JP2016011276A - Amide compound and its harmful arthropod control use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel compound that has control activity against harmful arthropod.SOLUTION: Provided is an amide compound represented by formula (I). [Xis N or CR; Xis N or CR; Xis N or CR; n is 1 or 2; Rto Rare each independently an alkyl group, a vinyl group, an alkoxy group or the like optionally substituted with halogen or the like; Rand Rare each independently C1-4 alkyl group optionally substituted with halogen, H, and the like; Y represents a single bond, O, or -S(O)-; u is 0 to 2; when Y is O or -S(O)-, m is 0, 1 to 9; Z is a hydrocarbon group optionally substituted with halogen, or is an organic functional group having a halogen atom or various organic functional groups or the like; when Y is a single bond, m is 0, and Z is a C1-C8 chain hydrocarbon group having various organic functional groups].

Description

The present invention relates to an amide compound and its use for controlling harmful arthropods.

  Patent Document 1 describes that certain amide compounds can be used for controlling ectoparasites.

WO2013 / 003505

An object of the present invention is to provide a compound having an excellent control effect against harmful arthropods.

〔式中、
Ｘ^１は、窒素原子またはＣＲ^１を表し、
Ｘ^２は、窒素原子またはＣＲ^２を表し、
Ｘ^３は、窒素原子またはＣＲ^３を表し（但しＸ^１、Ｘ^２、Ｘ^３のすべてが窒素原子を表すことはない）、
ｎは、１または２を表し、
Ｒ^１、Ｒ^２およびＲ^３は互いに独立して、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［２］式（Ｉ−ａ）

〔式中、
ｎは、１または２を表し、
Ｒ^２およびＲ^３は互いに独立して、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［３］式（Ｉ−ｂ）

〔式中、
ｎは、１または２を表し、
Ｒ^１およびＲ^３は互いに独立して、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［４］式（Ｉ−ｃ）

〔式中、
ｎは、１または２を表し、
Ｒ^１、Ｒ^２およびＲ^３は互いに独立して、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［５］Ｒ^１、Ｒ^２及びＲ^３が水素原子である［４］記載のアミド化合物。
［６］Ｒ^１、Ｒ^２及びＲ^３の少なくとも１つが群Ａより選ばれる１つの原子もしくは基である［４］記載のアミド化合物。
［７］式（Ｉ−ｄ）

〔式中、
ｎは、１または２を表し、
Ｒ^３は、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［８］式（Ｉ−ｅ）

〔式中、
ｎは、１または２を表し、
Ｒ^２は、水素原子または群Ａより選ばれる１個の原子もしくは基を表し、
Ｒ^４およびＲ^５は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、ハロゲン原子または水素原子を表し、
Ｙは、単結合、酸素原子または−Ｓ（Ｏ）_ｕ−を表し、
ｕは、０、１または２を表し、
Ｙが酸素原子、または−Ｓ（Ｏ）_ｕ−である場合、ｍは、０、１、２、３、４、５、６、７、８または９を表し、Ｚは、群Ｂより選ばれる１個の基または群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表し、
Ｙが単結合である場合、ｍは、０を表し、Ｚは、群Ｂより選ばれる１個の基を有するＣ１−Ｃ８鎖式炭化水素基を表す。
群Ａ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４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−Ｃ４アルキルチオ基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフェニル基、
シアノ基及びハロゲン原子からなる群。
群Ｂ：
群Ｃより選ばれる１個以上の原子または基を有していてもよいピリジル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいフリル基、
群Ｃより選ばれる１個以上の原子または基を有していてもよいチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいインダニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，２，３，４−テトラヒドロナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいキノリル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾフラニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいベンゾチエニル基、
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，３−ベンゾジオキソラニル基及び
群Ｃより選ばれる１個以上の原子若しくは基を有していてもよい１，４−ベンゾジオキサニル基からなる群。
群Ｃ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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Ｃ３−Ｃ１０シクロアルキル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルチオ基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４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−Ｃ４アルキルスルホニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルコキシカルボニル基、
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキルカルボニル基、
群Ｄより選ばれる１個以上の原子または基を有していてもよいビニル基、
群Ｄより選ばれる原子または基を有していてもよいエチニル基、
アミノ基、シアノ基、ニトロ基、カルボキシル基、ヒドロキシル基、−ＣＯＮＲ^６Ｒ^７基およびハロゲン原子からなる群（Ｒ^６およびＲ^７は互いに独立して、１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基、または水素原子を表す）。
群Ｄ：
１個以上のハロゲン原子を有していてもよいＣ１−Ｃ４アルキル基及びハロゲン原子からなる群。〕
で示されるアミド化合物。
［９］Ｙが単結合である［１］〜［８］いずれか一項記載のアミド化合物。
［１０］Ｙが酸素原子である［１］〜［８］いずれか一項記載のアミド化合物。
［１１］Ｙが−Ｓ（Ｏ）_ｕ−である［１］〜［８］いずれか一項記載のアミド化合物。
［１２］Ｙが酸素原子であり、ｍが１、２、３、４、５、６、７、８または９である［１］〜［８］いずれか一項記載のアミド化合物。
［１３］Ｙが−Ｓ（Ｏ）_ｕ−であり、ｍが１、２、３、４、５、６、７、８または９である［１］〜［８］いずれか一項記載のアミド化合物。
［１４］Ｙが単結合であり、ｍが０であり、Ｚが群Ｂより選ばれる１個の基を有するＣ２−Ｃ５鎖式炭化水素基である［１］〜［８］いずれか一項記載のアミド化合物。
［１５］Ｙが単結合であり、ｍが０であり、Ｚが群Ｂより選ばれる１個の基を有するＣ２鎖式炭化水素基である［１］〜［８］いずれか一項記載のアミド化合物。
［１６］Ｙが酸素原子であり、ｍが１または２であり、Ｚが群Ｂより選ばれる１個の基、または群Ｂより選ばれる１個の基を有するＣ１−Ｃ３鎖式炭化水素基である［１］〜［８］いずれか一項記載のアミド化合物。
［１７］Ｙが−Ｓ（Ｏ）_ｕ−であり、ｍが１または２であり、Ｚが群Ｂより選ばれる１個の基、または群Ｂより選ばれる１個の基を有するＣ１−Ｃ３鎖式炭化水素基である［１］〜［８］いずれか一項記載のアミド化合物。
［１８］群Ｂが、群Ｃより選ばれる１個以上の原子若しくは基を有していてもよいナフチル基である［１］〜［１７］いずれか一項記載のアミド化合物。
［１９］ｎが１である［１］〜［１８］いずれか一項記載のアミド化合物。
［２０］ｎが２である［１］〜［１８］いずれか一項記載のアミド化合物。
［２１］［１］〜［２０］いずれか一項記載のアミド化合物と不活性担体とを含有する有害節足動物防除剤。
［２２］［１］〜［２０］いずれか一項記載のアミド化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用する工程を含む有害節足動物の防除方法。 As a result of intensive studies to find a compound having an excellent control effect against harmful arthropods, the present inventors have found an amide compound represented by the following formula (I) (hereinafter sometimes referred to as the present compound). Was found to have an excellent control effect on harmful arthropods, and the present invention was completed.
That is, the present invention is as follows.
[1] Formula (I)

[Where,
X ¹ represents a nitrogen atom or CR ¹ ;
X ² represents a nitrogen atom or CR ² ,
X ³ represents a nitrogen atom or CR ³ (provided that all of X ¹ , X ² and X ³ do not represent a nitrogen atom),
n represents 1 or 2,
R ¹ , R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[2] Formula (Ia)

[Where,
n represents 1 or 2,
R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[3] Formula (Ib)

[Where,
n represents 1 or 2,
R ¹ and R ³ independently of each other represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group optionally having one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[4] Formula (Ic)

[Where,
n represents 1 or 2,
R ¹ , R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[5] The amide compound according to [4], wherein R ¹ , R ² and R ³ are hydrogen atoms.
[6] The amide compound according to [4], wherein at least one of R ¹ , R ² and R ³ is one atom or group selected from group A.
[7] Formula (Id)

[Where,
n represents 1 or 2,
R ³ represents a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[8] Formula (Ie)

[Where,
n represents 1 or 2,
R ² represents a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —;
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is selected from group B Represents a C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0, and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by
[9] The amide compound according to any one of [1] to [8], wherein Y is a single bond.
[10] The amide compound according to any one of [1] to [8], wherein Y is an oxygen atom.
[11] The amide compound according to any one of [1] to [8], wherein Y is —S (O) _u —.
[12] The amide compound according to any one of [1] to [8], wherein Y is an oxygen atom, and m is 1, 2, 3, 4, 5, 6, 7, 8 or 9.
[13] The amide according to any one of [1] to [8], wherein Y is —S (O) _u —, and m is 1, 2, 3, 4, 5, 6, 7, 8 or 9. Compound.
[14] Any one of [1] to [8], wherein Y is a single bond, m is 0, and Z is a C2-C5 chain hydrocarbon group having one group selected from Group B. The amide compound described.
[15] Any one of [1] to [8], wherein Y is a single bond, m is 0, and Z is a C2-chain hydrocarbon group having one group selected from group B. Amide compounds.
[16] A C1-C3 chain hydrocarbon group having Y as an oxygen atom, m being 1 or 2, and Z being one group selected from group B, or one group selected from group B The amide compound according to any one of [1] to [8].
[17] C1-C3 wherein Y is —S (O) _u —, m is 1 or 2, and Z is one group selected from group B or one group selected from group B The amide compound according to any one of [1] to [8], which is a chain hydrocarbon group.
[18] The amide compound according to any one of [1] to [17], wherein the group B is a naphthyl group which may have one or more atoms or groups selected from the group C.
[19] The amide compound according to any one of [1] to [18], wherein n is 1.
[20] The amide compound according to any one of [1] to [18], wherein n is 2.
[21] A harmful arthropod control agent comprising the amide compound according to any one of [1] to [20] and an inert carrier.
[22] A method for controlling harmful arthropods, comprising a step of applying an effective amount of the amide compound according to any one of [1] to [20] to harmful arthropods or habitats of harmful arthropods.

  Since the compound of the present invention has an excellent control effect against harmful arthropods, it is useful as an active ingredient of a harmful arthropod control agent.

The compound of the present invention may have an isomer derived from an asymmetric carbon atom and an isomer derived from a double bond, but the present invention has each isomer having harmful arthropod controlling activity and an arbitrary ratio. A mixture of isomers of

In the present invention, examples of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the present invention, examples of the “C1-C4 alkyl group optionally having one or more halogen atoms” include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl. Group, tert-butyl group, iodomethyl group, bromomethyl group, chloromethyl group, fluoromethyl group, difluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, trichloromethyl group, trifluoromethyl group, 2 , 2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group and 1,1,2,2,2-pentafluoroethyl group.

In the present invention, examples of the “C3-C10 cycloalkyl group optionally having one or more halogen atoms” include an adamantyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, A cyclooctyl group, a 1-fluorocyclopropyl group, a 1-methylcyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dimethylcyclopropyl group, and a 2,2,3,3-tetrachlorocyclopropyl group. Can be mentioned.

In the present invention, the “C1-C4 alkoxy group optionally having one or more halogen atoms” includes, for example,
Methoxy group, ethoxy group, propoxy group, isopropoxy group, isobutoxy group, difluoromethoxy group, trifluoromethoxy group, trichloromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoro Examples thereof include an ethoxy group and a 1,1,2,2,2-pentafluoroethoxy group.

In the present invention, the “C1-C4 alkylthio group optionally having one or more halogen atoms” includes, for example,
Methylthio group, ethylthio group, propylthio group, isopropylthio group, isobutylthio group, difluoromethylthio group, trifluoromethylthio group, trichloromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2- Examples include a tetrafluoroethylthio group and a 1,1,2,2,2-pentafluoroethylthio group.

In the present invention, the “C1-C4 alkylsulfinyl group optionally having one or more halogen atoms” includes, for example,
Methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, isobutylsulfinyl group, difluoromethylsulfinyl group, trifluoromethylsulfinyl group, trichloromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1, Examples include 1,2,2-tetrafluoroethylsulfinyl group and 1,1,2,2,2-pentafluoroethylsulfinyl group.

In the present invention, examples of the “C1-C4 alkylsulfonyl group optionally having one or more halogen atoms” include:
Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, isobutylsulfonyl group, difluoromethylsulfonyl group, trifluoromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1, Examples thereof include a 1,2,2-tetrafluoroethylsulfonyl group and a 1,1,2,2,2-pentafluoroethylsulfonyl group.

In the present invention, examples of the “C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms” include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, and a butoxycarbonyl group. , Tert-butoxycarbonyl group, difluoromethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 1,1,2,2-tetrafluoroethoxycarbonyl group and 1 , 1,2,2,2-pentafluoroethoxycarbonyl group.

In the present invention, examples of the “C1-C4 alkylcarbonyl group optionally having one or more halogen atoms” include a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, an isopropylcarbonyl group, a butylcarbonyl group, tert-butylcarbonyl group, difluoromethylcarbonyl group, trifluoromethylcarbonyl group, trichloromethylcarbonyl group, 2,2,2-trifluoroethylcarbonyl group, 1,1,2,2-tetrafluoroethylcarbonyl group and 1, A 1,2,2,2-pentafluoroethylcarbonyl group may be mentioned.

In the present invention, examples of the “vinyl group optionally having one or more atoms or groups selected from group D” include a vinyl group, a 2-fluorovinyl group, a 2,2-difluorovinyl group, and 2 , 2-dichlorovinyl group.

In the present invention, examples of the “ethynyl group optionally having one or more atoms or groups selected from group D” include ethynyl group, 1-propynyl group, 1-butynyl group, 1-pentynyl group, 2-iodoethynyl group, 2-bromoethynyl group, 2-chloroethynyl group, 2-fluoroethynyl group, trifluoromethyl-1-propynyl group, 3-methyl-1-butynyl group and 3,3-dimethyl-1- Butynyl is mentioned.

In the present invention, examples of the “phenyl group optionally having one or more atoms or groups selected from group C” include:
Phenyl group,
2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group,
2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group,
2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group,
2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group,
2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group,
2-trifluoromethylthiophenyl group, 3-trifluoromethylthiophenyl group, 4-trifluoromethylthiophenyl group,
2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group,
2-ethynylphenyl group, 3-ethynylphenyl group, 4-ethynylphenyl group,
2-vinylphenyl group, 3-vinylphenyl group, 4-vinylphenyl group,
2-acetylphenyl group, 3-acetylphenyl group, 4-acetylphenyl group,
2-methylsulfinyl group, 3-methylsulfinyl group, 4-methylsulfinyl group,
2-methylsulfonyl group, 3-methylsulfonyl group, 4-methylsulfonyl group,
2-methoxycarbonyl group, 3-methoxycarbonyl group, 4-methoxycarbonyl group,
2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group,
2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group,
2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group,
Is mentioned.

In the present invention, examples of the “pyridyl group optionally having one or more atoms or groups selected from group C” include 2-pyridyl group, 3-cyano-2-pyridyl group, 4-cyano- 2-pyridyl group, 5-cyano-2-pyridyl group, 6-cyano-2-pyridyl group,
3-nitro-2-pyridyl group, 4-nitro-2-pyridyl group, 5-nitro-2-pyridyl group, 6-nitro-2-pyridyl group,
3-carboxyl-2-pyridyl group, 4-carboxyl-2-pyridyl group, 5-carboxyl-2-pyridyl group, 6-carboxyl-2-pyridyl group,
3-hydroxyl-2-pyridyl group, 4-hydroxyl-2-pyridyl group, 5-hydroxyl-2-pyridyl group, 6-hydroxyl-2-pyridyl group,
3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group,
3-trifluoromethyl-2-pyridyl group, 4-trifluoromethyl-2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 6-trifluoromethyl-2-pyridyl group,
3-methoxy-2-pyridyl group, 4-methoxy-2-pyridyl group, 5-methoxy-2-pyridyl group, 6-methoxy-2-pyridyl group,
3-trifluoromethoxy-2-pyridyl group, 4-trifluoromethoxy-2-pyridyl group, 5-trifluoromethoxy-2-pyridyl group, 6-trifluoromethoxy-2-pyridyl group,
3-methoxycarbonyl-2-pyridyl group, 4-methoxycarbonyl-2-pyridyl group, 5-methoxycarbonyl-2-pyridyl group, 6-methoxycarbonyl-2-pyridyl group,
3-vinyl-2-pyridyl group, 4-vinyl-2-pyridyl group, 5-vinyl-2-pyridyl group, 6-vinyl-2-pyridyl group,
3- (2 ′, 2′-difluorovinyl) -2-pyridyl group, 4- (2 ′, 2′-difluorovinyl) -2-pyridyl group, 5- (2 ′, 2′-difluorovinyl) -2 -Pyridyl group, 6- (2 ', 2'-difluorovinyl) -2-pyridyl group,
3-ethynyl-2-pyridyl group, 4-ethynyl-2-pyridyl group, 5-ethynyl-2-pyridyl group, 6-ethynyl-2-pyridyl group,
3- (2′-fluoroethynyl) -2-pyridyl group, 4- (2′-fluoroethynyl) -2-pyridyl group, 5- (2′-fluoroethynyl) -2-pyridyl group, 6- (2 ′ -Fluoroethynyl) -2-pyridyl group,
3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group,
“One or more atoms selected from group C, such as 3-chloro-2-pyridyl group, 4-chloro-2-pyridyl group, 5-chloro-2-pyridyl group, 6-chloro-2-pyridyl group, etc. 2-pyridyl group optionally having a group ";
3-pyridyl group, 2-cyano-3-pyridyl group, 4-cyano-3-pyridyl group, 5-cyano-3-pyridyl group, 6-cyano-3-pyridyl group,
2-nitro-3-pyridyl group, 4-nitro-3-pyridyl group, 5-nitro-3-pyridyl group, 6-nitro-3-pyridyl group,
2-carboxyl-3-pyridyl group, 4-carboxyl-3-pyridyl group, 5-carboxyl-3-pyridyl group, 6-carboxyl-3-pyridyl group,
2-hydroxyl-3-pyridyl group, 4-hydroxyl-3-pyridyl group, 5-hydroxyl-3-pyridyl group, 6-hydroxyl-3-pyridyl group,
2-methyl-3-pyridyl group, 4-methyl-3-pyridyl group, 5-methyl-3-pyridyl group, 6-methyl-3-pyridyl group,
2-trifluoromethyl-3-pyridyl group, 4-trifluoromethyl-3-pyridyl group, 5-trifluoromethyl-3-pyridyl group, 6-trifluoromethyl-3-pyridyl group,
2-methoxy-3-pyridyl group, 4-methoxy-3-pyridyl group, 5-methoxy-3-pyridyl group, 6-methoxy-3-pyridyl group,
2-trifluoromethoxy-3-pyridyl group, 4-trifluoromethoxy-3-pyridyl group, 5-trifluoromethoxy-3-pyridyl group, 6-trifluoromethoxy-3-pyridyl group,
2-methoxycarbonyl-3-pyridyl group, 4-methoxycarbonyl-3-pyridyl group, 5-methoxycarbonyl-3-pyridyl group, 6-methoxycarbonyl-3-pyridyl group,
2-vinyl-3-pyridyl group, 4-vinyl-3-pyridyl group, 5-vinyl-3-pyridyl group, 6-vinyl-3-pyridyl group,
2- (2 ′, 2′-difluorovinyl) -3-pyridyl group, 4- (2 ′, 2′-difluorovinyl) -3-pyridyl group, 5- (2 ′, 2′-difluorovinyl) -3 -Pyridyl group, 6- (2 ', 2'-difluorovinyl) -3-pyridyl group,
2-ethynyl-3-pyridyl group, 4-ethynyl-3-pyridyl group, 5-ethynyl-3-pyridyl group, 6-ethynyl-3-pyridyl group,
2- (2′-fluoroethynyl) -3-pyridyl group, 4- (2′-fluoroethynyl) -3-pyridyl group, 5- (2′-fluoroethynyl) -3-pyridyl group, 6- (2 ′ -Fluoroethynyl) -3-pyridyl group,
2-fluoro-3-pyridyl group, 4-fluoro-3-pyridyl group, 5-fluoro-3-pyridyl group, 6-fluoro-3-pyridyl group,
“One or more atoms selected from group C, such as 2-chloro-3-pyridyl group, 4-chloro-3-pyridyl group, 5-chloro-3-pyridyl group, 6-chloro-3-pyridyl group, etc. A 3-pyridyl group optionally having a group ";
4-pyridyl group, 2-cyano-4-pyridyl group, 3-cyano-4-pyridyl group 2-nitro-4-pyridyl group, 3-nitro-4-pyridyl group,
2-carboxyl-4-pyridyl group, 3-carboxyl-4-pyridyl group,
2-hydroxyl-4-pyridyl group, 3-hydroxyl-4-pyridyl group,
2-methyl-4-pyridyl group, 3-methyl-4-pyridyl group,
2-trifluoromethyl-4-pyridyl group, 3-trifluoromethyl-4-pyridyl group,
2-methoxy-4-pyridyl group, 3-methoxy-4-pyridyl group,
2-trifluoromethoxy-4-pyridyl group, 3-trifluoromethoxy-4-pyridyl group,
2-methoxycarbonyl-4-pyridyl group, 3-methoxycarbonyl-4-pyridyl group,
2-vinyl-4-pyridyl group, 3-vinyl-4-pyridyl group,
2- (2 ′, 2′-difluorovinyl) -4-pyridyl group, 3- (2 ′, 2′-difluorovinyl) -4-pyridyl group,
2-ethynyl-4-pyridyl group, 3-ethynyl-4-pyridyl group,
2- (2′-fluoroethynyl) -4-pyridyl group, 3- (2′-fluoroethynyl) -4-pyridyl group,
2-fluoro-4-pyridyl group, 3-fluoro-4-pyridyl group,
"4-pyridyl group optionally having one or more atoms or groups selected from group C", such as 2-chloro-4-pyridyl group, 3-chloro-4-pyridyl group;
Is mentioned.

In the present invention, examples of the “furyl group optionally having one or more atoms or groups selected from group C” include 2-furyl group, 3-cyano-2-furyl group, 4-cyano- 2-furyl group, 5-cyano-2-furyl group,
3-nitro-2-furyl group, 4-nitro-2-furyl group, 5-nitro-2-furyl group,
3-carboxyl-2-furyl group, 4-carboxyl-2-furyl group, 5-carboxyl-2-furyl group,
3-hydroxyl-2-furyl group, 4-hydroxyl-2-furyl group, 5-hydroxyl-2-furyl group,
3-methyl-2-furyl group, 4-methyl-2-furyl group, 5-methyl-2-furyl group,
3-trifluoromethyl-2-furyl group, 4-trifluoromethyl-2-furyl group, 5-trifluoromethyl-2-furyl group,
3-methoxy-2-furyl group, 4-methoxy-2-furyl group, 5-methoxy-2-furyl group,
3-trifluoromethoxy-2-furyl group, 4-trifluoromethoxy-2-furyl group, 5-trifluoromethoxy-2-furyl group,
3-methoxycarbonyl-2-furyl group, 4-methoxycarbonyl-2-furyl group, 5-methoxycarbonyl-2-furyl group,
3-vinyl-2-furyl group, 4-vinyl-2-furyl group, 5-vinyl-2-furyl group,
3- (2 ′, 2′-difluorovinyl) -2-furyl group, 4- (2 ′, 2′-difluorovinyl) -2-furyl group, 5- (2 ′, 2′-difluorovinyl) -2 -Furyl group,
3-ethynyl-2-furyl group, 4-ethynyl-2-furyl group, 5-ethynyl-2-furyl group,
3- (2′-fluoroethynyl) -2-furyl group, 4- (2′-fluoroethynyl) -2-furyl group, 5- (2′-fluoroethynyl) -2-furyl group,
3-fluoro-2-furyl group, 4-fluoro-2-furyl group, 5-fluoro-2-furyl group,
Such as a 3-chloro-2-furyl group, a 4-chloro-2-furyl group, a 5-chloro-2-furyl group, etc. -Furyl group ";
3-furyl group, 2-cyano-3-furyl group, 4-cyano-3-furyl group, 5-cyano-3-furyl group,
2-nitro-3-furyl group, 4-nitro-3-furyl group, 5-nitro-3-furyl group,
2-carboxyl-3-furyl group, 4-carboxyl-3-furyl group, 5-carboxyl-3-furyl group,
2-hydroxyl-3-furyl group, 4-hydroxyl-3-furyl group, 5-hydroxyl-3-furyl group,
2-methyl-3-furyl group, 4-methyl-3-furyl group, 5-methyl-3-furyl group,
2-trifluoromethyl-3-furyl group, 4-trifluoromethyl-3-furyl group, 5-trifluoromethyl-3-furyl group,
2-methoxy-3-furyl group, 4-methoxy-3-furyl group, 5-methoxy-3-furyl group,
2-trifluoromethoxy-3-furyl group, 4-trifluoromethoxy-3-furyl group, 5-trifluoromethoxy-3-furyl group,
2-methoxycarbonyl-3-furyl group, 4-methoxycarbonyl-3-furyl group, 5-methoxycarbonyl-3-furyl group,
2-vinyl-3-furyl group, 4-vinyl-3-furyl group, 5-vinyl-3-furyl group,
2- (2 ′, 2′-difluorovinyl) -3-furyl group, 4- (2 ′, 2′-difluorovinyl) -3-furyl group, 5- (2 ′, 2′-difluorovinyl) -3 -Furyl group,
2-ethynyl-3-furyl group, 4-ethynyl-3-furyl group, 5-ethynyl-3-furyl group,
2- (2′-fluoroethynyl) -3-furyl group, 4- (2′-fluoroethynyl) -3-furyl group, 5- (2′-fluoroethynyl) -3-furyl group,
2-fluoro-3-furyl group, 4-fluoro-3-furyl group, 5-fluoro-3-furyl group,
“May have one or more atoms or groups selected from group C, such as 2-chloro-3-furyl group, 4-chloro-3-furyl group, 5-chloro-3-furyl group, etc. -Furyl group ";

In the present invention, examples of the “thienyl group optionally having one or more atoms or groups selected from group C” include 2-thienyl group, 3-cyano-2-thienyl group, 4-cyano- 2-thienyl group, 5-cyano-2-thienyl group,
3-nitro-2-thienyl group, 4-nitro-2-thienyl group, 5-nitro-2-thienyl group,
3-carboxyl-2-thienyl group, 4-carboxyl-2-thienyl group, 5-carboxyl-2-thienyl group,
3-hydroxyl-2-thienyl group, 4-hydroxyl-2-thienyl group, 5-hydroxyl-2-thienyl group,
3-methyl-2-thienyl group, 4-methyl-2-thienyl group, 5-methyl-2-thienyl group,
3-trifluoromethyl-2-thienyl group, 4-trifluoromethyl-2-thienyl group, 5-trifluoromethyl-2-thienyl group,
3-methoxy-2-thienyl group, 4-methoxy-2-thienyl group, 5-methoxy-2-thienyl group,
3-trifluoromethoxy-2-thienyl group, 4-trifluoromethoxy-2-thienyl group, 5-trifluoromethoxy-2-thienyl group,
3-methoxycarbonyl-2-thienyl group, 4-methoxycarbonyl-2-thienyl group, 5-methoxycarbonyl-2-thienyl group,
3-vinyl-2-thienyl group, 4-vinyl-2-thienyl group, 5-vinyl-2-thienyl group,
3- (2 ′, 2′-difluorovinyl) -2-thienyl group, 4- (2 ′, 2′-difluorovinyl) -2-thienyl group, 5- (2 ′, 2′-difluorovinyl) -2 A thienyl group,
3-ethynyl-2-thienyl group, 4-ethynyl-2-thienyl group, 5-ethynyl-2-thienyl group,
3- (2′-fluoroethynyl) -2-thienyl group, 4- (2′-fluoroethynyl) -2-thienyl group, 5- (2′-fluoroethynyl) -2-thienyl group,
3-fluoro-2-thienyl group, 4-fluoro-2-thienyl group, 5-fluoro-2-thienyl group,
Such as a 3-chloro-2-thienyl group, 4-chloro-2-thienyl group, 5-chloro-2-thienyl group, etc., which may have “one or more atoms or groups selected from group C 2 -Thienyl group ";
3-thienyl group, 2-cyano-3-thienyl group, 4-cyano-3-thienyl group, 5-cyano-3-thienyl group,
2-nitro-3-thienyl group, 4-nitro-3-thienyl group, 5-nitro-3-thienyl group,
2-carboxyl-3-thienyl group, 4-carboxyl-3-thienyl group, 5-carboxyl-3-thienyl group,
2-hydroxyl-3-thienyl group, 4-hydroxyl-3-thienyl group, 5-hydroxyl-3-thienyl group,
2-methyl-3-thienyl group, 4-methyl-3-thienyl group, 5-methyl-3-thienyl group,
2-trifluoromethyl-3-thienyl group, 4-trifluoromethyl-3-thienyl group, 5-trifluoromethyl-3-thienyl group,
2-methoxy-3-thienyl group, 4-methoxy-3-thienyl group, 5-methoxy-3-thienyl group,
2-trifluoromethoxy-3-thienyl group, 4-trifluoromethoxy-3-thienyl group, 5-trifluoromethoxy-3-thienyl group,
2-methoxycarbonyl-3-thienyl group, 4-methoxycarbonyl-3-thienyl group, 5-methoxycarbonyl-3-thienyl group,
2-vinyl-3-thienyl group, 4-vinyl-3-thienyl group, 5-vinyl-3-thienyl group,
2- (2 ′, 2′-difluorovinyl) -3-thienyl group, 4- (2 ′, 2′-difluorovinyl) -3-thienyl group, 5- (2 ′, 2′-difluorovinyl) -3 A thienyl group,
2-ethynyl-3-thienyl group, 4-ethynyl-3-thienyl group, 5-ethynyl-3-thienyl group,
2- (2′-fluoroethynyl) -3-thienyl group, 4- (2′-fluoroethynyl) -3-thienyl group, 5- (2′-fluoroethynyl) -3-thienyl group,
2-fluoro-3-thienyl group, 4-fluoro-3-thienyl group, 5-fluoro-3-thienyl group,
“May have one or more atoms or groups selected from group C, such as 2-chloro-3-thienyl group, 4-chloro-3-thienyl group, 5-chloro-3-thienyl group, etc. -Thienyl group ".

In the present invention, the “indanyl group optionally having one or more atoms or groups selected from group C” includes, for example,
1-indanyl group,
4-methyl-1-indanyl group, 5-methyl-1-indanyl group, 6-methyl-1-indanyl group, 7-methyl-1-indanyl group,
4-cyano-1-indanyl group, 5-cyano-1-indanyl group, 6-cyano-1-indanyl group, 7-cyano-1-indanyl group,
4-carboxyl-1-indanyl group, 5-carboxyl-1-indanyl group, 6-carboxyl-1-indanyl group, 7-carboxyl-1-indanyl group,
4-hydroxyl-1-indanyl group, 5-hydroxyl-1-indanyl group, 6-hydroxyl-1-indanyl group, 7-hydroxyl-1-indanyl group,
4-trifluoromethyl-1-indanyl group, 5-trifluoromethyl-1-indanyl group, 6-trifluoromethyl-1-indanyl group, 7-trifluoromethyl-1-indanyl group,
4-trifluoromethoxy-1-indanyl group, 5-trifluoromethoxy-1-indanyl group, 6-trifluoromethoxy-1-indanyl group, 7-trifluoromethoxy-1-indanyl group,
4-trifluoromethylthio-1-indanyl group, 5-trifluoromethylthio-1-indanyl group, 6-trifluoromethylthio-1-indanyl group, 7-trifluoromethylthio-1-indanyl group,
4-trifluoromethanesulfinyl-1-indanyl group, 5-trifluoromethanesulfinyl-1-indanyl group, 6-trifluoromethanesulfinyl-1-indanyl group, 7-trifluoromethanesulfinyl-1-indanyl group,
4-trifluoromethanesulfonyl-1-indanyl group, 5-trifluoromethanesulfonyl-1-indanyl group, 6-trifluoromethanesulfonyl-1-indanyl group, 7-trifluoromethanesulfonyl-1-indanyl group 4-fluoro-1-indanyl group Group, 5-fluoro-1-indanyl group, 6-fluoro-1-indanyl group, 7-fluoro-1-indanyl group 4-chloro-1-indanyl group, 5-chloro-1-indanyl group, 6-chloro- 1-indanyl group, 7-chloro-1-indanyl group 4-bromo-1-indanyl group, 5-bromo-1-indanyl group, 6-bromo-1-indanyl group, 7-bromo-1-indanyl group, etc. , “1-Indanyl group optionally having one or more atoms or groups selected from group C”;
2-indanyl group,
4-methyl-2-indanyl group, 5-methyl-2-indanyl group,
4-cyano-2-indanyl group, 5-cyano-2-indanyl group,
4-carboxyl-2-indanyl group, 5-carboxyl-2-indanyl group,
4-hydroxyl-2-indanyl group, 5-hydroxyl-2-indanyl group,
4-trifluoromethyl-2-indanyl group, 5-trifluoromethyl-2-indanyl group,
4-trifluoromethoxy-2-indanyl group, 5-trifluoromethoxy-2-indanyl group,
4-trifluoromethylthio-2-indanyl group, 5-trifluoromethylthio-2-indanyl group,
4-trifluoromethanesulfinyl-2-indanyl group, 5-trifluoromethanesulfinyl-2-indanyl group,
4-trifluoromethanesulfonyl-2-indanyl group, 5-trifluoromethanesulfonyl-2-indanyl group,
4-fluoro-2-indanyl group, 5-fluoro-2-indanyl group,
4-chloro-2-indanyl group, 5-chloro-2-indanyl group,
4-bromo-2-indanyl group, 5-bromo-2-indanyl group,
"2-indanyl group optionally having one or more atoms or groups selected from group C";
Is mentioned.

In the present invention, the “1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C” includes, for example,
1- (1,2,3,4-tetrahydronaphthyl) group, 1- (5-methyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-methyl-1,2,3,4) -Tetrahydronaphthyl) group, 1- (7-methyl-1,2,3,4-tetrahydronaphthyl) group, 1- (8-methyl-1,2,3,4-tetrahydronaphthyl) group,
1- (5-cyano-1,2,3,4-tetrahydronaphthyl) group, 1- (6-cyano-1,2,3,4-tetrahydronaphthyl) group, 1- (7-cyano-1,2 , 3,4-tetrahydronaphthyl) group, 1- (8-cyano-1,2,3,4-tetrahydronaphthyl) group,
1- (5-carboxyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-carboxyl-1,2,3,4-tetrahydronaphthyl) group, 1- (7-carboxyl-1,2) , 3,4-tetrahydronaphthyl) group, 1- (8-carboxyl-1,2,3,4-tetrahydronaphthyl) group,
1- (5-hydroxyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-hydroxyl-1,2,3,4-tetrahydronaphthyl) group, 1- (7-hydroxyl-1,2 , 3,4-tetrahydronaphthyl) group, 1- (8-hydroxyl-1,2,3,4-tetrahydronaphthyl) group,
1- (5-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 1- (7-trimethyl) Fluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 1- (8-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group,
1- (5-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 1- (6-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 1- (7-trimethyl) Fluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 1- (8-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group,
1- (5-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 1- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 1- (7-trimethyl) Fluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 1- (8-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group,
1- (5-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 1- (7-trifluoro) Lomethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 1- (8-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group,
1- (5-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 1- (6-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 1- (7-trifluoro) Lomethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 1- (8-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group,
"1- (1,2,3,4-tetrahydronaphthyl) group optionally having one or more atoms or groups selected from group C";
2- (1,2,3,4-tetrahydronaphthyl) group, 2- (5-methyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-methyl-1,2,3,4) -Tetrahydronaphthyl) group, 2- (7-methyl-1,2,3,4-tetrahydronaphthyl) group, 2- (8-methyl-1,2,3,4-tetrahydronaphthyl) group,
2- (5-cyano-1,2,3,4-tetrahydronaphthyl) group, 2- (6-cyano-1,2,3,4-tetrahydronaphthyl) group, 2- (7-cyano-1,2 , 3,4-tetrahydronaphthyl) group, 2- (8-cyano-1,2,3,4-tetrahydronaphthyl) group,
2- (5-carboxyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-carboxyl-1,2,3,4-tetrahydronaphthyl) group, 2- (7-carboxyl-1,2) , 3,4-tetrahydronaphthyl) group, 2- (8-carboxyl-1,2,3,4-tetrahydronaphthyl) group,
2- (5-hydroxyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-hydroxyl-1,2,3,4-tetrahydronaphthyl) group, 2- (7-hydroxyl-1,2) , 3,4-tetrahydronaphthyl) group, 2- (8-hydroxyl-1,2,3,4-tetrahydronaphthyl) group,
2- (5-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 2- (7-trimethyl) Fluoromethyl-1,2,3,4-tetrahydronaphthyl) group, 2- (8-trifluoromethyl-1,2,3,4-tetrahydronaphthyl) group,
2- (5-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 2- (6-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 2- (7-trimethyl) Fluoromethylthio-1,2,3,4-tetrahydronaphthyl) group, 2- (8-trifluoromethylthio-1,2,3,4-tetrahydronaphthyl) group,
2- (5-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 2- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 2- (7-trimethyl) Fluoromethoxy-1,2,3,4-tetrahydronaphthyl) group, 2- (8-trifluoromethoxy-1,2,3,4-tetrahydronaphthyl) group,
2- (5-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 2- (7-trifluoro) Lomethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group, 2- (8-trifluoromethanesulfinyl-1,2,3,4-tetrahydronaphthyl) group,
2- (5-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 2- (6-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 2- (7-trifluoro) Lomethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group, 2- (8-trifluoromethanesulfonyl-1,2,3,4-tetrahydronaphthyl) group,
"2- (1,2,3,4-tetrahydronaphthyl) group optionally having one or more atoms or groups selected from group C";
Is mentioned.

In the present invention, examples of the “naphthyl group optionally having one or more atoms or groups selected from group C” include 1-naphthyl group,
2-cyano-1-naphthyl group, 3-cyano-1-naphthyl group, 4-cyano-1-naphthyl group,
2-nitro-1-naphthyl group, 3-nitro-1-naphthyl group, 4-nitro-1-naphthyl group,
2-carboxyl-1-naphthyl group, 3-carboxyl-1-naphthyl group, 4-carboxyl-1-naphthyl group,
2-hydroxyl-1-naphthyl group, 3-hydroxyl-1-naphthyl group, 4-hydroxyl-1-naphthyl group,
2-methyl-1-naphthyl group, 3-methyl-1-naphthyl group, 4-methyl-1-naphthyl group,
2-trifluoromethyl-1-naphthyl group, 3-trifluoromethyl-1-naphthyl group, 4-trifluoromethyl-1-naphthyl group,
2-methoxy-1-naphthyl group, 3-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group,
2-trifluoromethoxy-1-naphthyl group, 3-trifluoromethoxy-1-naphthyl group, 4-trifluoromethoxy-1-naphthyl group,
2-trifluoromethylthio-1-naphthyl group, 3-trifluoromethylthio-1-naphthyl group, 4-trifluoromethylthio-1-naphthyl group,
2-trifluoromethylsulfinyl-1-naphthyl group, 3-trifluoromethylsulfinyl-1-naphthyl group, 4-trifluoromethylsulfinyl-1-naphthyl group,
2-trifluoromethylsulfonyl-1-naphthyl group, 3-trifluoromethylsulfonyl-1-naphthyl group, 4-trifluoromethylsulfonyl-1-naphthyl group,
2-methoxycarbonyl-1-naphthyl group, 3-methoxycarbonyl-1-naphthyl group, 4-methoxycarbonyl-1-naphthyl group,
2-vinyl-1-naphthyl group, 3-vinyl-1-naphthyl group, 4-vinyl-1-naphthyl group,
2- (2 ′, 2′-difluorovinyl) -1-naphthyl group, 3- (2 ′, 2′-difluorovinyl) -1-naphthyl group, 4- (2 ′, 2′-difluorovinyl) -1 A naphthyl group,
2-ethynyl-1-naphthyl group, 3-ethynyl-1-naphthyl group, 4-ethynyl-1-naphthyl group,
2- (2′-fluoroethynyl) -1-naphthyl group, 3- (2′-fluoroethynyl) -1-naphthyl group, 4- (2′-fluoroethynyl) -1-naphthyl group,
2-fluoro-1-naphthyl group, 3-fluoro-1-naphthyl group, 4-fluoro-1-naphthyl group,
“1 or more atoms or groups selected from group C 1 may be included, such as 2-chloro-1-naphthyl group, 3-chloro-1-naphthyl group, 4-chloro-1-naphthyl group, etc. -Naphthyl group ";
2-naphthyl group,
1-cyano-2-naphthyl group, 3-cyano-2-naphthyl group, 4-cyano-2-naphthyl group,
1-nitro-2-naphthyl group, 3-nitro-2-naphthyl group, 4-nitro-2-naphthyl group,
1-carboxyl-2-naphthyl group, 3-carboxyl-2-naphthyl group, 4-carboxyl-2-naphthyl group,
1-hydroxyl-2-naphthyl group, 3-hydroxyl-2-naphthyl group, 4-hydroxyl-2-naphthyl group,
1-methyl-2-naphthyl group, 3-methyl-2-naphthyl group, 4-methyl-2-naphthyl group,
1-trifluoromethyl-2-naphthyl group, 3-trifluoromethyl-2-naphthyl group, 4-trifluoromethyl-2-naphthyl group,
1-methoxy-2-naphthyl group, 3-methoxy-2-naphthyl group, 4-methoxy-2-naphthyl group,
1-trifluoromethoxy-2-naphthyl group, 3-trifluoromethoxy-2-naphthyl group, 4-trifluoromethoxy-2-naphthyl group,
1-trifluoromethylthio-2-naphthyl group, 3-trifluoromethylthio-2-naphthyl group, 4-trifluoromethylthio-2-naphthyl group,
1-trifluoromethylsulfinyl-2-naphthyl group, 3-trifluoromethylsulfinyl-2-naphthyl group, 4-trifluoromethylsulfinyl-2-naphthyl group,
1-trifluoromethylsulfonyl-2-naphthyl group, 3-trifluoromethylsulfonyl-2-naphthyl group, 4-trifluoromethylsulfonyl-2-naphthyl group,
1-methoxycarbonyl-2-naphthyl group, 3-methoxycarbonyl-2-naphthyl group, 4-methoxycarbonyl-2-naphthyl group,
1-vinyl-2-naphthyl group, 3-vinyl-2-naphthyl group, 4-vinyl-2-naphthyl group,
1- (2 ′, 2′-difluorovinyl) -2-naphthyl group, 3- (2 ′, 2′-difluorovinyl) -2-naphthyl group, 4- (2 ′, 2′-difluorovinyl) -2 A naphthyl group,
1-ethynyl-2-naphthyl group, 3-ethynyl-2-naphthyl group, 4-ethynyl-2-naphthyl group,
1- (2′-fluoroethynyl) -2-naphthyl group, 3- (2′-fluoroethynyl) -2-naphthyl group, 4- (2′-fluoroethynyl) -2-naphthyl group,
1-fluoro-2-naphthyl group, 3-fluoro-2-naphthyl group, 4-fluoro-2-naphthyl group,
1-chloro-2-naphthyl group, 3-chloro-2-naphthyl group, 4-chloro-2-naphthyl group, etc., “may have one or more atoms or groups selected from group C 2 -Naphthyl group ";

In the present invention, examples of the “quinolyl group optionally having one or more atoms or groups selected from group C” include a 2-quinolyl group,
5-cyano-2-quinolyl group, 6-cyano-2-quinolyl group, 7-cyano-2-quinolyl group, 8-cyano-2-quinolyl group,
5-nitro-2-quinolyl group, 6-nitro-2-quinolyl group, 7-nitro-2-quinolyl group, 8-nitro-2-quinolyl group,
5-carboxyl-2-quinolyl group, 6-carboxyl-2-quinolyl group, 7-carboxyl-2-quinolyl group, 8-carboxyl-2-quinolyl group,
5-hydroxyl-2-quinolyl group, 6-hydroxyl-2-quinolyl group, 7-hydroxyl-2-quinolyl group, 8-hydroxyl-2-quinolyl group,
5-methyl-2-quinolyl group, 6-methyl-2-quinolyl group, 7-methyl-2-quinolyl group, 8-methyl-2-quinolyl group,
5-trifluoromethyl-2-quinolyl group, 6-trifluoromethyl-2-quinolyl group, 7-trifluoromethyl-2-quinolyl group, 8-trifluoromethyl-2-quinolyl group,
5-methoxy-2-quinolyl group, 6-methoxy-2-quinolyl group, 7-methoxy-2-quinolyl group, 8-methoxy-2-quinolyl group,
5-trifluoromethoxy-2-quinolyl group, 6-trifluoromethoxy-2-quinolyl group, 7-trifluoromethoxy-2-quinolyl group, 8-trifluoromethoxy-2-quinolyl group,
5-methoxycarbonyl-2-quinolyl group, 6-methoxycarbonyl-2-quinolyl group, 7-methoxycarbonyl-2-quinolyl group, 8-methoxycarbonyl-2-quinolyl group,
5-vinyl-2-quinolyl group, 6-vinyl-2-quinolyl group, 7-vinyl-2-quinolyl group, 8-vinyl-2-quinolyl group,
5- (2 ′, 2′-difluorovinyl) -2-quinolyl group, 6- (2 ′, 2′-difluorovinyl) -2-quinolyl group, 7- (2 ′, 2′-difluorovinyl) -2 -Quinolyl group, 8- (2 ', 2'-difluorovinyl) -2-quinolyl group,
5-ethynyl-2-quinolyl group, 6-ethynyl-2-quinolyl group, 7-ethynyl-2-quinolyl group, 8-ethynyl-2-quinolyl group,
5- (2′-fluoroethynyl) -2-quinolyl group, 6- (2′-fluoroethynyl) -2-quinolyl group, 7- (2′-fluoroethynyl) -2-quinolyl group, 8- (2 ′ -Fluoroethynyl) -2-quinolyl group,
5-fluoro-2-quinolyl group, 6-fluoro-2-quinolyl group, 7-fluoro-2-quinolyl group, 8-fluoro-2-quinolyl group, 5,6,7,8-tetrafluoro-2-quinolyl Group,
“One or more atoms selected from group C, such as a 5-chloro-2-quinolyl group, a 6-chloro-2-quinolyl group, a 7-chloro-2-quinolyl group, and an 8-chloro-2-quinolyl group; A 2-quinolyl group optionally having a group ";
3-quinolyl group,
5-cyano-3-quinolyl group, 6-cyano-3-quinolyl group, 7-cyano-3-quinolyl group, 8-cyano-3-quinolyl group,
5-nitro-3-quinolyl group, 6-nitro-3-quinolyl group, 7-nitro-3-quinolyl group, 8-nitro-3-quinolyl group,
5-carboxyl-3-quinolyl group, 6-carboxyl-3-quinolyl group, 7-carboxyl-3-quinolyl group, 8-carboxyl-3-quinolyl group,
5-hydroxyl-3-quinolyl group, 6-hydroxyl-3-quinolyl group, 7-hydroxyl-3-quinolyl group, 8-hydroxyl-3-quinolyl group,
5-methyl-3-quinolyl group, 6-methyl-3-quinolyl group, 7-methyl-3-quinolyl group, 8-methyl-3-quinolyl group,
5-trifluoromethyl-3-quinolyl group, 6-trifluoromethyl-3-quinolyl group, 7-trifluoromethyl-3-quinolyl group, 8-trifluoromethyl-3-quinolyl group,
5-methoxy-3-quinolyl group, 6-methoxy-3-quinolyl group, 7-methoxy-3-quinolyl group, 8-methoxy-3-quinolyl group,
5-trifluoromethoxy-3-quinolyl group, 6-trifluoromethoxy-3-quinolyl group, 7-trifluoromethoxy-3-quinolyl group, 8-trifluoromethoxy-3-quinolyl group,
5-methoxycarbonyl-3-quinolyl group, 6-methoxycarbonyl-3-quinolyl group, 7-methoxycarbonyl-3-quinolyl group, 8-methoxycarbonyl-3-quinolyl group,
5-vinyl-3-quinolyl group, 6-vinyl-3-quinolyl group, 7-vinyl-3-quinolyl group, 8-vinyl-3-quinolyl group,
5- (2 ′, 2′-difluorovinyl) -3-quinolyl group, 6- (2 ′, 2′-difluorovinyl) -3-quinolyl group, 7- (2 ′, 2′-difluorovinyl) -3 -Quinolyl group, 8- (2 ', 2'-difluorovinyl) -3-quinolyl group,
5-ethynyl-3-quinolyl group, 6-ethynyl-3-quinolyl group, 7-ethynyl-3-quinolyl group, 8-ethynyl-3-quinolyl group,
5- (2′-fluoroethynyl) -3-quinolyl group, 6- (2′-fluoroethynyl) -3-quinolyl group, 7- (2′-fluoroethynyl) -3-quinolyl group, 8- (2 ′ -Fluoroethynyl) -3-quinolyl group,
5-fluoro-3-quinolyl group, 6-fluoro-3-quinolyl group, 7-fluoro-3-quinolyl group, 8-fluoro-3-quinolyl group, 5,6,7,8-tetrafluoro-3-quinolyl Group,
“One or more atoms selected from group C, such as a 5-chloro-3-quinolyl group, a 6-chloro-3-quinolyl group, a 7-chloro-3-quinolyl group, and an 8-chloro-3-quinolyl group; A 3-quinolyl group optionally having a group ";
4-quinolyl group, 2-cyano-4-quinolyl group, 3-cyano-4-quinolyl group,
2-nitro-4-quinolyl group, 3-nitro-4-quinolyl group,
2-carboxyl-4-quinolyl group, 3-carboxyl-4-quinolyl group,
2-hydroxyl-4-quinolyl group, 3-hydroxyl-4-quinolyl group,
2-methyl-4-quinolyl group, 3-methyl-4-quinolyl group,
2-trifluoromethyl-4-quinolyl group, 3-trifluoromethyl-4-quinolyl group,
2-methoxy-4-quinolyl group, 3-methoxy-4-quinolyl group,
2-trifluoromethoxy-4-quinolyl group, 3-trifluoromethoxy-4-quinolyl group,
2-methoxycarbonyl-4-quinolyl group, 3-methoxycarbonyl-4-quinolyl group,
2-vinyl-4-quinolyl group, 3-vinyl-4-quinolyl group,
2- (2 ′, 2′-difluorovinyl) -4-quinolyl group, 3- (2 ′, 2′-difluorovinyl) -4-quinolyl group,
2-ethynyl-4-quinolyl group, 3-ethynyl-4-quinolyl group,
2- (2′-fluoroethynyl) -4-quinolyl group, 3- (2′-fluoroethynyl) -4-quinolyl group,
2-fluoro-4-quinolyl group, 3-fluoro-4-quinolyl group,
“4-quinolyl group optionally having one or more atoms or groups selected from group C” such as 2-chloro-4-quinolyl group and 3-chloro-4-quinolyl group;

In the present invention, examples of the “benzofuranyl group optionally having one or more atoms or groups selected from group C” include a 2-benzofuranyl group,
4-cyano-2-benzofuranyl group, 5-cyano-2-benzofuranyl group, 6-cyano-2-benzofuranyl group, 7-cyano-2-benzofuranyl group,
4-nitro-2-benzofuranyl group, 5-nitro-2-benzofuranyl group, 6-nitro-2-benzofuranyl group, 7-nitro-2-benzofuranyl group,
4-carboxyl-2-benzofuranyl group, 5-carboxyl-2-benzofuranyl group, 6-carboxyl-2-benzofuranyl group, 7-carboxyl-2-benzofuranyl group,
4-hydroxyl-2-benzofuranyl group, 5-hydroxyl-2-benzofuranyl group, 6-hydroxyl-2-benzofuranyl group, 7-hydroxyl-2-benzofuranyl group,
4-methyl-2-benzofuranyl group, 5-methyl-2-benzofuranyl group, 6-methyl-2-benzofuranyl group, 7-methyl-2-benzofuranyl group,
4-trifluoromethyl-2-benzofuranyl group, 5-trifluoromethyl-2-benzofuranyl group, 6-trifluoromethyl-2-benzofuranyl group, 7-trifluoromethyl-2-benzofuranyl group,
4-methoxy-2-benzofuranyl group, 5-methoxy-2-benzofuranyl group, 6-methoxy-2-benzofuranyl group, 7-methoxy-2-benzofuranyl group,
4-trifluoromethoxy-2-benzofuranyl group, 5-trifluoromethoxy-2-benzofuranyl group, 6-trifluoromethoxy-2-benzofuranyl group, 7-trifluoromethoxy-2-benzofuranyl group,
4-methoxycarbonyl-2-benzofuranyl group, 5-methoxycarbonyl-2-benzofuranyl group, 6-methoxycarbonyl-2-benzofuranyl group), 7-methoxycarbonyl-2-benzofuranyl group,
4-vinyl-2-benzofuranyl group, 5-vinyl-2-benzofuranyl group, 6-vinyl-2-benzofuranyl group, 7-vinyl-2-benzofuranyl group,
4- (2 ′, 2′-difluorovinyl) -2-benzofuranyl group, 5- (2 ′, 2′-difluorovinyl) -2-benzofuranyl group, 6- (2 ′, 2′-difluorovinyl) -2 -Benzofuranyl group, 7- (2 ', 2'-difluorovinyl) -2-benzofuranyl group,
4-ethynyl-2-benzofuranyl group, 5-ethynyl-2-benzofuranyl group, 6-ethynyl-2-benzofuranyl group, 7-ethynyl-2-benzofuranyl group,
4- (2′-fluoroethynyl) -2-benzofuranyl group, 5- (2′-fluoroethynyl) -2-benzofuranyl group, 6- (2′-fluoroethynyl) -2-benzofuranyl group, 7- (2 ′ -Fluoroethynyl) -2-benzofuranyl group,
4-fluoro-2-benzofuranyl group, 5-fluoro-2-benzofuranyl group, 6-fluoro-2-benzofuranyl group, 7-fluoro-2-benzofuranyl group, 4,5,6,7-tetrafluoro-2-benzofuranyl group Group,
“One or more atoms selected from group C, such as 4-chloro-2-benzofuranyl group, 5-chloro-2-benzofuranyl group, 6-chloro-2-benzofuranyl group, 7-chloro-2-benzofuranyl group, etc. 2- (benzofuranyl group) optionally having a group;
3-benzofuranyl group,
4-cyano-3-benzofuranyl group, 5-cyano-3-benzofuranyl group, 6-cyano-3-benzofuranyl group, 7-cyano-3-benzofuranyl group,
4-nitro-3-benzofuranyl group, 5-nitro-3-benzofuranyl group, 6-nitro-3-benzofuranyl group, 7-nitro-3-benzofuranyl group,
4-carboxyl-3-benzofuranyl group, 5-carboxyl-3-benzofuranyl group, 6-carboxyl-3-benzofuranyl group, 7-carboxyl-3-benzofuranyl group,
4-hydroxyl-3-benzofuranyl group, 5-hydroxyl-3-benzofuranyl group, 6-hydroxyl-3-benzofuranyl group, 7-hydroxyl-3-benzofuranyl group,
4-methyl-3-benzofuranyl group, 5-methyl-3-benzofuranyl group, 6-methyl-3-benzofuranyl group, 7-methyl-3-benzofuranyl group,
4-trifluoromethyl-3-benzofuranyl group, 5-trifluoromethyl-3-benzofuranyl group, 6-trifluoromethyl-3-benzofuranyl group, 7-trifluoromethyl-3-benzofuranyl group,
4-methoxy-3-benzofuranyl group, 5-methoxy-3-benzofuranyl group, 6-methoxy-3-benzofuranyl group, 7-methoxy-3-benzofuranyl group,
4-trifluoromethoxy-3-benzofuranyl group, 5-trifluoromethoxy-3-benzofuranyl group, 6-trifluoromethoxy-3-benzofuranyl group, 7-trifluoromethoxy-3-benzofuranyl group,
4-methoxycarbonyl-3-benzofuranyl group, 5-methoxycarbonyl-3-benzofuranyl group, 6-methoxycarbonyl-3-benzofuranyl group, 7-methoxycarbonyl-3-benzofuranyl group,
4-vinyl-3-benzofuranyl group, 5-vinyl-3-benzofuranyl group, 6-vinyl-3-benzofuranyl group, 7-vinyl-3-benzofuranyl group,
4- (2 ′, 2′-difluorovinyl) -3-benzofuranyl group, 5- (2 ′, 2′-difluorovinyl) -3-benzofuranyl group, 6- (2 ′, 2′-difluorovinyl) -3 -Benzofuranyl group, 7- (2 ', 2'-difluorovinyl) -3-benzofuranyl group,
4-ethynyl-3-benzofuranyl group, 5-ethynyl-3-benzofuranyl group, 6-ethynyl-3-benzofuranyl group, 7-ethynyl-3-benzofuranyl group,
4- (2′-fluoroethynyl) -3-benzofuranyl group, 5- (2′-fluoroethynyl) -3-benzofuranyl group, 6- (2′-fluoroethynyl) -3-benzofuranyl group, 7- (2 ′ -Fluoroethynyl) -3-benzofuranyl group,
4-fluoro-3-benzofuranyl group, 5-fluoro-3-benzofuranyl group, 6-fluoro-3-benzofuranyl group, 7-fluoro-3-benzofuranyl group, 4,5,6,7-tetrafluoro-3-benzofuranyl group Group,
“One or more atoms selected from group C, such as 4-chloro-3-benzofuranyl group, 5-chloro-3-benzofuranyl group, 6-chloro-3-benzofuranyl group, 7-chloro-3-benzofuranyl group, etc. A 3-benzofuranyl group optionally having a group ”.

In the present invention, examples of the “benzothienyl group optionally having one or more atoms or groups selected from group C” include a 2-benzothienyl group,
4-cyano-2-benzothienyl group, 5-cyano-2-benzothienyl group, 6-cyano-2-benzothienyl group, 7-cyano-2-benzothienyl group,
4-nitro-2-benzothienyl group, 5-nitro-2-benzothienyl group, 6-nitro-2-benzothienyl group, 7-nitro-2-benzothienyl group,
4-carboxyl-2-benzothienyl group, 5-carboxyl-2-benzothienyl group, 6-carboxyl-2-benzothienyl group, 7-carboxyl-2-benzothienyl group,
4-hydroxyl-2-benzothienyl group, 5-hydroxyl-2-benzothienyl group, 6-hydroxyl-2-benzothienyl group, 7-hydroxyl-2-benzothienyl group,
4-methyl-2-benzothienyl group, 5-methyl-2-benzothienyl group, 6-methyl-2-benzothienyl group, 7-methyl-2-benzothienyl group,
4-trifluoromethyl-2-benzothienyl group, 5-trifluoromethyl-2-benzothienyl group, 6-trifluoromethyl-2-benzothienyl group, 7-trifluoromethyl-2-benzothienyl group,
4-methoxy-2-benzothienyl group, 5-methoxy-2-benzothienyl group, 6-methoxy-2-benzothienyl group, 7-methoxy-2-benzothienyl group,
4-trifluoromethoxy-2-benzothienyl group, 5-trifluoromethoxy-2-benzothienyl group, 6-trifluoromethoxy-2-benzothienyl group, 7-trifluoromethoxy-2-benzothienyl group,
4-methoxycarbonyl-2-benzothienyl group, 5-methoxycarbonyl-2-benzothienyl group, 6-methoxycarbonyl-2-benzothienyl group, 7-methoxycarbonyl-2-benzothienyl group,
4-vinyl-2-benzothienyl group, 5-vinyl-2-benzothienyl group, 6-vinyl-2-benzothienyl group, 7-vinyl-2-benzothienyl group,
4- (2 ′, 2′-difluorovinyl) -2-benzothienyl group, 5- (2 ′, 2′-difluorovinyl) -2-benzothienyl group, 6- (2 ′, 2′-difluorovinyl) -2-benzothienyl group, 7- (2 ′, 2′-difluorovinyl) -2-benzothienyl group,
4-ethynyl-2-benzothienyl group, 5-ethynyl-2-benzothienyl group, 6-ethynyl-2-benzothienyl group, 7-ethynyl-2-benzothienyl group,
4- (2′-fluoroethynyl) -2-benzothienyl group, 5- (2′-fluoroethynyl) -2-benzothienyl group, 6- (2′-fluoroethynyl) -2-benzothienyl group, 7- (2′-fluoroethynyl) -2-benzothienyl group,
4-fluoro-2-benzothienyl group, 5-fluoro-2-benzothienyl group, 6-fluoro-2-benzothienyl group, 7-fluoro-2-benzothienyl group, 4,5,6,7-tetrafluoro -2-benzothienyl group,
4-chloro-2-benzothienyl group, 5-chloro-2-benzothienyl group, 6-chloro-2-benzothienyl group, 7-chloro-2-benzothienyl group, etc., “one selected from group C 2-benzothienyl group optionally having the above atoms or groups ”;
3-benzothienyl group,
4-cyano-3-benzothienyl group, 5-cyano-3-benzothienyl group, 6-cyano-3-benzothienyl group, 7-cyano-3-benzothienyl group,
4-nitro-3-benzothienyl group, 5-nitro-3-benzothienyl group, 6-nitro-3-benzothienyl group, 7-nitro-3-benzothienyl group,
4-carboxyl-3-benzothienyl group, 5-carboxyl-3-benzothienyl group, 6-carboxyl-3-benzothienyl group, 7-carboxyl-3-benzothienyl group,
4-hydroxyl-3-benzothienyl group, 5-hydroxyl-3-benzothienyl group, 6-hydroxyl-3-benzothienyl group, 7-hydroxyl-3-benzothienyl group,
4-methyl-3-benzothienyl group, 5-methyl-3-benzothienyl group, 6-methyl-3-benzothienyl group, 7-methyl-3-benzothienyl group,
4-trifluoromethyl-3-benzothienyl group, 5-trifluoromethyl-3-benzothienyl group, 6-trifluoromethyl-3-benzothienyl group, 7-trifluoromethyl-3-benzothienyl group,
4-methoxy-3-benzothienyl group, 5-methoxy-3-benzothienyl group, 6-methoxy-3-benzothienyl group, 7-methoxy-3-benzothienyl group,
4-trifluoromethoxy-3-benzothienyl group, 5-trifluoromethoxy-3-benzothienyl group, 6-trifluoromethoxy-3-benzothienyl group, 7-trifluoromethoxy-3-benzothienyl group,
4-methoxycarbonyl-3-benzothienyl group, 5-methoxycarbonyl-3-benzothienyl group, 6-methoxycarbonyl-3-benzothienyl group, 7-methoxycarbonyl-3-benzothienyl group,
4-vinyl-3-benzothienyl group, 5-vinyl-3-benzothienyl group, 6-vinyl-3-benzothienyl group, 7-vinyl-3-benzothienyl group,
4- (2 ′, 2′-difluorovinyl) -3-benzothienyl group, 5- (2 ′, 2′-difluorovinyl) -3-benzothienyl group, 6- (2 ′, 2′-difluorovinyl) -3-benzothienyl group, 7- (2 ', 2'-difluorovinyl) -3-benzothienyl group,
4-ethynyl-3-benzothienyl group, 5-ethynyl-3-benzothienyl group, 6-ethynyl-3-benzothienyl group, 7-ethynyl-3-benzothienyl group,
4- (2′-fluoroethynyl) -3-benzothienyl group, 5- (2′-fluoroethynyl) -3-benzothienyl group, 6- (2′-fluoroethynyl) -3-benzothienyl group, 7- (2′-fluoroethynyl) -3-benzothienyl group,
4-fluoro-3-benzothienyl group, 5-fluoro-3-benzothienyl group, 6-fluoro-3-benzothienyl group, 7-fluoro-3-benzothienyl group, 4,5,6,7-tetrafluoro -3-benzothienyl group,
4-chloro-3-benzothienyl group, 5-chloro-3-benzothienyl group, 6-chloro-3-benzothienyl group, 7-chloro-3-benzothienyl group, etc., "one selected from group C A 3-benzothienyl group optionally having the above atoms or groups ”;
Is mentioned.

In the present invention, examples of the “1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C” include 4- (1,3-benzodioxolanyl). ) Group, 5- (1,3-benzodioxolanyl) group, 4- (2,2-dimethyl-1,3-benzodioxolanyl) group, 5- (2,2-dimethyl-1,3- Benzodioxolanyl) group 4- (2,2-difluoro-1,3-benzodioxolanyl) group, 5- (2,2-difluoro-1,3-benzodioxolanyl) group.

In the present invention, examples of the “1,4-benzodioxanyl group optionally having one or more atoms or groups selected from group C” include 2- (1,4-benzodioxanyl). ) Group, 5- (1,4-benzodioxanyl) group, 6- (1,4-benzodioxanyl) group.

Examples of the “C1-C8 chain hydrocarbon group” in “C1-C8 chain hydrocarbon group having one group selected from group B” include, for example, methyl group, ethyl group, isopropyl group, tert-butyl group Propyl group, sec-butyl group, isobutyl group, 1,1-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1,2,3-trimethylbutyl group, 1-ethylbutyl group, 2 -Ethylbutyl group, pentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1,1-dimethylpentyl group 2,2-dimethylpentyl group, 3,3-dimethylpentyl group, 4,4-dimethylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-propylpentyl group, 2- Propylpentyl, hexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1,1-dimethylhexyl, 2,2-dimethyl Hexyl group, 3,3-dimethylhexyl group, 4,4-dimethylhexyl group, 5,5-dimethylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 4-ethylhexyl group, heptyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 5-methylheptyl group Group, 6-methyl heptyl group, an octyl group, "C1-C8 alkyl group";

Vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2- Propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-1-butenyl group, 2-methyl-1 -Butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-3-butenyl group, 1,1-dimethyl-3-butenyl group, 1,1-dimethyl-2- Butenyl group, 1-ethyl-1-butenyl group, 1-ethyl-2-butenyl group, 1-ethyl-3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-1- Nthenyl group, 1-methyl-2-pentenyl group, 1-methyl-3-pentenyl group, 1-methyl-4-pentenyl group, 2-methyl-1-pentenyl group, 2-methyl-2-pentenyl group, 3- Methyl-2-pentenyl group, 3-methyl-3-pentenyl group, 4-methyl-3-pentenyl group, 4-methyl-4-pentenyl group, 1,1-dimethyl-2-pentenyl group, 1,1-dimethyl -3-pentenyl group, 1,1-dimethyl-4-pentenyl group, 1-ethyl-1-pentenyl group, 1-ethyl-2-pentenyl group, 1-ethyl-3-pentenyl group, 1-ethyl-4- A pentenyl group,
1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-methyl-1-hexenyl group, 1-methyl-2-hexenyl group, 1-methyl-3-hexenyl Group, 1-methyl-4-hexenyl group, 1-methyl-5-hexenyl group, 2-methyl-1-hexenyl group, 2-methyl-2-hexenyl group, 3-methyl-2-hexenyl group, 3-methyl -3-hexenyl group, 4-methyl-3-hexenyl group, 4-methyl-4-hexenyl group, 5-methyl-4-hexenyl group, 5-methyl-5-hexenyl group, 1,1-dimethyl-2- Hexenyl group, 1,1-dimethyl-3-hexenyl group, 1,1-dimethyl-4-hexenyl group, 1,1-dimethyl-5-hexenyl group, 1-ethyl-1-hexenyl group, 1-ethyl- - hexenyl group, 1-ethyl-3-hexenyl group, 1-ethyl-4-hexenyl group, 1-ethyl-5-hexenyl group,
1-heptenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 5-heptenyl group, 6-heptenyl group, 1-methyl-1-heptenyl group, 1-methyl-2-heptenyl group, 1- Methyl-3-heptenyl group, 1-methyl-4-heptenyl group, 1-methyl-5-heptenyl group, 1-methyl-6-heptenyl group, 2-methyl-1-heptenyl group, 2-methyl-2-heptenyl group Group, 3-methyl-2-heptenyl group, 3-methyl-3-heptenyl group, 4-methyl-3-heptenyl group, 4-methyl-4-heptenyl group, 5-methyl-4-heptenyl group, 5-methyl -5-heptenyl group, 6-methyl-5-heptenyl group, 6-methyl-6-heptenyl group,
1-octenyl group, 2-octenyl group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6-octenyl group, 7-octenyl group,
A "C2-C8 alkenyl group" such as;

Ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 1-butynyl group, 2-butynyl Group, 3-butynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2-butynyl group, 1,1-dimethyl-3-butynyl group, 1-ethyl 2-butynyl group, 1-ethyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-pentynyl group, 1-methyl-3- Pentynyl group, 1-methyl-4-pentynyl group, 1,1-dimethyl-2-pentynyl group, 1,1-dimethyl-3-pentynyl group, 1,1-dimethyl-4-pentynyl group, 1-ethyl-2 -Pentini Group, 1-ethyl-3-pentynyl group, 1-ethyl-4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 1-methyl-2 -Hexynyl group, 1-methyl-3-hexynyl group, 1-methyl-4-hexynyl group, 1-methyl-5-hexynyl group, 1,1-dimethyl-2-hexynyl group, 1,1-dimethyl-3- Hexynyl group, 1,1-dimethyl-4-hexynyl group, 1,1-dimethyl-5-hexynyl group, 1-ethyl-2-hexynyl group, 1-ethyl-3-hexynyl group, 1-ethyl-4-hexynyl 1-ethyl-5-hexynyl group, 1-heptynyl group, 2-heptynyl group, 3-heptynyl group, 4-heptynyl group, 5-heptynyl group, 6-heptynyl group, 1-methyl-2-hep Tinyl group, 1-methyl-3-heptynyl group, 1-methyl-4-heptynyl group, 1-methyl-5-heptynyl group, 1-methyl-6-heptynyl group, 1-octynyl group, 2-octynyl group, 3 -Octynyl group, 4-octynyl group, 5-octynyl group, 6-octynyl group, 7-octynyl group,
A “C 2 -C 8 alkynyl group”;
Is mentioned.

In the present invention, examples of the “C2 chain hydrocarbon group” in the “C2 chain hydrocarbon group having one group selected from group B” include an ethyl group, a vinyl group, and an ethynyl group.

In the present invention, the “C2-C5 chain hydrocarbon group” in the “C2-C5 chain hydrocarbon group having one group selected from group B” includes, for example,
Ethyl group, isopropyl group, tert-butyl group, propyl group, sec-butyl group, isobutyl group, 1,1-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group A "C2-C5 alkyl group" such as a group, butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, pentyl group;

Vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2- Propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-1-butenyl group, 2-methyl-1 -Butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-3-butenyl group,
“C2-C5 alkenyl group” such as 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group;

Ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 1-butynyl group, 2-butynyl Group, 3-butynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, etc. A C5 alkynyl group;
Is mentioned.

In the present invention, the “C1-C3 chain hydrocarbon group” in the “C1-C3 chain hydrocarbon group having one group selected from group B or one group selected from group B” For example,
Methyl group, ethyl group, propyl group, vinyl group, 1-propenyl group, 2-propenyl group, ethynyl group, 1-propynyl group, 2-propynyl group,
Is mentioned.

In the present invention, as the “C1-C8 chain hydrocarbon group optionally having one group selected from group B”, for example,

2-pyridylmethyl group, 1- (2′-pyridyl) ethyl group, 2- (2′-pyridyl) ethyl group, 3- (2′-pyridyl) propyl group, 4- (2′-pyridyl) butyl group, 5- (2′-pyridyl) pentyl group, 6- (2′-pyridyl) hexyl group, 7- (2′-pyridyl) heptyl group, 8- (2′-pyridyl) octyl group,

4-cyano-2-pyridylmethyl group, 4-nitro-2-pyridylmethyl group, 4-carboxyl-2-pyridylmethyl group, 4-hydroxyl-2-pyridylmethyl group, 4- (N-methylcarbamoyl) -2 -Pyridylmethyl group, 4- (N, N-dimethylcarbamoyl) -2-pyridylmethyl group, 4-methyl-2-pyridylmethyl group, 4-trifluoromethyl-2-pyridylmethyl group, 4-methoxy-2- Pyridylmethyl group, 4-trifluoromethoxy-2-pyridylmethyl group, 4-methylthio-2-pyridylmethyl group, 4-methylsulfinyl-2-pyridylmethyl group, 4-methylsulfonyl-2-pyridylmethyl group, 4- Methoxycarbonyl-2-pyridylmethyl group, 4-vinyl-2-pyridylmethyl group, 4- (2 ′, 2′-difluorovini ) -2-pyridylmethyl group, 4-ethynyl-2-pyridylmethyl group, 4- (2′-fluoroethynyl) -2-pyridylmethyl group, 4-fluoro-2-pyridylmethyl group, 4-chloro-2- A pyridylmethyl group,

5-cyano-2-pyridylmethyl group, 5-nitro-2-pyridylmethyl group, 5-carboxyl-2-pyridylmethyl group, 5-hydroxyl-2-pyridylmethyl group, 5- (N-methylcarbamoyl) -2 -Pyridylmethyl group, 5- (N, N-dimethylcarbamoyl) -2-pyridylmethyl group, 5-methyl-2-pyridylmethyl group, 5-trifluoromethyl-2-pyridylmethyl group, 5-methoxy-2- Pyridylmethyl group, 5-trifluoromethoxy-2-pyridylmethyl group, 5-methylthio-2-pyridylmethyl group, 5-methylsulfinyl-2-pyridylmethyl group, 5-methylsulfonyl-2-pyridylmethyl group, 5- Methoxycarbonyl-2-pyridylmethyl group, 5-vinyl-2-pyridylmethyl group, 5- (2 ′, 2′-difluorovini ) -2-pyridylmethyl group, 5-ethynyl-2-pyridylmethyl group, 5- (2′-fluoroethynyl) -2-pyridylmethyl group, 5-fluoro-2-pyridylmethyl group, 5-chloro-2- Pyridylmethyl group, 5,5-dichloro-2-pyridylmethyl group,

6-cyano-2-pyridylmethyl group, 6-nitro-2-pyridylmethyl group, 6-carboxyl-2-pyridylmethyl group, 6-hydroxyl-2-pyridylmethyl group, 6- (N-methylcarbamoyl) -2 -Pyridylmethyl group, 6- (N, N-dimethylcarbamoyl) -2-pyridylmethyl group, 6-methyl-2-pyridylmethyl group, 6-trifluoromethyl-2-pyridylmethyl group, 6-methoxy-2- Pyridylmethyl group, 6-trifluoromethoxy-2-pyridylmethyl group, 6-methylthio-2-pyridylmethyl group, 6-methylsulfinyl-2-pyridylmethyl group, 6-methylsulfonyl-2-pyridylmethyl group, 6- Methoxycarbonyl-2-pyridylmethyl group, 6-vinyl-2-pyridylmethyl group, 6- (2 ′, 2′-difluorovini ) -2-pyridylmethyl group, 6-ethynyl-2-pyridylmethyl group, 6- (2′-fluoroethynyl) -2-pyridylmethyl group, 6-fluoro-2-pyridylmethyl group, 6-chloro-2- Pyridylmethyl group, 6,6-dichloro-2-pyridylmethyl group,

3-pyridylmethyl group, 1- (3′-pyridyl) ethyl group, 2- (3′-pyridyl) ethyl group, 3- (3′-pyridyl) propyl group, 4- (3′-pyridyl) butyl group, 5- (3′-pyridyl) pentyl group, 6- (3′-pyridyl) hexyl group, 7- (3′-pyridyl) heptyl group, 8- (3′-pyridyl) octyl group,

5-cyano-3-pyridylmethyl group, 5-nitro-3-pyridylmethyl group, 5-carboxyl-3-pyridylmethyl group, 5-hydroxyl-3-pyridylmethyl group, 5- (N-methylcarbamoyl) -3 -Pyridylmethyl group, 5- (N, N-dimethylcarbamoyl) -3-pyridylmethyl group, 5-methyl-3-pyridylmethyl group, 5-trifluoromethyl-3-pyridylmethyl group, 5-methoxy-3- Pyridylmethyl group, 5-trifluoromethoxy-3-pyridylmethyl group, 5-methylthio-3-pyridylmethyl group, 5-methylsulfinyl-3-pyridylmethyl group, 5-methylsulfonyl-3-pyridylmethyl group, 5- Methoxycarbonyl-3-pyridylmethyl group, 5-vinyl-3-pyridylmethyl group, 5- (2 ′, 2′-difluorovini ) -3-pyridylmethyl group, 5-ethynyl-3-pyridylmethyl group, 5- (2′-fluoroethynyl) -3-pyridylmethyl group, 5-fluoro-3-pyridylmethyl group, 5-chloro-3- A pyridylmethyl group,

6-cyano-3-pyridylmethyl group, 6-nitro-3-pyridylmethyl group, 6-carboxyl-3-pyridylmethyl group, 6-hydroxyl-3-pyridylmethyl group, 6- (N-methylcarbamoyl) -3 -Pyridylmethyl group, 6- (N, N-dimethylcarbamoyl) -3-pyridylmethyl group, 6-methyl-3-pyridylmethyl group, 6-trifluoromethyl-3-pyridylmethyl group, 6-methoxy-3- Pyridylmethyl group, 6-trifluoromethoxy-3-pyridylmethyl group, 6-methylthio-3-pyridylmethyl group, 6-methylsulfinyl-3-pyridylmethyl group, 6-methylsulfonyl-3-pyridylmethyl group, 6- Methoxycarbonyl-3-pyridylmethyl group, 6-vinyl-3-pyridylmethyl group, 6- (2 ′, 2′-difluorovini ) -3-pyridylmethyl group, 6-ethynyl-3-pyridylmethyl group, 6- (2′-fluoroethynyl) -3-pyridylmethyl group, 6-fluoro-3-pyridylmethyl group, 6-chloro-3- A pyridylmethyl group,

4-pyridylmethyl group, 1- (4′-pyridyl) ethyl group, 2- (4′-pyridyl) ethyl group, 3- (4′-pyridyl) propyl group, 4- (4′-pyridyl) butyl group, 5- (4′-pyridyl) pentyl group, 6- (4′-pyridyl) hexyl group, 7- (4′-pyridyl) heptyl group, 8- (4′-pyridyl) octyl group,

2-cyano-4-pyridylmethyl group, 2-nitro-4-pyridylmethyl group, 2-carboxyl-4-pyridylmethyl group, 2-hydroxyl-4-pyridylmethyl group, 2- (N-methylcarbamoyl) -4 -Pyridylmethyl group, 2- (N, N-dimethylcarbamoyl) -4-pyridylmethyl group, 2-methyl-4-pyridylmethyl group, 2-trifluoromethyl-4-pyridylmethyl group, 2-methoxy-4- Pyridylmethyl group, 2-trifluoromethoxy-4-pyridylmethyl group, 2-methylthio-4-pyridylmethyl group, 2-methylsulfinyl-4-pyridylmethyl group, 2-methylsulfonyl-4-pyridylmethyl group, 2- Methoxycarbonyl-4-pyridylmethyl group, 2-vinyl-4-pyridylmethyl group, 2- (2 ′, 2′-difluorovini ) -4-pyridylmethyl group, 2-ethynyl-4-pyridylmethyl group, 2- (2′-fluoroethynyl) -4-pyridylmethyl group, 2-fluoro-4-pyridylmethyl group, 2-chloro-4- A pyridylmethyl group,

6-cyano-4-pyridylmethyl group, 6-nitro-4-pyridylmethyl group, 6-carboxyl-4-pyridylmethyl group, 6-hydroxyl-4-pyridylmethyl group, 6- (N-methylcarbamoyl) -4 -Pyridylmethyl group, 6- (N, N-dimethylcarbamoyl) -4-pyridylmethyl group, 6-methyl-4-pyridylmethyl group, 6-trifluoromethyl-4-pyridylmethyl group, 6-methoxy-4- Pyridylmethyl group, 6-trifluoromethoxy-4-pyridylmethyl group, 6-methylthio-4-pyridylmethyl group, 6-methylsulfinyl-4-pyridylmethyl group, 6-methylsulfonyl-4-pyridylmethyl group, 6- Methoxycarbonyl-4-pyridylmethyl group, 6-vinyl-4-pyridylmethyl group, 6- (2 ′, 2′-difluorovinyl ) -4-pyridylmethyl group, 6-ethynyl-4-pyridylmethyl group, 6- (2′-fluoroethynyl) -4-pyridylmethyl group, 6-fluoro-4-pyridylmethyl group, 6-chloro-4- A pyridylmethyl group,

2-furylmethyl group, 1- (2′-furyl) ethyl group, 2- (2′-furyl) ethyl group, 3- (2′-furyl) propyl group, 4- (2′-furyl) butyl group, 5- (2′-furyl) pentyl group, 6- (2′-furyl) hexyl group, 7- (2′-furyl) heptyl group, 8- (2′-furyl) octyl group,

4-cyano-2-furylmethyl group, 4-nitro-2-furylmethyl group, 4-carboxyl-2-furylmethyl group, 4-hydroxyl-2-furylmethyl group, 4- (N-methylcarbamoyl) -2 -Furylmethyl group, 4- (N, N-dimethylcarbamoyl) -2-furylmethyl group, 4-methyl-2-furylmethyl group, 4-trifluoromethyl-2-furylmethyl group, 4-methoxy-2- Furylmethyl group, 4-trifluoromethoxy-2-furylmethyl group, 4-methylthio-2-furylmethyl group, 4-methylsulfinyl-2-furylmethyl group, 4-methylsulfonyl-2-furylmethyl group, 4- Methoxycarbonyl-2-furylmethyl group, 4-vinyl-2-furylmethyl group, 4- (2 ′, 2′-difluorovinyl) -2-furylmethyl group, 4- Ethynyl-2-furylmethyl group, 4- (2'-fluoro-ethynyl) -2-furylmethyl group, 4-fluoro-2-furylmethyl group, 4-chloro-2-furylmethyl group,

3-furylmethyl group, 1- (3′-furyl) ethyl group, 2- (3′-furyl) ethyl group, 3- (3′-furyl) propyl group, 4- (3′-furyl) butyl group, 5- (3′-furyl) pentyl group, 6- (3′-furyl) hexyl group, 7- (3′-furyl) heptyl group, 8- (3′-furyl) octyl group,

4-cyano-3-furylmethyl group, 4-nitro-3-furylmethyl group, 4-carboxyl-3-furylmethyl group, 4-hydroxyl-3-furylmethyl group, 4- (N-methylcarbamoyl) -3 -Furylmethyl group, 4- (N, N-dimethylcarbamoyl) -3-furylmethyl group, 4-methyl-3-furylmethyl group, 4-trifluoromethyl-3-furylmethyl group, 4-methoxy-3- Furylmethyl group, 4-trifluoromethoxy-3-furylmethyl group, 4-methylthio-3-furylmethyl group, 4-methylsulfinyl-3-furylmethyl group, 4-methylsulfonyl-3-furylmethyl group, 4- Methoxycarbonyl-3-furylmethyl group, 4-vinyl-3-furylmethyl group, 4- (2 ′, 2′-difluorovinyl) -3-furylmethyl group, 4- Ethynyl-3-furylmethyl group, 4- (2'-fluoro-ethynyl) -3-furylmethyl group, 4-fluoro-3-furylmethyl group, 4-chloro-3-furylmethyl group,

2-thienylmethyl group, 1- (2′-thienyl) ethyl group, 2- (2′-thienyl) ethyl group, 3- (2′-thienyl) propyl group, 4- (2′-thienyl) butyl group, 5- (2′-thienyl) pentyl group, 6- (2′-thienyl) hexyl group, 7- (2′-thienyl) heptyl group, 8- (2′-thienyl) octyl group,

4-cyano-2-thienylmethyl group, 4-nitro-2-thienylmethyl group, 4-carboxyl-2-thienylmethyl group, 4-hydroxyl-2-thienylmethyl group, 4- (N-methylcarbamoyl) -2 -Thienylmethyl group, 4- (N, N-dimethylcarbamoyl) -2-thienylmethyl group, 4-methyl-2-thienylmethyl group, 4-trifluoromethyl-2-thienylmethyl group, 4-methoxy-2- Thienylmethyl group, 4-trifluoromethoxy-2-thienylmethyl group, 4-methylthio-2-thienylmethyl group, 4-methylsulfinyl-2-thienylmethyl group, 4-methylsulfonyl-2-thienylmethyl group, 4- Methoxycarbonyl-2-thienylmethyl group, 4-vinyl-2-thienylmethyl group, 4- (2 ′, 2′-difluorovini ) -2-thienylmethyl group, 4-ethynyl-2-thienylmethyl group, 4- (2'-fluoroethynyl) -2-thienylmethyl group, 4-fluoro-2-thienylmethyl group, 4-chloro-2- Thienylmethyl group,

3-thienylmethyl group, 1- (3′-thienyl) ethyl group, 2- (3′-thienyl) ethyl group, 3- (3′-thienyl) propyl group, 4- (3′-thienyl) butyl group, 5- (3′-thienyl) pentyl group, 6- (3′-thienyl) hexyl group, 7- (3′-thienyl) heptyl group, 8- (3′-thienyl) octyl group,

4-cyano-3-thienylmethyl group, 4-nitro-3-thienylmethyl group, 4-carboxyl-3-thienylmethyl group, 4-hydroxyl-3-thienylmethyl group, 4- (N-methylcarbamoyl) -3 -Thienylmethyl group, 4- (N, N-dimethylcarbamoyl) -3-thienylmethyl group, 4-methyl-3-thienylmethyl group, 4-trifluoromethyl-3-thienylmethyl group, 4-methoxy-3- Thienylmethyl group, 4-trifluoromethoxy-3-thienylmethyl group, 4-methylthio-3-thienylmethyl group, 4-methylsulfinyl-3-thienylmethyl group, 4-methylsulfonyl-3-thienylmethyl group, 4- Methoxycarbonyl-3-thienylmethyl group, 4-vinyl-3-thienylmethyl group, 4- (2 ′, 2′-difluorovini ) -3-thienylmethyl group, 4-ethynyl-3-thienylmethyl group, 4- (2'-fluoroethynyl) -3-thienylmethyl group, 4-fluoro-3-thienylmethyl group, 4-chloro-3- Thienylmethyl group,

1-indanylmethyl group, 1-indanylethyl group, 3- (1′-indanyl) propyl group, 4- (1′-indanyl) butyl group, 5- (1′-indanyl) pentyl group, 6- ( 1′-indanyl) hexyl group, 7- (1′-indanyl) heptyl group, 8- (1′-indanyl) octyl group,

2-indanylmethyl group, 2-indanylethyl group, 3- (2′-indanyl) propyl group, 4- (2′-indanyl) butyl group, 5- (2′-indanyl) pentyl group, 6- ( 2′-indanyl) hexyl group, 7- (2′-indanyl) heptyl group, 8- (2′-indanyl) octyl group,

1- (1,2,3,4-tetrahydronaphthyl) methyl group,
1- (1,2,3,4-tetrahydronaphthyl) ethyl group,
3- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] propyl group,
4- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] butyl group,
5- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] pentyl group,
6- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] hexyl group,
7- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] heptyl group,
8- [1 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] octyl group,

2- (1,2,3,4-tetrahydronaphthyl) methyl group,
2- (1,2,3,4-tetrahydronaphthyl) ethyl group,
3- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] propyl group,
4- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] butyl group,
5- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] pentyl group,
6- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] hexyl group,
7- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] heptyl group,
8- [2 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] octyl group,

5- (1,2,3,4-tetrahydronaphthyl) methyl group,
5- (1,2,3,4-tetrahydronaphthyl) ethyl group,
3- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] propyl group,
4- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] butyl group,
5- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] pentyl group,
6- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] hexyl group,
7- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] heptyl group,
8- [5 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] octyl group,

6- (1,2,3,4-tetrahydronaphthyl) methyl group,
6- (1,2,3,4-tetrahydronaphthyl) ethyl group,
3- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] propyl group,
4- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] butyl group,
5- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] pentyl group,
6- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] hexyl group,
7- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] heptyl group,
8- [6 ′-(1 ′, 2 ′, 3 ′, 4′-tetrahydronaphthyl)] octyl group,

1-naphthylmethyl group, 6-cyano-1-naphthylmethyl group, 6-nitro-1-naphthylmethyl group, 6-carboxyl-1-naphthylmethyl group, 6-hydroxyl-1-naphthylmethyl group, 6- (N -Methylcarboamido) -1-naphthylmethyl group, 6- (N, N-dimethylcarboamido) -1-naphthylmethyl group, 6-methyl-1-naphthylmethyl group, 6-trifluoromethyl-1-naphthylmethyl Group, 6-methoxy-1-naphthylmethyl group, 6-trifluoromethoxy-1-naphthylmethyl group, 6-methylthio-1-naphthylmethyl group, 6-methylsulfinyl-1-naphthylmethyl group, 6-methylsulfonyl- 1-naphthylmethyl group, 6-methoxycarbonyl-1-naphthylmethyl group, 6-vinyl-1-naphthylmethyl group, 6- (2 ′, 2′-difluorovinyl) -1-naphthylmethyl group, 6-ethynyl-1-naphthylmethyl group, 6- (2′-fluoroethynyl) -1-naphthylmethyl group, 6-fluoro-1-naphthylmethyl group, 6 -Chloro-1-naphthylmethyl group,
1-naphthylethyl group, 3- (1′-naphthyl) propyl group, 4- (1′-naphthyl) butyl group, 5- (1′-naphthyl) pentyl group, 6- (1′-naphthyl) hexyl group, 7- (1′-naphthyl) heptyl group, 8- (1′-naphthyl) octyl group,

2-naphthylmethyl group, 6-cyano-2-naphthylmethyl group, 6-nitro-2-naphthylmethyl group, 6-carboxyl-2-naphthylmethyl group, 6-hydroxyl-2-naphthylmethyl group, 6- (N -Methylcarboamido) -2-naphthylmethyl group, 6- (N, N-dimethylcarboamido) -2-naphthylmethyl group, 6-methyl-2-naphthylmethyl group, 6-trifluoromethyl-2-naphthylmethyl Group, 6-methoxy-2-naphthylmethyl group, 6-trifluoromethoxy-2-naphthylmethyl group, 6-methylthio-2-naphthylmethyl group, 6-methylsulfinyl-2-naphthylmethyl group, 6-methylsulfonyl- 2-naphthylmethyl group, 6-methoxycarbonyl-2-naphthylmethyl group, 6-vinyl-2-naphthylmethyl group, 6- (2 ′, 2′-difluorovinyl) -2-naphthylmethyl group, 6-ethynyl-2-naphthylmethyl group, 6- (2′-fluoroethynyl) -2-naphthylmethyl group, 6-fluoro-2-naphthylmethyl group, 6 -Chloro-2-naphthylmethyl group,
2-naphthylethyl group, 3- (2′-naphthyl) propyl group, 4- (2′-naphthyl) butyl group, 5- (2′-naphthyl) pentyl group, 6- (2′-naphthyl) hexyl group, 7- (2′-naphthyl) heptyl group, 8- (2′-naphthyl) octyl group,

2-quinolylmethyl group, 2-quinolylethyl group, 3- (2′-quinolyl) propyl group, 4- (2′-quinolyl) butyl group, 5- (2′-quinolyl) pentyl group, 6- (2′-quinolyl) ) Hexyl group, 7- (2′-quinolyl) heptyl group, 8- (2′-quinolyl) octyl group,

3-quinolylmethyl group, 3-quinolylethyl group, 3- (3′-quinolyl) propyl group, 4- (3′-quinolyl) butyl group, 5- (3′-quinolyl) pentyl group, 6- (3′-quinolyl) ) Hexyl group, 7- (3′-quinolyl) heptyl group, 8- (3′-quinolyl) octyl group,

4-quinolylmethyl group, 4-quinolylethyl group, 3- (4′-quinolyl) propyl group, 4- (4′-quinolyl) butyl group, 5- (4′-quinolyl) pentyl group, 6- (4′-quinolyl) ) Hexyl group, 7- (4′-quinolyl) heptyl group, 8- (4′-quinolyl) octyl group,

2-benzofuranylmethyl group, 2-benzofuranylethyl group, 3- (2′-benzofuranyl) propyl group, 4- (2′-benzofuranyl) butyl group, 5- (2′-benzofuranyl) pentyl group, 6 -(2'-benzofuranyl) hexyl group, 7- (2'-benzofuranyl) heptyl group, 8- (2'-benzofuranyl) octyl group,

3-benzofuranylmethyl group, 3-benzofuranylethyl group, 3- (3′-benzofuranyl) propyl group, 4- (3′-benzofuranyl) butyl group, 5- (3′-benzofuranyl) pentyl group, 6 -(3'-benzofuranyl) hexyl group, 7- (3'-benzofuranyl) heptyl group, 8- (3'-benzofuranyl) octyl group,

5-benzofuranylmethyl group, 5-benzofuranylethyl group, 3- (5′-benzofuranyl) propyl group, 4- (5′-benzofuranyl) butyl group, 5- (5′-benzofuranyl) pentyl group, 6 -(5'-benzofuranyl) hexyl group, 7- (5'-benzofuranyl) heptyl group, 8- (5'-benzofuranyl) octyl group,

6-benzofuranylmethyl group, 6-benzofuranylethyl group, 3- (6′-benzofuranyl) propyl group, 4- (6′-benzofuranyl) butyl group, 5- (6′-benzofuranyl) pentyl group, 6 -(6'-benzofuranyl) hexyl group, 7- (6'-benzofuranyl) heptyl group, 8- (6'-benzofuranyl) octyl group,

2-benzothienylmethyl group, 2-benzothienylethyl group, 3- (2′-benzothienyl) propyl group, 4- (2′-benzothienyl) butyl group, 5- (2′-benzothienyl) pentyl group, 6- (2′-benzothienyl) hexyl group, 7- (2′-benzothienyl) heptyl group, 8- (2′-benzothienyl) octyl group,

3-benzothienylmethyl group, 3-benzothienylethyl group, 3- (3′-benzothienyl) propyl group, 4- (3′-benzothienyl) butyl group, 5- (3′-benzothienyl) pentyl group, 6- (3′-benzothienyl) hexyl group, 7- (3′-benzothienyl) heptyl group, 8- (3′-benzothienyl) octyl group,

5-benzothienylmethyl group, 5-benzothienylethyl group, 3- (5′-benzothienyl) propyl group, 4- (5′-benzothienyl) butyl group, 5- (5′-benzothienyl) pentyl group, 6- (5′-benzothienyl) hexyl group, 7- (5′-benzothienyl) heptyl group, 8- (5′-benzothienyl) octyl group,

6-benzofuranylmethyl group, 6-benzothienylethyl group, 3- (6′-benzothienyl) propyl group, 4- (6′-benzothienyl) butyl group, 5- (6′-benzothienyl) pentyl group 6- (6′-benzothienyl) hexyl group, 7- (6′-benzothienyl) heptyl group, 8- (6′-benzothienyl) octyl group,

4- (1,3-benzodioxolanyl) methyl group, 4- (1,3-benzodioxolanyl) ethyl group, 3- [4 ′-(1 ′, 3′-benzodioxolanyl)] propyl Group, 4- [4 ′-(1 ′, 3′-benzodioxolanyl)] butyl group, 5- [4 ′-(1 ′, 3′-benzodioxolanyl)] pentyl group, 6- [4 '-(1', 3'-benzodioxolanyl)] hexyl group, 7- [4 '-(1', 3'-benzodioxolanyl)] heptyl group, 8- [4 '-(1', 3′-benzodioxolanyl)] octyl group,

5- (1,3-benzodioxolanyl) methyl group, 5- (1,3-benzodioxolanyl) ethyl group, 3- [5 ′-(1 ′, 3′-benzodioxolanyl)] propyl Group, 4- [5 ′-(1 ′, 3′-benzodioxolanyl)] butyl group, 5- [5 ′-(1 ′, 3′-benzodioxolanyl)] pentyl group, 6- [5 '-(1', 3'-benzodioxolanyl)] hexyl group, 7- [5 '-(1', 3'-benzodioxolanyl)] heptyl group, 8- [5 '-(1', 3′-benzodioxolanyl)] octyl group,
4- (2,2-dimethyl-1,3-benzodioxolanyl) methyl group, 4- (2,2-dimethyl-1,3-benzodioxolanyl) ethyl group, 3- [4 ′-(2 ', 2'-dimethyl-1', 3'-benzodioxolanyl)] propyl group, 4- [4 '-(2', 2'-dimethyl-1 ', 3'-benzodioxolanyl)] butyl Group, 5- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] pentyl group, 6- [4 ′-(2 ′, 2′-dimethyl-1 ′), 3′-benzodioxolanyl)] hexyl group, 7- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] heptyl group, 8- [4 ′-(2 ', 2'-dimethyl-1', 3'-benzodioxolanyl)] octyl group,

5- (2,2-dimethyl-1,3-benzodioxolanyl) methyl group, 5- (2,2-dimethyl-1,3-benzodioxolanyl) ethyl group, 3- [5 ′-(2 ', 2'-dimethyl-1', 3'-benzodioxolanyl)] propyl group, 4- [5 '-(2', 2'-dimethyl-1 ', 3'-benzodioxolanyl)] butyl 5- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] pentyl group, 6- [5 ′-(2 ′, 2′-dimethyl-1 ′), 3′-benzodioxolanyl)] hexyl group, 7- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] heptyl group, 8- [5 ′-(2 ', 2'-dimethyl-1', 3'-benzodioxolanyl)] octyl group,

4- (2,2-difluoro-1,3-benzodioxolanyl) methyl group, 4- (2,2-difluoro-1,3-benzodioxolanyl) ethyl group, 3- [4 ′-(2 ', 2'-difluoro-1', 3'-benzodioxolanyl)] propyl group, 4- [4 '-(2', 2'-difluoro-1 ', 3'-benzodioxolanyl)] butyl Group, 5- [4 '-(2', 2'-difluoro-1 ', 3'-benzodioxolanyl)] pentyl group, 6- [4'-(2 ', 2'-difluoro-1', 3′-benzodioxolanyl)] hexyl group, 7- [4 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] heptyl group, 8- [4 ′-(2 ', 2'-difluoro-1', 3'-benzodioxolanyl)] octyl group,

5- (2,2-dimethyl-1,3-benzodioxolanyl) methyl group, 5- (2,2-difluoro-1,3-benzodioxolanyl) ethyl group, 3- [5 ′-(2 ', 2'-difluoro-1', 3'-benzodioxolanyl)] propyl group, 4- [5 '-(2', 2'-difluoro-1 ', 3'-benzodioxolanyl)] butyl A 5- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] pentyl group, 6- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] hexyl group, 7- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] heptyl group, 8- [5 ′-(2 ', 2'-difluoro-1', 3'-benzodioxolanyl)] octyl group,

2- (1,4-benzodioxanyl) methyl group, 2- (1,4-benzodioxanyl) ethyl group, 3- [2 ′-(1 ′, 4′-benzodioxanyl)] propyl Group, 4- [2 ′-(1 ′, 4′-benzodioxanyl)] butyl group, 5- [2 ′-(1 ′, 4′-benzodioxanyl)] pentyl group, 6- [2 '-(1', 4'-benzodioxanyl)] hexyl group, 7- [2 '-(1', 4'-benzodioxanyl)] heptyl group, 8- [2 '-(1', 4′-benzodioxanyl)] octyl group,

5- (1,4-benzodioxanyl) methyl group, 5- (1,4-benzodioxanyl) ethyl group, 3- [5 ′-(1 ′, 4′-benzodioxanyl)] propyl Group, 4- [5 ′-(1 ′, 4′-benzodioxanyl)] butyl group, 5- [5 ′-(1 ′, 4′-benzodioxanyl)] pentyl group, 6- [5 '-(1', 4'-benzodioxanyl)] hexyl group, 7- [5 '-(1', 4'-benzodioxanyl)] heptyl group, 8- [5 '-(1', 4′-benzodioxanyl)] octyl group,

6- (1,4-benzodioxanyl) methyl group, 6- (1,4-benzodioxanyl) ethyl group, 3- [6 ′-(1 ′, 4′-benzodioxanyl)] propyl Group, 4- [6 ′-(1 ′, 4′-benzodioxanyl)] butyl group, 5- [6 ′-(1 ′, 4′-benzodioxanyl)] pentyl group, 6- [6 '-(1', 4'-benzodioxanyl)] hexyl group, 7- [6 '-(1', 4'-benzodioxanyl)] heptyl group, 8- [6 '-(1', 4′-benzodioxanyl)] octyl group,
Etc.

In the present invention, as the “C2-C5 chain hydrocarbon group having one group selected from group B”, for example,

1- (2′-pyridyl) ethyl group, 2- (2′-pyridyl) ethyl group, 3- (2′-pyridyl) propyl group, 4- (2′-pyridyl) butyl group, 5- (2′- Pyridyl) pentyl group,

1- (3′-pyridyl) ethyl group, 2- (3′-pyridyl) ethyl group, 3- (3′-pyridyl) propyl group, 4- (3′-pyridyl) butyl group, 5- (3′- Pyridyl) pentyl group,

1- (4′-pyridyl) ethyl group, 2- (4′-pyridyl) ethyl group, 3- (4′-pyridyl) propyl group, 4- (4′-pyridyl) butyl group, 5- (4′- Pyridyl) pentyl group,

1- (2′-furyl) ethyl group, 2- (2′-furyl) ethyl group, 3- (2′-furyl) propyl group, 4- (2′-furyl) butyl group, 5- (2′-) Furyl) pentyl group,

1- (3′-furyl) ethyl group, 2- (3′-furyl) ethyl group, 3- (3′-furyl) propyl group, 4- (3′-furyl) butyl group, 5- (3′-) Furyl) pentyl group,

1- (2′-thienyl) ethyl group, 2- (2′-thienyl) ethyl group, 3- (2′-thienyl) propyl group, 4- (2′-thienyl) butyl group, 5- (2′- Thienyl) pentyl group,

1- (3′-thienyl) ethyl group, 2- (3′-thienyl) ethyl group, 3- (3′-thienyl) propyl group, 4- (3′-thienyl) butyl group, 5- (3′- Thienyl) pentyl group,

1- (1′-naphthyl) ethyl group, 2- (1′-naphthyl) ethyl group, 3- (1′-naphthyl) propyl group, 4- (1′-naphthyl) butyl group, 5- (1′- Naphthyl) pentyl group,

1- (2′-naphthyl) ethyl group, 2- (2′-naphthyl) ethyl group, 3- (2′-naphthyl) propyl group, 4- (2′-naphthyl) butyl group, 5- (2-naphthyl) ) Pentyl group,

1- (2′-quinolyl) ethyl group, 2- (2′-quinolyl) ethyl group, 3- (2′-quinolyl) propyl group, 4- (2′-quinolyl) butyl group, 5- (2′- Quinolyl) pentyl group,

1- (3′-quinolyl) ethyl group, 2- (3′-quinolyl) ethyl group, 3- (3′-quinolyl) propyl group, 4- (3′-quinolyl) butyl group, 5- (3′- Quinolyl) pentyl group,

1- (2′-benzofuranyl) ethyl group, 2- (2′-benzofuranyl) ethyl group, 3- (2′-benzofuranyl) propyl group, 4- (2′-benzofuranyl) butyl group, 5- (2′- Benzofuranyl) pentyl group,

1- (2′-benzothienyl) ethyl group, 2- (2′-benzothienyl) ethyl group, 3- (2′-benzothienyl) propyl group, 4- (2′-benzothienyl) butyl group, 5- (2′-benzothienyl) pentyl group,

1- (3′-benzothienyl) ethyl group, 2- (3′-benzothienyl) ethyl group, 3- (3′-benzothienyl) propyl group, 4- (3′-benzothienyl) butyl group, 5- (3-benzothienyl) pentyl group,

1- [4 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [4 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 3- [4′- (1 ′, 3′-benzodioxolanyl)] propyl group, 4- [4 ′-(1 ′, 3′-benzodioxolanyl)] butyl group, 5- [4 ′-(1 ′, 3 ′) -Benzodioxolanyl)] pentyl group,

1- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3 ′) -Benzodioxolanyl)] ethyl group, 3- [4 '-(2', 2'-dimethyl-1 ', 3'-benzodioxolanyl)] propyl group, 4- [4- (2', 2 '-Dimethyl-1', 3'-benzodioxolanyl)] butyl group, 5- [4- (2 ', 2'-dimethyl-1', 3'-benzodioxolanyl)] pentyl group,

1- [4 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [4 ′-(2 ′, 2′-difluoro-1 ′, 3 ′) -Benzodioxolanyl)] ethyl group, 3- [4 '-(2', 2'-difluoro-1 ', 3'-benzodioxolanyl)] propyl group, 4- [4'-(2 ', 2′-difluoro-1 ′, 3′-benzodioxolanyl)] butyl group, 5- [4 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] pentyl group,

1- [5 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [5 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 3- [5′- (1 ′, 3′-benzodioxolanyl)] propyl group, 4- [5 ′-(1 ′, 3′-benzodioxolanyl)] butyl group, 5- [5 ′-(1 ′, 3 ′) -Benzodioxolanyl)] pentyl group,

1- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3 ′) -Benzodioxolanyl)] ethyl group, 3- [5 '-(2', 2'-dimethyl-1 ', 3'-benzodioxolanyl)] propyl group, 4- [5'-(2 ', 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] butyl group, 5- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] pentyl group,

1- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [5 ′-(2 ′, 2′-difluoro-1 ′, 3 ′) -Benzodioxolanyl)] ethyl group, 3- [5 '-(2', 2'-difluoro-1 ', 3'-benzodioxolanyl)] propyl group, 4- [5'-(2 ', 2′-difluoro-1 ′, 3′-benzodioxolanyl)] butyl group, 5- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] pentyl group,

1- [5 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 2- [5 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 3- [5′- (1 ′, 4′-benzodioxanyl)] propyl group, 4- [5 ′-(1 ′, 4′-benzodioxanyl)] butyl group, 5- [5 ′-(1 ′, 4 ′) -Benzodioxanyl)] pentyl group,

1- [6 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 2- [6 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 3- [6′- (1 ′, 4′-benzodioxanyl)] propyl group, 4- [6 ′-(1 ′, 4′-benzodioxanyl)] butyl group, 5- [6 ′-(1 ′, 4 ′) -Benzodioxanyl)] pentyl group,
Etc.

In the present invention, the “ethyl group or ethenyl group having one group selected from group B at the 2-position” includes, for example,
2- (2′-pyridyl) ethyl group, 2- (3′-pyridyl) ethyl group, 2- (4′-pyridyl) ethyl group,
2- (2′-furyl) ethyl group, 2- (3′-furyl) ethyl group,
2- (2′-thienyl) ethyl group, 2- (3′-thienyl) ethyl group,
2- (2′-pyridyl) ethenyl group, 2- (3′-pyridyl) ethenyl group, 2- (4′-pyridyl) ethenyl group,
2- (2′-furyl) ethenyl group, 2- (3′-furyl) ethenyl group,
2- (2′-thienyl) ethenyl group, 2- (3′-thienyl) ethenyl group,
Etc.

In the present invention, the “C2 chain hydrocarbon group having one group selected from group B” includes, for example,
1- (2′-pyridyl) ethyl group, 1- (3′-pyridyl) ethyl group, 1- (4′-pyridyl) ethyl group,
1- (2′-furyl) ethyl group, 1- (3′-furyl) ethyl group,
1- (2′-thienyl) ethyl group, 1- (3′-thienyl) ethyl group,
1- (2′-pyridyl) ethenyl group, 1- (3′-pyridyl) ethenyl group, 1- (4′-pyridyl) ethenyl group,
1- (2′-furyl) ethenyl group, 1- (3′-furyl) ethenyl group,
1- (2′-thienyl) ethenyl group, 1- (3′-thienyl) ethenyl group,
2- (2′-pyridyl) ethyl group, 2- (3′-pyridyl) ethyl group, 2- (4′-pyridyl) ethyl group,
2- (2′-furyl) ethyl group, 2- (3′-furyl) ethyl group,
2- (2′-thienyl) ethyl group, 2- (3′-thienyl) ethyl group,
2- (2′-pyridyl) ethenyl group, 2- (3′-pyridyl) ethenyl group, 2- (4′-pyridyl) ethenyl group,
2- (2′-furyl) ethenyl group, 2- (3′-furyl) ethenyl group,
2- (2′-thienyl) ethenyl group, 2- (3′-thienyl) ethenyl group,
Etc.

In the present invention, the “C1-C3 chain hydrocarbon group having one group selected from group B” includes, for example,

2-pyridylmethyl group, 1- (2'-pyridyl) ethyl group, 2- (2'-pyridyl) ethyl group, 3- (2'-pyridyl) propyl group,

3-pyridylmethyl group, 1- (3'-pyridyl) ethyl group, 2- (3'-pyridyl) ethyl group, 3- (3'-pyridyl) propyl group,

4-pyridylmethyl group, 1- (4′-pyridyl) ethyl group, 2- (4′-pyridyl) ethyl group, 3- (4′-pyridyl) propyl group, 4- (4′-pyridyl) butyl group, 5- (4′-pyridyl) pentyl group,

2-furylmethyl group, 1- (2'-furyl) ethyl group, 2- (2'-furyl) ethyl group, 3- (2'-furyl) propyl group,

3-furylmethyl group, 1- (3'-furyl) ethyl group, 2- (3'-furyl) ethyl group, 3- (3'-furyl) propyl group,

2-thienylmethyl group, 1- (2'-thienyl) ethyl group, 2- (2'-thienyl) ethyl group, 3- (2'-thienyl) propyl group,

3-thienylmethyl group, 1- (3'-thienyl) ethyl group, 2- (3'-thienyl) ethyl group, 3- (3'-thienyl) propyl group,

1-naphthylmethyl group, 1- (1'-naphthyl) ethyl group, 2- (1'-naphthyl) ethyl group, 3- (1'-naphthyl) propyl group,

2-naphthylmethyl group, 1- (2'-naphthyl) ethyl group, 2- (2'-naphthyl) ethyl group, 3- (2-naphthyl) propyl group

2-quinolylmethyl group, 1- (2'-quinolyl) ethyl group, 2- (2'-quinolyl) ethyl group, 3- (2'-quinolyl) propyl group,

3-quinolylmethyl group, 1- (3'-quinolyl) ethyl group, 2- (3'-quinolyl) ethyl group, 3- (3'-quinolyl) propyl group,

(2-benzofuranyl) methyl group, 1- (2'-benzofuranyl) ethyl group, 2- (2'-benzofuranyl) ethyl group, 3- (2'-benzofuranyl) propyl group,

(2-benzothienyl) methyl group, 1- (2'-benzothienyl) ethyl group, 2- (2'-benzothienyl) ethyl group, 3- (2'-benzothienyl) propyl group,

(3-benzothienyl) methyl group, 1- (3'-benzothienyl) ethyl group, 2- (3'-benzothienyl) ethyl group, 3- (3'-benzothienyl) propyl group,

4- (1,3-benzodioxolanyl) methyl group, 1- [4 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [4 ′-(1 ′, 3′-) Benzodioxolanyl)] ethyl group, 3- [4 ′-(1 ′, 3′-benzodioxolanyl)] propyl group,

4- (2,2-dimethyl-1,3-benzodioxolanyl) methyl group, 1- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group 2- [4 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group, 3-4 ′-(2 ′, 2′-dimethyl-1 ′, 3 ′ -Benzodioxolanyl)] propyl group,

4- (2,2-difluoro-1,3-benzodioxolanyl) methyl group, 1- [4 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group 2- [4 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group, 3- [4 ′-(2 ′, 2′-difluoro-1 ′, 3) '-Benzodioxolanyl)] propyl group,

5- (1,3-benzodioxolanyl) methyl group, 1- [5 ′-(1 ′, 3′-benzodioxolanyl)] ethyl group, 2- [5 ′-(1 ′, 3′-) Benzodioxolanyl)] ethyl group, 3- [5 ′-(1 ′, 3′-benzodioxolanyl)] propyl group,

5- (2,2-dimethyl-1,3-benzodioxolanyl) methyl group, 1- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group 2- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3′-benzodioxolanyl)] ethyl group, 3- [5 ′-(2 ′, 2′-dimethyl-1 ′, 3) '-Benzodioxolanyl)] propyl group,

5- (2,2-difluoro-1,3-benzodioxolanyl) methyl group, 1- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group 2- [5 ′-(2 ′, 2′-difluoro-1 ′, 3′-benzodioxolanyl)] ethyl group, 3- [5 ′-(2 ′, 2′-difluoro-1 ′, 3) '-Benzodioxolanyl)] propyl group,

5- (1,4-benzodioxanyl) methyl group, 1- [5 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 2- [5 ′-(1 ′, 4′-) Benzodioxanyl)] ethyl group, 3- [5 ′-(1 ′, 4′-benzodioxanyl)] propyl group,

6- (1,4-benzodioxanyl) methyl group, 1- [6 ′-(1 ′, 4′-benzodioxanyl)] ethyl group, 2- [6 ′-(1 ′, 4′-) Benzodioxanyl)] ethyl group, 3- [6 ′-(1 ′, 4′-benzodioxanyl)] propyl group,
Etc.

Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 3).

〔式中、Ｌは塩素原子、臭素原子またはヨウ素原子を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ、ｍ及びｎは［１］と同じ意味を表す。〕
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、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の無機塩類、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン等の第３級アミン類及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素、トルエン、キシレン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素、酢酸エチル、酢酸ブチル等のエステル、アセトニトリル、ブチロニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、ジメチルスルホキシド等のスルホキシド、水及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−２０〜１００℃の範囲である。
式（１）で示される化合物と、式（２）で示される化合物の使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、具体的には式（１）で示される化合物１モルに対して、式（２）で示される化合物が０．５〜３モルの割合である。
塩基は、式（１）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、本発明化合物を単離することができる。また単離された本発明化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Production method 1)
The compound of the present invention can be produced by reacting the compound represented by the formula (1) with the compound represented by the formula (2) in the presence of a base.

[Wherein, L represents a chlorine atom, a bromine atom or an iodine atom, and R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z, m and n represent the same meaning as [1]. ]
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 inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, Examples thereof include tertiary amines such as 1,5-diazabicyclo [4.3.0] non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane and octane, and aromatic carbonization such as toluene and xylene. Examples include hydrogen, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, water, and mixtures thereof. It is done.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of -20 to 100 ° C.
The use molar ratio of the compound represented by the formula (1) and the compound represented by the formula (2) can be arbitrarily set, but is preferably equimolar or a ratio close thereto, specifically represented by the formula (1). The compound shown by Formula (2) is a ratio of 0.5-3 mol with respect to 1 mol of compounds.
The base is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (1).
After completion of the reaction, the compound of the present invention can be isolated by adding the reaction mixture to water and then subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound of the present invention can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ、ｍ及びｎは［１］と同じ意味を表す。〕
反応は、通常縮合剤の存在下、必要に応じて塩基の存在下、溶媒中で行なわれる。
反応に用いられる縮合剤としては、例えば、ジシクロヘキシルカルボジイミド及び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及び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ホスフェートが挙げられる。
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、炭酸ナトリウム、炭酸カリウム等の炭酸塩、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、及び酢酸エチル、酢酸ブチル等のエステル及びこれらの混合物が挙げられる。
反応は、さらに必要に応じて式（３）で示される化合物１モルに対して、通常は０．０１モル〜１モルまで任意の割合、好ましくは０．０５モル〜０．２モルの割合の１−ヒドロキシベンゾトリアゾール、１−ヒドロキシ−７−アザベンゾトリアゾール、Ｎ−ヒドロキシコハク酸イミド等の存在下、行われる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−２０℃〜１００℃（但し、使用する溶媒の沸点が１００℃未満の場合には、−２０℃〜溶媒の沸点）の範囲である。
式（３）で示される化合物と、式（２）で示される化合物との使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、例えば式（３）で示される化合物１モルに対して式（２）で示される化合物が１モル〜３モルの割合である。
縮合剤は、式（３）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
塩基は、式（３）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、本発明合物を単離することができる。また単離された本発明化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Production method 2)
The compound of the present invention can be produced by reacting the compound represented by the formula (3) with the compound represented by the formula (2) in the presence of a condensing agent.

[Wherein R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z, m, and n represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in the presence of a condensing agent and optionally in the presence of a base.
Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate. .
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0]. There may be mentioned tertiary amines such as undec-7-ene and 1,5-diazabicyclo [4.3.0] non-5-ene, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, and chlorobenzene, Examples include acid amides such as N, N-dimethylformamide, esters such as ethyl acetate and butyl acetate, and mixtures thereof.
The reaction may be carried out at an optional ratio, usually from 0.01 mol to 1 mol, preferably from 0.05 mol to 0.2 mol, per 1 mol of the compound represented by formula (3), if necessary. The reaction is carried out in the presence of 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide and the like.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of −20 ° C. to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
The molar ratio of the compound represented by the formula (3) and the compound represented by the formula (2) can be arbitrarily set, but is preferably equimolar or a ratio close thereto, for example, the compound 1 represented by the formula (3) The compound represented by Formula (2) is 1 mol-3 mol with respect to mol.
The condensing agent is usually used in an arbitrary ratio from 1 mol to an excess amount, and preferably in a ratio of 1 mol to 3 mol, with respect to 1 mol of the compound represented by the formula (3).
The base is usually used in an arbitrary ratio from 1 mol to an excess amount, and preferably in a ratio of 1 mol to 3 mol, with respect to 1 mol of the compound represented by the formula (3).
After completion of the reaction, the compound of the present invention can be isolated by adding the reaction mixture to water and then subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound of the present invention can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｘ^１、Ｘ^２、Ｘ^３及びｎは前記と同じ意味を表し、Ｚ^１は群Ｂより選ばれる１個の基を表し、Ｚ^２は群Ｂより選ばれる１個の基を２位に有するエチル基またはエテニル基表す。〕
反応は、通常水素雰囲気下、水素化触媒の存在下、溶媒中で行なわれる。
反応に用いられる水素化触媒としては、例えばパラジウム−炭素、リンドラー触媒、ロジウムトリス（トリフェニルホスフィン）クロリド（ウィルキンソン触媒）、酸化白金(IV)水和物（アダムス触媒）等の遷移金属化合物が挙げられる。
反応に用いられる溶媒としては、例えばメタノール、エタノール、プロパノール等のアルコール、１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、トルエン、キシレン等の芳香族炭化水素、酢酸エチル、酢酸ブチル等のエステル、酢酸などの有機酸及びこれらの混合物が挙げられる。
反応は通常１〜１００気圧の水素雰囲気下で行われる。
反応の反応時間は、通常、５分〜２４時間の範囲である。
反応の反応温度は、通常、−２０〜１００℃（但し、使用する溶媒の沸点が１００℃未満の場合には、−２０℃〜溶媒の沸点）の範囲である。
反応に用いられる水素化触媒は、式（４）で示される化合物に対して通常０．０５ｗ／ｗ〜０．５ｗ／ｗの割合で使用される。
反応終了後は、反応混合物をろ過してから、濃縮する等の通常の後処理操作を施すことにより、本発明化合物を単離することができる。また単離された本発明化合物はクロマトグラフィ−、再結晶、蒸留等の操作によって精製することもできる。 (Production method 3)
Among the compounds of the present invention, a compound in which Y is a single bond, m is 0, and Z is an ethyl group or ethenyl group having one group selected from group B is a compound represented by the formula (4) Can be produced by subjecting to a reduction reaction.

[Wherein, X ¹ , X ² , X ³ and n represent the same meaning as described above, Z ¹ represents ^one group selected from group B, and Z ² represents one group selected from group B. Represents an ethyl group or an ethenyl group at the 2-position. ]
The reaction is usually carried out in a solvent in the presence of a hydrogenation catalyst under a hydrogen atmosphere.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium-carbon, Lindlar catalyst, rhodium tris (triphenylphosphine) chloride (Wilkinson catalyst), and platinum (IV) oxide hydrate (Adams catalyst). It is done.
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol and propanol, 1,4-dioxane, tetrahydrofuran, ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether, aromatic hydrocarbons such as toluene and xylene, and acetic acid. Examples thereof include esters such as ethyl and butyl acetate, organic acids such as acetic acid, and mixtures thereof.
The reaction is usually carried out in a hydrogen atmosphere at 1 to 100 atmospheres.
The reaction time of the reaction is usually in the range of 5 minutes to 24 hours.
The reaction temperature is usually in the range of −20 to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
The hydrogenation catalyst used for reaction is normally used in the ratio of 0.05 w / w-0.5 w / w with respect to the compound shown by Formula (4).
After completion of the reaction, the compound of the present invention can be isolated by subjecting the reaction mixture to normal post-treatment operations such as concentration and the like. The isolated compound of the present invention can also be purified by operations such as chromatography, recrystallization and distillation.

Next, the manufacturing method of the intermediate body used for manufacture of this invention compound is demonstrated.

〔式中、Ｌは塩素原子、臭素原子またはヨウ素原子を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、溶媒の存在下行われる。
反応に用いられるハロゲン化剤としては、例えば塩化チオニル、塩化オキサリル及びオキシ塩化リンが挙げられる。
反応に用いられる溶媒としては、例えば酢酸メチル、酢酸エチル等のエステル、１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、ヘキサン、ヘプタン等の脂肪族炭化水素、トルエン、キシレン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜２４時間の範囲である。
反応温度は、通常、０℃〜１００℃の範囲である。
ハロゲン化剤は、式（５）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜５モルの割合で使用される。
反応は、さらに必要に応じて式（５）で示される化合物１モルに対して、０．００１モル〜０．５モル、好ましくは０．０１モル〜０．１モルのＮ，Ｎ−ジメチルホルムアミド等の存在下、行われる。
反応終了後は、反応混合物をそのまま濃縮する等の後処理操作を行うことにより、式（１）で示される化合物を単離することができる。単離された式（１）で示される化合物は、通常精製することなく次の工程の反応に用いられるが、必要により蒸留等により精製することができる。 (Reference production method 1)
The compound represented by the formula (1) can be produced by reacting the compound represented by the formula (5) with a halogenating agent.

[Wherein, L represents a chlorine atom, a bromine atom or an iodine atom, and R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z and m represent the same meaning as [1]. ]
The reaction is usually carried out in the presence of a solvent under an inert gas atmosphere such as nitrogen.
Examples of the halogenating agent used in the reaction include thionyl chloride, oxalyl chloride, and phosphorus oxychloride.
Examples of the solvent used for the reaction include esters such as methyl acetate and ethyl acetate, ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane and heptane, toluene , Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, and mixtures thereof.
The reaction time is usually in the range of 5 minutes to 24 hours.
The reaction temperature is usually in the range of 0 ° C to 100 ° C.
The halogenating agent is generally used in an arbitrary ratio from 1 mol to an excess amount, and preferably in a ratio of 1 mol to 5 mol, with respect to 1 mol of the compound represented by the formula (5).
If necessary, the reaction is further performed in an amount of 0.001 mol to 0.5 mol, preferably 0.01 mol to 0.1 mol of N, N-dimethylformamide with respect to 1 mol of the compound represented by formula (5). Etc. in the presence of
After completion of the reaction, the compound represented by the formula (1) can be isolated by performing post-treatment operations such as concentrating the reaction mixture as it is. The isolated compound represented by the formula (1) is usually used for the reaction in the next step without purification, but can be purified by distillation or the like if necessary.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ及びｍは［１］と同じ意味を表す。〕
反応は、塩基の存在下、水及び有機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、水酸化リチウム、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、カリウム−ｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシドが挙げられる。
反応に用いられる溶媒としては例えば、１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、トルエン、キシレン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素、アセトニトリル、ブチロニトリル等のニトリル、メタノール、エタノール、プロパノール等のアルコール及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、０℃〜１００℃の範囲である。
塩基は、式（６）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜５モルの割合で使用される。
反応終了後は、反応混合物に塩酸等の酸性の水溶液を加えて中和し、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（５）で示される化合物を単離することができる。単離された式（５）で示される化合物は、クロマトグラフィー、再結晶、蒸留等によりさらに精製することもできるが、そのまま次の工程に用いることもできる。 (Reference production method 2)
The compound represented by the formula (5) can be produced by subjecting the compound represented by the formula (6) to a hydrolysis reaction in the presence of a base.

[Wherein, R ^a represents a methyl group or an ethyl group, and R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z and m represent the same meaning as [1]. ]
The reaction is performed in the presence of a base and water and an organic solvent.
Examples of the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkali metal alkoxides such as potassium tert-butoxide.
Examples of the solvent used in the reaction include 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ethers such as tert-butyl methyl ether, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, acetonitrile, Examples include nitriles such as butyronitrile, alcohols such as methanol, ethanol, and propanol, and mixtures thereof.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of 0 ° C to 100 ° C.
The base is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 5 mol, per 1 mol of the compound represented by the formula (6).
After completion of the reaction, the reaction mixture is neutralized by adding an acidic aqueous solution such as hydrochloric acid, and then subjected to usual post-treatment operations such as organic solvent extraction and concentration, to isolate the compound represented by the formula (5). be able to. The isolated compound represented by the formula (5) can be further purified by chromatography, recrystallization, distillation or the like, but can also be used in the next step as it is.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｗは脱離基（例えば塩素、臭素、ヨウ素、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基またはｐ−トルエンスルホニルオキシ基等）を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、塩基の存在下、溶媒中で行われる。
反応に用いられる塩基としては、例えば、ナトリウム、カリウム等のアルカリ金属、ｎ−ブチルリチウム等のアルキルリチウム類、水素化ナトリウム、水素化カリウム等の金属水素化合物、炭酸ナトリウム、炭酸カリウム等の炭酸塩、カリウム−ｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、１，４−ジオキサン、テトラヒドロフラン
、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等のエーテル
、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素、トルエン、キシレン等の芳香族炭化水素、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、アセトニトリル、ブチロニトリル等のニトリル、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−４０〜１００℃の範囲である。
式（７）で示される化合物と、式（８）で示される化合物の使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、具体的には式（７）で示される化合物１モルに対して、式（８）で示される化合物が０．５〜３モルの割合である。
塩基は、式（７）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（６）で示される化合物を単離することができる。また単離された式（６）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 3)
The compound represented by formula (6) can be produced by reacting the compound represented by formula (7) with the compound represented by formula (8) in the presence of a base.

[Wherein, R ^a represents a methyl group or an ethyl group, W represents a leaving group (for example, chlorine, bromine, iodine, methanesulfonyloxy group, trifluoromethanesulfonyloxy group, p-toluenesulfonyloxy group, etc.), R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z and m represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in the presence of a base under an inert gas atmosphere such as nitrogen.
Examples of the base used in the reaction include alkali metals such as sodium and potassium, alkyllithiums such as n-butyllithium, metal hydrides such as sodium hydride and potassium hydride, carbonates such as sodium carbonate and potassium carbonate , Alkali metal alkoxides such as potassium tert-butoxide, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4.3.0] nona-5 And tertiary amines such as -ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof Can be mentioned.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of -40 to 100 ° C.
The molar ratio of the compound represented by the formula (7) and the compound represented by the formula (8) can be arbitrarily set, but is preferably equimolar or a ratio close thereto, specifically represented by the formula (7). The compound shown by Formula (8) is a ratio of 0.5-3 mol with respect to 1 mol of compounds.
The base is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 3 mol, per 1 mol of the compound represented by the formula (7).
After completion of the reaction, the compound represented by the formula (6) can be isolated by adding the reaction mixture to water and subjecting it to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound represented by the formula (6) can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｗ^ａは脱離基（例えば、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基またはｐ−トルエンスルホニルオキシ基等）を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、塩基の存在下、溶媒中で行われる。
反応に用いられるスルホニル化剤としては、例えば塩化メタンスルホニル、塩化トリフルオロメタンスルホニル、塩化ｐ−トルエンスルホニル及びトリフルオロメタンスルホン酸無水物等が挙げられる。
反応に用いられる塩基としては、例えば、炭酸ナトリウム、炭酸カリウム等の炭酸塩、カリウム−ｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、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、クロロベンゼン等のハロゲン化炭化水素、酢酸エチル、酢酸ブチル等のエステル、アセトニトリル、ブチロニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−４０〜１００℃の範囲である。
スルホニル化剤は、式（９）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜３モルの割合で使用される。
塩基は、式（９）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（７−ａ）で示される化合物を単離することができる。また単離された式（７−ａ）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 4)
The compound represented by the formula (7-a) can be produced by reacting the compound represented by the formula (9) with a sulfonylating agent in the presence of a base.

[Wherein, R ^a represents a methyl group or an ethyl group, W ^a represents ^a leaving group (for example, methanesulfonyloxy group, trifluoromethanesulfonyloxy group, p-toluenesulfonyloxy group, etc.), R ⁴ , R ⁵ , X ¹ , X ² , X ³ and m represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in the presence of a base under an inert gas atmosphere such as nitrogen.
Examples of the sulfonylating agent used in the reaction include methanesulfonyl chloride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride, trifluoromethanesulfonic anhydride, and the like.
Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, alkali metal alkoxides such as potassium tert-butoxide, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undeca- Examples thereof include tertiary amines such as 7-ene and 1,5-diazabicyclo [4.3.0] non-5-ene, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, 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 and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof Is mentioned.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of -40 to 100 ° C.
The sulfonylating agent is generally used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 3 mol, per 1 mol of the compound represented by the formula (9).
The base is generally used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 3 mol, per 1 mol of the compound represented by the formula (9).
After completion of the reaction, the compound represented by the formula (7-a) can be isolated by adding the reaction mixture to water and subjecting it to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound represented by the formula (7-a) can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｗ^ｂは脱離基（例えば塩素、臭素またはヨウ素等）を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３及びｍは［１］と同じ意味を表す。〕
ハロゲン化反応としては例えば、
（１）塩化チオニル、オキシ塩化リン等を用いる方法
（２）ホスフィン存在下、ハロゲン化剤を用いる方法が挙げられる。
一例として、ホスフィン存在下、ハロゲン化剤を用いる方法を具体的に挙げる。
該反応は、通常窒素等の不活性気体雰囲気下、ホスフィンの存在下、必要に応じて塩基の存在下、溶媒中で行われる。
該反応に用いられるハロゲン化剤としては、例えば、ヨウ素、四臭化炭素及び四塩化炭素等が挙げられる。
反応に用いられるホスフィンとしては、例えば、トリブチルホスフィン、トリフェニルホスフィン等が挙げられる。
反応に用いられる塩基としては、例えば、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノン−５−エン等の第３級アミン及びイミダゾール、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が挙げられる。
反応に用いられる溶媒としては、例えば、１，４−ジオキサン、テトラヒドロフラン、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、トルエン、キシレン等の芳香族炭化水素、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、酢酸エチル、酢酸ブチル等のエステル、アセトニトリル、ブチロニトリル等のニトリル及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−２０〜１００℃の範囲である。
ハロゲン化剤は、式（９）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜５モルの割合で使用される。
必要に応じて用いられる塩基は、式（９）で示される化合物１モルに対して、通常は０．０１モルから過剰量まで任意の割合、好ましくは１〜５モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（７−ｂ）で示される化合物を単離することができる。また単離された式（７−ｂ）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 5)
The compound represented by the formula (7-b) can be produced by subjecting the compound represented by the formula (9) to a halogenation reaction.

[Wherein, R ^a represents a methyl group or an ethyl group, W ^b represents a leaving group (eg, chlorine, bromine, iodine, etc.), and R ⁴ , R ⁵ , X ¹ , X ² , X ³ and m represent It represents the same meaning as [1]. ]
Examples of the halogenation reaction include:
(1) Method using thionyl chloride, phosphorus oxychloride, etc. (2) A method using a halogenating agent in the presence of phosphine can be mentioned.
A specific example is a method using a halogenating agent in the presence of phosphine.
The reaction is usually carried out in a solvent in an inert gas atmosphere such as nitrogen, in the presence of phosphine, and optionally in the presence of a base.
Examples of the halogenating agent used in the reaction include iodine, carbon tetrabromide, carbon tetrachloride, and the like.
Examples of the phosphine used in the reaction include tributylphosphine and triphenylphosphine.
Examples of the base used in the reaction include triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4.3.0] non-5-ene. And nitrogen-containing aromatic compounds such as imidazole, pyridine, 4-dimethylaminopyridine and the like.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, 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, nitriles such as acetonitrile and butyronitrile, and mixtures thereof.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of -20 to 100 ° C.
The halogenating agent is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (9).
The base used as necessary is usually used in an arbitrary ratio from 0.01 mol to an excess amount, preferably in a ratio of 1 to 5 mol, with respect to 1 mol of the compound represented by the formula (9).
After completion of the reaction, the compound represented by the formula (7-b) can be isolated by adding the reaction mixture to water and subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound represented by the formula (7-b) can also be purified by procedures such as chromatography, recrystallization and distillation.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｗ^ｂは塩素原子、臭素原子またはヨウ素原子を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２及びＸ^３は［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、ラジカル開始剤の存在下、溶媒中で行われる。
反応に用いられるハロゲン化剤としては、例えば、臭素、ヨウ素、Ｎ−クロロコハク酸イミド、Ｎ−ブロモコハク酸イミド、Ｎ−ヨードコハク酸イミド等が挙げられる。
反応に用いられるラジカル開始剤としては、例えば、過酸化ベンゾイル、アゾビスイソブチロニトリル、ｔｅｒｔ−ブチルペルオキシド等が挙げられる。
反応に用いられる溶媒としては、例えば、１，４−ジオキサン、テトラヒドロフラン、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等のエーテル、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素、ベンゼン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素、アセトニトリル、ブチロニトリル等のニトリル及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、０〜１００℃の範囲である。
ハロゲン化剤は、式（１０−ａ）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜５モルの割合で使用される。
ラジカル開始剤は、式（１０−ａ）で示される化合物１モルに対して、通常は０．０１モルから過剰量まで任意の割合、好ましくは０．１〜１モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（７−ｃ）で示される化合物を単離することができる。また単離された式（７−ｃ）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 6)
The compound represented by the formula (7-c) can be produced by reacting the compound represented by the formula (10-a) with a halogenating agent in the presence of a radical initiator.

[Wherein, R ^a represents a methyl group or an ethyl group, W ^b represents a chlorine atom, a bromine atom or an iodine atom, and R ⁴ , R ⁵ , X ¹ , X ² and X ³ have the same meaning as [1]. Represents. ]
The reaction is usually carried out in a solvent in the presence of a radical initiator under an inert gas atmosphere such as nitrogen.
Examples of the halogenating agent used in the reaction include bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and the like.
Examples of the radical initiator used in the reaction include benzoyl peroxide, azobisisobutyronitrile, tert-butyl peroxide, and the like.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as benzene. , Halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile and butyronitrile, and mixtures thereof.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of 0 to 100 ° C.
The halogenating agent is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 5 mol, per 1 mol of the compound represented by the formula (10-a).
The radical initiator is usually used in an arbitrary ratio from 0.01 mol to an excess amount, preferably from 0.1 to 1 mol, per 1 mol of the compound represented by the formula (10-a).
After completion of the reaction, the compound represented by the formula (7-c) can be isolated by adding the reaction mixture to water and subjecting it to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound represented by the formula (7-c) can also be purified by procedures such as chromatography, recrystallization and distillation.

〔式中、Ｌ^ａは脱離基（例えば、ヨウ素原子、臭素原子、塩素原子またはトリフルオロメタンスルホニルオキシ基等）を表し、Ｘ^１、Ｘ^２、Ｘ^３、Ｚ^１及びｎは［１］と同じ意味を表す。〕
カップリング反応としては例えば、Ｓｏｎｏｇａｓｈｉｒａカップリング反応等が挙げられる。
Ｓｏｎｏｇａｓｈｉｒａ反応による方法を具体的に挙げる。
反応は、通常窒素等の不活性気体雰囲気下、通常遷移金属触媒、無機銅塩類及び塩基の存在下、溶媒中で行なわれる。
反応に用いられる遷移金属触媒としては、例えば酢酸パラジウム、パラジウムジクロリド、ジクロロビス（トリフェニルホスフィン）パラジウム、テトラキス（トリフェニルホスフィン）パラジウム等のパラジウム触媒等が挙げられる。
反応に用いられる無機銅塩類としては、臭化銅（Ｉ）、沃化銅（Ｉ）等が挙げられる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム等の炭酸塩、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノン−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、及び酢酸エチル、酢酸ブチル等のエステル及びこれらの混合物が挙げられる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、−２０℃〜１００℃（但し、使用する溶媒の沸点が１００℃未満の場合には、−２０℃〜溶媒の沸点）の範囲である。
反応に用いられる遷移金属触媒は、式（１１）で示される化合物１モルに対して通常０．００１〜０．５モルの割合で使用される。
反応に用いられる無機銅塩類は、式（１１）で示される化合物１モルに対して通常０．００１〜０．５モルの割合で使用される。
反応に用いられる式（１８）で示される化合物は、式（１１）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜５モルの割合で使用される。
反応に用いられる塩基は、式（１１）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（４）で示される化合物を得ることができる。また得られた式（４）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 7)
The compound represented by the formula (4) can be produced by subjecting the compound represented by the formula (11) and the compound represented by the formula (18) to a coupling reaction.

Wherein, ^{L a} is a leaving group (e.g., an iodine atom, a bromine atom, a chlorine atom or a trifluoromethanesulfonyloxy group, etc.) ^{represents, X 1, X 2, X} 3, Z 1 and n are as [1] Represents the same meaning. ]
Examples of the coupling reaction include a Sonogashira coupling reaction.
A method based on the Sonogashira reaction will be specifically mentioned.
The reaction is usually carried out in a solvent in an inert gas atmosphere such as nitrogen, usually in the presence of a transition metal catalyst, inorganic copper salts and a base.
Examples of the transition metal catalyst used in the reaction include palladium catalysts such as palladium acetate, palladium dichloride, dichlorobis (triphenylphosphine) palladium, and tetrakis (triphenylphosphine) palladium.
Examples of inorganic copper salts used in the reaction include copper (I) bromide and copper (I) iodide.
Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4. 3.0] Tertiary amines such as non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, and chlorobenzene, Examples include acid amides such as N, N-dimethylformamide, esters such as ethyl acetate and butyl acetate, and mixtures thereof.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of −20 ° C. to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
The transition metal catalyst used for the reaction is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the compound represented by the formula (11).
The inorganic copper salt used in the reaction is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the compound represented by the formula (11).
The compound represented by the formula (18) used in the reaction is usually in an arbitrary ratio from 1 mol to an excess amount, preferably in a ratio of 1 mol to 5 mol, with respect to 1 mol of the compound represented by the formula (11). used.
The base used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (11).
After completion of the reaction, the compound represented by the formula (4) can be obtained by adding the reaction mixture to water and subjecting it to usual post-treatment operations such as organic solvent extraction and concentration. The obtained compound represented by the formula (4) can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中Ｇは、エチニル基の保護基を表し、Ｌ^ａは脱離基（例えば、ヨウ素原子、臭素原子、塩素原子またはトリフルオロメタンスルホニルオキシ基等）を表し、Ｘ^１、Ｘ^２、Ｘ^３及びｎは［１］と同じ意味を表す。〕
エチニル基の保護基は、エチニル基の保護基として使用し得るすべての基を含み、たとえば、Ｗ．グリーン（Ｗ．Ｇｒｅｅｎ）ら、プロテクティブ・グループス・イン・オーガニック・シンセシス（Ｐｒｏｔｅｃｔｉｖｅ Ｇｒｏｕｐｓ ｉｎ Ｏｒｇａｎｉｃ Ｓｙｎｔｈｅｓｉｓ）第４版、第９２７〜９３３頁、２００７年、ジョン・ウィリイ・アンド・サンズ社（Ｊｏｈｎ Ｗｉｌｅｙ ＆ Ｓｏｎｓ，ＩＮＣ）に記載されている基が挙げられる。
該カップリング反応としては例えば、Ｓｏｎｏｇａｓｈｉｒａカップリング反応等が挙げられる。
Ｓｏｎｏｇａｓｈｉｒａ反応による方法を具体的に挙げる。
反応は、通常窒素等の不活性気体雰囲気下、通常遷移金属触媒、無機銅塩類、アルキン及び塩基の存在下、溶媒中で行なわれる。
反応に用いられる遷移金属触媒としては、例えば酢酸パラジウム、パラジウムジクロリド、ジクロロビス（トリフェニルホスフィン）パラジウム、テトラキス（トリフェニルホスフィン）パラジウム等のパラジウム触媒等が挙げられる。
該反応に用いられる無機銅塩類としては、臭化銅（Ｉ）、沃化銅（Ｉ）等が挙げられる。
該反応に用いられるアルキンとしては、アセチレン、１−プロピン、１−ブチン、１−ペンチン、シクロアルキルアセチレン、フェニルアセチレン、トリメチルシリルアセチレン等が挙げられる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム等の炭酸塩、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノン−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、及び酢酸エチル、酢酸ブチル等のエステル及びこれらの混合物が挙げられる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、−２０℃〜１００℃（但し、使用する溶媒の沸点が１００℃未満の場合には、−２０℃〜溶媒の沸点）の範囲である。
反応に用いられる遷移金属触媒は、式（１２）で示される化合物１モルに対して通常０．００１〜０．５モルの割合で使用される。
反応に用いられる無機銅塩類は、式（１２）で示される化合物１モルに対して通常０．００１〜０．５モルの割合で使用される。
反応に用いられるアルキンは、式（１２）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜５モルの割合で使用される。
反応に用いられる塩基の量は、式（１２）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（１３）で示される化合物を得ることができる。また得られた式（１３）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。
式（１０）で示される化合物は、Ｗ．グリーン（Ｗ．Ｇｒｅｅｎ）ら、プロテクティブ・グループス・イン・オーガニック・シンセシス（Ｐｒｏｔｅｃｔｉｖｅ Ｇｒｏｕｐｓ ｉｎ Ｏｒｇａｎｉｃ Ｓｙｎｔｈｅｓｉｓ）第４版、第９２７〜９３３頁、２００７年、ジョン・ウィリイ・アンド・サンズ社（Ｊｏｈｎ Ｗｉｌｅｙ ＆ Ｓｏｎｓ，ＩＮＣ）に記載の方法に準じて、式（１３）で示される化合物から製造することができる。 (Reference production method 8)
The compound represented by the formula (10) can be produced by deprotecting the compound represented by the formula (12) after the coupling reaction.

[In the formula, G represents a protecting group for an ethynyl group, La represents ^a leaving group (for example, an iodine atom, a bromine atom, a chlorine atom, or a trifluoromethanesulfonyloxy group), and X ¹ , X ² , X ³ And n represent the same meaning as [1]. ]
The protecting group for ethynyl group includes all groups that can be used as a protecting group for ethynyl group. W. Green et al., Protective Groups in Organic Synthesis 4th Edition, 927-933, 2007, John Wiley & Sons (John Wiley & Sons, Inc.) Sons, INC).
Examples of the coupling reaction include a Sonogashira coupling reaction.
A method based on the Sonogashira reaction will be specifically mentioned.
The reaction is usually carried out in a solvent in an inert gas atmosphere such as nitrogen, usually in the presence of a transition metal catalyst, inorganic copper salts, alkyne and base.
Examples of the transition metal catalyst used in the reaction include palladium catalysts such as palladium acetate, palladium dichloride, dichlorobis (triphenylphosphine) palladium, and tetrakis (triphenylphosphine) palladium.
Examples of inorganic copper salts used in the reaction include copper (I) bromide and copper (I) iodide.
Examples of the alkyne used in the reaction include acetylene, 1-propyne, 1-butyne, 1-pentyne, cycloalkylacetylene, phenylacetylene, and trimethylsilylacetylene.
Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4. 3.0] Tertiary amines such as non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, and chlorobenzene, Examples include acid amides such as N, N-dimethylformamide, esters such as ethyl acetate and butyl acetate, and mixtures thereof.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of −20 ° C. to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
The transition metal catalyst used for the reaction is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the compound represented by formula (12).
The inorganic copper salt used in the reaction is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the compound represented by formula (12).
The alkyne used in the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 5 mol, per 1 mol of the compound represented by the formula (12).
The amount of the base used in the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (12).
After completion of the reaction, the compound represented by the formula (13) can be obtained by adding the reaction mixture to water and subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The obtained compound represented by the formula (13) can also be purified by operations such as chromatography, recrystallization and distillation.
The compound represented by formula (10) is described in W.W. W. Green et al., Protective Groups in Organic Synthesis 4th Edition, 927-933, 2007, John Wiley & Sons (John Wiley & Sons, Inc.) According to the method described in Sons, INC), it can be produced from the compound represented by the formula (13).

〔式中、Ｌ^ａは脱離基（例えば、ヨウ素原子、臭素原子、塩素原子またはトリフルオロメタンスルホニルオキシ基等）を表し、Ｘ^１、Ｘ^２、Ｘ^３及びｎは［１］と同じ意味を表す。〕
反応は、通常縮合剤の存在下、必要に応じて塩基の存在下、溶媒中で行なわれる。
反応に用いられる縮合剤としては、例えば、ジシクロヘキシルカルボジイミド及び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及び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ホスフェートが挙げられる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム等の炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノン−５−エン等の第３級アミン類及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素類、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、及び酢酸エチル、酢酸ブチル等のエステル及びこれらの混合物が挙げられる。
反応は、さらに必要に応じて、式（１４）で示される化合物１モルに対して、通常は０．０１モル〜１モルまで任意の割合、好ましくは０．０５モル〜０．２モルの割合で１−ヒドロキシベンゾトリアゾール、１−ヒドロキシ−７−アザベンゾトリアゾール、Ｎ−ヒドロキシコハク酸イミド等を加えて行うこともできる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、−２０℃〜１００℃（但し、使用する溶媒の沸点が１００℃未満の場合には、−２０℃〜溶媒の沸点）の範囲である。
反応において、式（１４）で示される化合物と、式（２）で示される化合物との使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、例えば式（１４）で示される化合物１モルに対して式（２）で示される化合物が１モル〜３モルの割合である。
反応に用いられる縮合剤は、式（１４）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応に用いられる塩基は、式（１４）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（１２）で示される化合物を得ることができる。また得られた式式（１２）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 9)
The compound represented by the formula (12) can be produced by reacting the compound represented by the formula (14) with the compound represented by the formula (2) in the presence of a condensing agent.

Wherein, ^{L a} is a leaving group (e.g., an iodine atom, a bromine atom, a chlorine atom or a trifluoromethanesulfonyloxy group, etc.) ^represents, X ^1, X 2, ^{X 3} and n are the same meanings as [1] Represent. ]
The reaction is usually carried out in a solvent in the presence of a condensing agent and optionally in the presence of a base.
Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate. .
Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4. 3.0] Tertiary amines such as non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, and halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, and chlorobenzene. And acid amides such as N, N-dimethylformamide, and esters such as ethyl acetate and butyl acetate, and mixtures thereof.
The reaction may be carried out in any proportion, usually from 0.01 mol to 1 mol, preferably from 0.05 mol to 0.2 mol, if necessary, per 1 mol of the compound represented by formula (14). 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide and the like can also be added.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of −20 ° C. to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
In the reaction, the molar ratio of the compound represented by the formula (14) and the compound represented by the formula (2) can be arbitrarily set, but is preferably equimolar or a ratio close thereto, for example, the formula (14). The compound represented by the formula (2) is in a ratio of 1 mol to 3 mol with respect to 1 mol of the compound to be obtained.
The condensing agent used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (14).
The base used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (14).
After completion of the reaction, the compound represented by the formula (12) can be obtained by adding the reaction mixture to water and subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The obtained compound represented by the formula (12) can also be purified by operations such as chromatography, recrystallization, distillation and the like.

〔式中、Ｌ^ａは脱離基（例えば、ヨウ素原子、臭素原子、塩素原子またはトリフルオロメタンスルホニルオキシ基等）を表し、Ｒ^aはメチル基またはエチル基を表し、Ｘ^１、Ｘ^２、Ｘ^３及びｎは［１］と同じ意味を表す。〕
反応は、必要に応じて塩基の存在下、通常溶媒中で行われる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム等の炭酸塩、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノン−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド及びジメチルスルホキシド等のスルホキシド及びこれらの混合物が挙げられる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、０℃〜１５０℃（但し、使用する溶媒の沸点が１５０℃未満の場合には、０℃〜溶媒の沸点）の範囲である。
反応において、式（１５）で示される化合物と、式（２）で示される化合物との使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、例えば式（１６）で示される化合物１モルに対して式（２）で示される化合物が１モル〜３モルの割合である。
反応に用いられる塩基は、式（１５）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜５モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（１２）で示される化合物を得ることができる。また得られた式（１２）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 10)
The compound represented by the formula (12) can be produced by reacting the compound represented by the formula (15) with the compound represented by the formula (2).

Wherein, L ^a represents a leaving group (e.g., an iodine atom, a bromine atom, a chlorine atom or a trifluoromethanesulfonyloxy group, etc.) represents, R ^a represents a methyl group or an ethyl group, X ^{1, X 2,} X ³ and n represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in the presence of a base as necessary.
Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4. 3.0] Tertiary amines such as non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, and chlorobenzene, Examples include acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of 0 ° C. to 150 ° C. (however, when the boiling point of the solvent used is less than 150 ° C., it is 0 ° C. to the boiling point of the solvent).
In the reaction, the molar ratio of the compound represented by the formula (15) and the compound represented by the formula (2) can be arbitrarily set, but is preferably equimolar or a ratio close thereto, for example, the formula (16). The compound represented by the formula (2) is in a ratio of 1 mol to 3 mol with respect to 1 mol of the compound to be obtained.
The base used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 5 mol, per 1 mol of the compound represented by the formula (15).
After completion of the reaction, the compound represented by the formula (12) can be obtained by adding the reaction mixture to water and subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The obtained compound represented by the formula (12) can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、通常塩基の存在下、溶媒中で行われ、さらにドライアイスによる処理が行われる。
反応に用いられる塩基としては、ｎ−ブチルリチウム、ｓｅｃ−ブチルリチウム、ｔｅｒｔ−ブチルリチウム、２，４，６−トリメチルフェニルリチウム等の有機リチウム化合物、リチウムジイソプロピルアミド、リチウムヘキサメチルジシラジド等が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン等のエーテル及びこれらの混合物が挙げられる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、−１００℃〜４０℃の範囲である。
反応に用いられる塩基は、式（１５）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応に用いられるドライアイスは、式（１５）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合で使用される。
反応終了後は、反応混合物を水に加え、有機溶媒洗浄後、水層を塩酸等の酸性の水溶液により中和し、有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（５）で示される化合物を得ることができる。また得られた式（５）で示される化合物は、通常精製することなく次の工程の反応に用いられるが、必要によりクロマトグラフィ−、再結晶等の操作によって精製することもできる。 (Reference production method 11)
The compound represented by the formula (5) can be produced by reacting the compound represented by the formula (15) with a base and then reacting with dry ice (carbon dioxide).

[Wherein, R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z, and m represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in an inert gas atmosphere such as nitrogen, usually in the presence of a base, and further treated with dry ice.
Examples of the base used in the reaction include n-butyllithium, sec-butyllithium, tert-butyllithium, organolithium compounds such as 2,4,6-trimethylphenyllithium, lithium diisopropylamide, lithium hexamethyldisilazide and the like. Can be mentioned.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether and tetrahydrofuran, and mixtures thereof.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually in the range of −100 ° C. to 40 ° C.
The base used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (15).
The dry ice used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount with respect to 1 mol of the compound represented by the formula (15).
After completion of the reaction, the reaction mixture is added to water, washed with an organic solvent, the aqueous layer is neutralized with an acidic aqueous solution such as hydrochloric acid, and subjected to usual post-treatment operations such as organic solvent extraction and concentration, to obtain the formula ( The compound represented by 5) can be obtained. The obtained compound represented by the formula (5) is usually used for the reaction in the next step without purification, but can be purified by operations such as chromatography and recrystallization as necessary.

〔式中、Ｗは脱離基（例えば塩素、臭素、ヨウ素、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基またはｐ−トルエンスルホニルオキシ基等）を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３、Ｙ、Ｚ及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、塩基の存在下、溶媒中で行われる。
反応に用いられる塩基としては、例えば、ナトリウム、カリウム等のアルカリ金属、ｎ−ブチルリチウム等のアルキルリチウム、水素化ナトリウム、水素化カリウム等の金属水素化合物、炭酸ナトリウム、炭酸カリウム等の炭酸塩、カリウム−ｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド、トリエチルアミン、ジイソプロピルエチルアミン、１，８−ジアザビシクロ［５．４．０］ウンデカ−７−エン、１，５−ジアザビシクロ［４．３．０］ノナ−５−エン等の第３級アミン及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物が挙げられる。
反応に用いられる溶媒としては、例えば、１，４−ジオキサン、テトラヒドロフラン
、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等のエーテル、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、クロロベンゼン等のハロゲン化炭化水素、酢酸エチル、酢酸ブチル等のエステル、アセトニトリル、ブチロニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、ジメチルスルホキシド等のスルホキシド及びこれらの混合物が挙げられる。
反応時間は、通常、５分間〜７２時間の範囲である。
反応温度は、通常、−４０〜１００℃の範囲である。
式（１６）で示される化合物と、式（８）で示される化合物の使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比、具体的には式（１６）で示される化合物１モルに対して、式（８）で示される化合物が０．５〜３モルの割合である。
塩基は、式（１６）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、式（１５）で示される化合物を単離することができる。また単離された式（１５）で示される化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 12)
The compound represented by the formula (15) can be produced by reacting the compound represented by the formula (16) with the compound represented by the formula (8) in the presence of a base.

[Wherein W represents a leaving group (for example, chlorine, bromine, iodine, methanesulfonyloxy group, trifluoromethanesulfonyloxy group or p-toluenesulfonyloxy group), and R ⁴ , R ⁵ , X ¹ , X ² , X ³ , Y, Z and m represent the same meaning as [1]. ]
The reaction is usually carried out in a solvent in the presence of a base under an inert gas atmosphere such as nitrogen.
Examples of the base used in the reaction include alkali metals such as sodium and potassium, alkyllithiums such as n-butyllithium, metal hydrides such as sodium hydride and potassium hydride, carbonates such as sodium carbonate and potassium carbonate, Alkali metal alkoxides such as potassium tert-butoxide, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4.3.0] non-5 And tertiary amines such as ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, 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 and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof. Can be mentioned.
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of -40 to 100 ° C.
The molar ratio of the compound represented by the formula (16) and the compound represented by the formula (8) can be arbitrarily set, but is preferably an equimolar ratio or a ratio close thereto, specifically represented by the formula (16). The compound shown by Formula (8) is a ratio of 0.5-3 mol with respect to 1 mol of compounds.
The base is generally used in an arbitrary ratio from 1 mol to an excess amount, preferably 1 to 3 mol, per 1 mol of the compound represented by the formula (16).
After completion of the reaction, the compound represented by the formula (15) can be isolated by adding the reaction mixture to water and subjecting it to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound represented by the formula (15) can also be purified by operations such as chromatography, recrystallization and distillation.

〔式中、Ｒ^aはメチル基またはエチル基を表し、Ｚ^ａは群Ｂより選ばれる１個の基を表し、Ｙ^１は酸素原子または硫黄原子を表し、Ｒ^４、Ｒ^５、Ｘ^１、Ｘ^２、Ｘ^３及びｍは［１］と同じ意味を表す。〕
反応は、通常窒素等の不活性気体雰囲気下、光延試薬およびホスフィン化合物存在下、溶媒中で行われる。
反応に用いられる光延試薬としては、アゾジカルボン酸ジエチル（ＤＥＡＤ）、アゾジカルボン酸ジイソプロピル（ＤＩＡＤ）、Ｎ，Ｎ，Ｎ’，Ｎ’−テトライソプロピルアゾジカルボキサミド（ＴＩＰＡ）、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルアゾジカルボキサミド（ＴＭＡＤ）、１，１’−（アゾジカルボニル）ジピペリジン（ＡＤＤＰ）、１，６−ジメチル−１，５，７−ヘキサヒドロ−１，４，６，７−テトラゾシン−２，５−ジオン（ＤＨＴＤ）等のアゾ系光延試薬、（シアノメチレン）トリブチルホスホラン（ＣＭＢＰ）、（シアノメチレン）トリメチルホスホラン等のホスホラン系光延試薬等が挙げられる。
反応に用いられるホスフィン化合物としては、トリフェニルホスフィン等のトリアリールホスフィン、トリブチルホスフィン等のトリアルキルホスフィン等が挙げられる。
反応に用いられる溶媒としては、例えば、ベンゼン、トルエン等の芳香族炭化水素、ヘキサン等の炭化水素、ジエチルエーテル、テトラヒドロフラン、１，４−ジオキサン等のエーテル、クロロホルム、ジクロロメタン、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、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、及び酢酸エチル、酢酸ブチル等のエステル及びこれらの混合物が挙げられる。
反応の反応時間は、通常、５分間〜７２時間の範囲である。
反応の反応温度は、通常、−１０℃〜８０℃の範囲である。
反応に用いられる光延試薬は、式（９）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応に用いられるホスフィン化合物は、式（９）で示される化合物１モルに対して、通常は１モルから過剰量まで任意の割合、好ましくは１モル〜３モルの割合で使用される。
反応終了後は、反応混合物を水に加えた後に有機溶媒抽出、濃縮等の通常の後処理操作を施すことにより、本発明合物を単離することができる。また単離された本発明化合物はクロマトグラフィー、再結晶、蒸留等の操作によって精製することもできる。 (Reference production method 13)
The compound represented by the formula (6-a) can be produced by subjecting the compound represented by the formula (9) and the compound represented by the formula (8-a) to Mitsunobu reaction.

[Wherein, R ^a represents a methyl group or an ethyl group, Z ^a represents one group selected from group B, Y ¹ represents an oxygen atom or a sulfur atom, R ⁴ , R ⁵ , X ¹ , X ² , X ³ and m represent the same meaning as [1]. ]
The reaction is usually performed in a solvent in the presence of a Mitsunobu reagent and a phosphine compound in an inert gas atmosphere such as nitrogen.
Mitsunobu reagents used in the reaction include diethyl azodicarboxylate (DEAD), diisopropyl azodicarboxylate (DIAD), N, N, N ′, N′-tetraisopropyl azodicarboxamide (TIPA), N, N, N ′. , N′-tetramethylazodicarboxamide (TMAD), 1,1 ′-(azodicarbonyl) dipiperidine (ADDP), 1,6-dimethyl-1,5,7-hexahydro-1,4,6,7- Examples thereof include azo-based Mitsunobu reagents such as tetrazocine-2,5-dione (DHTD) and phospholane-based Mitsunobu reagents such as (cyanomethylene) tributylphosphorane (CMBP) and (cyanomethylene) trimethylphosphorane.
Examples of the phosphine compound used in the reaction include triarylphosphine such as triphenylphosphine, and trialkylphosphine such as tributylphosphine.
Examples of the solvent used for the reaction include aromatic hydrocarbons such as benzene and toluene, hydrocarbons such as hexane, ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane, chloroform, dichloromethane, 1,2-dichloroethane, Halogenated hydrocarbons such as chlorobenzene, acid amides such as N, N-dimethylformamide, esters such as ethyl acetate and butyl acetate, and mixtures thereof.
The reaction time of the reaction is usually in the range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually in the range of −10 ° C. to 80 ° C.
The Mitsunobu reagent used for the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (9).
The phosphine compound used in the reaction is usually used in an arbitrary ratio from 1 mol to an excess amount, preferably from 1 mol to 3 mol, per 1 mol of the compound represented by the formula (9).
After completion of the reaction, the compound of the present invention can be isolated by adding the reaction mixture to water and then subjecting to usual post-treatment operations such as organic solvent extraction and concentration. The isolated compound of the present invention can also be purified by operations such as chromatography, recrystallization and distillation.

Examples of harmful arthropods to which the compound of the present invention exhibits a controlling effect include harmful insects and harmful mites. More specifically, the following are mentioned.
Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera) planthoppers such as, green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens) leafhoppers such as, cotton aphid (Aphis gossypii) Aphids such as peach mosquito aphids (Myzus persicae), Nezoa antennata, Riptortus clavetus, Eysarcoris larvae ris parvus), Plautia crossota green bug (Plautia stali), brown marmorated stink bug (Halyomorpha mista) red streaks Miridae (Stenotus rubrovittatus), stink bugs such as Trigonotylus caelestialium (Trigonotylus ruficornis), greenhouse whitefly (Trialeurodes vaporariorum), silverleaf whitefly (Bemisia whiteflies such as argentifolii, Aonidiella aurantii, Santoze scales (Comstockcaspis perniciosa), Citrus snow scale (Unaspis citri), Ruby rots (Ceroplaste) s rubens), scale insects such as Icerya purchasi, bed bugs, bed bugs such as bed bugs (Cimex electrarius), lice, etc .;

Lepidoptera: rice stem borer (Chilo suppressalis), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Pyralidae such as Indian meal moth (Plodia interpunctella), common cutworm (Spodoptera litura), armyworm (Pseudaletia separata), Trichoplusia spp., Heliotis genus, Helicobelpa genus moths, white butterflies (Pieris rapae), white butterflies, Adoxofies genus, Nashihime shinsukii (Grapholita molesta), codling moth (Cydia pomonella), etc., peach sinc ensis), mosquito moths such as Lionettia genus, Limantria genus, Euproctinis genus moths, moths such as Plutella xylostella, cotton moths such as Pectinophora gossypiella, cunea), tigers such as tiger (Tinea bissellella), and so on.

Diptera: Culex pipiens pallens, Culex tritaenor hyeschus, Culex quasius es, etc. Houseflies such as Anopheles, Chironomid, Housefly (Musca domestica), Muscina stabulans, etc. Lirio Hyzaglyflies such as myza trifolii), fruit flies, Drosophila, flies such as Drosophila flies (Megella spiracularis), flies such as Drosophila such as Drosophila such as Clogmia albipuncta;

Coleoptera: Western corn root worms (Diabrotica virgifera virgifera), Southern corn root worms (Diabrotica undecimuccita wiard), etc. Weevil such as Sitophilus zeamais, Rice weevil (Lissohoptrus oryzophilus), Azuki beetle (Callosobrchuchus chiensis), Chilobole moss, Tenebrio molit aneum, etc., Olema oryzae, Auracophora femaris, Phyllotreta stomata, etc. , Epilacunas such as Epilachna vigintioctopuncta, Oysterworm, Nagashimushimushi, Leopard beetle, Longicorn beetle, Paederus fuscipes, etc .;

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

Thrips of the order Thrips palmi, Tripas tabaci, Franklinella occidentalis, Franklin, etc.
Hymenoptera: Monomorium phalaosis, Formica fusca japonica, Ochellelus glaben, Phytomidae, Phitomae (Phitomidae) japonica) and the like;

Straight-eyed pests: keratoids, grasshoppers, crickets, etc .;
Lepidoptera: Cat fleas (Ctenocephalides felis), Dog fleas (Ctenocephalides canis), Human fleas (Pulex irritans), Xenopsilla cheopes, etc.
Lice insect pests: Pediculus humanus corporis, phethyrus pubis, cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), pig lice
Termite pests: Yamato termites (Reticulites spertermus), Western termites (Cantopterites teremite) (Reticulitermes tibias), Subteranian termites such as dessert Subteranian termite (Heterotermes aureus), Dora such as American termite minor (Incitermes minor) Wood terpolymers mites such, Nevada dump wood coater termite (Zootermopsis nevadensis) Dump Wood terpolymers mitogen such as such;

Mite order pests: Tetanychus urticae, Kanzawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), mite spider mite (Panonychus ulmi), spider mite (Aponicus mite) Mites (Aculus schleechtendali), mites (Polyphagotaronemusus latus), mites, terrestrial mites, mites (Haemaphysalis longis), Mites Merikan dog ticks (Dermacentor varis), Tick ticks (Haemphysalis flava), Tick ticks (Dermacetor taiusicus), Tick ticks (Ixodes ovasus) Tick such as Amblyomma americanum, Rhipicephalus sanguineus, Mite, Tyrophagus putrescentiae, Mite, Dermatode mite hagoides farinae), D. pteronyssinus (Dermatophagoides ptrenyssnus) house dust mite such as, Hosotsumedani (Cheyletus eruditus), Stag Tsumedani (Cheyletus malaccensis), Tsumedani such as Minami Tsumedani (Cheyletus moorei), house dust mite (Ornithonyssus bacoti), Torisashidani (Ornithonyssus sylvairum), Cucumbers such as Dermanyssus gallinae, tsutsugamushi such as Leptotrophidium akamushi;
Spiders: Chiracanthium japonicum, Latroectus hasseltii, etc .;

Lip and leg class: Geeu (Thereunema hilgendorfi), Tobismadede (Scolopendra subspinepes), etc .;
Double leg class: Oxidus gracilis, Nedyopus tambanus, etc .;
Isopods: Armadillium vulgare, etc .;

  The harmful arthropod control agent of the present invention contains the compound of the present invention and an inert carrier. In the present invention, the inert carrier represents a bulking agent, a diluent or the like used in the field of prevention and agriculture. The harmful arthropod control agent of the present invention is usually prepared by mixing the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier, and if necessary, for surfactants and other preparations. Adjuvants are added and formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poison baits, resin formulations and the like. These preparations usually contain 0.01 to 95% by weight of the compound of the present invention.

  Examples of the solid carrier used for formulation 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.), chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), etc.

  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 carbonization Hydrogen (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, isobutyrate) Nitriles), 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 gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

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

  Other adjuvants for preparation include sticking 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 -Mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

  The harmful arthropod can be controlled by applying the harmful arthropod control agent of the present invention directly to the harmful arthropod and / or in the habitat of the harmful arthropod.

  The harmful arthropod control method of the present invention is carried out by applying an effective amount of the compound of the present invention to the harmful arthropod or the habitat of the harmful arthropod. In the harmful arthropod control method of the present invention, the compound of the present invention is usually used in the form of the harmful arthropod control agent of the present invention.

Examples of habitats for harmful arthropods include paddy fields, fields, orchards, non-agricultural land, and houses.
The above application can be carried out by the same application method as before as long as the compound of the present invention can be brought into contact with or ingested by a harmful arthropod.
Examples of such application methods include spraying treatment, soil treatment, seed treatment, and hydroponic liquid treatment.

When the harmful arthropod control agent of the present invention is used for controlling harmful arthropods in the agricultural field, the application amount is the amount of the compound of the present invention per 10,000 m ² and is usually 1 to 10,000 g. When the harmful arthropod 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 10,000 ppm, and applied. Granules, powders, etc. are usually applied as they are.

  These preparations and water dilutions of these preparations may be sprayed directly on harmful arthropods or plants such as crops to be protected from harmful arthropods, and harmful arthropods that inhabit the soil of cultivated land. You may treat to this soil in order to control.

  Moreover, it can also process by the method of wrapping the resin formulation processed into the sheet form or the string form around the crop, stretching over the crop vicinity, and laying on the stock soil.

When the harmful arthropod control agent of the present invention is used for controlling harmful arthropods living in the house, the amount applied is usually the amount of the compound of the present invention per 1 m ² of treatment area when treated on the surface. The amount of the compound of the present invention per 1 m ³ of the treatment space is usually 0.01 to 500 mg. When the harmful arthropod 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 0.1 to 1000 ppm, and applied. Apply oils, aerosols, smoke, poison baits, etc. as they are.

The compound of the present invention can be used in farmland where the following crops are 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.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Bridegroom,
Foliage plant,
Fruit trees; pears (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, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

  The crop includes a genetically modified crop.

  The harmful arthropod control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.

Active Ingredients of Insecticides (1) Organophosphorus Compounds Acephate, Aluminum Phosphide, Butathiofos, Cadosafos, Chlorethoxyfos, Chlorfenvinphos, Chlorfenvinphos (Chlorpyrifos), Chlorpyrifos-methyl (Chlorpyrifos-methyl), Cyanophos (Cyanophos: CYAP), Diazinon (Diazinon), DCIP (Dichlorodiisopropylene ether), Diclofenthion (V: D) ), Dimethoate, dimethylvinphos, disulfoton, EPN, etion, ethoprofos, etrimfos, fention (MPP), EP, Phosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenfos, methulfenfos, methulfenfos MTP), monocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphosmethyl (pirimithiopimethiopimethiopimethiopimethiopimethiopimethiopimethiopimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisonepimethypisone (Pyridafenthion), quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos, pyraclofos, phosphite, sulthio Tebupirimfos, temefos, tetrachlorbinphos (tetrach1orvinphos), terbufos, thiomethon, trichlorfon (DEP), bamidithios (vamidothionate, vamidothionate) .
(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbothofen, carbothofen, carbothofen (Fenobucarb), phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), metocarb (metholcarb) rb), oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), and aldicarb (aldicarb).
(3) Pyrethroid compounds Acrinathrin, allethrin, beta-cyfluthrin, bifenthrin, cycloprotorin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin, cyfluthrin ), Deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flufenprote Flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, rethrethrin, rethrethrin, pylletrin Cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, phenothrin. rin), cyphenothrin, alpha-cypermethrin, zeta-cyperthrin, lambda-cyhalothrin, gamma cyhalothrin (gammathrin) ), Tau-fluvalinate, metofluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS) , 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-eni Lucyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropane Carboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) cyclo Propanecarboxylate.
(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, and bisultap.
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam, thiacloprid (thiacloprid), dinoteurin (dinothurine)
(6) Benzoylurea compound Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucyclolone (Flufenoxuron), hexaflumuron, lufenuron, novaluron, novifluuron, teflubenzuron, triflumuron, and triflumuron.
(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
(8) Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
(11) Other insecticide active ingredients Machine oil (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr Ritranol, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupirahydroprene , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosul, spiromidol, spinomidol tolfenpyrad, triazamate, flubendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen calcium lime ulfide, chlordane, DDT, DSP, flufenerium, flonicamid, flurimfen, formatenate, metam-ammonium, metam-ammonium sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfoxafluor, sulfur, metafluon, sulfur ), Spirotetramat (sp rotetramat), pyrifluquinazon (pyrifluquinazone), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), cyan tiger Niri Prowl (cyantraniliprole).

Active ingredients of acaricides: acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate (BS), chinomethionate (BS), chloromethionate (BS) chlorfenson, clofentezine, cyflumetofene, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarbene roximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactin complex (pyridene), pyridaben (pyriben) (Tetradifon), spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cienopyrafen.

Active ingredients of nematicides DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imiciafos.

Active ingredients of fungicides Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Tebuconazole, Tebuconazole, Tebuconazole , Bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumazole, triflumizole Tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, tericonazole, triticonazole, triticonazole Azole fungicidal compounds such as flutriafol;
Cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin;
Benzimidazolic fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl;
Procymidone; cyprodinil; pyrimethanil; dietofencarb; thiuram; fluazilonyl; Captan; mepanipyrim; fenpiclonil; fludioxonil; diclofluraned; folppet; cresoxime- azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyracrostrobin; dimoxystrobin; dimoxystrobin; dimoxystrobin; Pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; samamide; samamide; iprovalicarb; benthiavaricarb; cyazofamid; mandipropamid; boscaliden; (Bifafen); cyflufenamide; proquinazid; isotianil and thiadinil.

Active ingredients of plant growth regulators Ethephon, chlormequat-chloride, mepiquat-chloride, gibberellin A3 (Gibberellin A3), abscisic acid Kinetin, benzyladenine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, 4-oxo-4- (2-phenylethyl) aminobutyric acid, 5- (trifluoro) Methyl) benzo [b] thiophene-2-carboxylate and 5- (trifluoromethyl) benzo [b] thio Fen-2-carboxylic acid.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (phenothio1), mecoprop, fluroxypyr, triclopyr, clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, metabenthuron , Cumyluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimethamethrin (dimethymetrine) ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
(8) Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
(9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butyrate, beniocarb, esprocarb, molinate, dimipeperate (Swep), chlorpropham, phenmedifam, phenisopham, piributicarb, and asuram.
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobanzanide.
(11) Chloroacetanilide herbicidal compounds acetochlor, acechlor, butachlor, dimethenamide, propachlor, metazachlor, metrachlor or totrachlor pretilachlor), tenylchlor (theny1ch1or), and petoxamide.
(12) Diphenyl ether herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxythonifen, and clomethoxythonipheni.
(13) Cyclic imide herbicidal compounds oxadiazon, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumi-lacyl-pentyl Oxazine (flumioxazin), pyraflufen-ethyl, oxadiargyl (oxadiargy1), pentoxazone (pentoxazone), fluthiacet-methyl (butafenzilben) zone), and saflufenacil (saflufenacil).
(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefriltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-propyl Fluazifop-butyl, haloxyhop-methyl, and quizalofop-ethyl, metamihop.
(17) Trionoxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloxydimim, cycloxidim, texydimym (Traxydim), and profoxydim.
(18) sulfonylurea herbicidal compounds chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron methyl (18) tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, urmisyl Nicosulfuron (nico) ulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron (th), thulfuron (thulsulfuron), prosulfuron (thulsulfuron) , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurium, sulfosulfurium Azulsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesulfuron methyl Trisulfursulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compounds imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, and imazakin (p), imazaquin (p)
(20) Sulfonamide herbicidal compounds flumetslam, metosulam, dicloslam, floraslam, chloransrammethyl, penoxsulox, penoxsulox, and penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methy1, pyribenzoximid, pyrifalidomid And pyrimisulfan.
(22) Other herbicidal compounds bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethyline, cinmethyline (cinthyl) tripiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone (proflubazone) Nasset (mefenacet), flufenacet (flufenacet), fentrazamide (fentrazamide), caffenstrole (cafenstrom), indanophan (indanofan), oxadichromemephone (oxaneclomefone), fidarate (benduresate) (Norflurazon), flurtamon, diflufenican, picolinafen, beflubutamide, clomazone, amicarbazone , Pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), amino cyclo Pila crawl (aminocyclopyrachlor), type phen carbazone (ipfencarbazone), and Mechiozorin (methiozolin).

Active ingredient of synergist piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-decylimidazole), WARF-anti-resistant (TBRF-antiresistant), TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenyl group Tenon (t-phenylbutone), diethyl maleate, DMC, FDMC, ETP, and ETN.

  Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited to these examples.

  First, the manufacture example of this invention compound and the manufacture example of the intermediate body used for manufacture of this invention compound are shown below. In the present invention, TMS represents tetramethylsilane.

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−（（Ｚ）−２−（３−チエニル）ビニル）ピリジン−２−カルボン酸アミド（以下、本発明化合物（１）と記す。）２８０ｍｇを得た。 Production Example 1
N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg, 1.60 mmol), 1-hexene (1 mL) and palladium-carbon (100 mg) in ethanol (30 mL) ). After stirring at room temperature for 15 minutes under a hydrogen atmosphere, insolubles were removed by filtration using Celite. The obtained filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography.

N- (tetrahydrofuran-3-ylmethyl) -5-((Z) -2- (3-thienyl) vinyl) pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (1)) 280 mg Got.

Compound (1) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.68-1.78 (m, 1H), 2.06-2.15 (m, 1H), 2.57-2.69 (m , 1H), 3.45-3.57 (m, 2H), 3.62 (dd, J = 8.8, 5.6 Hz, 1H), 3.75-3.82 (m, 1H), 3.87-3.96 (m, 2H), 6.51 (d, J = 12.0 Hz, 1H), 6.88 (d, J = 12.0 Hz, 1H), 6.93 (dd , J = 5.2, 3.6 Hz, 1H), 6.98-7.01 (m, 1H), 7.14-7.17 (m, 1H), 7.81-7.87 (m , 1H), 8.13-8.21 (m, 2H), 8.50-8.54 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−[（Ｚ）−２−（２−チエニル）ビニル]ピリジン−２−カルボン酸アミド（以下、本発明化合物（２）と記す。）１８０ｍｇを得た。 Production Example 2
In Production Example 1, N- (tetrahydrofuran-3-ylmethyl) -5- (2) was used instead of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg). -Thienylethynyl) pyridine-2-carboxylic acid amide (580 mg) was reacted in the same manner as

N- (tetrahydrofuran-3-ylmethyl) -5-[(Z) -2- (2-thienyl) vinyl] pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (2)) 180 mg Got.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.67-1.77 (m, 1H), 2.06-2.14 (m, 1H), 2.56-2.66 (m , 1H), 3.47-3.53 (m, 2H), 3.59-3.65 (m, 1H), 3.74-3.82 (m, 1H), 3.86-3.95 (M, 2H), 6.52 (d, J = 12.0 Hz, 1H), 6.75 (d, J = 12.0 Hz, 1H), 6.81 (dd, J = 5.0, 1.4 Hz, 1H), 7.14-7.16 (m, 1H), 7.19-7.22 (m, 1H), 7.73-7.77 (m, 1H), 8.08 −8.11 (m, 1H), 8.13 (brs, 1H), 8.43-8.45 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−[２−（３−チエニル）エチル]ピリジン−２−カルボン酸アミド（以下、本発明化合物（３）と記す。）１２５ｍｇを得た。 Production Example 3
In Production Example 1, instead of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg), N- (tetrahydrofuran-3-ylmethyl) -5-[( Z) -2- (3-thienyl) vinyl] pyridine-2-carboxylic acid amide (200 mg) was used, and the reaction time was 1 hour 30 minutes.

As a result, 125 mg of N- (tetrahydrofuran-3-ylmethyl) -5- [2- (3-thienyl) ethyl] pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (3)) was obtained.

Compound (3) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.66-1.77 (m, 1H), 2.06-2.14 (m, 1H), 2.57-2.65 (m , 1H), 2.96-3.01 (m, 4H), 3.44-3.55 (m, 2H), 3.61 (dd, J = 8.7, 5.5 Hz, 1H), 3.74-3.81 (m, 1H), 3.86-3.95 (m, 2H), 6.88-6.92 (m, 2H), 7.27-7.29 (m, 1H) ), 7.57-7.61 (m, 1H), 8.07-8.11 (m, 1H), 8.14 (brs, 1H), 8.30-8.32 (m, 1H) .

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−６−[（Ｚ）−２−（２−チエニル）ビニル]ピリダジン−３−カルボン酸アミド（以下、本発明化合物（４）と記す。）８６ｍｇを得た。 Production Example 4
In Production Example 1, N- (tetrahydrofuran-3-ylmethyl) -6- (2) was used instead of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg). -Thienylethynyl) pyridazine-3-carboxylic acid amide (330 mg) was used to carry out the reaction in the same manner.

N- (tetrahydrofuran-3-ylmethyl) -6-[(Z) -2- (2-thienyl) vinyl] pyridazine-3-carboxylic acid amide (hereinafter referred to as the present compound (4)) 86 mg Got.

The present compound (4)
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.69-1.79 (m, 1H), 2.08-2.17 (m, 1H), 2.59-2.71 (m , 1H), 3.54-3.59 (m, 2H), 3.64 (dd, J = 8.7, 5.5 Hz, 1H), 3.76-3.83 (m, 1H), 3.87-3.98 (m, 2H), 6.57 (d, J = 12.4 Hz, 1H), 7.05 (dd, J = 5.0, 3.7 Hz, 1H), 7 .15 (d, J = 12.4 Hz, 1H), 7.30 (d, J = 3.7 Hz, 1H), 7.37 (d, J = 5.0 Hz, 1H), 7.62 (D, J = 8.7 Hz, 1H), 8.22 (d, J = 8.7 Hz, 1H), 8.38 (br s, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−６−[２−（２−チエニル）エチル]ピリダジン−３−カルボン酸アミド（以下、本発明化合物（５）と記す。）６５ｍｇを得た。 Production Example 5
In Production Example 1, N- (tetrahydrofuran-3-ylmethyl) -6- (2) was used instead of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg). -Thienylethynyl) pyridazine-3-carboxylic acid amide (200 mg) was used, and the reaction time was 1 hour and 20 minutes.

65 mg of N- (tetrahydrofuran-3-ylmethyl) -6- [2- (2-thienyl) ethyl] pyridazine-3-carboxylic acid amide (hereinafter referred to as the present compound (5)) represented by the formula (1) was obtained.

Compound (5) of the present invention
MS (m / z): [M + H] ⁺ 318.

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−[２−（２−チエニル）エチル]−ピリジン−２−カルボン酸アミド（以下、本発明化合物（６）と記す。）１２５ｍｇを得た。 Production Example 6
In Production Example 1, instead of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (500 mg), N- (tetrahydrofuran-3-ylmethyl) -5-[( Z) -2- (2-thienyl) vinyl] pyridine-2-carboxylic acid amide (280 mg) and the reaction time was 1 hour 30 minutes.

125 mg of N- (tetrahydrofuran-3-ylmethyl) -5- [2- (2-thienyl) ethyl] -pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (6)) represented by the formula (1) was obtained. .

The present compound (6)
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.66-1.76 (m, 1H), 2.06-2.14 (m, 1H), 2.56-2.66 (m , 1H), 3.02-3.09 (m, 2H), 3.14-3.21 (m, 2H), 3.43-3.56 (m, 2H), 3.61 (dd, J = 8.7, 5.5 Hz, 1H), 3.74-3.81 (m, 1H), 3.86-3.95 (m, 2H), 6.71-6.73 (m, 1H) ), 6.88-6.92 (m, 1H), 7.13-7.15 (m, 1H), 7.59-7.64 (m, 1H), 8.10 (d, J = 8) 0.0 Hz, 1H), 8.14 (br s, 1H), 8.32-8.35 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−（２’−チエニルメトキシメチル）−ピリジン−２−カルボン酸アミド（以下、本発明化合物（７）と記す。）２０７ｍｇを得た。 Production Example 7
5- (2′-thienylmethoxymethyl) -pyridine-2-carboxylic acid (235 mg, 0.94 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (181 mg, 1.32 mmol), triethylamine (0.26 mL, 1. 89 mmol) and 1-hydroxybenzotriazole (13 mg, 0.09 mmol) were added to chloroform (amylene-added product) (2.5 mL). To the mixture was added 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (253 mg, 1.32 mmol) at room temperature, and the mixture was stirred overnight at room temperature. Then, it concentrated under pressure reduction. Dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

207 mg of N- (tetrahydrofuran-3-ylmethyl) -5- (2′-thienylmethoxymethyl) -pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (7)) represented by the formula (1) was obtained.

Compound (7) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.66-1.77 (m, 1H), 2.04-2.14 (m, 1H), 2.55-2.68 (m , 1H), 3.44-3.56 (m, 2H), 3.61 (dd, 1H), 3.74-3.81 (m, 1H), 3.86-3.96 (m, 2H) ), 4.62 (s, 2H), 4.77 (s, 2H), 6.99-7.02 (m, 1H), 7.03-7.05 (m, 1H), 7.34 ( dd, 1H), 7.84 (dd, 1H), 8.16-8.20 (m, 2H), 8.51-8.52 (m, 1H).

で示されるＮ−（テトラヒドロピラン−４−イルメチル）−５−（２’−チエニルメトキシメチル）−ピリジン−２−カルボン酸アミド（以下、本発明化合物（８）と記す。）１５４ｍｇを得た。 Production Example 8
In Production Example 7, tetrahydropyran-4-ylmethylamine (152 mg, 1.32 mmol) was used instead of tetrahydrofuran-3-ylmethylamine hydrochloride (181 mg, 1.32 mmol), and the same reaction was carried out. formula

154 mg of N- (tetrahydropyran-4-ylmethyl) -5- (2′-thienylmethoxymethyl) -pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (8)) represented by the formula (1) was obtained.

Compound (8) of the present invention
¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.35 to 1.47 (m, 2H), 1.66-1.73 (m, 2H), 1.84 to 1.97 ( m, 1H), 3.35-3.44 (m, 4H), 3.99 (d, 2H), 4.62 (s, 2H), 4.77 (s, 2H), 6.99-7. .02 (m, 1H), 7.03-7.05 (m, 1H), 7.32-7.35 (m, 1H), 7.82-7.86 (m, 1H), 8.15 (Brs, 1H), 8.17-8.20 (m, 1H), 8.50-8.52 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−ブロモピリジン−２−カルボン酸アミド１６．９５ｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：１．７０（ｍ，１Ｈ）、２．０９（ｍ，１Ｈ）、２．６１（ｍ，１Ｈ）、３．４９（ｍ，２Ｈ）、３．６１（ｄｄ，１Ｈ，Ｊ ＝ ８．８，５．４ Ｈｚ）、３．７８（ｍ，１Ｈ）、３．９０（ｍ，２Ｈ）、７．９８（ｍ，１Ｈ）、８．０６（ｂｒｓ，１Ｈ）、８．１０（ｍ，１Ｈ）、８．６１（ｍ，１Ｈ）． Reference production example 1
To a suspension of 5-bromopyridine-2-carboxylic acid (15.00 g, 74.3 mmol) in ethyl acetate (200 mL) was added thionyl chloride (6.2 mL, 85.4 mmol) and N, N-dimethylformamide (about 0. 2 mL) was added, and the mixture was stirred at 75 ° C. for 2 hours 30 minutes. After concentration under reduced pressure, the mixture was diluted with toluene (150 mL). After cooling to 5 ° C. or lower, (tetrahydrofuran-3-yl) methylamine hydrochloride (11.24 g, 81.7 mmol) and 2 mol / L aqueous sodium hydroxide solution (100 mL) were added simultaneously, and the mixture was stirred at 5 ° C. or lower for 2 hours. Water was added and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. By suspending the residue in diisopropyl ether and filtering the precipitate, the following formula

16.95 g of N- (tetrahydrofuran-3-ylmethyl) -5-bromopyridine-2-carboxylic acid amide represented by formula (1) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.70 (m, 1H), 2.09 (m, 1H), 2.61 (m, 1H), 3.49 (m, 2H) 3.61 (dd, 1H, J = 8.8, 5.4 Hz), 3.78 (m, 1H), 3.90 (m, 2H), 7.98 (m, 1H), 8. 06 (brs, 1H), 8.10 (m, 1H), 8.61 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−エチニルピリジン−２−カルボン酸アミド１．６０ｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：１．７５−１．６６（ｍ，１Ｈ）、２．０４−２．１４（ｍ，１Ｈ）、２．５６−２．６７（ｍ，１Ｈ）、３．３５（ｓ，１Ｈ）、３．４６−３．５６（ｍ，２Ｈ）、３．６１（ｄｄ，Ｊ ＝ ８．９， ５．５ Ｈｚ，１Ｈ）、３．７４−３．８１（ｍ，１Ｈ）、３．８６−３．９５（ｍ，２Ｈ）、７．９３（ｄｄ，Ｊ ＝ ８．１， ２．０ Ｈｚ，１Ｈ）、８．１３（ｂｒｓ，１Ｈ）、８．１６（ｄ，Ｊ ＝ ８．１ Ｈｚ，１Ｈ）、８．６１−８．６４（ｍ，１Ｈ）． Reference production example 2
Under a nitrogen atmosphere, trimethylsilylacetylene (1) was added to a solution of N- (tetrahydrofuran-3-ylmethyl) -5-bromopyridine-2-carboxylic acid amide (3.00 g, 10.5 mmol) in N, N-dimethylformamide (10 mL). .34 g, 13.7 mmol), triethylamine (4.4 mL, 31.6 mmol), copper iodide (36 mg, 0.53 mmol) and dichlorobis (triphenylphosphine) palladium (369 mg, 0.53 mmol) were added, and 1 at room temperature was added. After stirring for hours, water was added, and the mixture was extracted with a mixed solution of ethyl acetate / hexane = 1/1. The organic layer was washed successively with 1 mol / L hydrochloric acid and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. Methanol (20 mL) and potassium carbonate (4.02 g, 29.1 mmol) were added to the obtained crude product, and after stirring at room temperature for 1 hour and 30 minutes, toluene (50 mL) was added and concentrated under reduced pressure. Ethyl acetate was added to the concentrate, and the ethyl acetate solution was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

1.60 g of N- (tetrahydrofuran-3-ylmethyl) -5-ethynylpyridine-2-carboxylic acid amide represented by formula (1) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.75-1.66 (m, 1H), 2.04-2.14 (m, 1H), 2.56-2.67 (m , 1H), 3.35 (s, 1H), 3.46-3.56 (m, 2H), 3.61 (dd, J = 8.9, 5.5 Hz, 1H), 3.74- 3.81 (m, 1H), 3.86-3.95 (m, 2H), 7.93 (dd, J = 8.1, 2.0 Hz, 1H), 8.13 (brs, 1H) 8.16 (d, J = 8.1 Hz, 1H), 8.61-8.64 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−（２−チエニルエチニル）ピリジン−２−カルボン酸アミド（以下、本発明化合物（９）と記す。）５８０ｍｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）１．６７−１．７７（ｍ，１Ｈ）、２．０６−２．１５（ｍ，１Ｈ）、２．５７−２．６８（ｍ，１Ｈ）、３．４５−３．５７（ｍ，２Ｈ）、３．６２（ｄｄ，Ｊ ＝ ８．７，５．５Ｈｚ，１Ｈ）、３．７８（ｄｄ，Ｊ ＝ １５．５，７．９ Ｈｚ，１Ｈ）、３．８７−３．９６（ｍ，２Ｈ）、７．０４−７．０８（ｍ，１Ｈ）、７．３５−７．３９（ｍ，２Ｈ）、７．９２−７．９６（ｍ，１Ｈ）、８．１４（ｂｒｓ，１Ｈ）、８．１６−８．２０（ｍ，１Ｈ）、８．６４−８．６６（ｍ，１Ｈ）． Production Example 9
To a solution of N- (tetrahydrofuran-3-ylmethyl) -5-ethynylpyridine-2-carboxylic acid amide (400 mg, 1.74 mmol) in N, N-dimethylformamide (5 mL) under a nitrogen atmosphere was added 2-iodothiophene (401 mg). , 1.91 mmol), triethylamine (0.7 mL, 5.21 mmol), copper iodide (6 mg, 0.09 mmol) and dichlorobis (triphenylphosphine) palladium (61 mg, 0.09 mmol), and stirred at room temperature for 3 hours. Then, water was added and extracted with ethyl acetate. The organic layer was washed successively with 1 mol / L hydrochloric acid and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

580 mg of N- (tetrahydrofuran-3-ylmethyl) -5- (2-thienylethynyl) pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (9)) represented by the formula:
¹ H-NMR (CDCl ₃ , TMS) δ (ppm) 1.67-1.77 (m, 1H), 2.06-2.15 (m, 1H), 2.57-2.68 (m, 1H), 3.45-3.57 (m, 2H), 3.62 (dd, J = 8.7, 5.5 Hz, 1H), 3.78 (dd, J = 15.5, 7.9). Hz, 1H), 3.87-3.96 (m, 2H), 7.04-7.08 (m, 1H), 7.35-7.39 (m, 2H), 7.92-7. 96 (m, 1H), 8.14 (brs, 1H), 8.16-8.20 (m, 1H), 8.64-8.66 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−５−（３−チエニルエチニル）ピリジン−２−カルボン酸アミド（以下、本発明化合物（１０）と記す。）５０６ｍｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）１．６７−１．７７（ｍ，１Ｈ）、２．０４−２．１５（ｍ，１Ｈ）、２．５７−２．６８（ｍ，１Ｈ）、３．４５−３．５７（ｍ，２Ｈ）、３．６２（ｄｄ，Ｊ ＝ ８．９，５．５Ｈｚ，１Ｈ）、３．７５−３．８２（ｍ，１Ｈ）、３．８６−３．９６（ｍ，２Ｈ）、７．２３（ｄｄ，Ｊ ＝ ５．０，１．１Ｈｚ，１Ｈ）、７．３５（ｄｄ，Ｊ ＝ ５．０，３．０Ｈｚ，１Ｈ）、
７．６１（ｄｄ，Ｊ ＝ ３．０，１．１Ｈｚ，１Ｈ）、７．９４（ｄｄ，Ｊ ＝ ８．０，２．１Ｈｚ，１Ｈ）、８．１４（ｂｒｓ，１Ｈ）、８．１７−８．１８（ｍ，１Ｈ）、８．６４−８．６６（ｍ，１Ｈ）． Production Example 10
In Reference Production Example 3, 3-iodothiophene (401 mg, 1.91 mmol) was used instead of 2-iodothiophene (401 mg, 1.91 mmol), and the same reaction was carried out.

506 mg of N- (tetrahydrofuran-3-ylmethyl) -5- (3-thienylethynyl) pyridine-2-carboxylic acid amide (hereinafter referred to as the present compound (10)) represented by the formula:
¹ H-NMR (CDCl ₃ , TMS) δ (ppm) 1.67-1.77 (m, 1H), 2.04-2.15 (m, 1H), 2.57-2.68 (m, 1H), 3.45-3.57 (m, 2H), 3.62 (dd, J = 8.9, 5.5 Hz, 1H), 3.75-3.82 (m, 1H), 3. 86-3.96 (m, 2H), 7.23 (dd, J = 5.0, 1.1 Hz, 1H), 7.35 (dd, J = 5.0, 3.0 Hz, 1H),
7.61 (dd, J = 3.0, 1.1 Hz, 1H), 7.94 (dd, J = 8.0, 2.1 Hz, 1H), 8.14 (brs, 1H), 8.17 -8.18 (m, 1H), 8.64-8.66 (m, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−６−クロロピリダジン−３−カルボン酸アミド５．１０ｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：１．７１（ｍ，１Ｈ）、２．１１（ｍ，１Ｈ）、２．６３（ｍ，１Ｈ）、３．５６（ｍ，２Ｈ）、３．６２（ｄｄ，１Ｈ，Ｊ ＝ ８．９，５．３ Ｈｚ）、３．７９（ｍ，１Ｈ）、３．９１（ｍ，２Ｈ）、７．７０（ｄ，１Ｈ，Ｊ ＝ ８．８ Ｈｚ）、８．１７（ｂｒｓ，１Ｈ）、８．２８（ｄ，１Ｈ，Ｊ ＝ ８．８ Ｈｚ） Reference production example 3
6-chloropyridazine-3-carboxylic acid (5.00 g, 31.5 mmol), (tetrahydrofuran-3-yl) methylamine hydrochloride (4.77 g, 34.7 mmol) and 1-hydroxybenzotriazole (426 mg, 3. 15 mmol) was added to chloroform (100 mL), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (6.95 g, 36.3 mmol) was added, and then triethylamine (9.1 mL, 47.3 mmol) was added, and the mixture was stirred for 3 hours in the range of 5 ° C. to room temperature, water was added, and the mixture was extracted twice with chloroform. The organic layers were combined, washed successively with 1 mol / L hydrochloric acid and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

Thus, 5.10 g of N- (tetrahydrofuran-3-ylmethyl) -6-chloropyridazine-3-carboxylic acid amide represented by the formula (1) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.71 (m, 1H), 2.11 (m, 1H), 2.63 (m, 1H), 3.56 (m, 2H) 3.62 (dd, 1H, J = 8.9, 5.3 Hz), 3.79 (m, 1H), 3.91 (m, 2H), 7.70 (d, 1H, J = 8) .8 Hz), 8.17 (brs, 1H), 8.28 (d, 1H, J = 8.8 Hz)

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−６−エチニルピリダジン−３−カルボン酸アミド６１０ｍｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：１．６７−１．７６（ｍ，２Ｈ）、２．０７−２．１６（ｍ，１Ｈ）、２．５８−２．６９（ｍ，１Ｈ）、３．５２−３．５４（ｍ，３Ｈ）、３．５９−３．６４（ｍ，１Ｈ）、３．７５−３．８２（ｍ，１Ｈ）、３．８６−３．９７（ｍ，２Ｈ）、７．７８（ｄ，１Ｈ，Ｊ ＝ ８．７ Ｈｚ）、８．３０（ｄ，１Ｈ，Ｊ ＝ ８．７ Ｈｚ）、８．３１（ｂｒｓ，１Ｈ）． Reference production example 4
To a solution of N- (tetrahydrofuran-3-ylmethyl) -6-chloropyridazine-3-carboxylic acid amide (2.00 g, 8.28 mmol) in N, N-dimethylformamide (10 mL) was added trimethylsilylacetylene (1.06 g, 10 .8 mmol), triethylamine (3.5 mL, 24.8 mmol), copper iodide (17 mg, 0.25 mmol) and dichlorobis (triphenylphosphine) palladium (174 mg, 0.25 mmol) were added, and 45-50 under nitrogen atmosphere. After stirring for 4 hours within the range of ° C., water was added and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1 mol / L hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. Methanol (20 mL) and potassium carbonate (1.72 g, 12.4 mmol) were added to the resulting crude product, and the mixture was stirred at room temperature for 2 hours, diluted with toluene, and reduced pressure conditions. Concentrated down. Ethyl acetate was added to the resulting suspension, washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

610 mg of N- (tetrahydrofuran-3-ylmethyl) -6-ethynylpyridazine-3-carboxylic acid amide represented by formula (1) was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.67-1.76 (m, 2H), 2.07-2.16 (m, 1H), 2.58-2.69 (m , 1H), 3.52-3.54 (m, 3H), 3.59-3.64 (m, 1H), 3.75-3.82 (m, 1H), 3.86-3.97. (M, 2H), 7.78 (d, 1H, J = 8.7 Hz), 8.30 (d, 1H, J = 8.7 Hz), 8.31 (brs, 1H).

で示されるＮ−（テトラヒドロフラン−３−イルメチル）−６−（２−チエニルエチニル）ピリダジン−３−カルボン酸アミド（以下、本発明化合物（１１）と記す。）３３０ｍｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：１．６８−１．７８（ｍ，１Ｈ）、２．０７−２．１７（ｍ，１Ｈ）、２．５９−２．７０（ｍ，１Ｈ）、３．５５−３．５９（ｍ，２Ｈ）、３．６３（ｄｄ，Ｊ ＝ ８．７，５．５ Ｈｚ，１Ｈ）、３．７６−３．８２（ｍ，１Ｈ）、３．８７−３．９７（ｍ，２Ｈ）、７．１０（ｄｄ，Ｊ ＝ ５．０，３．７ Ｈｚ，１Ｈ）、７．４７（ｄｄ，Ｊ ＝ ５．０，１．１ Ｈｚ，１Ｈ）、７．５１（ｄｄ，Ｊ ＝ ３．７，１．１ Ｈｚ，１Ｈ）、７．７８（ｄ，Ｊ ＝ ８．６ Ｈｚ，１Ｈ）、８．２９（ｄ，Ｊ ＝ ８．６ Ｈｚ，１Ｈ）、８．３１（ｂｒｓ，１Ｈ）． Production Example 11
To a solution of N- (tetrahydrofuran-3-ylmethyl) -6-ethynylpyridazine-3-carboxylic acid amide (400 mg, 1.73 mmol) in N, N-dimethylformamide (5 mL) was added 2-iodothiophene (436 mg, 2.08 mmol). ), Triethylamine (0.7 mL, 5.2 mmol), copper iodide (6 mg, 0.09 mmol) and dichlorobis (triphenylphosphine) palladium (61 mg, 0.09 mmol), and added under nitrogen atmosphere at 40-50 ° C. After stirring for 1 hour within the range, water was added and the mixture was extracted with ethyl acetate.
The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

N- (tetrahydrofuran-3-ylmethyl) -6- (2-thienylethynyl) pyridazine-3-carboxylic acid amide (hereinafter, referred to as the present compound (11)) represented by the formula:
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.68-1.78 (m, 1H), 2.07-2.17 (m, 1H), 2.59-2.70 (m , 1H), 3.55-3.59 (m, 2H), 3.63 (dd, J = 8.7, 5.5 Hz, 1H), 3.76-3.82 (m, 1H), 3.87-3.97 (m, 2H), 7.10 (dd, J = 5.0, 3.7 Hz, 1H), 7.47 (dd, J = 5.0, 1.1 Hz, 1H), 7.51 (dd, J = 3.7, 1.1 Hz, 1H), 7.78 (d, J = 8.6 Hz, 1H), 8.29 (d, J = 8.6) Hz, 1H), 8.31 (brs, 1H).

で示される５−メタンスルホニルオキシメチルピリジン−２−カルボン酸メチル６４３ｍｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ＴＭＳ）δ（ｐｐｍ）：３．０６（ｓ，３Ｈ）、４．０４（ｓ，３Ｈ）、５．３４（ｓ，２Ｈ）、７．９４（ｄｄ， Ｊ ＝ ８．１，２．１Ｈｚ，１Ｈ）、８．２０（ｄ，Ｊ ＝ ８．１ Ｈｚ，１Ｈ）、８．７７（ｄ，Ｊ ＝ ２．１ Ｈｚ，１Ｈ）． Reference production example 5
To a solution of methyl 5-hydroxymethylpyridine-2-carboxylate (0.50 g, 2.99 mmol) in chloroform (12 mL) was added triethylamine (0.54 mL, 3.89 mmol). Under ice water cooling, methanesulfonyl chloride (0.30 mL, 3.89 mmol) was slowly added dropwise, followed by stirring for 20 minutes. Water was poured into the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and the organic layer was dried over sodium sulfate. Concentrate under reduced pressure, suspend the residue in a mixture of diisopropyl ether and hexane, and collect the precipitate by filtration.

As a result, 643 mg of methyl 5-methanesulfonyloxymethylpyridine-2-carboxylate was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 3.06 (s, 3H), 4.04 (s, 3H), 5.34 (s, 2H), 7.94 (dd, J = 8.1, 2.1 Hz, 1H), 8.20 (d, J = 8.1 Hz, 1H), 8.77 (d, J = 2.1 Hz, 1H).

で示される５−（２’−チエニルメトキシメチル）−ピリジン−２−カルボン酸４８９ｍｇを得た。 Reference production example 6
To a solution of 2-thienylmethanol (1.40 g, 12.2 mmol) in THF (10 mL) was added potassium tert-butoxide (1.32 g, 12.2 mmol), and while stirring, 5-methanesulfonyloxymethylpyridine- Methyl 2-carboxylate (1.00 g, 4.08 mmol) was added. After stirring at room temperature for 2 hours and 30 minutes, methyl-tert-butyl ether (MTBE) and water were added to the reaction solution, and the mixture was washed with MTBE. The aqueous layer was adjusted to pH 1-2 with about 35% hydrochloric acid, and the aqueous layer was saturated with sodium chloride. The mixture was extracted twice with ethyl acetate, and the ethyl acetate layer was washed with saturated brine and dried over sodium sulfate. After concentration under reduced pressure, the mixture is suspended in a mixed solvent of ethyl acetate and diisopropyl ether, and the precipitate is collected by filtration.

489 mg of 5- (2′-thienylmethoxymethyl) -pyridine-2-carboxylic acid represented by

  Next, specific examples of the compound of the present invention are exemplified below. However, R and n in a formula represent one of the combinations shown below.

Compounds represented by formula (I-A1-1) to formula (I-A1-112);
Compounds represented by formula (I-A2-1) to formula (I-A2-112);
Compounds represented by formula (I-A3-1) to formula (I-A3-112);
Compounds represented by formula (I-A4-1) to formula (I-A4-112);
Compounds represented by formula (I-A5-1) to formula (I-A5-112);
Compounds represented by formula (I-A6-1) to formula (I-A6-112);
Compounds represented by formula (I-A7-1) to formula (I-A7-112);
Compounds represented by formula (I-A8-1) to formula (I-A8-112);
Compounds represented by formula (I-A9-1) to formula (I-A9-112);
Compounds represented by formula (I-A10-1) to formula (I-A10-112);
Compounds represented by formula (I-A11-1) to formula (I-A11-112);
Compounds represented by formula (I-A12-1) to formula (I-A12-112);
Compounds represented by formula (I-A13-1) to formula (I-A13-112);
Compounds represented by formula (I-A14-1) to formula (IA-14-112);
Compounds represented by formula (I-A15-1) to formula (I-A15-112);
Compounds represented by formula (I-A16-1) to formula (I-A16-112);
Compounds of formula (I-A17-1) to formula (I-A17-112);
Compounds represented by formula (I-A18-1) to formula (I-A18-112);
Compounds represented by formula (I-A19-1) to formula (IA19-112);
Compounds of formula (I-A20-1) to formula (I-A20-112);
Compounds represented by formula (I-A21-1) to formula (I-A21-112);
Compounds represented by formula (I-A22-1) to formula (I-A22-112);
Compounds represented by formula (I-A23-1) to formula (I-A23-112);
Compounds represented by formula (I-A24-1) to formula (I-A24-112);
Compounds represented by formula (I-A25-1) to formula (I-A25-112);
Compounds represented by formula (I-A26-1) to formula (I-A26-112);
Compounds represented by formula (I-A27-1) to formula (IA27-112);
Compounds represented by formula (I-A28-1) to formula (IA28-112);
Compounds represented by formula (I-A29-1) to formula (I-A29-112);
Compounds represented by formula (I-A30-1) to formula (I-A30-112);
Compounds represented by formula (I-A31-1) to formula (I-A31-112);
Compounds represented by formula (I-A32-1) to formula (I-A32-112);
Compounds represented by formula (I-A33-1) to formula (I-A33-112);
Compounds represented by formula (I-A34-1) to formula (I-A34-112);
Compounds represented by formula (I-A35-1) to formula (IA35-112);
Compounds represented by formula (I-A36-1) to formula (IA36-112);
Compounds represented by formula (I-A37-1) to formula (IA37-112);
Compounds represented by formula (I-A38-1) to formula (IA38-112);
Compounds represented by formula (I-A39-1) to formula (IA39-112);
Compounds represented by formula (I-A40-1) to formula (IA40-112);
Compounds represented by formula (I-A41-1) to formula (I-A41-112);
Compounds represented by formula (I-A42-1) to formula (I-A42-112);
Compounds represented by formula (I-A43-1) to formula (IA43-112);
Compounds of formula (I-A44-1) to formula (I-A44-112);
Compounds represented by formula (I-A45-1) to formula (I-A45-112);
Compounds represented by formula (I-A46-1) to formula (I-A46-112);
Compounds represented by formula (I-A47-1) to formula (I-A47-112);
Compounds represented by formula (I-A48-1) to formula (I-A48-112);
Compounds represented by formula (I-A49-1) to formula (I-A49-112);
Compounds represented by formula (I-A50-1) to formula (I-A50-112);
Compounds represented by formula (I-A51-1) to formula (I-A51-112);
Compounds represented by formula (I-A52-1) to formula (I-A52-112);
Compounds represented by formula (I-A53-1) to formula (I-A53-112);
Compounds represented by formula (I-A54-1) to formula (I-A54-112).

Compounds represented by formula (I-B1-1) to formula (I-B1-112);
Compounds represented by formula (I-B2-1) to formula (I-B2-112);
Compounds represented by formula (I-B3-1) to formula (I-B3-112);
Compounds represented by formula (I-B4-1) to formula (I-B4-112);
Compounds represented by formula (I-B5-1) to formula (I-B5-112);
Compounds represented by formula (I-B6-1) to formula (I-B6-112);
Compounds represented by formula (I-B7-1) to formula (I-B7-112);
Compounds represented by formula (I-B8-1) to formula (I-B8-112);
Compounds represented by formula (I-B9-1) to formula (I-B9-112);
Compounds represented by formula (I-B10-1) to formula (I-B10-112);
Compounds represented by formula (I-B11-1) to formula (I-B11-112);
Compounds represented by formula (I-B12-1) to formula (I-B12-112);
Compounds represented by formula (I-B13-1) to formula (I-B13-112);
Compounds represented by formula (I-B14-1) to formula (I-B14-112);
Compounds represented by formula (I-B15-1) to formula (I-B15-112);
Compounds represented by formula (I-B16-1) to formula (I-B16-112);
Compounds represented by formula (I-B17-1) to formula (I-B17-112);
Compounds represented by formula (I-B18-1) to formula (I-B18-112);
Compounds represented by formula (I-B19-1) to formula (I-B19-112);
Compounds represented by formula (I-B20-1) to formula (I-B20-112);
Compounds represented by formula (I-B21-1) to formula (I-B21-112);
Compounds represented by formula (I-B22-1) to formula (I-B22-112);
Compounds represented by formula (I-B23-1) to formula (I-B23-112);
Compounds represented by formula (I-B24-1) to formula (I-B24-112);
Compounds represented by formula (I-B25-1) to formula (I-B25-112);
Compounds represented by formula (I-B26-1) to formula (I-B26-112);
Compounds represented by formula (I-B27-1) to formula (I-B27-112);
Compounds represented by formula (I-B28-1) to formula (I-B28-112);
Compounds represented by formula (I-B29-1) to formula (I-B29-112);
Compounds represented by formula (I-B30-1) to formula (I-B30-112);
Compounds represented by formula (I-B31-1) to formula (I-B31-112);
Compounds represented by formula (I-B32-1) to formula (I-B32-112);
Compounds represented by formula (I-B33-1) to formula (I-B33-112);
Compounds represented by formula (I-B34-1) to formula (I-B34-112);
Compounds represented by formula (I-B35-1) to formula (I-B35-112);
Compounds represented by formula (I-B36-1) to formula (I-B36-112);
Compounds represented by formula (I-B37-1) to formula (I-B37-112);
Compounds represented by formula (I-B38-1) to formula (I-B38-112);
Compounds represented by formula (I-B39-1) to formula (I-B39-112);
Compounds represented by formula (I-B40-1) to formula (I-B40-112);
Compounds represented by formula (I-B41-1) to formula (I-B41-112);
Compounds represented by formula (I-B42-1) to formula (I-B42-112);
Compounds represented by formula (I-B43-1) to formula (I-B43-112);
Compounds represented by formula (I-B44-1) to formula (I-B44-112);
Compounds represented by formula (I-B45-1) to formula (I-B45-112);
Compounds represented by formula (I-B46-1) to formula (I-B46-112);
Compounds represented by formula (I-B47-1) to formula (I-B47-112);
Compounds represented by formula (I-B48-1) to formula (I-B48-112);
Compounds represented by formula (I-B49-1) to formula (I-B49-112);
Compounds represented by formula (I-B50-1) to formula (I-B50-112);
Compounds represented by formula (I-B51-1) to formula (I-B51-112);
Compounds represented by formula (I-B52-1) to formula (I-B52-112);
Compounds represented by formula (I-B53-1) to formula (I-B53-112);
Compounds represented by formula (I-B54-1) to formula (I-B54-112).

Compounds represented by formula (I-C1-1) to formula (I-C1-112);
Compounds represented by formula (I-C2-1) to formula (I-C2-112);
Compounds represented by formula (I-C3-1) to formula (I-C3-112);
Compounds represented by formula (I-C4-1) to formula (I-C4-112);
Compounds represented by formula (I-C5-1) to formula (I-C5-112);
Compounds represented by formula (I-C6-1) to formula (I-C6-112);
Compounds represented by formula (I-C7-1) to formula (I-C7-112);
Compounds represented by formula (I-C8-1) to formula (I-C8-112);
Compounds represented by formula (I-C9-1) to formula (I-C9-112);
Compounds represented by formula (I-C10-1) to formula (I-C10-112);
Compounds represented by formula (I-C11-1) to formula (I-C11-112);
Compounds represented by formula (I-C12-1) to formula (I-C12-112);
Compounds represented by formula (I-C13-1) to formula (I-C13-112);
Compounds represented by formula (I-C14-1) to formula (I-C14-112);
Compounds represented by formula (I-C15-1) to formula (I-C15-112);
Compounds represented by formula (I-C16-1) to formula (I-C16-112);
Compounds represented by formula (I-C17-1) to formula (I-C17-112);
Compounds represented by formula (I-C18-1) to formula (I-C18-112);
Compounds represented by formula (I-C19-1) to formula (I-C19-112);
Compounds represented by formula (I-C20-1) to formula (I-C20-112);
Compounds represented by formula (I-C21-1) to formula (I-C21-112);
Compounds represented by formula (I-C22-1) to formula (I-C22-112);
Compounds represented by formula (I-C23-1) to formula (I-C23-112);
Compounds represented by formula (I-C24-1) to formula (I-C24-112);
Compounds represented by formula (I-C25-1) to formula (I-C25-112);
Compounds represented by formula (I-C26-1) to formula (I-C26-112);
Compounds represented by formula (I-C27-1) to formula (I-C27-112);
Compounds represented by formula (I-C28-1) to formula (I-C28-112);
Compounds represented by formula (I-C29-1) to formula (I-C29-112);
Compounds represented by formula (I-C30-1) to formula (I-C30-112);
Compounds represented by formula (I-C31-1) to formula (I-C31-112);
Compounds represented by formula (I-C32-1) to formula (I-C32-112);
Compounds represented by formula (I-C33-1) to formula (I-C33-112);
Compounds represented by formula (I-C34-1) to formula (I-C34-112);
Compounds represented by formula (I-C35-1) to formula (I-C35-112);
Compounds represented by formula (I-C36-1) to formula (I-C36-112);
Compounds represented by formula (I-C37-1) to formula (I-C37-112);
Compounds represented by formula (I-C38-1) to formula (I-C38-112);
Compounds represented by formula (I-C39-1) to formula (I-C39-112);
Compounds of formula (I-C40-1) to formula (I-C40-112);
Compounds represented by formula (I-C41-1) to formula (I-C41-112);
Compounds represented by formula (I-C42-1) to formula (I-C42-112);
Compounds represented by formula (I-C43-1) to formula (I-C43-112);
Compounds represented by formula (I-C44-1) to formula (I-C44-112);
Compounds represented by formula (I-C45-1) to formula (I-C45-112);
Compounds represented by formula (I-C46-1) to formula (I-C46-112);
Compounds represented by formula (I-C47-1) to formula (I-C47-112);
Compounds of formula (I-C48-1) to formula (I-C48-112);
Compounds represented by formula (I-C49-1) to formula (I-C49-112);
Compounds represented by formula (I-C50-1) to formula (I-C50-112);
Compounds represented by formula (I-C51-1) to formula (I-C51-112);
Compounds represented by formula (I-C52-1) to formula (I-C52-112);
Compounds represented by formula (I-C53-1) to formula (I-C53-112);
Compounds represented by formula (I-C54-1) to formula (I-C54-112);
Compounds represented by formula (I-C55-1) to formula (I-C55-112);
Compounds represented by formula (I-C56-1) to formula (I-C56-112);
Compounds represented by formula (I-C57-1) to formula (I-C57-112);
Compounds of formula (I-C58-1) to formula (I-C58-112);
Compounds of formula (I-C59-1) to formula (I-C59-112);
Compounds of formula (I-C60-1) to formula (I-C60-112);
Compounds represented by formula (I-C61-1) to formula (I-C61-112);
Compounds represented by formula (I-C62-1) to formula (I-C62-112);
Compounds represented by formula (I-C63-1) to formula (I-C63-112);
Compounds represented by formula (I-C64-1) to formula (I-C64-112);
Compounds represented by formula (I-C65-1) to formula (I-C65-112);
Compounds of formula (I-C66-1) to formula (I-C66-112);
Compounds of formula (I-C67-1) to formula (I-C67-112);
Compounds represented by formula (I-C68-1) to formula (I-C68-112);
Compounds of formula (I-C69-1) to formula (I-C69-112);
Compounds represented by formula (I-C70-1) to formula (I-C70-112);
Compounds of formula (I-C71-1) to formula (I-C71-112);
Compounds represented by formula (I-C72-1) to formula (I-C72-112);
Compounds represented by formula (I-C73-1) to formula (I-C73-112);
Compounds represented by formula (I-C74-1) to formula (I-C74-112);
Compounds represented by formula (I-C75-1) to formula (I-C75-112);
Compounds represented by formula (I-C76-1) to formula (I-C76-112);
Compounds represented by formula (I-C77-1) to formula (I-C77-112);
Compounds represented by formula (I-C78-1) to formula (I-C78-112);
Compounds of formula (I-C79-1) to formula (I-C79-112);
Compounds represented by formula (I-C80-1) to formula (I-C80-112);
Compounds of formula (I-C81-1) to formula (I-C81-112);
Compounds represented by formula (I-C82-1) to formula (I-C82-112);
Compounds represented by formula (I-C83-1) to formula (I-C831-112);
Compounds represented by formula (I-C84-1) to formula (I-C84-112);
Compounds represented by formula (I-C85-1) to formula (I-C85-112);
Compounds represented by formula (I-C86-1) to formula (I-C86-112);
Compounds of formula (I-C87-1) to formula (I-C87-112);
Compounds of formula (I-C88-1) to formula (I-C88-112);
Compounds of formula (I-C89-1) to formula (I-C89-112);
Compounds represented by formula (I-C90-1) to formula (I-C90-112);
Compounds represented by formula (I-C91-1) to formula (I-C91-112);
Compounds represented by formula (I-C92-1) to formula (I-C92-112);
Compounds represented by formula (I-C93-1) to formula (I-C93-112);
Compounds of formula (I-C94-1) to formula (I-C94-112);
Compounds of formula (I-C95-1) to formula (I-C95-112);
Compounds represented by formula (I-C96-1) to formula (I-C96-112);
Compounds of formula (I-C97-1) to formula (I-C97-112);
Compounds represented by formula (I-C98-1) to formula (I-C98-112);
Compounds represented by formula (I-C99-1) to formula (I-C99-112);
Compounds represented by formula (I-C100-1) to formula (I-C100-112);
Compounds of formula (I-C101-1) to formula (I-C101-112);
Compounds represented by formula (I-C102-1) to formula (I-C102-112);
Compounds represented by formula (I-C103-1) to formula (I-C103-112);
Compounds represented by formula (I-C104-1) to formula (I-C104-112);
Compounds represented by formula (I-C105-1) to formula (I-C105-112);
Compounds represented by formula (I-C106-1) to formula (I-C106-112);
Compounds represented by formula (I-C107-1) to formula (I-C107-112);
Compounds represented by formula (I-C108-1) to formula (I-C108-112);
Compounds of formula (I-C109-1) to formula (I-C109-112);
Compounds represented by formula (I-C110-1) to formula (I-C110-112);
Compounds represented by formula (I-C111-1) to formula (I-C111-112);
Compounds represented by formula (I-C112-1) to formula (I-C112-112);
Compounds represented by formula (I-C113-1) to formula (I-C113-112);
Compounds represented by formula (I-C114-1) to formula (I-C114-112);
Compounds of formula (I-C115-1) to formula (I-C115-112);
Compounds represented by formula (I-C116-1) to formula (I-C116-112);
Compounds represented by formula (I-C117-1) to formula (I-C117-112);
Compounds of formula (I-C118-1) to formula (I-C118-112);
Compounds represented by formula (I-C119-1) to formula (I-C119-112);
Compounds represented by formula (I-C120-1) to formula (I-C120-112);
Compounds represented by formula (I-C121-1) to formula (I-C121-112);
Compounds represented by formula (I-C122-1) to formula (I-C122-112);
Compounds represented by formula (I-C123-1) to formula (I-C123-112);
Compounds represented by formula (I-C124-1) to formula (I-C124-112);
Compounds of formula (I-C125-1) to formula (I-C125-112);
Compounds of formula (I-C126-1) to formula (I-C126-112);
Compounds represented by formula (I-C127-1) to formula (I-C127-112);
Compounds represented by formula (I-C128-1) to formula (I-C128-112);
Compounds represented by formula (I-C129-1) to formula (I-C129-112);
Compounds represented by formula (I-C130-1) to formula (I-C130-112);
Compounds represented by formula (I-C131-1) to formula (I-C131-112);
Compounds represented by formula (I-C132-1) to formula (I-C132-112);
Compounds represented by formula (I-C133-1) to formula (I-C133-112);
Compounds represented by formula (I-C134-1) to formula (I-C134-112);
Compounds of formula (I-C135-1) to formula (I-C135-112);
Compounds represented by formula (I-C136-1) to formula (I-C136-112);
Compounds represented by formula (I-C137-1) to formula (I-C137-112);
Compounds of formula (I-C138-1) to formula (I-C138-112);
Compounds of formula (I-C139-1) to formula (I-C139-112);
Compounds of formula (I-C140-1) to formula (I-C140-112);
Compounds represented by formula (I-C141-1) to formula (I-C141-112);
Compounds represented by formula (I-C142-1) to formula (I-C142-112);
Compounds represented by formula (I-C143-1) to formula (I-C143-112);
Compounds represented by formula (I-C144-1) to formula (I-C144-112);
Compounds represented by formula (I-C145-1) to formula (I-C145-112);
Compounds of formula (I-C146-1) to formula (I-C146-112);
Compounds represented by formula (I-C147-1) to formula (I-C147-112).

Compounds represented by formula (I-D1-1) to formula (I-D1-112);
Compounds represented by formula (I-D2-1) to formula (I-D2-112);
Compounds represented by formula (I-D3-1) to formula (I-D3-112);
Compounds represented by formula (I-D4-1) to formula (I-D4-112);
Compounds represented by formula (I-D5-1) to formula (I-D5-112);
Compounds represented by formula (I-D6-1) to formula (I-D6-112);
Compounds represented by formula (I-D7-1) to formula (I-D7-112);
Compounds represented by formula (I-D8-1) to formula (I-D8-112);
Compounds represented by formula (I-D9-1) to formula (I-D9-112);
Compounds represented by formula (I-D10-1) to formula (I-D10-112);
Compounds represented by formula (I-D11-1) to formula (I-D11-112);
Compounds represented by formula (I-D12-1) to formula (I-D12-112);
Compounds represented by formula (I-D13-1) to formula (I-D13-112);
Compounds represented by formula (I-D14-1) to formula (I-D14-112);
Compounds represented by formula (I-D15-1) to formula (I-D15-112);
Compounds represented by formula (I-D16-1) to formula (I-D16-112).

Compounds represented by formula (I-E1-1) to formula (I-E1-112);
Compounds represented by formula (I-E2-1) to formula (I-E2-112);
Compounds represented by formula (I-E3-1) to formula (I-E3-112);
Compounds represented by formula (I-E4-1) to formula (I-E4-112);
Compounds represented by formula (I-E5-1) to formula (I-E5-112);
Compounds represented by formula (I-E6-1) to formula (I-E6-112);
Compounds represented by formula (I-E7-1) to formula (I-E7-112);
Compounds represented by formula (I-E8-1) to formula (I-E8-112);
Compounds represented by formula (I-E9-1) to formula (I-E9-112);
Compounds of formula (I-E10-1) to formula (IE10-112);
Compounds represented by formula (I-E11-1) to formula (I-E11-112);
Compounds represented by formula (I-E12-1) to formula (I-E12-112);
Compounds represented by formula (IE13-1) to formula (IE13-112);
Compounds represented by formula (IE14-1) to formula (IE14-112);
Compounds represented by formulas (IE15-1) to (IE15-112);
Compounds represented by formula (IE16-1) to formula (IE16-112).

Compounds represented by formula (I-A1) to formula (I-A54), compounds represented by formula (I-B1) to formula (I-B54), formulas (I-C1) to (I-C147) Examples of R and n in the compounds represented by the formulas (I-D1) to (I-D16) and the compounds represented by the formulas (I-E1) to (I-E16) are shown below. In the following, a branch number, a group represented by R, and n are described in order in [].

[Branch number, R, n] = [1, a1, 1], [2, a1, 2], [3, a2, 1], [4, a3, 1], [5, a4, 1], [ 6, a4, 2], [7, a5, 1], [8, a6, 1], [9, a7, 1], [10, a8, 1], [11, a9, 1], [12, a10, 1], [13, a11, 1], [14, a12, 1], [15, a13, 1], [16, a14, 1], [17, a15, 1], [18, a15, 2], [19, a16, 1], [20, a17, 1], [21, a18, 1], [22, a19, 1], [23, a19, 2], [24, a20, 1] , [25, a21, 1], [26, a22, 1], [27, a23, 1], [28, a24, 1], [29, a25, 1], [30, a26, 1], [ 31, a27, 1], [32, a28, 1], [33, a28, 2], [34, a29, 1], [35, a29, 2], [36, a30, 1], [37, a31, 1], [38, a32, 1], [39, a33, 1], [40, a34, 1], [41, a35, 1], [42, a36, 1], [43, a36, 2], [44, a37, 1], [45, a37, 2], [46, a38, 1], [47, a38, 2], [49, a39, 1], [50, a39, 2] , [51, a40, 1], [52, a40, 2], [53, a41, 1], [54, a41, 2], [55, a42, 1], [56, a42, 2], [ 57, a43, 1], [58, a43, 2], [59, a44, 1], [60, a4 4, 2], [61, a45, 1], [62, a45, 2], [63, a46, 1], [64, a46, 2], [65, a47, 1], [66, a47, 2], [67, a48, 1], [68, a48, 2], [69, a49, 1], [70, a49, 2], [71, a50, 1], [72, a50, 2] , [73, a51, 1], [74, a51, 2], [75, a52, 1], [76, a52, 2], [77, a53, 1], [78, a53, 2], [ 79, a54, 1], [80, a54, 2], [81, a55, 1], [82, a55, 2], [83, a56, 1], [84, a56, 2], [85, a57, 1], [86, a57, 2], [87, a58, 1], [88, a58, 2], [89, a59, 1], [90, a59, 2], [91, a60, 1], [92, a60, 2], [93, a61, 1], [94, a61, 2], [95, a62, 1], [96, a62, 2], [97, a63, 1] , [98, a63, 2], [99, a64, 1], [100, a64, 2], [101, a65, 1], [102, a65, 2], [103, a66, 1], [ 104, a66, 2], [105, a67, 1], [106, a67, 2], [107, a68, 1], [108, a68, 2], [109, a69, 1], [110, a69, 2], [111, a70, 1], [112, a70, 2].

Each symbol of a1 to a70 described as a group represented by R represents the following group.

For example, I-A1-1 represents a compound represented by the formula (I-A1) in which R is a1 and n is 1, and is represented by the following formula.

  Next, formulation examples are shown. In addition, a part shows a weight part.

Formulation Example 1
20 parts of any one of the compounds (1) to (11) of the present invention are dissolved in 65 parts of xylene, 15 parts of Solpol 3005X (Toho Chemical Registration) is added, and the mixture is stirred well to obtain an emulsion.

Formulation Example 2
Solvent 3005X 5 parts is added to 40 parts of any one of the compounds (1) to (11) of the present invention and mixed well to mix 32 parts of Carplex # 80 (synthetic hydrous silicon oxide, Shionogi & Co., registered trademark), 300 mesh. Add 23 parts of diatomaceous earth and stir and mix with a juice mixer to obtain a wettable powder.

Formulation Example 3
1.5 parts of any one of the compounds (1) to (11) of the present invention and 1 part of Toxeal GUN (synthetic hydrous silicon oxide, manufactured by Tokuyama Co., Ltd.), Ryax 85A (sodium lignin sulfonate, manufactured by West vaco chemicals) 2 parts, 30 parts of bentonite Fuji (Bentonite, manufactured by Hojun Co., Ltd.) and 65.5 parts of Katsuyama A clay (Kaolin clay, manufactured by Katsumiyama Mining Co., Ltd.) are thoroughly pulverized and mixed. Granulate with a granulator and dry to obtain 1.5% granules.

Formulation Example 4
After mixing 10 parts of any one of the compounds (1) to (11) of the present invention, 10 parts of phenylxylylethane and 0.5 part of Sumidur L-75 (tolylene diisocyanate, manufactured by Sumika Bayer Urethane Co., Ltd.) The mixture is added to 20 parts of a 10% aqueous solution of gum arabic and stirred with a homomixer to obtain an emulsion having an average particle size of 20 μm. To this, 2 parts of ethylene glycol is added, and further stirred in a warm bath at 60 ° C. for 24 hours to obtain a microcapsule slurry. On the other hand, 0.2 part of Xanthan gum and 1.0 part of Beegum R (aluminum magnesium silicate, Vanderbilt Company registered trademark) are dispersed in 56.3 parts of ion-exchanged water to obtain a thickener solution. 42.5 parts of the microcapsule slurry and 57.5 parts of the thickener solution are mixed to obtain a microcapsule.

Formulation Example 5
After mixing 10 parts of any one of the compounds (1) to (11) of the present invention and 10 parts of phenylxylylethane, the mixture was added to 20 parts of a 10% aqueous solution of polyethylene glycol and stirred with a homomixer. An emulsion with a particle size of 3 μm is obtained. On the other hand, 0.2 parts of Xanthan gum and 1.0 part of Beegum R (aluminum magnesium silicate, Vanderbilt Company registered trademark) are dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution. 40 parts of the emulsion solution and 60 parts of the thickener solution are mixed to obtain a flowable agent.

Formulation Example 6
5 parts of any one of the compounds (1) to (11) of the present invention are mixed with 3 parts of Carplex # 80 (synthetic hydrous silicon oxide fine powder, registered trademark of Shionogi Pharmaceutical), PAP (mixture of monoisopropyl phosphate and diisopropyl phosphate) ) Add 0.3 parts and 91.7 parts of talc (300 mesh) and stir and mix with a juice mixer to obtain a powder.

Formulation Example 7
0.1 part of any one of the compounds (1) to (11) of the present invention is dissolved in 10 parts of isopropyl alcohol, and this is mixed with 89.9 parts of deodorized kerosene to obtain an oil agent.

Formulation Example 8
One of the compounds (1) to (11) of the present invention, 1 part of dichloromethane, 5 parts of dichloromethane and 34 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, and attached with a valve part, and then propellant through the valve part. 60 parts of (liquefied petroleum gas) are pressure-filled to obtain an oily aerosol.

Formulation Example 9
One of the compounds (1) to (11) of the present invention 0.6 parts, 5 parts of xylene, 3.4 parts of deodorized kerosene and 1 part of Atmos 300 (emulsifier, registered trademark of Atlas Chemical Co., Ltd.) Then, 50 parts of water is filled in an aerosol container, and 40 parts of a propellant (liquefied petroleum gas) is pressurized and filled through a valve part to obtain an aqueous aerosol.

Formulation Example 10
0.3 g of any one of the compounds (1) to (11) of the present invention is dissolved in 20 ml of acetone, and this is mixed with a base material for incense (tab powder: rice cake powder: wood powder = 4: 3: 3) After uniformly stirring and mixing with 99.7 g, 100 ml of water is added, and the kneaded mixture is molded and dried to obtain an insecticidal incense.

Formulation Example 11
Acetone is added to 0.8 g of any one of the compounds (1) to (11) of the present invention and 0.4 g of piperonyl butoxide to dissolve to make a total of 10 ml. 0.5 ml of this solution was impregnated uniformly into a 2.5 cm × 1.5 cm, 0.3 cm thick electric insecticidal mat substrate (a mixture of cotton linter and pulp filled into a plate). Get an electric insecticidal matting agent.

Formulation Example 12
3 parts of any one of the compounds (1) to (11) of the present invention are dissolved in 97 parts of deodorized kerosene to obtain a liquid agent, which is put in a vinyl chloride container so that the upper part can be heated with a heater. By inserting (inorganic powder hardened with a binder and sintered), parts used for a liquid absorption core type heat transpiration apparatus are obtained.

Formulation Example 13
100 mg of any one of the compounds (1) to (11) of the present invention is dissolved in an appropriate amount of acetone, impregnated into a porous ceramic plate of 4.0 cm × 4.0 cm, thickness 1.2 cm, and heated smoke Get.

Formulation Example 14
100 μg of any one of the compounds (1) to (11) of the present invention is dissolved in an appropriate amount of acetone, and uniformly applied to a filter paper having a size of 2 cm × 2 cm and a thickness of 0.3 mm. Get the agent.

Formulation Example 15
Mixing 10 parts of any one of the compounds (1) to (11) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water, and finely pulverizing them by a wet pulverization method. To obtain a formulation.

  Next, the harmful arthropod controlling effect of the compound of the present invention is shown as a test example.

Test example 1
The oils of the present compounds (1) to (5) and (7) obtained in Formulation Example 7 are mixed with isopropyl alcohol / deodorized kerosene = 1/9 so that the active ingredient concentration is 2.0% w / v. The test drug solution was prepared by diluting with the solution.
10 German cockroaches (5 males and 5 females) are placed in a test container with a buttered inner wall (diameter: 8.75 cm, height: 7.5 cm, bottom 16 mesh wire mesh), and the container is used for testing. It was installed at the bottom of the chamber (bottom: 46 cm × 46 cm, height: 70 cm). From a height of 60 cm above the upper surface of the container, 1.5 ml of a test drug solution was sprayed using a spray gun (a spraying pressure of 0.42 kg / cm ² ). The container was removed from the test chamber 30 seconds after spraying, and the number of insects knocked down after 2 minutes, 5 minutes, and 15 minutes was counted to determine the knockdown rate. The knockdown rate was calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100
As a result, in the treatment of the compounds (1) to (5) and (7) of the present invention, the knockdown rate of the test insects within 15 minutes was 80% or more.

Test example 2
The oils of the present compounds (1) and (2) obtained in Formulation Example 7 are diluted with a mixture of isopropyl alcohol / deodorized kerosene = 1/9 so that the active ingredient concentration is 2.0% w / v. Then, a test chemical solution was prepared.
Ten adult house flies (5 males and 5 females) were released in a polyethylene cup (bottom diameter: 10.6 cm) and covered with 16 mesh nylon goose. The polyethylene cup was placed at the bottom of a test chamber (bottom: 46 cm × 46 cm, height: 70 cm). From the height of 30 cm above the upper surface of the polyethylene cup, 0.5 ml of the test drug solution was sprayed using a spray gun (spray pressure 0.9 kg / cm ² ). Immediately after spraying, the cup was removed from the test chamber, and the number of insects knocked down after 2, 5 and 15 minutes was counted to determine the knockdown rate. The knockdown rate was calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100
As a result, in the treatment with the compounds (1) and (2) of the present invention, the knockdown rate of the test insects within 15 minutes was 80% or more.

Test example 3
The oils of the present compounds (1) to (7) obtained in Formulation Example 7 are diluted with a mixture of isopropyl alcohol / deodorized kerosene = 1/9 so that the active ingredient concentration is 0.1% w / v. Then, a test chemical solution was prepared.
Ten adult oyster mosquitoes were released in a polyethylene cup (bottom diameter 10.6 cm) and covered with 16 mesh nylon goose. The polyethylene cup was placed at the bottom of a test chamber (bottom: 46 cm × 46 cm, height: 70 cm). From the height of 30 cm above the upper surface of the polyethylene cup, 0.5 ml of the test drug solution was sprayed using a spray gun (spray pressure 0.4 kg / cm ² ). Immediately after spraying, the cup was removed from the test chamber, and the number of insects knocked down after 2, 5 and 15 minutes was counted to determine the knockdown rate. The knockdown rate was calculated by the following formula.
Knockdown rate (%) = (number of knockdown insects / number of test insects) × 100
As a result, in the treatment with the compounds (1) to (7) of the present invention, the knockdown rate of the test insects within 15 minutes was 80% or more.

  The compound of the present invention has a controlling effect on harmful arthropods and is useful as an active ingredient of a harmful arthropod controlling agent.

Claims (22)

Formula (I)

[Where,
X ¹ represents a nitrogen atom or CR ¹ ;
X ² represents a nitrogen atom or CR ² ;
X ³ represents a nitrogen atom or CR ³ (provided that all of X ¹ , X ² and X ³ do not represent a nitrogen atom),
n represents 1 or 2,
R ¹ , R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is one selected from Group B Or a C1-C8 chain hydrocarbon group having one group selected from the group
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by Formula (Ia)

[Where,
n represents 1 or 2,
R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is one selected from Group B Or a C1-C8 chain hydrocarbon group having one group selected from the group
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by Formula (Ib)

[Where,
n represents 1 or 2,
R ¹ and R ³ independently of each other represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is one selected from Group B Or a C1-C8 chain hydrocarbon group having one group selected from the group
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by Formula (Ic)

[Where,
n represents 1 or 2,
R ¹ , R ² and R ³ each independently represent a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is 1 selected from group B A C1-C8 chain hydrocarbon group having one group or one group selected from group B;
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by The amide compound according to claim 4, wherein R ¹ , R ² and R ³ are hydrogen atoms. The amide compound according to claim 4, wherein at least one of R ¹ , R ² and R ³ is one atom or group selected from group A. Formula (Id)

[Where,
n represents 1 or 2,
R ³ represents a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is one selected from Group B Or a C1-C8 chain hydrocarbon group having one group selected from the group
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by Formula (Ie)

[Where,
n represents 1 or 2,
R ² represents a hydrogen atom or one atom or group selected from group A;
R ⁴ and R ⁵ independently of each other represent a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
Y represents a single bond, an oxygen atom or —S (O) _u —,
u represents 0, 1 or 2;
When Y is an oxygen atom or —S (O) _u —, m represents 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and Z is one selected from Group B Or a C1-C8 chain hydrocarbon group having one group selected from the group
When Y is a single bond, m represents 0 and Z represents a C1-C8 chain hydrocarbon group having one group selected from Group B.
Group A:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A phenyl group optionally having one or more atoms or groups selected from group C;
A group consisting of a cyano group and a halogen atom.
Group B:
A pyridyl group optionally having one or more atoms or groups selected from group C;
A furyl group optionally having one or more atoms or groups selected from group C;
A thienyl group optionally having one or more atoms or groups selected from group C;
An indanyl group optionally having one or more atoms or groups selected from group C;
A 1,2,3,4-tetrahydronaphthyl group optionally having one or more atoms or groups selected from group C;
A naphthyl group optionally having one or more atoms or groups selected from group C;
A quinolyl group optionally having one or more atoms or groups selected from group C;
A benzofuranyl group optionally having one or more atoms or groups selected from group C;
A benzothienyl group optionally having one or more atoms or groups selected from group C;
1,3-benzodioxolanyl group optionally having one or more atoms or groups selected from group C, and one or more atoms or groups selected from group C, A group consisting of 4-benzodioxanyl groups.
Group C:
A C1-C4 alkyl group optionally having one or more halogen atoms,
A C3-C10 cycloalkyl group optionally having one or more halogen atoms,
A C1-C4 alkoxy group optionally having one or more halogen atoms,
A C1-C4 alkylthio group optionally having one or more halogen atoms,
A C1-C4 alkylsulfinyl group optionally having one or more halogen atoms,
A C1-C4 alkylsulfonyl group optionally having one or more halogen atoms,
A C1-C4 alkoxycarbonyl group optionally having one or more halogen atoms,
A C1-C4 alkylcarbonyl group optionally having one or more halogen atoms,
A vinyl group optionally having one or more atoms or groups selected from group D;
An ethynyl group optionally having an atom or group selected from group D;
A group consisting of an amino group, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a —CONR ⁶ R ⁷ group and a halogen atom (R ⁶ and R ⁷ independently of one another have one or more halogen atoms. May represent a C1-C4 alkyl group or a hydrogen atom).
Group D:
A group consisting of a C1-C4 alkyl group which may have one or more halogen atoms and a halogen atom. ]
An amide compound represented by The amide compound according to any one of claims 1 to 8, wherein Y is a single bond. Y is an oxygen atom, The amide compound as described in any one of Claims 1-8. Y is -S (O) _u- , The amide compound as described in any one of Claims 1-8. The amide compound according to any one of claims 1 to 8, wherein Y is an oxygen atom, and m is 1, 2, 3, 4, 5, 6, 7, 8 or 9. The amide compound according to any one of claims 1 to 8, wherein Y is -S (O) _u- , and m is 1, 2, 3, 4, 5, 6, 7, 8 or 9. The amide compound according to any one of claims 1 to 8, wherein Y is a single bond, m is 0, and Z is a C2-C5 chain hydrocarbon group having one group selected from group B. The amide compound according to any one of claims 1 to 8, wherein Y is a single bond, m is 0, and Z is a C2-chain hydrocarbon group having one group selected from group B. Y is an oxygen atom, m is 1 or 2, and Z is a C1-C3 chain hydrocarbon group having one group selected from group B or one group selected from group B. The amide compound as described in any one of claim | item 1 -8. C1-C3 chain carbonization wherein Y is —S (O) _u —, m is 1 or 2, and Z is one group selected from group B or one group selected from group B It is a hydrogen group, The amide compound as described in any one of Claims 1-8. The amide compound according to any one of claims 1 to 17, wherein the group B is a naphthyl group which may have one or more atoms or groups selected from the group C. The amide compound according to claim 1, wherein n is 1. n is 2, The amide compound as described in any one of Claims 1-18. A harmful arthropod control agent comprising the amide compound according to any one of claims 1 to 20 and an inert carrier. A method for controlling harmful arthropods, comprising a step of applying an effective amount of the amide compound according to any one of claims 1 to 20 to harmful arthropods or habitats of harmful arthropods.