling, and stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl). 1.78 g of phenyl] benzamide were obtained.
2-Ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] benzamide

¹ H-NMR (CDCl ₃ ) δ: 9.89 (1H, s), 9.71 (1H, s), 8.05 (1H, dd), 7.58 (1H, dd), 7.51 ( 1H, ddd), 7.48-7.41 (3H, m), 7.12 (1H, d), 2.99 (2H, q), 1.31 (3H, t).
Production Example 67-2
A mixture of 1.78 g of 2-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] benzamide, 1.79 g of DMEAD, 1.88 g of triphenylphosphine and 20 ml of THF is stirred for 30 minutes at room temperature and For 1 hour. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.33 g of 2- (2-ethylsulfanylphenyl) -5- (trifluoromethylsulfanyl) benzoxazole.
2- (2-Ethylsulfanylphenyl) -5- (trifluoromethylsulfanyl) benzoxazole

¹ H-NMR (CDCl ₃ ) δ: 8.21 (1H, d), 8.17 (1H, dd), 7.67 (1H, dd), 7.64 (1H, d), 7.52- 7.46 (1H, m), 7.43 (1H, dd), 7.31-7.27 (1H, m), 3.07 (2H, q), 1.45 (3H, t).
Production Example 67-3
To a mixture of 1.15 g of 2- (2-ethylsulfanylphenyl) -5- (trifluoromethylsulfanyl) benzoxazole and 25 ml of chloroform, 2.04 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling. After the addition, the mixture was stirred at room temperature for one and a half days. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 0.38 g of 2- (2-ethylsulfonylphenyl) -5- (trifluoromethylsulfanyl) benzoxazole and 2- (2-ethylsulfonylphenyl) -5- ( 0.55 g of trifluoromethylsulfinyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic compound 131) was obtained.
2- (2-Ethylsulfonylphenyl) -5- (trifluoromethylsulfanyl) benzoxazole

¹ H-NMR (CDCl ₃ ) δ: 8.28-8.24 (1H, m), 8.16-8.13 (1H, m), 7.9-7.95 (1H, m), 7 .85-7.76 (2H, m), 7.73 (1H, dd), 7.66 (1H, d), 3.83 (2H, q), 1.40 (3H, t).
This condensed heterocyclic compound 131

¹ H-NMR (CDCl ₃ ) δ: 8.30-8.25 (2H, m), 8.01-7.97 (1H, m), 7.87-7.79 (4H, m), 3 .82 (2H, q), 1.41 (3H, t).

Hereinafter, ¹ H-NMR data of the present condensed heterocyclic compounds shown in Table 1 are shown.
The present condensed heterocyclic compound 66
¹ H-NMR (CDCl ₃ ) δ: 8.51 (1H, s), 8.22 (1H, s), 7.55-7.50 (2H, m), 7.47-7.43 (1H M), 7.38-7.32 (1H, m), 5.81 (1H, dq), 3.76 (3H, s), 2.88 (2H, q), 1.24 (3H, t).
The present condensed heterocyclic compound 67
¹ H-NMR (CDCl ₃ ) δ: 8.55 (1H, d), 8.26 (1H, d), 8.21 (1H, d), 7.83 (1H, t), 7.69 ( 1H, t), 7.60 (1H, d), 5.84 (1H, dq), 3.88 (3H, s), 3.42-3.30 (1H, m), 3.03-2 .91 (1H, m), 1.33-1.25 (3H, m).
This condensed heterocyclic compound 68
¹ H-NMR (CDCl ₃ ) δ: 8.53 (1H, s), 8.26-8.16 (2H, m), 7.88-7.78 (2H, m), 7.59-7 .53 (1H, m), 5.82 (1H, dq), 3.70 (3H, s), 3.44 (2H, q), 1.26 (3H, t).
This condensed heterocyclic compound 69
¹ H-NMR (CDCl ₃ ) δ: 8.68 (1H, d), 8.29 (1 H, d), 7.74-7.68 (1 H, m), 7.49-7.40 (2H M), 3.73 (3H, s), 2.74 (2H, q), 1.06 (3H, t).
The present condensed heterocyclic compound 70
¹ H-NMR (CDCl ₃ ) δ: 8.64 (1H, s), 8.24 (1H, s), 7.65 (1H, d), 7.58 (1H, t), 7.39 ( 1H, d), 3.72 (3H, s), 3.63-3.47 (1H, m), 3.37-3.22 (1H, m), 1.38-1.30 (3H, m).
The present condensed heterocyclic compound 71
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.33-8.32 (1H, m), 7.52-7.49 (1H, m), 7 .47-7.43 (2H, m), 3.79 (3H, s), 2.85 (2H, q), 1.23 (3H, t).
The present condensed heterocyclic compound 72
¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.33-8.31 (1H, m), 8.20 (1H, d), 7.81-7 .78 (1H, m), 7.60 (1H, d), 3.93 (3H, s), 3.42-3.32 (1H, m), 3.02-2.92 (1H, m ), 1.31 (3H, t).
This condensed heterocyclic compound 73
¹ H-NMR (CDCl ₃ ) δ: 8.76-8.75 (1H, m), 8.29-8.28 (1H, m), 8.16 (1H, d), 7.80-7 .77 (1H, m), 7.57 (1H, d), 3.75 (3H, s), 3.40 (2H, q), 1.26 (3H, t).
The present condensed heterocyclic compound 74
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.33-8.31 (1H, m), 7.51-7.45 (1H, m), 7 .36-7.31 (2H, m), 3.75 (3H, s), 2.78 (2H, q), 1.10 (3H, t).
This condensed heterocyclic compound 75
¹ H-NMR (CDCl ₃ ) δ: 8.73-8.71 (1H, m), 8.29-8.27 (1H, m), 7.70-7.64 (1H, m), 7 .44-7.38 (1H, m), 7.33 (1H, d), 3.81 (3H, s), 3.53-3.43 (1H, m), 3.42-3.31 (1H, m), 1.33 (3H, t).
The present condensed heterocyclic compound 76
¹ H-NMR (CDCl ₃ ) δ: 8.73-8.72 (1H, m), 8.28-8.26 (1H, m), 7.84-7.78 (1H, m), 7 .55-7.49 (1H, m), 7.38-7.35 (1H, m), 3.77 (3H, s), 3.50-3.34 (2H, m), 1.34 (3H, t).
This condensed heterocyclic compound 77
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.37-8.35 (1H, m), 7.54-7.48 (1H, m), 7 .27-7.24 (1H, m), 7.09-7.03 (1H, m), 3.77 (3H, d), 2.93 (2H, q), 1.28 (3H, t ).
The present condensed heterocyclic compound 78
¹ H-NMR (CDCl ₃ ) δ: 8.79-8.76 (1H, m), 8.35-8.32 (1H, m), 8.03 (1H, d), 7.87-7 .80 (1H, m), 7.43 (1H, t), 3.84 (3H, d), 3.51-3.40 (1H, m), 3.13-3.02 (1H, m ), 1.33 (3H, t).
This condensed heterocyclic compound 79
¹ H-NMR (CDCl ₃ ) δ: 8.77-8.75 (1H, m), 8.32-8.30 (1H, m), 8.07-8.04 (1H, m), 7 .86-7.80 (1H, m), 7.62-7.57 (1H, m), 3.76 (3H, s), 3.69-3.58 (1H, m), 3.41 -3.31 (1H, m), 1.29 (3H, t).
This condensed heterocyclic compound 80
¹ H-NMR (CDCl ₃ ) δ: 8.71-8.69 (1H, m), 8.31-8.30 (1H, m), 7.35-7.31 (2H, m), 7 19-7.15 (1H, m), 3.76 (3H, s), 2.85 (2H, q), 2.46 (3H, s), 1.22 (3H, t).
This condensed heterocyclic compound 81
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.73 (1H, m), 8.30-8.28 (1H, m), 8.06-8.05 (1H, m), 7 .49-7.48 (2H, m), 3.88 (3H, s), 3.42-3.32 (1H, m), 3.00-2.90 (1H, m), 2.58 (3H, s), 1.32 (3H, t).
This condensed heterocyclic compound 82
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.27-8.26 (1H, m), 8.03-8.02 (1H, m), 7 .64-7.61 (1H, m), 7.44 (1H, d), 3.70 (3H, s), 3.41 (2H, q), 2.59 (3H, s), 1. 26 (3H, t).
This condensed heterocyclic compound 83
¹ H-NMR (CDCl ₃ ) δ: 8.75-8.74 (1H, m), 8.35-8.34 (1H, m), 7.66-7.65 (1H, m), 7 .61-7.55 (2H, m), 3.80 (3H, s), 2.95 (2H, q), 1.28 (3H, t).
This condensed heterocyclic compound 84
¹ H-NMR (CDCl ₃ ) δ: 8.80-8.78 (1H, m), 8.54-8.53 (1H, m), 8.35-8.34 (1H, m), 7 .95-7.91 (1H, m), 7.79 (1H, d), 3.95 (3H, s), 3.52-3.41 (1H, m), 3.09-2.99 (1H, m), 1.33 (3H, t).
The present condensed heterocyclic compound 85
¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.47-8.46 (1H, m), 8.31-8.30 (1H, m), 8 10-8.07 (1H, m), 7.76 (1H, d), 3.76 (3H, s), 3.48 (2H, q), 1.28 (3H, t).
The present condensed heterocyclic compound 86
¹ H-NMR (CDCl ₃ ) δ: 8.51 (1H, d), 8.19 (1H, d), 7.53-7.42 (3H, m), 7.38-7.29 (1H M), 3.73 (3H, s), 2.97-2.83 (4H, m), 1.33-1.19 (6H, m).
The present condensed heterocyclic compound 87
¹ H-NMR (CDCl ₃ ) δ: 8.96 (1H, d), 8.54 (1H, d), 8.28-8.18 (1H, m), 7.91-7.80 (2H M), 7.63-7.55 (1H, m), 3.74 (3H, s), 3.43 (2H, q), 3.24 (2H, q), 1.38 (3H, t), 1.26 (3H, t).
This condensed heterocyclic compound 88
¹ H-NMR (CDCl ₃ ) δ: 8.53 (1H, d), 8.23 (1H, d), 7.54-7.42 (3H, m), 7.38-7.29 (1H , M), 3.74 (3H, s), 3.33-3.22 (1H, m), 2.87 (2H, q), 1.30 (6H, d), 1.24 (3H, t).
This condensed heterocyclic compound 89
¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, d), 8.51 (1H, d), 8.22 (1H, dd), 7.92-7.81 (2H, m), 7.62 (1H, dd), 3.75 (3H, s), 3.43 (2H, q), 3.36-3.26 (1H, m), 1.38 (6H, d), 1 .26 (3H, t).
The present condensed heterocyclic compound 90
¹ H-NMR (CDCl ₃ ) δ: 8.69-8.68 (1H, m), 8.33-8.31 (1H, m), 7.70-7.68 (1H, m), 7 .62-7.55 (2H, m), 3.79 (3H, s), 2.97 (2H, q), 1.29 (3H, t).
The present condensed heterocyclic compound 91
¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, d), 8.52 (1H, d), 8.25 (1H, d), 7.78 (1H, dd), 7.67 ( 1H, d), 3.76 (2H, q), 1.40 (3H, t).
This condensed heterocyclic compound 92
¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, d), 8.56 (1H, d), 7.56-7.42 (3H, m), 7.39-7.33 (1H M), 3.77 (3H, s), 2.89 (2H, q), 1.25 (3H, t).
This condensed heterocyclic compound 93
¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, d), 8.53 (1H, d), 8.26 (1H, dd), 7.84 (1H, td), 7.71 ( 1H, td), 7.60 (1H, dd), 3.89 (3H, s), 3.42-3.32 (1H, m), 3.05-2.96 (1H, m), 1 .31 (3H, t).
This condensed heterocyclic compound 94
¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, d), 8.50 (1H, d), 8.23 (1H, dd), 7.87-7.80 (2H, m), 7.56 (1H, dd), 3.71 (3H, s), 3.45 (2H, q), 1.26 (3H, t).
This condensed heterocyclic compound 95
¹ H-NMR (CDCl ₃ ) δ: 8.72-8.70 (1H, m), 8.51-8.49 (1H, m), 8.29-8.27 (1H, m), 8 .13-8.09 (1H, m), 7.74-7.71 (1H, m), 3.74 (3H, s), 3.49 (2H, q), 1.29 (3H, t ).
The present condensed heterocyclic compound 96
¹ H-NMR (CDCl ₃ ) δ: 8.09 (1H, s), 7.59-7.42 (5H, m), 7.37-7.31 (1H, m), 3.69 (3H , S), 2.85 (2H, q), 1.23 (3H, t).
This condensed heterocyclic compound 97
¹ H-NMR (CDCl ₃ ) δ: 8.22 (1H, d), 8.07 (1H, s), 7.80 (1H, t), 7.67 (1H, t), 7.62- 7.52 (3H, m), 3.79 (3H, s), 3.37-3.26 (1H, m), 3.01-2.89 (1H, m), 1.27 (3H, t).
This condensed heterocyclic compound 98
¹ H-NMR (CDCl ₃ ) δ: 8.20-8.18 (1H, m), 8.06 (1H, s), 7.82-7.74 (2H, m), 7.59-7 .52 (3H, m), 3.61 (3H, s), 3.43 (2H, brs), 1.22 (3H, t).
This condensed heterocyclic compound 99
¹ H-NMR (CDCl ₃ ) δ: 8.65-8.64 (1H, m), 8.29-8.28 (1H, m), 7.35-7.31 (2H, m), 7 18-7.15 (1H, m), 3.76 (3H, s), 2.86 (2H, q), 2.46 (3H, s), 1.23 (3H, t).
The present condensed heterocyclic compound 100
¹ H-NMR (CDCl ₃ ) δ: 8.69-8.68 (1H, m), 8.28-8.26 (1H, m), 8.07-8.05 (1H, m), 7 .50-7.48 (2H, m), 3.89 (3H, s), 3.44-3.33 (1H, m), 3.01-2.92 (1H, m), 2.58 (3H, s), 1.32 (3H, t).
This condensed heterocyclic compound 101
¹ H-NMR (CDCl ₃ ) δ: 8.68-8.66 (1H, m), 8.25-8.23 (1H, m), 8.04-8.02 (1H, m), 7 .65-7.61 (1H, m), 7.45-7.42 (1H, m), 3.71 (3H, s), 3.47-3.38 (2H, m), 2.59 (3H, s), 1.26 (3H, t).
The present condensed heterocyclic compound 102
¹ H-NMR (CDCl ₃ ) δ: 8.81 (1H, d), 8.55 (1H, d), 8.07-8.00 (1H, m), 7.59-7.53 (1H M), 7.52-7.45 (1H, m), 7.41-7.33 (1H, m), 2.99 (2H, q), 1.35 (3H, t).
This condensed heterocyclic compound 103
¹ H-NMR (CDCl ₃ ) δ: 8.85 (1H, d), 8.59 (1H, d), 8.15 (1H, d), 7.75 (1H, s), 7.59 ( 1H, d), 3.05 (2H, q), 1.38 (3H, t).
The condensed heterocyclic compound 104
¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, d), 8.50 (1H, d), 8.28-8.22 (1H, m), 7.85-7.76 (2H M), 7.74-7.70 (1H, m), 3.74 (2H, q), 1.37 (3H, t).
The present condensed heterocyclic compound 105
¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, s), 8.57-8.49 (2H, m), 8.07 (1H, d), 7.88 (1H, d), 3.77 (2H, q), 1.40 (3H, t).
This condensed heterocyclic compound 106
¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, d), 8.61 (1H, d), 7.45-7.34 (3H, m), 2.91 (2H, q), 1.27 (3H, t).
The present condensed heterocyclic compound 107
¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 7.86 (1H, dd), 7.73 ( 1H, t), 3.40 (2H, q), 1.28 (3H, t).
The present condensed heterocyclic compound 108
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.28-8.26 (1H, m), 8.05-8.03 (1H, m), 7 .67-7.64 (1H, m), 7.46 (1H, d), 3.71 (3H, s), 3.41 (2H, q), 2.88 (2H, q), 1. 37 (3H, t), 1.26 (3H, t).
The present condensed heterocyclic compound 109
¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.46-8.44 (1H, m), 8.31-8.30 (1H, m), 8 .09-8.05 (1H, m), 7.76 (1H, d), 3.75 (3H, s), 3.48 (2H, q), 1.27 (3H, t).
The present condensed heterocyclic compound 110
¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, s), 8.33 (1H, s), 8.25 (1H, dd), 8.21 (1H, dd), 7.73- 7.58 (2H, m), 3.47-3.36 (1H, m), 3.13-3.01 (1H, m), 1.57-0.71 (3H, m).
This condensed heterocyclic compound 111
¹ H-NMR (CDCl ₃ ) δ: 8.76 (1H, d), 8.51 (1H, d), 8.29 (1H, d), 8.10 (1H, dd), 7.74 ( 1H, d), 4.22 (2H, q), 3.55 (2H, q), 1.42 (3H, t), 1.30 (3H, t).
This condensed heterocyclic compound 112
¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, s), 7.67 (1H, s), 7.62 (1H, d), 7.59-7.57 (2H, m), 7.52 (1H, d), 3.70 (3H, s), 2.92 (2H, q), 1.27 (3H, t).
This condensed heterocyclic compound 113
¹ H-NMR (CDCl ₃ ) δ: 8.53 (1H, s), 8.10 (1H, s), 7.93 (1H, d), 7.75 (1H, d), 7.65 ( 1H, d), 7.57 (1H, d), 3.85 (3H, s), 3.52-3.41 (1H, m), 3.05-2.95 (1H, m), 1 .32 (3H, t).
This condensed heterocyclic compound 114
¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, s), 8.10-8.05 (2H, m), 7.74 (1H, d), 7.62 (1H, d), 7.53 (1H, d), 3.63 (3H, s), 3.47 (2H, q), 1.25 (3H, t).
This condensed heterocyclic compound 115
¹ H-NMR (CDCl ₃ ) δ: 8.83-8.74 (3H, m), 8.54 (1H, dd), 8.31-8.29 (1H, m), 7.95-7 .86 (2H, m), 7.68 (1H, d), 7.41-7.37 (1H, m), 3.75 (3H, s), 3.49 (2H, q), 1. 30 (3H, t).
The present condensed heterocyclic compound 116
¹ H-NMR (CDCl ₃ ) δ: 8.74-8.72 (1H, m), 8.28-8.25 (1H, m), 8.07-8.05 (1H, m), 7 .69-7.66 (1H, m), 7.47 (1H, d), 3.72 (3H, s), 3.41 (2H, q), 3.18-3.10 (1H, m ), 1.37 (6H, d), 1.26 (3H, t).
The present condensed heterocyclic compound 117
¹ H-NMR (CDCl ₃ ) δ: 8.77-8.75 (1H, m), 8.38-8.36 (1H, m), 8.31-8.29 (1H, m), 8 .02-7.99 (1H, m), 7.69 (1H, d), 6.85 (1H, t), 3.73 (3H, s), 3.54-3.33 (2H, m ), 1.28 (3H, t).
The present condensed heterocyclic compound 118
¹ H-NMR (CDCl ₃ ) δ: 8.68-8.66 (1H, m), 8.31-8.30 (1H, m), 7.48 (1H, d), 7.29-7 .26 (1H, m), 7.21-7.17 (1H, m), 3.80 (3H, s), 2.93 (2H, q), 1.29 (3H, t).
This condensed heterocyclic compound 119
¹ H-NMR (CDCl ₃ ) δ: 8.72-8.71 (1H, m), 8.30-8.29 (1H, m), 8.14-8.12 (1H, m), 7 .68 (1H, d), 7.55-7.51 (1H, m), 3.93 (3H, s), 3.50-3.40 (1H, m), 3.08-2.98 (1H, m), 1.33 (3H, t).
The present condensed heterocyclic compound 120
¹ H-NMR (CDCl ₃ ) δ: 8.71-8.69 (1H, m), 8.27-8.26 (1H, m), 8.09-8.07 (1H, m), 7 .70-7.66 (1H, m), 7.62 (1H, d), 3.74 (3H, s), 3.47 (2H, q), 1.28 (3H, t).
This condensed heterocyclic compound 121
¹ H-NMR (CDCl ₃ ) δ: 8.11 (1H, s), 7.67 (1H, s), 7.61-7.56 (3H, m), 7.53 (1H, d), 3.70 (3H, s), 2.93 (2H, q), 1.28 (3H, t).
The present condensed heterocyclic compound 122
¹ H-NMR (CDCl ₃ ) δ: 8.53 (1H, d), 8.09 (1H, s), 7.93 (1H, dd), 7.74 (1H, d), 7.64 ( 1H, d), 7.59 (1H, d), 3.85 (3H, s), 3.51-3.40 (1H, m), 3.06-2.97 (1H, m), 1 .32 (3H, t).
This condensed heterocyclic compound 123
¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, d), 8.10-8.04 (2H, m), 7.73 (1H, d), 7.60 (1H, d), 7.55 (1H, d), 3.64 (3H, s), 3.47 (2H, q), 1.25 (3H, t).
The condensed heterocyclic compound 124
¹ H-NMR (CDCl ₃ ) δ: 9.06-9.04 (1H, m), 8.87 (1H, d), 8.77-8.75 (1H, m), 8.59 (1H , Dd), 8.31-8.30 (1H, m), 8.14-8.11 (1H, m), 8.07-8.04 (1H, m), 7.72 (1H, d). ), 3.76 (3H, s), 3.51 (2H, q), 1.31 (3H, t).
This condensed heterocyclic compound 125
¹ H-NMR (CDCl ₃ ) δ: 8.67-8.66 (1H, m), 8.40-8.39 (1H, m), 7.47 (1H, d), 7.29-7 .26 (1H, m), 7.21-7.16 (1H, m), 3.78 (3H, s), 2.93 (2H, q), 1.29 (3H, t).
The present condensed heterocyclic compound 126
¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.39 (1H, d), 8.13-8.12 (1H, m), 7.67 (1H, d), 7.54-7.50 (1H, m), 3.91 (3H, s), 3.49-3.39 (1H, m), 3.06-2.96 (1H, m), 1. 33 (3H, t).
The present condensed heterocyclic compound 127
¹ H-NMR (CDCl ₃ ) δ: 8.70 (1H, d), 8.36 (1H, d), 8.09-8.07 (1H, m), 7.70-7.66 (1H M), 7.62 (1H, d), 3.72 (3H, s), 3.46 (2H, q), 1.28 (3H, t).
This condensed heterocyclic compound 128
¹ H-NMR (CDCl ₃ ) δ: 8.53 (1H, s), 8.19-8.13 (2H, m), 8.07 (1H, dd), 7.77 (1H, dd), 7.69 (1H, d), 3.91 (2H, q), 1.44 (3H, t).
The present condensed heterocyclic compound 129
¹ H-NMR (CDCl ₃ ) δ: 8.54 (1H, s), 8.33 (1H, s), 8.17 (1H, d), 8.10 (1H, d), 7.89 ( 2H, s), 3.91 (2H, q), 1.45 (3H, t).

Below, the formulation example of the pest control composition of this invention is shown. In the following formulation examples, the present insecticidal compounds 1 to 119 mean the following.

[Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

[Continuation of Table 2]

尚、上記の構造式において、Ｍｅはメチル基、Ｅｔはエチル基を意味する。 [Continuation of Table 2]

In the above structural formula, Me means a methyl group, and Et means an ethyl group.

Formulation Example 1
5 parts of any one of the present condensed heterocyclic compounds 1 to 131 and 5 parts of the present insecticidal compound 20 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and polyoxyethylene styryl phenyl ether 14 And 6 parts of calcium dodecylbenzenesulfonate are added and mixed to obtain each emulsion.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 10 parts of any one of the condensed heterocyclic compounds 1 to 131 and the insecticidal compound 21 are mixed. Add 10 parts and mix to obtain each wettable powder.

Formulation Example 3
1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 1 part of the present insecticidal compound 22 are added 1 part of a synthetic silicon hydroxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay. Mix. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.

Formulation Example 4
1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 1 part of the present insecticidal compound 23 are dissolved in an appropriate amount of acetone. Add 7 parts, mix well, and evaporate and remove acetone to obtain each powder.

Formulation Example 5
35 parts of a mixture (weight ratio 1: 1) of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon, 5 parts of any one of the present condensed heterocyclic compounds 1 to 131, 5 parts of the present insecticidal compound 24, and water Each flowable agent is obtained by mixing 55 parts and finely pulverizing by a wet pulverization method.

Formulation Example 6
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 1 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 7
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 2 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 8
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 3 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 9
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 4 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 10
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 5 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 11
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 6 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 12
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 7 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 13
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 8 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 14
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 9 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 15
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 10 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 16
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 11 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 17
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 12 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 18
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 13 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 19
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 14 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 20
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 15 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 21
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 16 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 22
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 17 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 23
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 18 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 24
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 19 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 25
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 20 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 26
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 21 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 27
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 22 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 28
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 23 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 29
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 24 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 30
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 25 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 31
0.1 part of any one of the present condensed heterocyclic compounds 1-131 and 0.1 part of the present insecticidal compound 26 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 32
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 27 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 33
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 28 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 34
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 29 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 35
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 30 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 36
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 31 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 37
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 32 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 38
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 33 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 39
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 34 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 40
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 35 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 41
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 36 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 42
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 37 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 43
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 38 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 44
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 39 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 45
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 40 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 46
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 41 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 47
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 42 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 48
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 43 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 49
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 44 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 50
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 45 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 51
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 46 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 52
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 47 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 53
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 48 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 54
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 49 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 55
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 50 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 56
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 51 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 57
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 52 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 58
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 53 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 59
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 54 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 60
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 55 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 61
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 56 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 62
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 57 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 63
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 58 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 64
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 59 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 65
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 60 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 66
0.1 part of any one of the present condensed heterocyclic compounds 1-131 and 0.1 part of the present insecticidal compound 61 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 67
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 62 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 68
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 63 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 69
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 64 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 70
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 65 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 71
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 66 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 72
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 67 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 73
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 68 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 74
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 69 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 75
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 70 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 76
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 71 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 77
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 72 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 78
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 73 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 79
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 74 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 80
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 75 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 81
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 76 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 82
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 77 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 83
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 78 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 84
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 79 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 85
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 80 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 86
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 81 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 87
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 82 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 88
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 83 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 89
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 84 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 90
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 85 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 91
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 86 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 92
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 87 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 93
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 88 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 94
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 89 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 95
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 90 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 96
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 91 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 97
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 92 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 98
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 93 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 99
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 94 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 100
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 95 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 101
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 96 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 102
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 97 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 103
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 98 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 104
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 99 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 105
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 100 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 106
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 101 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 107
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 102 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 108
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 103 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 109
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 104 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 110
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 105 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 111
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 106 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 112
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 107 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 113
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 108 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 114
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 109 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 115
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 110 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 116
0.1 part of any one of the present condensed heterocyclic compounds 1-131 and 0.1 part of the present insecticidal compound 111 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 117
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 112 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 118
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 113 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 119
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 114 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 120
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 115 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 121
0.1 part of any one of the condensed heterocyclic compounds 1 to 131 and 0.1 part of the insecticidal compound 116 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 122
0.1 part of any one of the condensed heterocyclic compounds 1-131 and 0.1 part of the insecticidal compound 117 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 123
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 118 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 124
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 part of the present insecticidal compound 119 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 125
10 mg of any one of the present condensed heterocyclic compounds 1-131 and 10 mg of the present insecticidal compound 36 are dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (solid feed powder CE-2 for breeding, Japan Treat to 5g, and mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 126
0.1 part of any one of the present condensed heterocyclic compounds 1 to 131, 0.1 part of the present insecticidal compound 11 and 49.8 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can and equipped with an aerosol valve. Thereafter, 25 parts of dimethyl ether and 25 parts of LPG are filled, shaken, and an oil aerosol is obtained by mounting the actuator.

Formulation Example 127
0.6 part of any one of the present condensed heterocyclic compounds 1 to 131, 0.6 part of the present insecticidal compound 12, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), xylene 5 parts, 3.33 parts of deodorized kerosene and 1 part of an emulsifier {Atmos 300 (registered trademark name of Atmos Chemical)} and 50 parts of distilled water are filled in an aerosol container, and a valve is attached. Then, 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

Formulation Example 128
A porous ceramic plate having a size of 4.0 × 4.0 cm and a thickness of 1.2 cm is prepared by dissolving 0.1 g of any one of the present condensed heterocyclic compounds 1 to 131 and 0.1 g of the present insecticidal compound 13 in 2 ml of propylene glycol. So as to obtain a heating smoke.

Formulation Example 129
Any one of the present condensed heterocyclic compounds 1-131, 3 parts of the present insecticidal compound 14 and ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, 95 parts by Sumitomo Chemical Co., Ltd. were melt-kneaded with a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product was extruded from an extrusion molding machine through a molding die to form a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm. obtain.

Formulation Example 130
Any one of the condensed heterocyclic compounds 1 to 131, 2 parts, 3 parts of the insecticidal compound 15 and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product Is extruded through a molding die from an extrusion molding machine to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 131
Any one of the condensed heterocyclic compounds 1-131 100 mg, the insecticidal compound 16 100 mg, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg and 2.5 mg of magnesium stearate are mixed and the resulting mixture is compressed to an appropriate size to obtain a tablet.

Formulation Example 132
25 mg of any one of the present condensed heterocyclic compounds 1 to 131, 50 mg of the present insecticidal compound 17, 60 mg of lactose, 25 mg of corn starch, 6 mg of carmellose calcium, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is hard Capsules are obtained by filling shell gelatin capsules or hydroxypropyl methylcellulose capsules.

Formulation Example 133
Any one of the condensed heterocyclic compounds 1-131 1000 mg, the insecticidal compound 18 1000 mg, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, VeegumK ( Vanderbilt Co.) 100 mg, fragrance 35 mg, and colorant 500 mg are added with distilled water to a final volume of 100 ml and mixed to obtain a suspension for oral administration.

Formulation Example 134
2% by weight of any one of the condensed heterocyclic compounds 1-131 and 3% by weight of the insecticidal compound 52 are dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol, and 30% by weight of propylene glycol. After adding a phosphate buffer so that the pH of the solution becomes 6.0 to 6.5, water is added until the final volume is obtained to obtain a solution for oral administration.

Formulation Example 135
5% by weight of aluminum distearate is dispersed by heating in 57% by weight of fractionated coconut oil and 3% by weight of polysorbate 85. This is cooled to room temperature and 25% by weight of saccharin in the oil vehicle is dispersed. To this, 5% by weight of any one of the present condensed heterocyclic compounds 1 to 131 and 5% by weight of the present insecticidal compound 56 are distributed to obtain a paste preparation for oral administration.

Formulation Example 136
5% by weight of any one of the present condensed heterocyclic compounds 1 to 131 and 5% by weight of the present insecticidal compound 58 are mixed with 90% by weight of limestone powder to obtain granules for oral administration using a wet granule formation method.

Formulation Example 137
5 parts of any one of the present condensed heterocyclic compounds 1 to 131 and 5 parts of the present insecticidal compound 61 are dissolved in 75 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution. .

Formulation Example 138
10 parts of any one of the present condensed heterocyclic compounds 1 to 131 and 10 parts of the present insecticidal compound 67 are dissolved in 60 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed with this to give a pour-on solution. Get.

Formulation Example 139
0.5 part of any one of the present condensed heterocyclic compounds 1 to 131 and 0.5 part of the present insecticidal compound 68, 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine), propylene After adding 20 parts of glycol and sufficiently stirring and mixing until a uniform solution is obtained, 19.0 parts of water is added and further sufficiently stirring and mixing to obtain a shampoo agent of a uniform solution.

Formulation Example 140
Any one of the present condensed heterocyclic compounds 1 to 131, 0.15% by weight, 0.15% by weight of the present insecticidal compound 69, 95% by weight of animal feed, and dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) And 4.85% by weight of the mixture consisting of) is sufficiently stirred and mixed to obtain an animal feed premix.

Formulation Example 141
3.6 g of any one of the condensed heterocyclic compounds 1 to 131, 3.6 g of the insecticidal compound 70, and 92.8 g of Phosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C. Pour into shape and cool and solidify to obtain a suppository.

  Next, the pest control effect of the pest control composition of the present invention can be confirmed by, for example, the following test method.

Test example 1
The condensed heterocyclic compounds 1 to 131 are each dissolved in 10 μL of a mixed solvent of xylene, dimethylformamide, and a surfactant (trade name: Solpol 3005X, manufactured by Toho Chemical Industry) having a volume ratio of 4: 4: 1 per 1 mg. Then, it is diluted with water containing 0.02% by volume of a spreading agent (trade name: Cyndyne, manufactured by Sumitomo Chemical Co., Ltd.) so that the concentration of the present condensed heterocyclic compound is 500 ppm.
Further, each of the present insecticidal compounds 1 to 119 was dissolved in 10 μL of a mixed solvent of xylene, dimethylformamide and a surfactant (trade name: Solpol 3005X, manufactured by Toho Chemical Industry) having a volume ratio of 4: 4: 1 per 1 mg. Thereafter, the solution is diluted with water containing 0.02% by volume of a spreading agent (trade name: Cinderine, manufactured by Sumitomo Chemical Co., Ltd.) so that the concentration of the insecticidal compound is 500 ppm.
A test drug solution is prepared by appropriately mixing the water diluted solution of the condensed heterocyclic compound and the water diluted solution of the insecticidal compound.
Cabbage (Brassicae oleracea) leaf disk (1.5 cm in diameter) is placed in each well of a 24-well microplate (manufactured by Becton Dickinson), and 40 μL of the test drug solution is sprayed per well. After air-drying, 5 koganaga second-instar larvae (Plutella xylostella) were released per well, and each well was covered with a paper towel and then covered. Two days after release, the number of live insects in each well is observed.

Test example 2
A filter paper of the same size is laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of a test chemical prepared by the method described in Test Example 1 is dropped on the filter paper, and 30 mg of sucrose is uniformly added as a bait. Release 10 female Musca domestica females into the polyethylene cup and cap. After 24 hours, the life of the house fly is examined to determine the death rate.

Test example 3
A filter paper of the same size is laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of a test chemical prepared by the method described in Test Example 1 is dropped on the filter paper, and 30 mg of sucrose is uniformly added as a bait. Two adult male German cockroaches (Blattala germanica) are released into the polyethylene cup and covered. After 6 days, investigate the life and death of German cockroaches and determine the death rate.

Test example 4
0.7 ml of a test chemical prepared by the method described in Test Example 1 is added to 100 ml of ion-exchanged water (active ingredient concentration 3.5 ppm). In the liquid, 20 larvae of Culex pipiens parallels are released, and after 1 day, the life and death are examined to determine the mortality rate.

Test Example 5
Any one of the present condensed heterocyclic compounds 1 to 131 and any one of the present insecticidal compounds 1 to 119 are weighed into a screw tube (Marume No. 5; 27 × 55 mm) to a total of 2 mg, Add 0.2 mL of acetone, cover and dissolve. The screw tube is rotated and inverted to coat the chemical solution so that the entire inner wall is uniform. After removing the lid and allowing it to air dry for about 2 hours, 5 groups of non-blood-sucking young ticks (Haemaphysalis longicornis) are released and covered. The lethal number is examined after 2 days.

  Pests can be controlled with the pest control composition of the present invention.

Claims (4)

Formula (1)

[Where:
A ¹ represents —NR ⁶ —, an oxygen atom or a sulfur atom,
A ² represents a nitrogen atom or = CH-,
R ¹ , R ² , R ³ and R ⁴ are the same or different and are each a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, one or more atoms selected from group Z, or A phenyl group which may have a group, a 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR ⁷ , -S (O) _m R ⁷ , halogen An atom or a hydrogen atom (provided that at least two of R ¹ , R ² , R ³ and R ⁴ represent a hydrogen atom);
R ⁵ represents a C1-C3 chain hydrocarbon group, —OR ⁷ , —S (O) _m R ⁷ , or a halogen atom, which may have one or more atoms or groups selected from group X. ,
R ⁶ may have a C1-C3 chain hydrocarbon group optionally having one or more atoms or groups selected from group W, or may have one or more atoms or groups selected from group W. Represents a C3-C6 alicyclic hydrocarbon group or a hydrogen atom,
R ⁷ represents a C1-C3 chain hydrocarbon group which may have one or more halogen atoms or a hydrogen atom,
m represents 0, 1 or 2, and n represents 0, 1 or 2.
Here, in —S (O) _m R ⁷ , when m is 1 or 2, R ⁷ does not represent a hydrogen atom.
Group X: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms An optionally substituted C2-C3 alkynyloxy group, a C1-C3 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C3 alkylsulfinyl optionally having one or more halogen atoms A group consisting of a group, a C1-C3 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group and a halogen atom;
Group Z: C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, C1-C3 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C3 alkylsulfanyl group optionally having one or more, a C1-C3 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C3 optionally having one or more halogen atoms A group consisting of an alkylsulfonyl group, a cyano group, a nitro group and a halogen atom.
Group W: C1-C3 alkoxy group optionally having one or more halogen atoms, C2-C3 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A group consisting of an optionally substituted C2-C3 alkynyloxy group, a halogen atom and a hydroxy group. ]
A compound represented by
A pest control composition comprising one or more insecticidal compounds selected from the group (A).
Group (A)
A-1 (Pyrethroid compound):
Pyrethrin, allethrin, plaretrin, imiprothrin, resmethrin, tetramethrin, phenothrin, ciphenothrin, flumethrin, metfurthrin, transfluthrin, profluthrin, dimefluthrin, empentrin, framethrin, meperfluthrin, 2,3,5,6-tetrafluoro-4- (methoxy Methyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2- Dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3-tetramethyl Cyclopropane carbox Rate;
A-2 (other series of compounds):
Fenitrothion, Dichlorvos, Propoxur, Bistrifluron, Diflubenzuron, Hexaflumuron, Amidoflumet, Chlorfenapyr, Cyromazine, Hydroprene, Metoprene, Indoxacarb, Metoxadiazone, Etoxazole, Piperonylbutoxide, N- (2-Ethylhexyl) -5-norbornene-2 , 3-Dicarboximide, a compound represented by the following formula

[Wherein Cy is a phenyl group optionally substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group optionally substituted with a group selected from groups E1 to E2, and group E1. Represents a 3- to 7-membered cycloalkyl group which may be substituted with a group selected from -E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3, and Q ¹ a halogen atom substituted by C1~C4 may chain hydrocarbon group, a halogen atom or a hydrogen atom, Q ² is optionally substituted C1~C4 chain hydrocarbon group with a halogen atom, -C (= G) Q ^{4 represents} a cyano group, a halogen atom or a hydrogen atom, Q ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom, G represents an oxygen atom or a sulfur atom, Q ⁴ is still at a halogen atom A C1-C4 alkyl group which may be substituted, a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, or a halogen atom Good C3-C6 alkynyloxy group, C1-C4 alkylamino group optionally substituted with a halogen atom, Di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, Hydroxyl group, Amino group, C2 -C5 represents a cyclic amino group or a hydrogen atom, k represents 0 or 1, h represents 0, 1 or 2, and group E1 is a C1-C6 chain optionally substituted with a group selected from group L wherein the hydrocarbon group, C3 -C6 cycloalkyl group which may be substituted with a halogen ^{atom, -OQ 5, -SQ 5, -S} (= O) Q 5, -S (= O) 2 Q 5, -C (= O) Q ^6, -O (= O) Q ^7, a cyano group, a nitro group, a group of monovalent radicals consisting of hydroxyl group and a halogen atom, the group E2 is a group optionally substituted by C2-C6 alkanediyl also selected from the group L A group of divalent groups consisting of a group, a 1,3-butadiene-1,4-diyl group, -GTG-G- and -TGGT- which may be substituted with a group selected from group L Group E3 represents a group of divalent groups consisting of ═O, ═NO—Q ⁵ , ═C═CH ₂ and ═C (Q ⁸ ) Q ⁹ , T represents a methylene group or an ethylene group, Q ⁵ represents a C1-C4 chain hydrocarbon group which may be substituted with a group selected from Group L or a C3-C6 cycloalkyl group which may be substituted with a group selected from Group L, Q ⁶ is C1-C4 alkoxy group optionally substituted with a halogen atom, C3-C6 alkyl optionally substituted with a halogen atom A kenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, a C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) optionally substituted with a halogen atom ) amino group, optionally substituted C1~C4 alkyl group with a halogen atom, a hydroxyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁷ is C1 which may optionally be substituted with a halogen atom -C4 alkoxy group, C3-C6 alkenyloxy group optionally substituted with a halogen atom, C3-C6 alkynyloxy group optionally substituted with a halogen atom, C1-C4 alkyl optionally substituted with a halogen atom Amino group, di (C1-C4 alkyl) amino group optionally substituted with halogen atom, halogen source In substituted C1~C4 may alkyl group, an amino group, a C2~C5 cyclic amino group or a hydrogen atom, Q ⁸ and Q ⁹ are the same or different, C1 to which may be substituted with a halogen atom A C4 alkoxy group, a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom; Group L is a C1-C4 alkoxy optionally substituted with a hydroxyl group or a halogen atom A C3-C6 alkenyloxy group optionally substituted with a halogen atom, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, an amino group, a C1-C4 alkyl optionally substituted with a halogen atom amino groups, optionally substituted with a halogen atom di (C1 -C4 alkyl) amino group, C2-C5 cyclic amino group, -C (= O) Q ⁶ -OC (= O) Q ⁷
And a group consisting of halogen atoms. ], A compound represented by the following formula

[Wherein, k, h, Q ¹ , Q ² and Q ³ are the same as above, Q ¹¹ is a C1-C5 haloalkyl group having at least one fluorine atom, and C3-C5 optionally substituted with a halogen atom] An alkenyl group, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, a C3-C5 alkynyl group optionally substituted with a halogen atom, or a C3-C5 alkynyloxy group optionally substituted with a halogen atom. Q ¹² represents a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, a C1-C4 alkylthio group which may be substituted with a halogen atom, Represents a halogen atom or a hydrogen atom (provided that Q ¹¹ may be a C3-C5 alkenyloxy group or a halogen atom optionally substituted by a halogen atom); If it is optionally substituted C3-C5 alkynyloxy group in the child, Q ¹² is a is C1-C4 may be an alkyl group or a hydrogen atom substituted with a halogen atom.), Q ¹³ is C1-C4 alkyl Represents a group, a halogen atom or a hydrogen atom. ], A compound represented by the following formula

[Wherein L ³ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a hydrogen atom, and L ⁴ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or a C1 represents C1-C6 alkyl group substituted with -C6 alkoxy group, L ⁵ and L ⁶ are the same or different, represent a methyl group or a hydrogen atom. ],
Compound represented by the following formula

[Wherein, X ¹ represents a 2-methylpropyl group or 2-methyl-1-propenyl group, X ² represents a methyl group, X ³ represents a 2-methyl-1-propenyl group, and X ⁴ represents methyl Represents a group. ] The pest according to claim 1, wherein the ratio of the content of the compound represented by the formula (1) and one or more insecticidal compounds selected from the group (A) is 100: 1 to 1: 100 by weight. Control composition. The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) and one or more insecticidal compounds selected from the group (A) is 10: 1 to 1:10 by weight. Control composition. The pest control method which has a process in the habitat of a pest or a pest in the effective amount of the pest control composition in any one of Claims 1-3.