JP2018016593A - Pest control composition and pest control method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pest control composition having excellent pest control effect.SOLUTION: A pest control composition contains a bipyridine compound represented by the following formula (I) [where each symbol represents a definition in the specifications] or an N oxide compound thereof, and at least one compound selected from the following groups a to d. The group a is: bactericides. The group b is: insecticidal, acaricidal, and nematicidal agents. The group c is: phytotoxicity reducing agents. The group d is: plant growth regulators.SELECTED DRAWING: None

Description

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

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

The Pesticide Manual-17th edition (BCPC); ISBN 978-1-901396-88-1

  It is an object of the present invention to provide a pest control composition having an excellent control effect against pests.

As a result of examining to find a pest control composition having an excellent control effect against pests, one or more compounds selected from the following formula (I) or N oxide compounds thereof and the following group a to the following group d: It has been found that a pest control composition containing any of the above compounds has an excellent control effect against pests.
That is, the present invention includes the following [1] to [7].

［式中、
Ｒ¹は、Ｃ２−Ｃ１０ハロアルキル基、Ｃ３−Ｃ１０ハロアルケニル基、Ｃ３−Ｃ１０ハロアルキニル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルコキシ）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルファニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルフィニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルホニル）Ｃ２−Ｃ５アルキル基、群Ｇより選ばれる１以上の置換基を有する（Ｃ３−Ｃ７シクロアルキル）Ｃ１−Ｃ３アルキル基、又は群Ｇより選ばれる１以上の置換基を有するＣ３−Ｃ７シクロアルキル基を表し、
Ｒ²は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、シクロプロピルメチル基、又はシクロプロピル基を表し、
Ｒ³は、群Ｂより選ばれる１以上の置換基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、ＯＲ¹²、ＮＲ¹¹Ｒ¹²、ＮＲ^11aＲ^12a、ＮＲ²⁴ＮＲ¹¹Ｒ¹²、ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、Ｎ＝ＣＨＮＲ¹⁵Ｒ¹⁶、Ｎ＝Ｓ（Ｏ）_xＲ¹⁵Ｒ¹⁶、Ｓ（Ｏ）_yＲ¹⁵、Ｃ（Ｏ）ＯＲ¹⁷、Ｃ（Ｏ）ＮＲ¹¹Ｒ¹²、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ⁶は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、ＯＲ¹⁸、ＮＲ¹⁸Ｒ¹⁹、Ｃ（Ｏ）ＯＲ²⁵、ＯＣ（Ｏ）Ｒ²⁰、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ¹¹、Ｒ¹⁷、Ｒ¹⁸、Ｒ¹⁹、Ｒ²⁰、Ｒ²⁴、及びＲ²⁵は、各々独立して、水素原子又は１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基を表し、
Ｒ¹²は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｆより選ばれる１の置換基を有するＣ１−Ｃ６アルキル基、又はＳ（Ｏ）₂Ｒ²³を表し、
Ｒ²³は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基を表し、
Ｒ^11a及びＲ^12aはそれらが結合する窒素原子と一緒になって、３−７員非芳香族複素環基｛該３−７員非芳香族複素環はアジリジン環、アゼチジン環、ピロリジン環、イミダゾリン環、イミダゾリジン環、ピペリジン環、テトラヒドロピリミジン環、ヘキサヒドロピリミジン環、ピペラジン環、アゼパン環、オキサゾリジン環、イソオキサゾリジン環、１，３−オキサジナン環、モルホリン環、１，４−オキサゼパン環、チアゾリジン環、イソチアゾリジン環、１，３−チアジナン環、チオモルホリン環、又は１，４−チアゼパン環を表し、群Ｅより選ばれる１以上の置換基を有していてもよい。｝を形成し、
Ｒ¹³は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、又は群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基を表し、
Ｒ¹⁴は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、又はフェニルＣ１−Ｃ３アルキル基｛フェニルＣ１−Ｃ３アルキル基におけるフェニル部分は、群Ｄより選ばれる１以上の置換基を有していてもよい。｝を表し、
Ｒ¹⁵、及びＲ¹⁶は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表し、
ｎ及びｙは、各々独立して、０、１、又は２を表し、
ｘは、０又は１を表し、
ｐ及びｑは、各々独立して、０、１、２、又３を表し、ｐが２又は３である場合、複数のＲ⁶は同一でも異なっていてもよく、ｑが２又は３である場合、複数のＲ³は同一でも異なっていてもよい。
群Ｂ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６シクロアルキル基、シアノ基、ヒドロキシ基、及びハロゲン原子からなる群。
群Ｄ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、ヒドロキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、スルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、アミノ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、Ｃ（Ｏ）Ｒ²¹、ＯＣ（Ｏ）Ｒ²¹、Ｃ（Ｏ）ＯＲ²¹、シアノ基、ニトロ基、及びハロゲン原子からなる群。｛Ｒ²¹、及びＲ²²は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表す｝
群Ｅ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、ハロゲン原子、オキソ基、ヒドロキシ基、シアノ基、及びニトロ基からなる群。
群Ｆ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、シアノ基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、及び群Ｃより選ばれる１以上の置換基を有していてもよい３−７員非芳香族複素環基からなる群。
群Ｃ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、及びハロゲン原子からなる群。
群Ｇ：ハロゲン原子、及びＣ１−Ｃ６ハロアルキル基からなる群。］

群ａ；殺菌剤
群ｂ；殺虫・殺ダニ・殺センチュウ剤
群ｃ；薬害軽減剤
群ｄ；植物生長調節剤
［２］前記式（Ｉ）で示されるビピリジン化合物又はそのＮオキシド化合物と、前記群ａ乃至前記群ｄより選ばれる１種以上の化合物との含有量の比が、重量比で１００００：１〜１：１００である［１］に記載の組成物。
［３］下記式（Ｉ）で示されるビピリジン化合物又はそのＮオキシド化合物と、下記群ａ乃至下記群ｄより選ばれる１種以上の化合物とを保持してなる植物の種子又は栄養繁殖器官。
式（Ｉ）：

［式中、
Ｒ¹は、Ｃ２−Ｃ１０ハロアルキル基、Ｃ３−Ｃ１０ハロアルケニル基、Ｃ３−Ｃ１０ハロアルキニル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルコキシ）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルファニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルフィニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルホニル）Ｃ２−Ｃ５アルキル基、群Ｇより選ばれる１以上の置換基を有する（Ｃ３−Ｃ７シクロアルキル）Ｃ１−Ｃ３アルキル基、又は群Ｇより選ばれる１以上の置換基を有するＣ３−Ｃ７シクロアルキル基を表し、
Ｒ²は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、シクロプロピルメチル基、又はシクロプロピル基を表し、
Ｒ³は、群Ｂより選ばれる１以上の置換基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、ＯＲ¹²、ＮＲ¹¹Ｒ¹²、ＮＲ^11aＲ^12a、ＮＲ²⁴ＮＲ¹¹Ｒ¹²、ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、Ｎ＝ＣＨＮＲ¹⁵Ｒ¹⁶、Ｎ＝Ｓ（Ｏ）_xＲ¹⁵Ｒ¹⁶、Ｓ（Ｏ）_yＲ¹⁵、Ｃ（Ｏ）ＯＲ¹⁷、Ｃ（Ｏ）ＮＲ¹¹Ｒ¹²、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ⁶は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、ＯＲ¹⁸、ＮＲ¹⁸Ｒ¹⁹、Ｃ（Ｏ）ＯＲ²⁵、ＯＣ（Ｏ）Ｒ²⁰、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ¹¹、Ｒ¹⁷、Ｒ¹⁸、Ｒ¹⁹、Ｒ²⁰、Ｒ²⁴、及びＲ²⁵は、各々独立して、水素原子又は１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基を表し、
Ｒ¹²は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｆより選ばれる１の置換基を有するＣ１−Ｃ６アルキル基、又はＳ（Ｏ）₂Ｒ²³を表し、
Ｒ²³は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基を表し、
Ｒ^11a及びＲ^12aはそれらが結合する窒素原子と一緒になって、３−７員非芳香族複素環基｛該３−７員非芳香族複素環はアジリジン環、アゼチジン環、ピロリジン環、イミダゾリン環、イミダゾリジン環、ピペリジン環、テトラヒドロピリミジン環、ヘキサヒドロピリミジン環、ピペラジン環、アゼパン環、オキサゾリジン環、イソオキサゾリジン環、１，３−オキサジナン環、モルホリン環、１，４−オキサゼパン環、チアゾリジン環、イソチアゾリジン環、１，３−チアジナン環、チオモルホリン環、又は１，４−チアゼパン環を表し、群Ｅより選ばれる１以上の置換基を有していてもよい。｝を形成し、
Ｒ¹³は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、又は群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基を表し、
Ｒ¹⁴は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、又はフェニルＣ１−Ｃ３アルキル基｛フェニルＣ１−Ｃ３アルキル基におけるフェニル部分は、群Ｄより選ばれる１以上の置換基を有していてもよい。｝を表し、
Ｒ¹⁵、及びＲ¹⁶は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表し、
ｎ及びｙは、各々独立して、０、１、又は２を表し、
ｘは、０又は１を表し、
ｐ及びｑは、各々独立して、０、１、２、又３を表し、ｐが２又は３である場合、複数のＲ⁶は同一でも異なっていてもよく、ｑが２又は３である場合、複数のＲ³は同一でも異なっていてもよい。
群Ｂ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６シクロアルキル基、シアノ基、ヒドロキシ基、及びハロゲン原子からなる群。
群Ｄ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、ヒドロキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、スルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、アミノ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、Ｃ（Ｏ）Ｒ²¹、ＯＣ（Ｏ）Ｒ²¹、Ｃ（Ｏ）ＯＲ²¹、シアノ基、ニトロ基、及びハロゲン原子からなる群。｛Ｒ²¹、及びＲ²²は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表す｝
群Ｅ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、ハロゲン原子、オキソ基、ヒドロキシ基、シアノ基、及びニトロ基からなる群。
群Ｆ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、シアノ基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、及び群Ｃより選ばれる１以上の置換基を有していてもよい３−７員非芳香族複素環基からなる群。
群Ｃ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、及びハロゲン原子からなる群。
群Ｇ：ハロゲン原子、及びＣ１−Ｃ６ハロアルキル基からなる群。］

群ａ；殺菌剤
群ｂ；殺虫・殺ダニ・殺センチュウ剤
群ｃ；薬害軽減剤
群ｄ；植物生長調節剤
［４］前記式（Ｉ）で示されるビピリジン化合物又はそのＮオキシド化合物の保持量が、植物の種子又は栄養繁殖器官１ｋｇあたり、０．０００００１〜５０ｇである［３］に記載の植物の種子又は栄養繁殖器官。
［５］下記式（Ｉ）で示されるビピリジン化合物又はそのＮオキシド化合物と、下記群ａ乃至下記群ｄより選ばれる１種以上の化合物とを、植物又は植物の栽培地に施用する工程を含む、有害生物防除方法。
式（Ｉ）：

［式中、
Ｒ¹は、Ｃ２−Ｃ１０ハロアルキル基、Ｃ３−Ｃ１０ハロアルケニル基、Ｃ３−Ｃ１０ハロアルキニル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルコキシ）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルファニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルフィニル）Ｃ２−Ｃ５アルキル基、１以上のハロゲン原子を有する（Ｃ１−Ｃ５アルキルスルホニル）Ｃ２−Ｃ５アルキル基、群Ｇより選ばれる１以上の置換基を有する（Ｃ３−Ｃ７シクロアルキル）Ｃ１−Ｃ３アルキル基、又は群Ｇより選ばれる１以上の置換基を有するＣ３−Ｃ７シクロアルキル基を表し、
Ｒ²は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、シクロプロピルメチル基、又はシクロプロピル基を表し、
Ｒ³は、群Ｂより選ばれる１以上の置換基を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、ＯＲ¹²、ＮＲ¹¹Ｒ¹²、ＮＲ^11aＲ^12a、ＮＲ²⁴ＮＲ¹¹Ｒ¹²、ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）Ｒ¹³、ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＯＲ¹⁴、ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、ＮＲ²⁴ＮＲ¹¹Ｃ（Ｏ）ＮＲ¹⁵Ｒ¹⁶、Ｎ＝ＣＨＮＲ¹⁵Ｒ¹⁶、Ｎ＝Ｓ（Ｏ）_xＲ¹⁵Ｒ¹⁶、Ｓ（Ｏ）_yＲ¹⁵、Ｃ（Ｏ）ＯＲ¹⁷、Ｃ（Ｏ）ＮＲ¹¹Ｒ¹²、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ⁶は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、ＯＲ¹⁸、ＮＲ¹⁸Ｒ¹⁹、Ｃ（Ｏ）ＯＲ²⁵、ＯＣ（Ｏ）Ｒ²⁰、シアノ基、ニトロ基、又はハロゲン原子を表し、
Ｒ¹¹、Ｒ¹⁷、Ｒ¹⁸、Ｒ¹⁹、Ｒ²⁰、Ｒ²⁴、及びＲ²⁵は、各々独立して、水素原子又は１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基を表し、
Ｒ¹²は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、群Ｆより選ばれる１の置換基を有するＣ１−Ｃ６アルキル基、又はＳ（Ｏ）₂Ｒ²³を表し、
Ｒ²³は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基を表し、
Ｒ^11a及びＲ^12aはそれらが結合する窒素原子と一緒になって、３−７員非芳香族複素環基｛該３−７員非芳香族複素環はアジリジン環、アゼチジン環、ピロリジン環、イミダゾリン環、イミダゾリジン環、ピペリジン環、テトラヒドロピリミジン環、ヘキサヒドロピリミジン環、ピペラジン環、アゼパン環、オキサゾリジン環、イソオキサゾリジン環、１，３−オキサジナン環、モルホリン環、１，４−オキサゼパン環、チアゾリジン環、イソチアゾリジン環、１，３−チアジナン環、チオモルホリン環、又は１，４−チアゼパン環を表し、群Ｅより選ばれる１以上の置換基を有していてもよい。｝を形成し、
Ｒ¹³は、水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、又は群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基を表し、
Ｒ¹⁴は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、１以上のハロゲン原子を有していてもよい（Ｃ３−Ｃ６シクロアルキル）Ｃ１−Ｃ３アルキル基、又はフェニルＣ１−Ｃ３アルキル基｛フェニルＣ１−Ｃ３アルキル基におけるフェニル部分は、群Ｄより選ばれる１以上の置換基を有していてもよい。｝を表し、
Ｒ¹⁵、及びＲ¹⁶は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表し、
ｎ及びｙは、各々独立して、０、１、又は２を表し、
ｘは、０又は１を表し、
ｐ及びｑは、各々独立して、０、１、２、又３を表し、ｐが２又は３である場合、複数のＲ⁶は同一でも異なっていてもよく、ｑが２又は３である場合、複数のＲ³は同一でも異なっていてもよい。
群Ｂ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６シクロアルキル基、シアノ基、ヒドロキシ基、及びハロゲン原子からなる群。
群Ｄ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６鎖式炭化水素基、ヒドロキシ基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、スルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルファニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルフィニル基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキルスルホニル基、アミノ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、Ｃ（Ｏ）Ｒ²¹、ＯＣ（Ｏ）Ｒ²¹、Ｃ（Ｏ）ＯＲ²¹、シアノ基、ニトロ基、及びハロゲン原子からなる群。｛Ｒ²¹、及びＲ²²は、各々独立して、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表す｝
群Ｅ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、ハロゲン原子、オキソ基、ヒドロキシ基、シアノ基、及びニトロ基からなる群。
群Ｆ：１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、ＮＨＲ²¹、ＮＲ²¹Ｒ²²、シアノ基、群Ｄより選ばれる１以上の置換基を有していてもよいフェニル基、群Ｄより選ばれる１以上の置換基を有していてもよい５もしくは６員芳香族複素環基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ７シクロアルキル基、及び群Ｃより選ばれる１以上の置換基を有していてもよい３−７員非芳香族複素環基からなる群。
群Ｃ：１以上のハロゲン原子で置換されていてもよいＣ１−Ｃ６鎖式炭化水素基、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルコキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルケニルオキシ基、１以上のハロゲン原子を有していてもよいＣ３−Ｃ６アルキニルオキシ基、及びハロゲン原子からなる群。
群Ｇ：ハロゲン原子、及びＣ１−Ｃ６ハロアルキル基からなる群。］

群ａ；殺菌剤
群ｂ；殺虫・殺ダニ・殺センチュウ剤
群ｃ；薬害軽減剤
群ｄ；植物生長調節剤
［６］植物が、遺伝子組換え植物である、［３］又は［４］に記載の植物の種子又は栄養繁殖器官。
［７］植物が、種子又は栄養繁殖器官である、［５］に記載の有害生物防除方法。
［８］植物が、遺伝子組換え植物である、［５］又は［７］に記載の有害生物防除方法。 [1] A bipyridine compound represented by the following formula (I) or an N oxide compound thereof;
A pest control composition containing one or more compounds selected from the following group a to the following group d.
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide / acaricide / nematocide group c; safener group d; plant growth regulator [2] bipyridine compound represented by the formula (I) or its N oxide compound, and The composition according to [1], wherein the ratio of the content with one or more compounds selected from group a to group d is 10,000: 1 to 1: 100 by weight.
[3] A plant seed or vegetative propagation organ comprising a bipyridine compound represented by the following formula (I) or an N oxide compound thereof and one or more compounds selected from the following group a to the following group d.
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide / acaricide / nematocide group c; safener group d; plant growth regulator [4] Amount of bipyridine compound represented by the above formula (I) or its N oxide compound The plant seed or vegetative propagation organ according to [3], wherein the amount is 0.000001 to 50 g per 1 kg of plant seed or vegetative propagation organ.
[5] including a step of applying a bipyridine compound represented by the following formula (I) or an N oxide compound thereof and one or more compounds selected from the following group a to the following group d to a plant or a plant cultivation site: , Pest control methods.
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide / acaricide / nematocide group c; safener group d; plant growth regulator [6] The plant is a genetically modified plant in [3] or [4] Seeds or vegetative propagation organs of the described plants.
[7] The pest control method according to [5], wherein the plant is a seed or a vegetative propagation organ.
[8] The pest control method according to [5] or [7], wherein the plant is a genetically modified plant.

  According to the present invention, seeds or vegetative propagation organs and plants grown from them can be protected from pests.

  The pest control composition of the present invention (hereinafter referred to as the present composition) comprises a bipyridine compound represented by the formula (I) or an N oxide compound thereof (hereinafter referred to as the present bipyridine compound), a fungicide, and an insecticide. -It contains at least one compound selected from the group consisting of an acaricide / nematocide, a safener and a plant growth regulator.

Examples of substituents used in the description of the present specification will be described below.
“It may have one or more halogen atoms” means that when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
In this specification, the expression “CX-CY” means that the number of carbon atoms is X to Y. For example, the expression “C1-C6” means that the number of carbon atoms is 1 to 6.

  The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The “chain hydrocarbon group” represents an alkyl group, an alkenyl group, and an alkynyl group.
Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group and a hexyl group are mentioned.
Examples of the “alkenyl group” include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, Examples include 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group and 5-hexenyl group.
Examples of the “alkynyl group” include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 4-pentynyl group and 5-hexynyl group.
The “C2-C10 haloalkyl group” represents a group in which a hydrogen atom of a C2-C10 alkyl group is substituted with a halogen atom, and examples thereof include a chloroethyl group, a 2,2,2-trifluoroethyl group, and 2-bromo-1 1,2,2-tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group and perfluorodecyl group. Can be mentioned.

  Examples of the “cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

Examples of the “3-7-membered non-aromatic heterocyclic group” include an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidin Ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, or 1,4-thiazepane ring Examples of the 3-7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from group E include the groups shown below.

Examples of the N oxide compound include a compound represented by the formula (Id), a compound represented by the formula (Ie), and a compound represented by the formula (If).

Examples of the “phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may have one or more substituents selected from group D}” include, for example, a benzyl group, 2-fluorobenzyl Group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, 2- [4- (trifluoromethyl) phenyl] ethyl group.
“(C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms” represents a group in which (C1-C5 alkoxy) and / or (C2-C5 alkyl) has one or more halogen atoms, For example, 2,2-difluoro-3- (2,2,2-trichloroethoxy) propyl group,
2- (2,2,2-trichloroethoxy) ethyl group, 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, 2,2-difluoro-3- (2,2,2-tri Fluoroethoxy) propyl group, 2- (2,2,2-trifluoroethoxy) ethyl group, 2,2-difluoro-3-methoxypropyl group.
“(C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfanyl) and / or (C2-C5 alkyl) has one or more halogen atoms. For example, a 2,2-difluoro-2- (trifluoromethylthio) ethyl group.
“(C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfinyl) and / or (C2-C5 alkyl) has one or more halogen atoms. For example, 2,2-difluoro-2- (trifluoromethanesulfinyl) ethyl group.
“(C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfonyl) and / or (C2-C5 alkyl) has one or more halogen atoms. For example, a 2,2-difluoro-2- (trifluoromethanesulfonyl) ethyl group.
“(C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G” means that (C3-C7 cycloalkyl) and / or (C1-C3 alkyl) is one or more groups. Represents a group having one or more substituents selected from G, for example, (2,2-difluorocyclopropyl) methyl group, [1- (trifluoromethyl) cyclopropyl] methyl group, [2- (trifluoromethyl) ) Cyclopropyl] methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and 2-cyclopropyl-3,3,3-trifluoropropyl group.
Examples of the “C3-C7 cycloalkyl group having one or more substituents selected from group G” include a 2,2-difluorocyclopropyl group and a 1- (2,2,2-trifluoroethyl) cyclopropyl group. And 4- (trifluoromethyl) cyclohexyl group.
“5- or 6-membered aromatic heterocyclic group” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, and the 5-membered aromatic heterocyclic group is a pyrrolyl group, a furyl group, a thienyl group, or a pyrazolyl group. Represents a group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. Represent.
“5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms” means pyrrolyl group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group, and tetrazolyl group Represents.

Examples of the bipyridine compound include the following compounds.

In the present bipyridine compound, a compound wherein R ² is a C1-C6 alkyl group optionally having one or more halogen atoms;
In the bipyridine compound, a compound wherein R ² is a C1-C6 alkyl group;
In the bipyridine compound, a compound wherein R ² is an ethyl group;

｛図中Ｒ²⁶は、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基を表す。｝ In the present bipyridine compound, q is 0, 1, or 2, and R ³ is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group B, selected from group Q 1-membered 5-membered aromatic heterocyclic group (this 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a compound that is a halogen atom;
Group Q:

{In the figure, R ²⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms. }

In the present bipyridine compound, R ¹ is a C2-C10 haloalkyl group, or a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ is a C1-C6 alkyl group optionally having one or more substituents selected from group B, a C2-C6 alkenyl group optionally having one or more substituents selected from group B, 1 5-membered aromatic heterocyclic group selected from group Q (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C ( O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S ( O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ¹¹ R ¹² , a cyano group, a nitro group, or a halogen atom,
a compound wherein p is 0, 1, or 2;

In the present bipyridine compound, R ¹ is a C2-C10 haloalkyl group, or a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ is a C1-C6 alkyl group optionally having one or more substituents selected from group B, a C2-C6 alkenyl group optionally having one or more substituents selected from group B, 5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a halogen atom,
p is 0, 1, or 2;
A compound in which R ⁶ is OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , a cyano group, a nitro group, or a halogen atom;

In the present bipyridine compound, R ¹ is a C2-C6 alkyl group having two or more fluorine atoms, or a (C1-C5 alkoxy) C2-C5 alkyl group having one or more fluorine atoms,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ is a C1-C6 alkyl group optionally having one or more substituents selected from group B, a C2-C6 alkenyl group optionally having one or more substituents selected from group B, 5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a halogen atom,
a compound in which p is 0, 1, or 2 and R ⁶ is a cyano group or a halogen atom;

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having 4 or more fluorine atoms, or a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group,
R ² is an ethyl group,
q is 0, 1, or 2;
R ³ has a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A triazole group, NR ¹¹ R ¹² , or a halogen atom,
A compound in which R ¹¹ and R ¹² are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and p is 0;

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having 4 or more fluorine atoms,
R ² is an ethyl group, q is 0 or 1,
R ³ is a C1-C6 alkyl group having one or more halogen atoms, 1,2,4-triazol-1-yl group optionally having one or more halogen atoms, NR ¹¹ R ¹² , or a halogen atom And
R ¹¹ and R ¹² are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms,
A compound wherein p is 0.

  Next, the manufacturing method of this bipyridine compound is demonstrated.

  As a manufacturing method of this bipyridine compound, the following manufacturing methods are mentioned, for example.

［式中、記号は前記と同じ意味を表す。］ Manufacturing method 1
In this bipyridine compound, a compound in which n = 1 (hereinafter referred to as the present bipyridine compound (Ib)) and a compound in which n = 2 (hereinafter referred to as the present bipyridine compound (Ic)) are n = 0. (Hereinafter referred to as the present bipyridine compound (Ia)) and an oxidant.

[Wherein the symbols have the same meaning as described above. ]

First, a method for producing the bipyridine compound (Ib) from the bipyridine compound (Ia) will be described.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons).
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid (hereinafter referred to as mCPBA).
In the reaction, the oxidizing agent is usually used in a ratio of 1 to 1.2 mol per 1 mol of the bipyridine compound (Ia).
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. The obtained bipyridine compound (Ib) can be obtained by drying and concentrating the obtained organic layer.

Next, a method for producing the bipyridine compound (Ic) from the bipyridine compound (Ib) will be described.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
In the reaction, the oxidizing agent is usually used at a ratio of 1 to 2 moles with respect to 1 mole of the present bipyridine compound (Ib).
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. By drying and concentrating the organic layer, the bipyridine compound (Ic) can be obtained.

Moreover, this bipyridine compound (Ic) can be manufactured by one step reaction (one pot) by making this bipyridine compound (Ia) and an oxidizing agent react.
The reaction is carried out according to the method for producing the bipyridine compound (Ic) from the bipyridine compound (Ib) using an oxidizing agent in a proportion of usually 2 to 5 mol per 1 mol of the bipyridine compound (Ia). be able to.

［式中、記号は前記と同じ意味を表す。］ Manufacturing method 2
The bipyridine compound represented by the formula (Id) (hereinafter referred to as the present bipyridine compound (Id)), the bipyridine compound represented by the formula (Ie) (hereinafter referred to as the present bipyridine compound (Ie)), and the formula The bipyridine compound represented by (If) (hereinafter referred to as the present bipyridine compound (If)) can be produced by reacting the bipyridine compound (Ic) with an oxidizing agent.

[Wherein the symbols have the same meaning as described above. ]

The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
For the reaction, the oxidizing agent is usually used at a ratio of 1 to 10 mol per 1 mol of the bipyridine compound (Ic).
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. By drying and concentrating the obtained organic layer, this bipyridine compound (Id), this bipyridine compound (Ie), and the mixture of this bipyridine compound (If) can be obtained. This bipyridine compound (Id), this bipyridine compound (Ie), and this bipyridine compound (If) can be isolated by subjecting this mixture to chromatography, recrystallization, and the like.

［式中、Ｖはハロゲン原子を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばジメチルホルムアミド（以下、ＤＭＦと記す。）、Ｎ−メチルピロリドン（以下、ＮＭＰと記す）、ジメチルスルホキシド（以下、ＤＭＳＯと記す。）等の非プロトン性極性溶媒（以下、非プロトン性極性溶媒と記す。）が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類（以下、アルカリ金属水素化物類と記す。）が挙げられる。
反応には、化合物（Ｍ−１）１モルに対して、化合物（Ｒ−１）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉａ）を得ることができる。
該反応において、Ｖはフッ素原子又は塩素原子が好ましい。 Production method 3
The bipyridine compound (Ia) includes a compound represented by the formula (M-1) (hereinafter referred to as the compound (M-1)) and a compound represented by the formula (R-1) (hereinafter referred to as the compound (R-1)). And) in the presence of a base.

[Wherein V represents a halogen atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include aprotic polar solvents such as dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), and dimethyl sulfoxide (hereinafter referred to as DMSO). Hereinafter, it is referred to as an aprotic polar solvent.).
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).
In the reaction, with respect to 1 mol of compound (M-1), compound (R-1) is usually used at a ratio of 1 to 10 mol, and the base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V is preferably a fluorine atom or a chlorine atom.

［式中、Ｖ¹は塩素原子、臭素原子、又はヨウ素原子を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えば炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩類（以下、アルカリ金属炭酸塩類と記す。）が挙げられる。
反応には、化合物（Ｍ−２）１モルに対して、化合物（Ｒ−２）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉａ）を得ることができる。 Manufacturing method 4
This bipyridine compound (Ia) is a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)). And) in the presence of a base.

[Wherein, V ¹ represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates such as potassium carbonate and cesium carbonate (hereinafter referred to as alkali metal carbonates).
In the reaction, with respect to 1 mol of compound (M-2), compound (R-2) is usually used at a ratio of 1 to 10 mol, and the base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、Ｖ²はＣ１−Ｃ１０ペルフルオロアルカンスルホニルオキシ基を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えばアルカリ金属炭酸塩類が挙げられる。
反応には、化合物（Ｍ−３）１モルに対して、化合物（Ｒ−３）が通常１〜１０モルの割合で用いられ、塩基が通常０．１〜５モルの割合で用いられる。
反応温度は、通常−２０℃〜１２０℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉ）を得ることができる。 Manufacturing method 5
The bipyridine compound represented by the formula (I) (hereinafter referred to as the present bipyridine compound (I)) is composed of the compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) and the formula. It can be produced by reacting a compound represented by (R-3) (hereinafter referred to as compound (R-3)) in the presence of a base.

[Wherein, V ² represents a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates.
For the reaction, the compound (R-3) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 0.1 to 5 mol with respect to 1 mol of the compound (M-3).
The reaction temperature is usually in the range of -20 ° C to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water of the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えばアルカリ金属水素化物類が挙げられる。
反応には、化合物（Ｍ−４）１モルに対して、化合物（Ｒ−４）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉ）を得ることができる。
該反応において、Ｖはフッ素原子が好ましい。 Manufacturing method 6
This bipyridine compound (I) includes a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) and a compound represented by formula (R-4) (hereinafter referred to as compound (R-4)). And) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal hydrides.
In the reaction, with respect to 1 mol of compound (M-4), compound (R-4) is usually used at a ratio of 1 to 10 mol, and the base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V is preferably a fluorine atom.

［式中、Ｒ³⁴、Ｒ³⁵、及びＲ³⁶は、それぞれ独立して水素原子、１以上のハロゲン原子を有していてもよいＣ１−Ｃ６アルキル基、群Ｄより選ばれる１以上の原子又は基を有していてもよいフェニル基、又は群Ｄより選ばれる１以上の原子もしくは基を有していてもよい５もしくは６員芳香族複素環基を表し、その他の記号は前記と同じ意味を表す。］ Manufacturing method 7
A compound represented by the formula (Ig) (hereinafter referred to as the present bipyridine compound (Ig)) can be produced according to the method described below.

[Wherein R ³⁴ , R ³⁵ , and R ³⁶ each independently represent a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, one or more atoms selected from group D, or Represents a phenyl group which may have a group, or a 5- or 6-membered aromatic heterocyclic group which may have one or more atoms or groups selected from group D, and other symbols have the same meanings as described above Represents. ]

First, Step 1 will be described.
In Step 1, a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)) and a compound represented by formula (R-5) (hereinafter referred to as compound (R-5)). And react.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include alcohols, aprotic polar solvents, and mixtures thereof.
In the reaction, compound (R-5) is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the residue obtained by concentrating the reaction mixture is directly used in Step 2.

Next, Step 2 will be described.
The bipyridine compound (Ig) can be produced by reacting the residue obtained in Step 1, methanesulfonyl chloride and triethylamine.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers (hereinafter referred to as ethers) such as tetrahydrofuran and methyl-tert-butyl ether (hereinafter referred to as MTBE).
For the reaction, methanesulfonyl chloride is usually used in a proportion of 1 to 10 mol and triethylamine is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ig) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
はじめに、化合物（Ｍ−５）から式（Ｍ−６）で示される化合物（以下、化合物（Ｍ−６）と記す。）を製造する方法について記す。
化合物（Ｍ−６）は、化合物（Ｍ−５）と式（Ｒ−６）で示される化合物（以下、化合物（Ｒ−６）と記す。）とを反応させることにより製造することができる。
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばハロゲン化炭化水素が挙げられる。
反応には、化合物（Ｍ−５）１モルに対して、化合物（Ｒ−６）が通常１〜１０モルの割合で用いられる。
反応温度は、通常０〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に重曹水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ−６）を単離することができる。 Manufacturing method 8
A compound represented by the formula (Ih) (hereinafter referred to as the present bipyridine compound (Ih)) can be produced, for example, according to the following method.

[Wherein the symbols have the same meaning as described above. ]
First, a method for producing a compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)) from compound (M-5) will be described.
Compound (M-6) can be produced by reacting compound (M-5) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)).
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
In the reaction, compound (R-6) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M-6) can be isolated by performing post-treatment operations such as adding sodium bicarbonate water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Subsequently, a method for producing the bipyridine compound (Ih) from the compound (M-6) will be described. This bipyridine compound (Ih) can be produced by reacting compound (M-6) with a halogenating agent.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the halogenating agent used in the reaction include N-bromosuccinimide and N-chlorosuccinimide.
In the reaction, benzoyl peroxide may be added as necessary.
In the reaction, with respect to 1 mol of the compound (M-6), the halogenating agent is usually used in a proportion of 1 to 10 mol, and benzoyl peroxide is usually used in a proportion of 0.1 to 0.5 mol.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine is added to the reaction mixture by performing post-treatment operations such as adding sodium methoxide until the exotherm subsides, then adding water, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (Ih) can be isolated.

［式中、Ｒ³⁷はＣ１−Ｃ６アルキル基を表し、その他の記号は前記と同じ意味を表す。］
はじめに、Ｓｔｅｐ１について記載する。式（Ｍ−７）で示される化合物（以下、化合物（Ｍ−７）と記す。）と式（Ｒ−７）で示される化合物（以下、化合物（Ｒ−７）と記す。）とを塩基存在下で反応させる。
化合物（Ｒ−７）は、国際公開第２００９／０５４７４２号記載の方法に準じて製造することができる。
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばハロゲン化炭化水素類が挙げられる。
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、ピリジン等の有機塩基類（以下、有機塩基類と記す。）が挙げられる。
反応には、化合物（Ｍ−７）１モルに対して、化合物（Ｒ−７）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常−５０〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行って得られる残渣をＳｔｅｐ２で用いる。 Manufacturing method 9
Examples of the method for producing the compound represented by the formula (Ii) (hereinafter referred to as the present bipyridine compound (Ii)) include the following methods.

[Wherein, R ³⁷ represents a C1-C6 alkyl group, and other symbols have the same meaning as described above. ]
First, Step 1 will be described. A compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) and a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)) as a base. React in the presence.
Compound (R-7) can be produced according to the method described in International Publication No. 2009/054742.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the base used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases).
In the reaction, with respect to 1 mol of compound (M-7), compound (R-7) is usually used at a ratio of 1 to 10 mol, and base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of −50 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, a residue obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer is used in Step 2.

Next, Step 2 will be described.
The bipyridine compound (Ii) can be produced by reacting the residue obtained in Step 1 with ammonia.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include alcohols, water, and mixtures thereof.
As the ammonia used in the reaction, an aqueous ammonia solution, an ammonia methanol solution, or the like can be used.
In the reaction, ammonia is usually used at a ratio of 1 to 100 mol with respect to 1 mol of the compound (M-7).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ii) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
該反応は、必要に応じて溶媒を用いることができる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応には、化合物（Ｍ−５）１モルに対して、化合物（Ｒ−８）が通常１〜１０モルの割合で用いられる。
反応温度は、通常０〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉｊ）を単離することができる。 Manufacturing method 10
The compound represented by the formula (Ij) (hereinafter referred to as the present bipyridine compound (Ij)) is composed of the compound (M-5) and the compound represented by the formula (R-8) (hereinafter referred to as the compound (R-8)). It can be manufactured by reacting.

[Wherein the symbols have the same meaning as described above. ]
In the reaction, a solvent can be used as necessary. Examples of the solvent used for the reaction include aprotic polar solvents.
In the reaction, compound (R-8) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ij) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、Ｘ³はフッ素原子、塩素原子、又はＳ（Ｏ）₂Ｒ¹⁵を表し、ｒは０、１又は２を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、アルカリ金属炭酸塩類、アルカリ金属水素化物類等が挙げられる。
反応には、本ビピリジン化合物（Ｉｋ）１モルに対して、化合物（Ｒ−１２）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常０〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉｐ）を単離することができる。 Manufacturing method 11
A compound represented by the formula (Ip) (hereinafter referred to as the present bipyridine compound (Ip)) is a compound represented by the formula (Ik) (hereinafter referred to as the present bipyridine compound (Ik)) and a formula (R-12). ) (Hereinafter, referred to as compound (R-12)) is allowed to react in the presence of a base.

[Wherein, X ³ represents a fluorine atom, a chlorine atom, or S (O) ₂ R ¹⁵ ; r represents 0, 1 or 2; and other symbols represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates and alkali metal hydrides.
For the reaction, the compound (R-12) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ip) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、アセトニトリル等のニトリル類（以下、ニトリル類と記す。）、非プロトン性極性溶媒及びこれらの混合物が挙げられる。
反応には、必要に応じて塩基を加えて行うこともできる。反応に用いられる塩基としては、アルカリ金属炭酸塩類、アルカリ金属水素化物類、有機塩基類等が挙げられる。
反応には、本ビピリジン化合物（Ｉｍ）を製造するとき、本ビピリジン化合物（Ｉｋ）１モルに対して、化合物（Ｒ−９）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応には、本ビピリジン化合物（Ｉｎ）を製造するとき、本ビピリジン化合物（Ｉｋ）化合物１モルに対して、化合物（Ｒ−１０）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応には、本ビピリジン化合物（Ｉｏ）を製造するとき、本ビピリジン化合物（Ｉｋ）化合物１モルに対して、化合物（Ｒ−１１）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合で用いられる。
反応温度は、通常０〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉｍ）、本ビピリジン化合物（Ｉｎ）、又は本ビピリジン化合物（Ｉｏ）を得ることができる。 Production method 12
The compound represented by the formula (Im) (hereinafter referred to as the present bipyridine compound (Im)) is composed of the bipyridine compound (Ik) and the compound represented by the formula (R-9) (hereinafter referred to as the compound (R-9)). It can be manufactured by reacting.
The compound represented by the formula (In) (hereinafter referred to as the present bipyridine compound (In)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-10) (hereinafter referred to as the compound (R-10)). It can be manufactured by reacting.
The compound represented by the formula (Io) (hereinafter referred to as the present bipyridine compound (Io)) is composed of the bipyridine compound (Ik) and the compound represented by the formula (R-11) (hereinafter referred to as the compound (R-11)). It can be manufactured by reacting.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, nitriles such as acetonitrile (hereinafter referred to as nitriles), aprotic polar solvents, and mixtures thereof.
The reaction can be carried out by adding a base as necessary. Examples of the base used for the reaction include alkali metal carbonates, alkali metal hydrides, organic bases and the like.
In the reaction, when the bipyridine compound (Im) is produced, the ratio of the compound (R-9) is usually 1 to 10 mol and the base is usually 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik). Used in proportions.
In the reaction, when the bipyridine compound (In) is produced, the ratio of the compound (R-10) is usually 1 to 10 mol and the base is usually 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik) compound. It is used in the ratio.
In the reaction, when the bipyridine compound (Io) is produced, the compound (R-11) is usually in a ratio of 1 to 10 mol and the base is usually 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik). It is used in the ratio.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Im), the bipyridine compound (In), or the present bipyridine compound (In) is obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. This bipyridine compound (Io) can be obtained.

［式中、Ｂ¹及びＢ²は各々独立して窒素原子又はＣＲ³³を表し、Ｒ³¹、Ｒ³²、及びＲ³³は、各々独立して水素原子、又は群Ｄより選ばれる１の置換基を表し、その他の記号は前記と同じ意味を表す。］
該反応は、化合物（Ｒ−１２）に代えて化合物（Ｒ−１３）を用い、製造法１１に記載の方法に準じて実施することができる。 Production method 13
The compound represented by the formula (Iq) (hereinafter referred to as the present bipyridine compound (Iq)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-13) (hereinafter referred to as the compound (R-13)). In the presence of a base.

[Wherein, B ¹ and B ² each independently represent a nitrogen atom or CR ³³ , and R ³¹ , R ³² , and R ³³ each independently represent a hydrogen atom or one substituent selected from Group D And other symbols have the same meaning as described above. ]
This reaction can be carried out according to the method described in Production Method 11, using compound (R-13) instead of compound (R-12).

［式中、記号は前記と同じ意味を表す。］ Manufacturing method 14
The compound represented by the formula (Is) (hereinafter referred to as the present bipyridine compound (Is)) and the compound represented by the formula (It) (hereinafter referred to as the present bipyridine compound (It)) are prepared according to the following method. Can be manufactured.

[Wherein the symbols have the same meaning as described above. ]

First, a compound represented by formula (Ir) (hereinafter referred to as the present bipyridine compound (Ir)) and a compound represented by formula (R-14) (hereinafter referred to as compound (R-14)) were reacted. A method for producing the present bipyridine compound (Is) is described.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include nitriles.
In the reaction, a base can be used as necessary. Examples of the base used for the reaction include organic bases.
For the reaction, the compound (R-14) is usually used in a proportion of 1 to 5 mol and the base is used in a proportion of 0.1 to 5 mol with respect to 1 mol of the bipyridine compound (Ir).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Is) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

It continues and describes the method of manufacturing this bipyridine compound (It) by making this bipyridine compound (Is) and a base react.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include alcohols, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is used in a proportion of 0.1 to 5 mol with respect to 1 mol of the bipyridine compound (Is).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (It) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば非プロトン性極性溶媒が挙げられる。
反応に用いられる塩基としては、例えばアルカリ金属炭酸塩類が挙げられる。
反応に用いられる還元剤としては、例えばヒドロキシメタンスルフィン酸ナトリウムが挙げられる。
反応には、化合物（Ｍ−２２）１モルに対して、化合物（Ｒ−２）が通常１〜１０モルの割合、塩基が通常１〜１０モルの割合、還元剤が通常１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本ビピリジン化合物（Ｉａ）を得ることができる。 Production method 15
The present bipyridine compound (Ia) is obtained by reacting a compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) with compound (R-2) in the presence of a base and a reducing agent. Can be manufactured.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the base used for the reaction include alkali metal carbonates.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate.
In the reaction, with respect to 1 mole of the compound (M-22), the ratio of the compound (R-2) is usually 1 to 10 moles, the base is usually 1 to 10 moles, and the reducing agent is usually 1 to 10 moles. Used in proportions.
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Hereafter, it describes about the manufacturing method of each intermediate body.

［式中、Ｖ³は塩素原子、臭素原子又はヨウ素原子を表し、ＭはＳｎ（ｎ−Ｃ₄Ｈ₉）₃を表し、その他の記号は前記と同じ意味を表す。］
化合物（Ｍ−９）は、例えば国際公開第０３／０２４９６１号に記載の方法、又はOrganic Process Research & Development, 2004, 8, 192-200に記載の方法に準じて製造することができる。
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばトルエン、キシレン等の芳香族炭化水素類が挙げられる。
反応に用いられる金属触媒としては、テトラキス（トリフェニルホスフィン）パラジウム（０）、１，１’−ビス（ジフェニルホスフィノ）フェロセンパラジウム（ＩＩ）ジクロリド等のパラジウム触媒が挙げられる。
反応に用いられる無機ハロゲン化物としては、フッ化カリウム、フッ化ナトリウム等のアルカリ金属フッ化物、塩化リチウム、塩化ナトリウム等のアルカリ金属塩化物が挙げられる。
反応には、化合物（Ｍ−８）１モルに対して、化合物（Ｍ−９）が通常１〜１０モルの割合、金属触媒が通常０．０１〜０．５モルの割合、無機ハロゲン化物が通常０．１〜５モルの割合で用いられる。
反応温度は、通常−２０℃〜２００℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ−１）を得ることができる。 Reference manufacturing method 1
Compound (M-1) is a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) and a compound represented by formula (M-9) (hereinafter referred to as compound (M-9). ) Can be produced by reacting in the presence of a metal catalyst and an inorganic halide.

[Wherein V ³ represents a chlorine atom, a bromine atom or an iodine atom, M represents Sn (n—C ₄ H ₉ ) ₃ , and other symbols represent the same meaning as described above. ]
Compound (M-9) can be produced, for example, according to the method described in WO 03/024961 or the method described in Organic Process Research & Development, 2004, 8, 192-200.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aromatic hydrocarbons such as toluene and xylene.
Examples of the metal catalyst used in the reaction include palladium catalysts such as tetrakis (triphenylphosphine) palladium (0) and 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride.
Examples of the inorganic halide used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride, and alkali metal chlorides such as lithium chloride and sodium chloride.
In the reaction, with respect to 1 mol of the compound (M-8), the compound (M-9) is usually in a proportion of 1 to 10 mol, the metal catalyst is usually in a proportion of 0.01 to 0.5 mol, and the inorganic halide is contained. Usually, it is used in a proportion of 0.1 to 5 mol.
The reaction temperature is usually in the range of -20 ° C to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, compound (M-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ−１０）と化合物（Ｒ−３）とを該反応させる方法は、製造法５に記載の方法に準ずる。 Reference manufacturing method 2
Compound (M-8) is produced by reacting a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) and compound (R-3) in the presence of a base. can do.

[Wherein the symbols have the same meaning as described above. ]
The method of reacting compound (M-10) and compound (R-3) is in accordance with the method described in Production Method 5.

［式中、Ｒ^xはメチル基又はエチル基を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばハロゲン化炭化水素類が挙げられる。
反応に用いられる酸としては、三塩化ホウ素、三臭化ホウ素等のハロゲン化ホウ素類が挙げられる。
反応には、化合物（Ｍ−１１）１モルに対して、酸が通常０．１〜１０モルの割合で用いられる。
反応温度は、通常−２０℃〜１５０℃の範囲である。反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ−３）を得ることができる。 Reference manufacturing method 3
Compound (M-3) can be produced by reacting a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) with an acid.

[Wherein R ^x represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the acid used for the reaction include boron halides such as boron trichloride and boron tribromide.
For the reaction, the acid is usually used in a proportion of 0.1 to 10 mol per 1 mol of the compound (M-11).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ−１３）は、化合物（Ｍ−８）に代えて式（Ｍ−１２）で示される化合物（以下、化合物（Ｍ−１２）と記す。）を用い、参考製造法１に記載の方法に準じて製造することができる。
化合物（Ｍ−１２）は、Ｈｅｔｅｒｏｃｙｃｌｅｓ，１９９０，３０，８７５−８８４に記載の方法に準じて製造することにより得られる。また、市販されている化合物（Ｍ−１２）を用いてもよい。
化合物（Ｍ−１１ａ）は、化合物（Ｍ−１）に代えて化合物（Ｍ−１３）を用い、製造法３に記載の方法に準じて製造することができる。
化合物（Ｍ−１１ｂ）及び化合物（Ｍ−１１ｃ）は、本ビピリジン化合物（Ｉａ）に代えて化合物（Ｍ−１１ａ）を用い、製造法１に記載の方法に準じて製造することができる。 Reference production method 4
In the compound (M-11), a compound in which n is 0 (hereinafter referred to as a compound (M-11a)), a compound in which n is 1 (hereinafter referred to as a compound (M-11b)), and n Is a compound (hereinafter referred to as compound (M-11c)) can be produced according to the following method.

[Wherein the symbols have the same meaning as described above. ]
As the compound (M-13), a compound represented by the formula (M-12) (hereinafter referred to as the compound (M-12)) is used instead of the compound (M-8), and described in the reference production method 1. It can be produced according to the method.
A compound (M-12) is obtained by manufacturing according to the method as described in Heterocycles, 1990, 30, 875-884. A commercially available compound (M-12) may also be used.
Compound (M-11a) can be produced according to the method described in Production Method 3, using Compound (M-13) instead of Compound (M-1).
Compound (M-11b) and Compound (M-11c) can be produced according to the method described in Production Method 1, using Compound (M-11a) instead of Bipyridine Compound (Ia).

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ−１５）は、化合物（Ｍ−５）に代えて式（Ｍ−１４）で示される化合物（以下、化合物（Ｍ−１４）と記す。）を用い、製造法７に記載の方法に準じて製造することができる。 Reference production method 5
The compound represented by the formula (M-15) (hereinafter referred to as the compound (M-15)) can be produced according to the method described below.

[Wherein the symbols have the same meaning as described above. ]
The method according to Production Method 7, wherein the compound (M-15) is a compound represented by the formula (M-14) (hereinafter referred to as the compound (M-14)) instead of the compound (M-5) It can be manufactured according to.

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ−１７）は、化合物（Ｍ−７）に代えて化合物（Ｍ−１６）を用い、製造法９に記載の方法に準じて製造することができる。 Reference manufacturing method 6
A compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) is a compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) and a compound. It can manufacture by making it react with ammonia, after making (R-12) react.

[Wherein the symbols have the same meaning as described above. ]
Compound (M-17) can be produced according to the method described in production method 9, using compound (M-16) in place of compound (M-7).

［式中、記号は前記と同じ意味を表す。］
化合物（Ｍ−１８）は、化合物（Ｍ−５）に代えて化合物（Ｍ−１４）を用い、製造法１０に記載の方法に準じて製造することができる。 Reference manufacturing method 7
A compound represented by formula (M-18) (hereinafter referred to as compound (M-18)) can be produced by reacting compound (M-14) with compound (R-8).

[Wherein the symbols have the same meaning as described above. ]
Compound (M-18) can be produced according to the method described in production method 10 using compound (M-14) in place of compound (M-5).

［式中、Ｒ³⁸はハロゲン原子、又はＯＲ¹を表し、その他の記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。
反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、アルコール類、非プロトン性極性溶媒、水及びこれらの混合物が挙げられる。
反応に用いられる酸としては、例えば塩酸、硫酸が挙げられる。
反応には、化合物（Ｍ−１７）１モルに対して、酸が通常０．１〜５モルの割合で用いられる。
反応温度は、通常０℃〜１００℃の範囲である。反応時間は通常０．５〜１２時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ−１９）を得ることができる。 Reference production method 8
A compound represented by formula (M-19) (hereinafter referred to as compound (M-19)) is a compound represented by formula (M-20) (hereinafter referred to as compound (M-20)). It can be produced by reacting in the presence of an acid.

[Wherein, R ³⁸ represents a halogen atom or OR ¹ , and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, alcohols, aprotic polar solvents, water, and mixtures thereof.
Examples of the acid used for the reaction include hydrochloric acid and sulfuric acid.
For the reaction, the acid is usually used at a ratio of 0.1 to 5 mol with respect to 1 mol of the compound (M-17).
The reaction temperature is usually in the range of 0 ° C to 100 ° C. The reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, the compound (M-19) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

［式中、記号は前記と同じ意味を表す。］
該反応は、通常溶媒中で行われる。
反応に用いられる溶媒としては、例えばエーテル類、ヘキサン及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えばｎ−ブチルリチウムが挙げられる。
反応には、化合物（Ｍ−２１）１モルに対して、化合物（Ｒ−１６）が通常１〜５モルの割合、塩基が通常１〜５モルの割合で用いられる。
反応温度は、通常−７８℃〜１００℃の範囲である。反応時間は通常０．５〜１２時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ−２０）を得ることができる。
化合物（Ｍ−２１）は、既知の方法により製造することができる。また、市販されている化合物（Ｍ−２１）を用いてもよい。 Reference manufacturing method 9
Compound (M-20) includes a compound represented by formula (M-21) (hereinafter referred to as compound (M-21)) and a compound represented by formula (R-16) (hereinafter referred to as compound (R-)). 16).) Can be reacted in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used for the reaction include ethers, hexane, and a mixture thereof.
Examples of the base used for the reaction include n-butyllithium.
In the reaction, with respect to 1 mol of compound (M-21), compound (R-16) is usually used at a ratio of 1 to 5 mol, and the base is usually used at a ratio of 1 to 5 mol.
The reaction temperature is usually in the range of -78 ° C to 100 ° C. The reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, the compound (M-20) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
Compound (M-21) can be produced by a known method. Moreover, you may use the compound (M-21) marketed.

［式中、記号は前記と同じ意味を表す。］ Reference production method 10
Compound (M-2) and compound (M-22) can be produced by reacting compound (M-1) with a sulfurizing agent.

[Wherein the symbols have the same meaning as described above. ]

The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aprotic polar solvents.
Examples of the sulfurizing agent used in the reaction include sodium sulfide and sodium hydrogen sulfide.
In the reaction, the sulfurizing agent is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (M-1).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M-2) and the compound (M-22) are obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. be able to.
In the reaction, V is preferably a fluorine atom or a chlorine atom.

［式中、Ｖ⁴は塩素原子又は臭素原子を表し、Ｖ⁵はフッ素原子又はヨウ素原子を表し、その他の記号は前記と同じ意味を表す。］
はじめに、化合物（Ｍ−３）から化合物（Ｍ−４ａ）を製造する方法について記載する。
化合物（Ｍ−４ａ）は、化合物（Ｍ−３）とオキシ塩化リン又はオキシ臭化リンとを反応させることにより製造することができる。
該反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば芳香族炭化水素類が挙げられる。オキシ塩化リンを用いる場合、オキシ塩化リンを溶媒として用いる事もできる。
反応には、化合物（Ｍ−３）１モルに対して、オキシ塩化リン又はオキシ臭化リンが通常１〜１０モルの割合で用いられる。
反応温度は、通常０℃〜１５０℃の範囲である。反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ−４ａ）を得ることができる。 Reference production method 11
In the compound (M-4), a compound in which V is a chlorine atom or a bromine atom (hereinafter referred to as compound (M-4a)), and a compound in which V is a fluorine atom or iodine atom (hereinafter referred to as compound (M-4b) ) Can be produced according to the method described below.

[Wherein, V ⁴ represents a chlorine atom or a bromine atom, V ⁵ represents a fluorine atom or an iodine atom, and other symbols represent the same meaning as described above. ]
First, a method for producing the compound (M-4a) from the compound (M-3) will be described.
Compound (M-4a) can be produced by reacting compound (M-3) with phosphorus oxychloride or phosphorus oxybromide.
The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include aromatic hydrocarbons. When using phosphorus oxychloride, phosphorus oxychloride can also be used as a solvent.
In the reaction, phosphorous oxychloride or phosphorous oxybromide is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (M-3).
The reaction temperature is usually in the range of 0 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M-4a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

It continues and describes the method to manufacture a compound (M-4b) from a compound (M-4a).
Compound (M-4b) can be produced by reacting compound (M-4a) with an inorganic fluoride or inorganic iodide.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include nitriles, aprotic polar solvents, and mixtures thereof.
As an inorganic fluoride used for reaction, potassium fluoride is mentioned, for example.
Examples of the inorganic iodide used in the reaction include sodium iodide.
In the reaction, an inorganic fluoride or an inorganic iodide is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (M-4a).
The reaction temperature is usually in the range of 0 ° C to 250 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, compound (M-4b) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

  Next, specific examples of the bipyridine compound are shown below.

［式中、Ｒ²⁰¹はＲ¹を表し、Ｒ²⁰²はＲ²を表し、Ｒ²⁰³、Ｒ²⁰⁴、及びＲ²⁰⁵は、各々独立して水素原子、又はＲ³を表し、Ｒ²⁰⁶、Ｒ²⁰⁷、及びＲ²⁰⁸は、各々独立して水素原子、又はＲ⁶を表し、ｎは０、１、又は２を表す。］
で示される化合物。 Formula (200)

[Wherein R ²⁰¹ represents R ¹ , R ²⁰² represents R ² , R ²⁰³ , R ²⁰⁴ , and R ²⁰⁵ each independently represent a hydrogen atom or R ³ , R ²⁰⁶ , R ²⁰⁷ , And R ²⁰⁸ each independently represents a hydrogen atom or R ⁶ , and n represents 0, 1, or 2. ]
A compound represented by

In the compound represented by the formula (200), n is 2, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are [Table 1] to This bipyridine compound (hereinafter referred to as compound group SX1) which is any combination described in [Table 11].

In the compound represented by the formula (200), n is 1, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are [Table 1] to This bipyridine compound (hereinafter referred to as compound group SX2) which is any combination described in [Table 11].
In the compound represented by the formula (200), n is 0, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are [Table 1] to This bipyridine compound (hereinafter referred to as compound group SX3), which is any combination described in [Table 11].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX4), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX5).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX6) in which any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX7), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX8), which are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19], and the present bipyridine compound (hereinafter referred to as compound group SX9).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX10).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX11), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX12), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX13), which are any combination described in [Table 12] to [Table 19].

［式中、記号は前記の意味を示す。］
で示される化合物 Formula (201)

[Wherein the symbols have the above-mentioned meanings. ]
Compound represented by

In the compound represented by the formula (201), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are described in [Table 1] to [Table 11]. This bipyridine compound (hereinafter referred to as compound group SX14).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19], and the present bipyridine compound (hereinafter referred to as compound group SX15).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX16).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX17), which are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX18), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX19), which are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX20).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX21).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ^{204, R 205, R 206,} R 207 and R ²⁰⁸ are [Table 12] - the bipyridine compound which is either a combination according to Table 19] (hereinafter, referred to as compound group SX22).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX23) in which any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX24), which is any combination described in [Table 12] to [Table 19].

［式中、記号は前記の意味を示す。］
で示される化合物 Formula (202)

[Wherein the symbols have the above-mentioned meanings. ]
Compound represented by

In the compound represented by the formula (202), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are described in [Table 1] to [Table 11]. The bipyridine compound (hereinafter referred to as compound group SX25) which is any combination of

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX26).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound (hereinafter, referred to as compound group SX27) wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX28), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX29), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX30), which are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX31).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX32).

In the compound represented by formula (202), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX33) in which any combination of [Table 12] to [Table 19] is described.

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX34), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX35) in any combination described in [Table 12] to [Table 19].

［式中、記号は前記の意味を示す。］
で示される化合物 Formula (203)

[Wherein the symbols have the above-mentioned meanings. ]
Compound represented by

In the compound represented by the formula (203), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are described in [Table 1] to [Table 11]. The bipyridine compound (hereinafter referred to as compound group SX36), which is a combination of any of the above.

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19], and the present bipyridine compound (hereinafter referred to as compound group SX37).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX38).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX39), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX40), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX41), which are any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19], and the present bipyridine compound (hereinafter referred to as compound group SX42).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX43).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX44), which is any combination described in [Table 12] to [Table 19].

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX45) in which any combination described in [Table 12] to [Table 19].

In the compound represented by formula (203), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in [Table 12] to [Table 19] (hereinafter referred to as compound group SX46).

Next, production examples of the present bipyridine compound are shown below.

¹H-NMR (CDCl₃) δ: 8.32 (1H, d), 7.54 (1H, dd), 7.39 (1H, d), 5.15-4.96 (1H, m). Production Example 1-1
A mixture of 1.0 g of 2-chloro-5-hydroxypyridine, 110 mg of potassium hydroxide, 19 mL of methanol, and 19 mL of DMSO was stirred at room temperature for 12 hours under a hexafluoropropene atmosphere. Water was added to the resulting reaction mixture and extracted with MTBE. The obtained organic layer was dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure to obtain 2.0 g of Intermediate 1 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.32 (1H, d), 7.54 (1H, dd), 7.39 (1H, d), 5.15-4.96 (1H, m).

¹H-NMR (CDCl₃) δ: 8.60-8.56 (1H, m), 7.24-7.19 (1H, m), 7.18-7.12 (1H, m), 1.66-1.47 (6H, m), 1.42-1.23 (6H, m), 1.23-1.09 (6H, m), 0.97-0.80 (9H, m). Production Example 1-2
To a mixture of 16 g of 1,4-diazabicyclo [2,2,2] octane and 640 mL of MTBE, 80 mL of 1.6 M n-butyllithium hexane solution was added dropwise at −45 ° C. in a nitrogen atmosphere. After stirring at −45 ° C. for 2 hours, 11 mL of 3-fluoropyridine was added dropwise to the reaction mixture. Furthermore, after stirring at -45 degreeC for 2 hours, it cooled to -50 degreeC and 35 mL tributyltin chloride was dripped. After stirring at −50 ° C. for 1 hour, the temperature was raised to room temperature. A saturated aqueous ammonium chloride solution was added to the obtained mixture at room temperature, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The obtained organic layer was concentrated under reduced pressure to obtain 50 g of a mixture containing intermediate 2 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.60-8.56 (1H, m), 7.24-7.19 (1H, m), 7.18-7.12 (1H, m), 1.66-1.47 (6H, m), 1.42-1.23 ( 6H, m), 1.23-1.09 (6H, m), 0.97-0.80 (9H, m).

¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, dd), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt). Production Example 1-3
A mixture of 1.2 g of intermediate 1, 2.5 g of intermediate 2, 500 mg of tetrakistriphenylphosphine palladium (0), 160 mg of copper iodide, 270 mg of anhydrous lithium chloride, and 14 mL of toluene was heated under reflux. Stir for hours. The resulting reaction mixture was allowed to cool to room temperature, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 820 mg of intermediate 3 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, dd), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt).

¹H-NMR (CDCl₃) δ: 8.64 (1H, d), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, dd), 7.68 (1H, dd), 7.28 (1H, dd), 5.18-4.98 (1H, m), 2.92 (2H, q), 1.33 (3H, t). Production Example 1-4
200 μL of ethanethiol was added dropwise to a suspension of sodium hydride (60%, oily) 110 mg and DMF 5 mL under ice cooling. After stirring for 10 minutes under ice-cooling, a mixture of 820 mg of Intermediate 3 and 5 mL of DMF was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 5 hours. To the obtained reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 680 mg of the present bipyridine compound 9 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.64 (1H, d), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, dd), 7.68 (1H, dd), 7.28 (1H, dd ), 5.18-4.98 (1H, m), 2.92 (2H, q), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.60-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 5.18-4.99 (1H, m), 3.52-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
本ビピリジン化合物１１

¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.53 (1H, d), 8.50 (1H, dd), 7.91 (1H, d), 7.74 (1H, dd), 7.58 (1H, dd), 5.18-4.99 (1H, m), 3.87 (2H, q), 1.38 (3H, t). Production Example 2
To a mixed solution of 530 mg of the present bipyridine compound 9 and 5 mL of chloroform, 520 mg of mCPBA (70%) was added under ice cooling. After stirring for 6 hours under ice-cooling, sodium sulfite and saturated aqueous sodium hydrogen carbonate solution were sequentially added, and the mixture was extracted with chloroform. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 210 mg of the present bipyridine compound 10 represented by the following formula and 340 mg of the present bipyridine compound 11 represented by the following formula.
This bipyridine compound 10

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.60-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 5.18-4.99 (1H, m), 3.52-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
This bipyridine compound 11

¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, dd), 8.53 (1H, d), 8.50 (1H, dd), 7.91 (1H, d), 7.74 (1H, dd), 7.58 (1H, dd ), 5.18-4.99 (1H, m), 3.87 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.57-8.54 (1H, m), 8.51-8.49 (1H, m), 7.96 (1H, dd), 7.56-7.49 (1H, m), 7.35-7.28 (2H, m), 3.94-3.91 (3H, m). Production Example 3-1
In place of Intermediate 1, 2-bromo-5-methoxypyridine was used, and Intermediate 4 represented by the following formula was obtained according to the method described in Production Example 1-3.

¹ H-NMR (CDCl ₃ ) δ: 8.57-8.54 (1H, m), 8.51-8.49 (1H, m), 7.96 (1H, dd), 7.56-7.49 (1H, m), 7.35-7.28 (2H, m), 3.94-3.91 (3H, m).

¹H-NMR (CDCl₃) δ: 8.86 (1H, dd), 8.48 (1H, dd), 8.31 (1H, d), 7.83 (1H, d), 7.51 (1H, dd), 7.36 (1H, dd), 3.94-3.87 (5H, m), 1.37 (3H, t). Production Example 3-2
To a mixture of 510 mg of intermediate 4, 110 mg of sodium hydride (oil, 60%), and 5 mL of DMF, 200 μL of ethanethiol was added dropwise under ice cooling. The mixture was warmed to room temperature and stirred for 4 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure.
To a solution obtained by diluting the obtained residue with chloroform, 1.4 g of mCPBA (70%) was added under ice cooling. The reaction mixture was stirred at room temperature for 10 hours. To the obtained reaction mixture, sodium sulfite and saturated aqueous sodium hydrogen carbonate solution were sequentially added, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 490 mg of intermediate 5 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.48 (1H, dd), 8.31 (1H, d), 7.83 (1H, d), 7.51 (1H, dd), 7.36 (1H, dd ), 3.94-3.87 (5H, m), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.86 (1H, dd), 8.50 (1H, dd), 8.12 (1H, d), 7.67 (1H, d), 7.54 (1H, dd), 7.08 (1H, dd), 6.64 (1H, br s), 3.94 (2H, q), 1.39 (3H, t). Production Example 3-3
To 5 mL of 1.0 M boron tribromide dichloromethane solution, 490 mg of Intermediate 5 was added under ice cooling. The mixture was warmed to room temperature and stirred for 2 days. To the obtained reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added under ice cooling, and the mixture was extracted with chloroform. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 300 mg of Intermediate 6 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.50 (1H, dd), 8.12 (1H, d), 7.67 (1H, d), 7.54 (1H, dd), 7.08 (1H, dd ), 6.64 (1H, br s), 3.94 (2H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd), 6.08 (1H, tt), 4.48 (2H, t), 3.89 (2H, q), 1.38 (3H, t). Production Example 3-4
To a mixture of 100 mg of Intermediate 6, 190 mg of cesium carbonate, and 2 mL of DMF, 150 mg of 2,2,3,3-tetrafluoropropyl = trifluoromethanesulfonate (hereinafter referred to as Reagent A) is added under ice cooling. It was. After stirring at room temperature for 10 hours, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 140 mg of the present bipyridine compound 7 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 6.08 (1H, tt), 4.48 (2H, t), 3.89 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd), 4.54 (2H, t), 3.89 (2H, q), 1.38 (3H, t). Production Example 4
Using 2,2,3,3,3-pentafluoropropyl = trifluoromethanesulfonate instead of reagent A, the bipyridine compound 8 represented by the following formula was obtained according to the method described in Production Example 3-4. .

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.54 (2H, t), 3.89 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.55 (1H, dd), 7.42 (1H, dd), 5.33-5.08 (1H, m), 4.59-4.36 (2H, m), 3.89 (2H, q), 1.38 (3H, t). Production Example 5
This bipyridine compound 14 represented by the following formula is used according to the method described in Production Example 3-4 using 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate instead of reagent A. Got.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.55 (1H, dd), 7.42 (1H, dd ), 5.33-5.08 (1H, m), 4.59-4.36 (2H, m), 3.89 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.33 (1H, d), 7.55 (1H, dd), 7.39 (1H, d), 5.97 (1H, dt). Production Example 6-1
Intermediate 7 represented by the following formula was obtained according to the method described in Production Example 1-1 using (trifluorovinyl) (trifluoromethyl) ether instead of hexafluoropropene.

¹ H-NMR (CDCl ₃ ) δ: 8.33 (1H, d), 7.55 (1H, dd), 7.39 (1H, d), 5.97 (1H, dt).

¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, d), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt). Production Example 6-2
Intermediate 8 represented by the following formula was obtained according to the method described in Production Example 1-3 using Intermediate 7 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, d), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt).

¹H-NMR (CDCl₃) δ: 8.65 (1H, s), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, d), 7.69 (1H, dd), 7.31-7.26 (1H, m), 6.00 (1H, dd), 2.92 (2H, q), 1.33 (3H, t). Production Example 6-3
This bipyridine compound 22 represented by the following formula was obtained according to the method described in Production Example 1-4 using Intermediate 8 instead of Intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, s), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, d), 7.69 (1H, dd), 7.31-7.26 (1H , m), 6.00 (1H, dd), 2.92 (2H, q), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.61-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 6.01 (1H, dt), 3.51-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
本ビピリジン化合物２４

¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.54 (1H, d), 8.50 (1H, dd), 7.91 (1H, dd), 7.74 (1H, dd), 7.59 (1H, dd), 6.00 (1H, dt), 3.87 (2H, q), 1.38 (3H, t). Production Example 7
This bipyridine compound 22 was used in place of this bipyridine compound 9, and the bipyridine compound 23 represented by the following formula and the bipyridine compound 24 represented by the following formula were obtained according to the method described in Production Example 2.
This bipyridine compound 23

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.61-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 6.01 (1H , dt), 3.51-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
This bipyridine compound 24

¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, dd), 8.54 (1H, d), 8.50 (1H, dd), 7.91 (1H, dd), 7.74 (1H, dd), 7.59 (1H, dd ), 6.00 (1H, dt), 3.87 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.13 (1H, d), 7.45 (1H, d), 7.19 (1H, dd), 4.46 (2H, t). Production Example 8-1
A mixture of 10 g of 2-bromo-5-hydroxypyridine, 26 g of cesium carbonate, and 29 mL of DMF, 22 g of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate (hereinafter referred to as reagent B) under ice cooling. ) Was added dropwise. The reaction mixture was stirred at room temperature for 2 days, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with MTBE. The obtained organic layer was washed successively with 1M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 17 g of intermediate 9 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, d), 7.45 (1H, d), 7.19 (1H, dd), 4.46 (2H, t).

¹H-NMR (CDCl₃) δ: 8.59-8.55 (1H, m), 8.54 (1H, d), 8.01 (1H, dd), 7.58-7.52 (1H, m), 7.40 (1H, dd), 7.38-7.33 (1H, m), 4.55 (2H, t). Production Example 8-2
Intermediate 10 represented by the following formula was obtained according to the method described in Production Example 1-3 using Intermediate 9 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.59-8.55 (1H, m), 8.54 (1H, d), 8.01 (1H, dd), 7.58-7.52 (1H, m), 7.40 (1H, dd), 7.38 -7.33 (1H, m), 4.55 (2H, t).

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 8.43 (1H, dd), 8.02 (1H, dd), 7.70 (1H, dd), 7.41 (1H, dd), 7.28-7.23 (1H, m), 4.54 (2H, td), 2.91 (2H, q), 1.32 (3H, t). Production Example 8-3
This bipyridine compound 27 represented by the following formula was obtained according to the method described in Production Example 1-4 using Intermediate 10 instead of Intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.47 (1H, dd), 8.43 (1H, dd), 8.02 (1H, dd), 7.70 (1H, dd), 7.41 (1H, dd), 7.28-7.23 (1H , m), 4.54 (2H, td), 2.91 (2H, q), 1.32 (3H, t).

Production Example 8-4
According to the method described in Production Example 2, this bipyridine compound 30 represented by the following formula can be synthesized using this bipyridine compound 27 instead of the present bipyridine compound 9.
This bipyridine compound 30

¹H-NMR (CDCl₃) δ: 8.12 (1H, d), 7.44 (1H, dd), 7.17 (1H, dd), 6.03 (1H, tt), 4.40 (2H, tt). Production Example 9-1
Intermediate 18 represented by the following formula was obtained according to the method described in Production Example 8-1, using reagent A instead of reagent B.

¹ H-NMR (CDCl ₃ ) δ: 8.12 (1H, d), 7.44 (1H, dd), 7.17 (1H, dd), 6.03 (1H, tt), 4.40 (2H, tt).

¹H-NMR (CDCl₃) δ: 8.59-8.52 (2H, m), 8.04-7.99 (1H, m), 7.59-7.52 (1H, m), 7.42-7.32 (2H, m), 6.25-5.93 (1H, m), 4.54-4.45 (2H, m). Production Example 9-2
In accordance with the method described in Production Example 1-3, Intermediate 19 represented by the following formula was obtained using Intermediate 18 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.59-8.52 (2H, m), 8.04-7.99 (1H, m), 7.59-7.52 (1H, m), 7.42-7.32 (2H, m), 6.25-5.93 ( 1H, m), 4.54-4.45 (2H, m).

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 8.43 (1H, dd), 8.00 (1H, d), 7.70 (1H, dd), 7.39 (1H, dd), 7.28-7.23 (1H, m), 6.09 (1H, tt), 4.48 (2H, t), 2.91 (2H, q), 1.32 (3H, t). Production Example 9-3
This bipyridine compound 26 represented by the following formula was obtained according to the method described in Production Example 1-4 using Intermediate 19 instead of Intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, d), 8.43 (1H, dd), 8.00 (1H, d), 7.70 (1H, dd), 7.39 (1H, dd), 7.28-7.23 (1H m), 6.09 (1H, tt), 4.48 (2H, t), 2.91 (2H, q), 1.32 (3H, t).

Production Example 9-4
The bipyridine compound 29 represented by the following formula can be synthesized according to the method described in Production Example 2 using the bipyridine compound 26 instead of the bipyridine compound 9.
This bipyridine compound 29

¹H-NMR (CDCl₃) δ: 8.57 (1H, d), 8.19 (1H, dd), 7.62-7.55 (1H, m), 4.97 (2H, s), 3.30 (2H, q), 1.47 (3H, t). Production Example 10-1
To a mixture of 100 mL of 1.6 M n-butyllithium hexane solution and 160 mL of THF, a mixture of 23 g of ethyl methyl sulfone and 20 mL of THF was added dropwise at −78 ° C. The reaction mixture was gradually warmed to 0 ° C and then re-cooled to -78 ° C. To this reaction mixture, a mixture of 20 g of 5-fluoro-2-cyanopyridine and 20 mL of THF was added dropwise at -78 ° C. After gradually warming to room temperature, 2N hydrochloric acid was added to the reaction mixture and stirred for 30 minutes. The obtained mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 40 g of intermediate 16 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.57 (1H, d), 8.19 (1H, dd), 7.62-7.55 (1H, m), 4.97 (2H, s), 3.30 (2H, q), 1.47 (3H , t).

¹H-NMR (CDCl₃) δ: 8.88 (1H, dd), 8.52-8.46 (2H, m), 7.87 (1H, dd), 7.62-7.54 (2H, m), 3.86 (2H, q), 1.38 (3H, t). Production Example 10-2
To a mixture of 11 mL of oxalyl chloride and 86 mL of chloroform, 10 mL of DMF was added dropwise under ice cooling. After stirring for 30 minutes under ice cooling, 33 mL of butyl vinyl ether was added dropwise to the mixture. After warming to room temperature and stirring for 2 hours, a mixture of 10 g of Intermediate 16, 42 mL of triethylamine and 30 mL of chloroform was added dropwise to this mixture under ice cooling. The mixture was warmed to room temperature and stirred for 1 hour. The resulting mixture was added to a saturated aqueous ammonium chloride solution and extracted with chloroform. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was diluted with 30 mL of ethanol, and 10 mL of 28% aqueous ammonia solution was added at room temperature. The mixture was heated and stirred at 60 ° C. for 2.5 hours, allowed to cool to room temperature, added to saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 9.4 g of intermediate 17 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, dd), 8.52-8.46 (2H, m), 7.87 (1H, dd), 7.62-7.54 (2H, m), 3.86 (2H, q), 1.38 (3H, t).

本ビピリジン化合物２

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.86 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd), 4.48 (2H, q), 3.89 (2H, q), 1.38 (3H, t). Production Example 10-3
To a mixture of 400 mg intermediate 17, 90 mg sodium hydride (60%, oil), and 2 mL NMP was added 230 mg 2,2,2-trifluoroethanol under ice cooling. The mixture was heated and stirred at 70 ° C. for 2 days. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 170 mg of the present bipyridine compound 2 represented by the following formula.

This bipyridine compound 2

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.86 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.48 (2H, q), 3.89 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.93 (1H, dd), 8.37 (1H, dd), 8.04 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 7.05 (1H, dd), 4.50 (2H, t), 3.76-3.64 (1H, m), 3.61-3.49 (1H, m), 1.35 (3H, t).
本ビピリジン化合物２１４

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 8.43 (1H, d), 7.97 (1H, dd), 7.69 (1H, d), 7.50 (1H, dd), 7.43 (1H, dd), 4.54 (2H, t), 3.44 (2H, q), 1.30 (3H, t).
本ビピリジン化合物２２４

¹H-NMR (CDCl₃) δ: 8.49 (1H, dd), 8.14 (1H, d), 7.91 (1H, dd), 7.57 (1H, dd), 7.42 (1H, d), 7.07 (1H, dd), 4.51 (2H, t), 3.36-3.18 (2H, m), 1.28 (3H, t). Production Example 11
To a mixture of 2.0 g of the present bipyridine compound 8, 6 mL of sulfuric acid, and 2 mL of water, 630 μL of 30% aqueous hydrogen peroxide was added under ice cooling. After stirring at room temperature for 2 days, the reaction mixture was added to ice water. The obtained mixture was extracted with chloroform, and the organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.2 g of the present bipyridine compound 204 represented by the following formula, 0.6 g of the present bipyridine compound 214, and 0.2 g of the present bipyridine compound 224.
The bipyridine compound 204

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, dd), 8.37 (1H, dd), 8.04 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 7.05 (1H, dd ), 4.50 (2H, t), 3.76-3.64 (1H, m), 3.61-3.49 (1H, m), 1.35 (3H, t).
The bipyridine compound 214

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, dd), 8.43 (1H, d), 7.97 (1H, dd), 7.69 (1H, d), 7.50 (1H, dd), 7.43 (1H, dd ), 4.54 (2H, t), 3.44 (2H, q), 1.30 (3H, t).
The bipyridine compound 224

¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, dd), 8.14 (1H, d), 7.91 (1H, dd), 7.57 (1H, dd), 7.42 (1H, d), 7.07 (1H, dd ), 4.51 (2H, t), 3.36-3.18 (2H, m), 1.28 (3H, t).

¹H-NMR (CDCl₃) δ: 8.86 (1H, dd), 8.49 (1H, dd), 7.86 (1H, d), 7.56 (1H, dd), 7.42 (1H, d), 4.56 (2H, t), 3.98 (2H, q), 1.44 (3H, t).
本ビピリジン化合物１９４

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 7.47 (1H, d), 7.42 (1H, d), 7.39 (1H, d), 4.56 (2H, t), 3.70 (2H, q), 1.40 (3H, t). Production Example 12
15 mL of phosphorus oxychloride was added to a mixture of 6.8 g of the present bipyridine compound 204 and the present bipyridine compound 224 (mixing ratio, the present bipyridine compound 204: this bipyridine compound 224 = 100: 1), and the mixture was heated and stirred at 110 ° C. for 4 hours. . The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform, and a saturated aqueous sodium hydrogen carbonate solution was added. This mixture was extracted with chloroform, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6.7 g of the present bipyridine compound 169 represented by the following formula and 0.07 g of the present bipyridine compound 194.
The bipyridine compound 169

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.49 (1H, dd), 7.86 (1H, d), 7.56 (1H, dd), 7.42 (1H, d), 4.56 (2H, t ), 3.98 (2H, q), 1.44 (3H, t).
The bipyridine compound 194

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, d), 7.47 (1H, d), 7.42 (1H, d), 7.39 (1H, d), 4.56 (2H, t), 3.70 (2H, q ), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.42 (1H, dd), 8.37 (1H, d), 7.91 (1H, d), 7.54 (1H, dd), 7.41 (1H, dd), 4.54 (2H, t), 3.92 (2H, q), 1.38 (3H, t). Production Example 13
To 3.7 g of the present bipyridine compound 214, 10 mL of phosphorus oxychloride was added, and the mixture was heated and stirred at 110 ° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform, and a saturated aqueous sodium hydrogen carbonate solution was added. This mixture was extracted with chloroform, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.0 g of the present bipyridine compound 79 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.42 (1H, dd), 8.37 (1H, d), 7.91 (1H, d), 7.54 (1H, dd), 7.41 (1H, dd), 4.54 (2H, t ), 3.92 (2H, q), 1.38 (3H, t).

¹H-NMR (CDCl₃) δ: 8.35 (1H, dd), 8.29 (1H, d), 7.83 (1H, dd), 7.40 (1H, dd), 6.88 (1H, d), 4.54 (2H, td), 4.03 (3H, s), 3.83 (2H, q), 1.36 (3H, t). Production Example 14
To a mixture of 500 mg of the present bipyridine compound 79 and 2 mL of DMF, 0.1 mL of 28% sodium methoxide methanol solution was added under ice cooling. After stirring at room temperature for 2 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 230 mg of the present bipyridine compound 94 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.35 (1H, dd), 8.29 (1H, d), 7.83 (1H, dd), 7.40 (1H, dd), 6.88 (1H, d), 4.54 (2H, td ), 4.03 (3H, s), 3.83 (2H, q), 1.36 (3H, t).

¹H-NMR (CDCl₃) δ: 9.23 (1H, s), 8.67 (1H, d), 8.41 (1H, dd), 8.17 (1H, s), 8.10 (1H, d), 7.90 (1H, dd), 7.47 (1H, dd), 4.57 (2H, td), 3.93 (2H, q), 1.41 (3H, t). Production Example 15
To a mixture of 200 mg of the present bipyridine compound 79 and 2 mL of DMF, 39 mg of 1H-1,2,4-triazole and 22 mg of sodium hydride (60% oil) were added in an ice bath. After stirring at room temperature for 24 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 160 mg of the present bipyridine compound 104 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.23 (1H, s), 8.67 (1H, d), 8.41 (1H, dd), 8.17 (1H, s), 8.10 (1H, d), 7.90 (1H, dd ), 7.47 (1H, dd), 4.57 (2H, td), 3.93 (2H, q), 1.41 (3H, t).

¹H-NMR (CDCl₃) δ: 8.35 (1H, d), 8.12 (1H, d), 7.77 (1H, d), 7.44 (1H, s), 7.40 (1H, dd), 6.52 (1H, d), 5.40 (1H, t), 4.77 (2H, d), 4.54 (2H, t), 3.77 (2H, q), 1.35 (3H, t). Production Example 16
To a mixture of 200 mg of the present bipyridine compound 79, 0.96 mL of diisopropylethylamine, and 1 mL of acetonitrile, 960 mg of 2-chloro-5- (aminomethyl) thiazole hydrobromide was added under ice cooling. After stirring at 80 ° C. for 5 days, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 200 mg of the present bipyridine compound 89 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.35 (1H, d), 8.12 (1H, d), 7.77 (1H, d), 7.44 (1H, s), 7.40 (1H, dd), 6.52 (1H, d ), 5.40 (1H, t), 4.77 (2H, d), 4.54 (2H, t), 3.77 (2H, q), 1.35 (3H, t).

¹H-NMR (CDCl₃) δ: 8.34 (1H, d), 8.13 (1H, d), 7.71 (1H, dd), 7.38 (1H, dd), 6.58 (1H, d), 5.01 (2H, s), 4.52 (2H, td), 3.66 (2H, q), 1.32 (3H, t). Production Example 17
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of NMP, 0.09 mL of 28% aqueous ammonia solution was added at room temperature. The reaction mixture was stirred at 80 ° C. for 3 days. After allowing to cool to room temperature, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 110 mg of the present bipyridine compound 59 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.34 (1H, d), 8.13 (1H, d), 7.71 (1H, dd), 7.38 (1H, dd), 6.58 (1H, d), 5.01 (2H, s ), 4.52 (2H, td), 3.66 (2H, q), 1.32 (3H, t).

¹H-NMR (CDCl₃) δ: 8.80 (1H, d), 8.48 (1H, d), 8.37 (1H, d), 7.88 (1H, dd), 7.42 (1H, dd), 4.54 (2H, td), 3.94 (2H, q), 1.55 (6H, s), 1.40 (3H, t). Production Example 18
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of DMF, 0.13 mL of 50% aqueous dimethylamine solution was added at room temperature. The reaction mixture was stirred at 60 ° C. for 4 hours. After allowing to cool to room temperature, the reaction mixture was subjected to silica gel chromatography to obtain 200 mg of the bipyridine compound 69.

¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.48 (1H, d), 8.37 (1H, d), 7.88 (1H, dd), 7.42 (1H, dd), 4.54 (2H, td ), 3.94 (2H, q), 1.55 (6H, s), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.34 (1H, d), 8.17 (1H, d), 7.75 (1H, d), 7.40 (1H, dd), 6.61 (1H, d), 5.18 (1H, t), 4.54 (2H, t), 4.28-4.16 (2H, m), 3.79 (2H, q), 1.36 (3H, t). Production Example 19
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of NMP, 0.2 mL of 2,2,2-trifluoroethylamine was added at room temperature. The reaction mixture was stirred at 120 ° C. for 4 days. After allowing to cool to room temperature, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 180 mg of the present bipyridine compound 74 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.34 (1H, d), 8.17 (1H, d), 7.75 (1H, d), 7.40 (1H, dd), 6.61 (1H, d), 5.18 (1H, t ), 4.54 (2H, t), 4.28-4.16 (2H, m), 3.79 (2H, q), 1.36 (3H, t).

¹H-NMR (CDCl₃) δ: 8.88 (1H, dd), 8.51 (1H, dd), 8.12 (1H, d), 7.61 (1H, dd), 7.55 (1H, d), 4.66 (2H, t), 3.90 (2H, q), 1.45 (3H, t). Production Example 20
To a mixture of 500 mg of the present bipyridine compound 204, 240 mg of triethylamine, and 3 mL of acetonitrile, 360 mg of trimethylsilylcyanide was added at room temperature. This mixture was heated and stirred at 80 ° C. for 34 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with ethyl acetate, and saturated aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 180 mg of the present bipyridine compound 179 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, dd), 8.51 (1H, dd), 8.12 (1H, d), 7.61 (1H, dd), 7.55 (1H, d), 4.66 (2H, t ), 3.90 (2H, q), 1.45 (3H, t).

¹H-NMR (CDCl₃) δ: 8.86 (1H, dd), 8.47 (1H, dd), 7.83 (1H, d), 7.55 (1H, dd), 7.47 (1H, d), 4.51 (2H, t), 3.78 (2H, q), 2.33 (3H, s), 1.36 (3H, t). Production Example 21
5 mL of acetic anhydride was added to 1.0 g of the present bipyridine compound 204, and the mixture was heated and stirred at 100 ° C. for 20 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with ethyl acetate, and saturated aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 980 mg of the present bipyridine compound 174 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.47 (1H, dd), 7.83 (1H, d), 7.55 (1H, dd), 7.47 (1H, d), 4.51 (2H, t ), 3.78 (2H, q), 2.33 (3H, s), 1.36 (3H, t).

¹H-NMR (CDCl₃) δ: 11.08 (1H, s), 8.89 (1H, dd), 8.60 (1H, d), 7.61 (1H, dd), 7.32-7.24 (1H, br m), 7.11 (1H, d), 4.71 (2H, t), 3.15 (2H, q), 1.18 (3H, t). Production Example 22
To a mixture of 660 mg of the present bipyridine compound 174 and methanol 7 mL, 600 mg of potassium carbonate was added at room temperature, stirred at room temperature for 1.5 hours, and then adjusted to pH 4 with 2N hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 530 mg of the present bipyridine compound 159 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 11.08 (1H, s), 8.89 (1H, dd), 8.60 (1H, d), 7.61 (1H, dd), 7.32-7.24 (1H, br m), 7.11 ( 1H, d), 4.71 (2H, t), 3.15 (2H, q), 1.18 (3H, t).

¹H-NMR (CDCl₃) δ: 8.88 (1H, d), 8.46 (1H, d), 7.57 (1H, dd), 7.34 (1H, d), 7.28 (1H, d), 4.52 (2H, t), 4.00 (3H, s), 3.62 (2H, q), 1.34 (3H, t). Production Example 23
To a mixture of 340 mg of the present bipyridine compound 159, 400 mg cesium carbonate, and 3 mL DMF, 0.98 mL iodomethane was added at room temperature. After stirring at room temperature for 1 day, the reaction mixture was subjected to silica gel chromatography to obtain 250 mg of the present bipyridine compound 164 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, d), 8.46 (1H, d), 7.57 (1H, dd), 7.34 (1H, d), 7.28 (1H, d), 4.52 (2H, t ), 4.00 (3H, s), 3.62 (2H, q), 1.34 (3H, t).

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.71 (1H, dd), 7.33 (1H, dd), 6.04 (1H, tt), 4.49 (2H, t). Production Example 24-1
To a mixture of 30 g of 2-cyano-5-fluoropyridine, 54 g of 2,2,3,3-tetrafluoro-1-propanol, and 90 mL of NMP, 130 g of cesium carbonate was added under ice cooling, and then the temperature was raised to room temperature. Stir at room temperature for 1.5 hours. The resulting mixture was heated to 60 ° C. and further stirred at 60 ° C. for 5 hours, and then water was added to the reaction mixture, followed by extraction with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was recrystallized with an isopropanol / hexane solvent to obtain 47 g of an intermediate 11 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, d), 7.71 (1H, dd), 7.33 (1H, dd), 6.04 (1H, tt), 4.49 (2H, t).

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.69 (1H, d), 7.33 (1H, dd), 6.79 (2H, s), 6.05 (1H, tt), 5.28 (1H, s), 4.48 (2H, t), 3.10 (2H, q), 1.40 (3H, t). Production Example 24-2
To a mixture of 11 g of ethyl methyl sulfone and 50 mL of THF, 59 mL of 1.6 Mn-butyllithium hexane solution was added under ice cooling, followed by stirring for 15 minutes under ice cooling. This mixture was added to a mixture of 20 g of intermediate 11 and 50 mL of THF under ice cooling, and stirred for 10 minutes under ice cooling. This mixture was added to water and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized with an ethyl acetate / hexane solvent to obtain 18 g of intermediate 12 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.36 (1H, d), 7.69 (1H, d), 7.33 (1H, dd), 6.79 (2H, s), 6.05 (1H, tt), 5.28 (1H, s ), 4.48 (2H, t), 3.10 (2H, q), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.37 (1H, d), 7.99 (1H, d), 7.89 (1H, d), 7.43 (1H, dd), 6.08 (1H, tt), 4.49 (2H, t), 4.01 (2H, q), 1.41 (3H, t). Production Example 24-3
A mixture of 200 mg of Intermediate 12 and 2 mL of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one was heated and stirred at 100 ° C. for 4.5 hours. This mixture was subjected to silica gel column chromatography to obtain 100 mg of the present bipyridine compound 53 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.37 (1H, d), 7.99 (1H, d), 7.89 (1H, d), 7.43 (1H, dd), 6.08 (1H, tt ), 4.49 (2H, t), 4.01 (2H, q), 1.41 (3H, t).

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 7.73-7.71 (1H, m), 7.35 (1H, dd), 4.56 (2H, td). Production Example 25-1
In place of 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,3-pentafluoropropanol is used, and is represented by the following formula according to the method described in Production Example 24-1. Intermediate 13 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, d), 7.73-7.71 (1H, m), 7.35 (1H, dd), 4.56 (2H, td).

¹H-NMR (CDCl₃) δ: 8.37 (1H, d), 7.69 (1H, d), 7.34 (1H, dd), 6.79 (2H, s), 5.28 (1H, s), 4.54 (2H, t), 3.10 (2H, q), 1.40 (3H, t). Production Example 25-2
In place of Intermediate 11, Intermediate 13 was used, and Intermediate 14 represented by the following formula was obtained according to the method described in Production Example 24-2.

¹ H-NMR (CDCl ₃ ) δ: 8.37 (1H, d), 7.69 (1H, d), 7.34 (1H, dd), 6.79 (2H, s), 5.28 (1H, s), 4.54 (2H, t ), 3.10 (2H, q), 1.40 (3H, t).

¹H-NMR (CDCl₃) δ: 8.69 (1H, dd), 8.39 (1H, d), 7.99 (1H, dd), 7.89 (1H, d), 7.44 (1H, dd), 4.55 (2H, td), 4.01 (2H, q), 1.41 (3H, t). Production Example 25-3
This bipyridine compound 54 represented by the following formula was obtained according to the method described in Production Example 24-3, using Intermediate 14 instead of Intermediate 12.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, dd), 8.39 (1H, d), 7.99 (1H, dd), 7.89 (1H, d), 7.44 (1H, dd), 4.55 (2H, td ), 4.01 (2H, q), 1.41 (3H, t).

¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.36 (1H, d), 8.30 (1H, d), 7.84 (1H, d), 7.42 (1H, dd), 6.04-5.93 (1H, m), 5.23-5.18 (2H, m), 4.54 (2H, t), 3.87 (2H, q), 3.55 (2H, d), 1.37 (3H, t). Production Example 26
A mixture of 3.0 g of intermediate 14, 830 μL of acrolein, and 10 mL of ethanol was stirred at 60 ° C. for 2 hours. The mixture was concentrated under reduced pressure to obtain 3.8 g of residue. Of this residue, 500 mg was mixed with 2 mL of THF, and 620 μL of triethylamine and 220 μL of methanesulfonyl chloride were added at room temperature. This mixture was heated and stirred at 60 ° C. for 1 hour. 2N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 47 mg of the present bipyridine compound 99 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.36 (1H, d), 8.30 (1H, d), 7.84 (1H, d), 7.42 (1H, dd), 6.04-5.93 (1H , m), 5.23-5.18 (2H, m), 4.54 (2H, t), 3.87 (2H, q), 3.55 (2H, d), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.81-7.78 (2H, m), 7.33 (1H, dd), 4.52 (2H, t), 3.49-3.31 (2H, m), 3.11-3.02 (3H, m), 1.29 (3H, t). Production Example 27
To a mixture of 8.5 g of intermediate 14 and 30 mL of chloroform, 9.4 g of α- (trifluoromethyl) acryloyl chloride was added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Hexane was added to the mixture and then filtered. The filtrate was added to saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized with an ethyl acetate / hexane solution to obtain 21 g of intermediate 15 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.36 (1H, d), 7.81-7.78 (2H, m), 7.33 (1H, dd), 4.52 (2H, t), 3.49-3.31 (2H, m), 3.11 -3.02 (3H, m), 1.29 (3H, t).

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 8.41 (1H, s), 7.92 (1H, d), 7.41 (1H, dd), 4.57 (2H, t), 3.45 (2H, q), 1.33 (3H, t). Production Example 28
To a mixture of 10 g of intermediate 15 and chloroform (30 mL), 4.4 g of N-bromosuccinimide and 10 mg of benzoyl peroxide were added at room temperature, and the mixture was heated and stirred at 60 ° C. for 30 minutes. The mixture was allowed to cool to room temperature and sodium methoxide was added until the exotherm subsided. Water was added to this mixture and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 14 g of the bipyridine compound 114 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, d), 8.41 (1H, s), 7.92 (1H, d), 7.41 (1H, dd), 4.57 (2H, t), 3.45 (2H, q ), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 8.75 (1H, s), 8.40 (1H, d), 8.03 (1H, d), 7.44 (1H, dd), 4.56 (2H, t), 4.01 (2H, q), 1.43 (3H, t). Production Example 29
23 g of phosphorus oxychloride was added to 4.4 g of the present bipyridine compound 114, and the mixture was stirred for 2 days while heating under reflux. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.7 g of the present bipyridine compound 109 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, s), 8.40 (1H, d), 8.03 (1H, d), 7.44 (1H, dd), 4.56 (2H, t), 4.01 (2H, q ), 1.43 (3H, t).

¹H-NMR (CDCl₃) δ: 9.02 (1H, s), 8.99 (1H, s), 8.44 (1H, d), 8.23 (1H, s), 8.01 (1H, d), 7.47 (1H, dd), 4.58 (2H, t), 4.05 (2H, q), 1.47 (3H, t). Production Example 30
To a mixture of 500 mg of the present bipyridine compound 109, 46 mg of 1H-1,2,4-triazole and 2 mL of DMSO, 240 mg of cesium carbonate was added at room temperature and stirred for 30 minutes. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 240 mg of the present bipyridine compound 154 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.02 (1H, s), 8.99 (1H, s), 8.44 (1H, d), 8.23 (1H, s), 8.01 (1H, d), 7.47 (1H, dd ), 4.58 (2H, t), 4.05 (2H, q), 1.47 (3H, t).

¹H-NMR (CDCl₃) δ: 8.44 (1H, s), 8.35 (1H, s), 7.78 (1H, d), 7.39 (1H, d), 5.52 (2H, s), 4.53 (2H, t), 3.79 (2H, q), 1.37 (3H, t). Production Example 31
This bipyridine compound 109 was used in place of the present bipyridine compound 79, and was carried out according to the method described in Production Example 17 to obtain the present bipyridine compound 124 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.44 (1H, s), 8.35 (1H, s), 7.78 (1H, d), 7.39 (1H, d), 5.52 (2H, s), 4.53 (2H, t ), 3.79 (2H, q), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.35-8.35 (2H, m), 7.86 (1H, dd), 7.40 (1H, dd), 5.48 (1H, s), 4.54 (2H, td), 3.83 (2H, q), 3.15 (3H, d), 1.37 (3H, t). Production Example 32
The present bipyridine compound 109 is used in place of the present bipyridine compound 79, and 40% methylamine-methanol solution is used in place of the 50% dimethylamine aqueous solution. Bipyridine compound 129 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.35-8.35 (2H, m), 7.86 (1H, dd), 7.40 (1H, dd), 5.48 (1H, s), 4.54 (2H, td), 3.83 (2H , q), 3.15 (3H, d), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.36 (1H, d), 7.81 (1H, d), 7.42 (1H, dd), 5.62 (1H, s), 4.55 (2H, t), 4.42-4.33 (2H, m), 3.89 (2H, q), 1.39 (3H, t). Production Example 33
This bipyridine compound 109 was used in place of this bipyridine compound 79, and was carried out according to the method described in Production Example 19, to obtain the present bipyridine compound 139 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.47 (1H, d), 8.36 (1H, d), 7.81 (1H, d), 7.42 (1H, dd), 5.62 (1H, s), 4.55 (2H, t ), 4.42-4.33 (2H, m), 3.89 (2H, q), 1.39 (3H, t).

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.37 (1H, d), 7.82 (1H, d), 7.41 (1H, dd), 6.74 (1H, s), 4.55 (2H, t), 4.19 (2H, d), 3.80 (2H, q), 1.37 (3H, t). Production Example 34
To a mixture of 1.0 g of the present bipyridine compound 109, 820 μL of diisopropylethylamine, and 5 mL of THF, 160 μL of hydrazine monohydrate was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 620 mg of the present bipyridine compound 144 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, d), 8.37 (1H, d), 7.82 (1H, d), 7.41 (1H, dd), 6.74 (1H, s), 4.55 (2H, t ), 4.19 (2H, d), 3.80 (2H, q), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.36 (1H, d), 7.71 (1H, d), 7.65 (2H, d), 7.50 (1H, t), 7.41 (1H, dd), 7.34 (1H, d), 7.00 (2H, d), 4.58 (2H, t), 3.81 (2H, q), 2.29 (3H, s), 1.33 (3H, t). Production Example 35
To a mixture of 550 mg of the present bipyridine compound 144, 110 μL of pyridine, and acetonitrile 10 mL, 250 mg of p-toluenesulfonyl chloride was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 730 mg of the present bipyridine compound 149 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, d), 8.36 (1H, d), 7.71 (1H, d), 7.65 (2H, d), 7.50 (1H, t), 7.41 (1H, dd ), 7.34 (1H, d), 7.00 (2H, d), 4.58 (2H, t), 3.81 (2H, q), 2.29 (3H, s), 1.33 (3H, t).

¹H-NMR (CDCl₃) δ: 9.10 (1H, s), 8.73 (1H, s), 8.40 (1H, d), 7.97 (1H, d), 7.46-7.44 (1H, m), 4.56 (2H, t), 3.99 (2H, q), 1.42 (3H, t). Production Example 36
To a mixture of 630 mg of the present bipyridine compound 149, 1 mL of water, and 2 mL of ethylene glycol, 78 mg of sodium hydroxide was added at room temperature, and the mixture was stirred at 90 ° C. for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 350 mg of the present bipyridine compound 39 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.10 (1H, s), 8.73 (1H, s), 8.40 (1H, d), 7.97 (1H, d), 7.46-7.44 (1H, m), 4.56 (2H , t), 3.99 (2H, q), 1.42 (3H, t).

¹H-NMR (CDCl₃) δ: 8.59 (1H, d), 8.38 (1H, t), 7.90 (1H, dd), 7.42 (1H, dd), 4.55 (2H, t), 4.16 (3H, s), 3.91 (2H, q), 1.40 (3H, t). Production Example 37
This bipyridine compound 109 was used in place of this bipyridine compound 79, and was carried out according to the method described in Production Example 14, to obtain the present bipyridine compound 119 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, d), 8.38 (1H, t), 7.90 (1H, dd), 7.42 (1H, dd), 4.55 (2H, t), 4.16 (3H, s ), 3.91 (2H, q), 1.40 (3H, t).

ＬＣ−ＭＳ：Ｍ＋Ｈ：３３７
中間体２１

¹H-NMR (DMSO-D₆) δ: 8.57 (2H, d), 8.52 (2H, dd), 8.32 (2H, d), 8.05 (2H, dd), 7.78 (2H, dd), 7.41 (2H, dd), 5.06 (4H, t).
ＬＣ−ＭＳ：Ｍ＋Ｈ：６７１ Production Example 38-1
To a mixture of 3.4 g of the intermediate 10 and NMP 36 mL, 5.0 g of sodium hydrogen sulfide n hydrate (manufactured by Wako Pure Chemical Industries, Ltd.) was added at room temperature. The reaction mixture was heated and stirred at 80 ° C. for 12 hours. The resulting reaction mixture was allowed to cool to room temperature, water was added, and 2N hydrochloric acid was further added to adjust to pH 4. The resulting mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated. The resulting solution was stirred at room temperature under an air atmosphere for 12 hours. The obtained solution was subjected to silica gel chromatography to obtain a trace amount of intermediate 20 represented by the following formula and 2.5 g of intermediate 21 represented by the following formula.
Intermediate 20

LC-MS: M + H: 337
Intermediate 21

¹ H-NMR (DMSO-D ₆ ) δ: 8.57 (2H, d), 8.52 (2H, dd), 8.32 (2H, d), 8.05 (2H, dd), 7.78 (2H, dd), 7.41 (2H , dd), 5.06 (4H, t).
LC-MS: M + H: 671

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 8.43 (1H, dd), 8.02 (1H, dd), 7.71 (1H, dd), 7.41 (1H, dd), 7.24 (1H, dd), 4.55 (2H, td), 2.82 (2H, d), 1.07-0.97 (1H, m), 0.63-0.57 (2H, m), 0.31-0.26 (2H, m). Production Example 38-2
To a mixture of 200 mg of Intermediate 21, 240 mg of potassium carbonate, and 1.2 mL of DMF, 190 mg of (bromomethyl) cyclopropane and 270 mg of sodium hydroxymethanesulfinate dihydrate were sequentially added at room temperature. The reaction mixture was heated to 80 ° C. and stirred for 10 hours. The reaction mixture was allowed to cool to room temperature, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 150 mg of the present bipyridine compound 279 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, d), 8.43 (1H, dd), 8.02 (1H, dd), 7.71 (1H, dd), 7.41 (1H, dd), 7.24 (1H, dd ), 4.55 (2H, td), 2.82 (2H, d), 1.07-0.97 (1H, m), 0.63-0.57 (2H, m), 0.31-0.26 (2H, m).

¹H-NMR (CDCl₃) δ: 8.86 (1H, dd), 8.56 (1H, dd), 8.34 (1H, d), 7.88 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd), 4.54 (2H, td), 3.82 (2H, d), 1.20-1.08 (1H, m), 0.62-0.55 (2H, m), 0.37-0.31 (2H, m). Production Example 38-3
The bipyridine compound 280 represented by the following formula was obtained according to the method described in Production Example 2 using the bipyridine compound 279 instead of the bipyridine compound 9.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.56 (1H, dd), 8.34 (1H, d), 7.88 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.54 (2H, td), 3.82 (2H, d), 1.20-1.08 (1H, m), 0.62-0.55 (2H, m), 0.37-0.31 (2H, m).

¹H NMR(CDCl₃)δ ppm: 1.47 (3H, t), 3.29 (2H, q), 4.96 (2H, s), 7.87 (1H, dd), 8.08 (1H, dd), 8.68 (1H, dd) Production Example 39-1
The following intermediate 22 was obtained according to the method described in Production Example 10-1 using 5-chloro-2-cyanopyridine instead of 5-fluoro-2-cyanopyridine.

¹ H NMR (CDCl ₃ ) δ ppm: 1.47 (3H, t), 3.29 (2H, q), 4.96 (2H, s), 7.87 (1H, dd), 8.08 (1H, dd), 8.68 (1H, dd )

¹H NMR(CDCl₃)δ ppm: 1.38 (3H, t), 3.87 (2H, q), 7.57 (1H, dd), 7.81 (1H, dd), 7.85 (1H, dd), 8.49 (1H, dd), 8.58 (1H, dd), 8.88 (1H, dd) Production Example 39-2
The following intermediate body 23 was obtained according to the method described in Production Example 10-2 using the intermediate body 22 instead of the intermediate body 16.

¹ H NMR (CDCl ₃ ) δ ppm: 1.38 (3H, t), 3.87 (2H, q), 7.57 (1H, dd), 7.81 (1H, dd), 7.85 (1H, dd), 8.49 (1H, dd ), 8.58 (1H, dd), 8.88 (1H, dd)

¹H-NMR (CDCl₃) δ: 8.79 (1H, d), 8.04-7.98 (2H, m), 4.97(2H, s), 3.28 (2H, q), 1.46 (3H, t). Production Example 40-1
The following intermediate 24 was obtained according to the method described in Production Example 10-1 using 2-cyano-5-bromopyridine instead of 5-fluoro-2-cyanopyridine.

¹ H-NMR (CDCl ₃ ) δ: 8.79 (1H, d), 8.04-7.98 (2H, m), 4.97 (2H, s), 3.28 (2H, q), 1.46 (3H, t).

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.68 (1H, d), 8.49 (1H, dd), 8.01-7.98 (1H, m), 7.74 (1H, d), 7.56 (1H, dd), 3.86 (2H, q), 1.37 (3H, t). Production Example 40-2
The following intermediate 25 was obtained according to the method described in Production Example 10-2 using the intermediate 24 instead of the intermediate 16.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.68 (1H, d), 8.49 (1H, dd), 8.01-7.98 (1H, m), 7.74 (1H, d), 7.56 (1H , dd), 3.86 (2H, q), 1.37 (3H, t).

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.16 (1H, d), 7.38 (1H, dd), 6.05 (1H, tt), 4.96 (2H, s), 4.52 (2H, t), 3.29 (2H, q), 1.47 (3H, t). Production Example 41-1
In place of 5-fluoro-2-cyanopyridine, 2-cyano-5- (2,2,3,3-tetrafluoropropoxy) pyridine was used, and according to the method described in Production Example 10-1, the following Intermediate 25 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.43 (1H, d), 8.16 (1H, d), 7.38 (1H, dd), 6.05 (1H, tt), 4.96 (2H, s), 4.52 (2H, t ), 3.29 (2H, q), 1.47 (3H, t).

Production Example 41-2
This bipyridine compound 7 was obtained according to the method described in Production Example 10-2 using Intermediate 25 instead of Intermediate 16.

¹H-NMR (CDCl₃) δ: 8.44 (1H, t), 8.16 (1H, dd), 7.39 (1H, dd), 4.96 (2H, s), 4.58 (2H, td), 3.29 (2H, q), 1.47 (3H, t). Production Example 42-1
In place of 5-fluoro-2-cyanopyridine, 2-cyano-5- (2,2,3,3,3-pentafluoropropoxy) pyridine was used and according to the method described in Production Example 10-1, The following intermediate 26 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.44 (1H, t), 8.16 (1H, dd), 7.39 (1H, dd), 4.96 (2H, s), 4.58 (2H, td), 3.29 (2H, q ), 1.47 (3H, t).

Production Example 42-2
This bipyridine compound 8 was obtained according to the method described in Production Example 10-2 using Intermediate 26 instead of Intermediate 16.

〔式中、Ｒ²⁰¹、Ｒ²⁰²、Ｒ²⁰³、Ｒ²⁰⁴、Ｒ²⁰⁵、Ｒ²⁰⁶、Ｒ²⁰⁷、Ｒ²⁰⁸、及びｎは、下記の［表２０］〜［表３８］に記載のいずれかの組み合わせを表す。〕で示される化合物は、前述の方法に準じて製造することができる。 Formula (200)

[Wherein R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n are any combination described in the following [Table 20] to [Table 38]. Represents. ] Can be manufactured according to the above-mentioned method.

〔式中、Ｒ²⁰¹、Ｒ²⁰²、Ｒ²⁰³、Ｒ²⁰⁴、Ｒ²⁰⁵、Ｒ²⁰⁶、Ｒ²⁰⁷、Ｒ²⁰⁸、及びｎは、下記の［表３９］に記載のいずれかの組み合わせを表す。〕で示される化合物は、前述の方法に準じて製造することができる。 Formula (201)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination described in the following [Table 39]. ] Can be manufactured according to the above-mentioned method.

〔式中、Ｒ²⁰¹、Ｒ²⁰²、Ｒ²⁰³、Ｒ²⁰⁴、Ｒ²⁰⁵、Ｒ²⁰⁶、Ｒ²⁰⁷、Ｒ²⁰⁸、及びｎは、下記の［表４０］に記載のいずれかの組み合わせを表す。〕で示される化合物は、前述の方法に準じて製造することができる。 Formula (202)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination described in the following [Table 40]. ] Can be manufactured according to the above-mentioned method.

〔式中、Ｒ²⁰¹、Ｒ²⁰²、Ｒ²⁰³、Ｒ²⁰⁴、Ｒ²⁰⁵、Ｒ²⁰⁶、Ｒ²⁰⁷、Ｒ²⁰⁸、及びｎは、下記の［表４１］に記載のいずれかの組み合わせを表す。〕で示される化合物は、前述の方法に準じて製造することができる。 Formula (203)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination described in the following [Table 41]. ] Can be manufactured according to the above-mentioned method.

The bipyridine compound may be in the form of a salt and can be produced by mixing with an acid such as hydrochloric acid, sulfuric acid, methanesulfonic acid and the like.
The bipyridine compound or a salt of the bipyridine compound can be formulated alone or mixed with other agrochemical active ingredients and applied by the methods described herein. Moreover, the agricultural chemical formulation containing this bipyridine compound or the salt of this bipyridine compound and the agricultural chemical formulation containing another agricultural chemical active ingredient can be mixed, and it can apply by the method as described in this specification. Further, the formulated bipyridine compound or the salt of the bipyridine compound and the other formulated pesticidal active ingredient can be applied at regular intervals without mixing.
As a salt of this bipyridine compound,
The hydrochloride of any one of the bipyridine compounds 1 to 347;
A sulfate of any one of the present bipyridine compounds 1 to 347;
A phosphate of any one of the bipyridine compounds 1 to 347;
Nitrate of any one of the present bipyridine compounds 1 to 347;
Inorganic acid salts, etc.
A methanesulfonate salt of any one of the bipyridine compounds 1 to 347;
A paratoluenesulfonate salt of any one of the present bipyridine compounds 1 to 347;
A benzenesulfonate salt of any one of the bipyridine compounds 1 to 347;
Camphorsulfonic acid salt of any one of the present bipyridine compounds 1 to 347;
And the like, and the like.
The bipyridine compound or a salt of the bipyridine compound can be formulated into a crystalline or amorphous form and applied by the method described herein.

  Next, 1 or more types of compounds chosen from the group a thru | or the group d used for pest control in combination with this bipyridine compound in this invention composition are shown.

The group a in this specification is a group consisting of the bactericides listed in the following (a1) to (a15).
(A1) DMI fungicide (demethylation inhibitor)
Azaconazole, bittertanol, bromconazole, cyproconazole, difenoconazole, dinicoconazole, dinicoconazole, dinicoconazole. (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriazole (flu) riafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, microbutanol (myclonazole) Oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, prothioconazole Pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconiole, triazimefonol, triazimefone, triazimefonol , Triticonazole, 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1,2,4-triazol-1-yl) propan-2-ol (CAS registration number 1417782-03-6, hereinafter referred to as α2), 2- [4- (4-chlorophenoxy) -2- (trif (Luoromethyl) phenyl] -3-methyl-1- (1,2,4-triazol-1-yl) butan-2-ol (CAS registration number 1417782-28-1, hereinafter referred to as α3), 2-{[3 -(2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione (CAS Registry Number 1342260) -19-8, hereinafter referred to as α4), 1-{[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4- Triazol-5-yl thiocyanato (CAS registration number 1342260-26-7, hereinafter referred to as α5), 5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1, 2,4-triazol-1-ylmethyl) cyclopentanol (CAS registration number 1394057-11-4, hereinafter referred to as α6), 2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- ( 1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (CAS registration number 1394057-13-6, hereinafter referred to as α7), methyl = 3-[(4-chlorophenyl) methyl] -2-hydroxy- 1-methyl-2- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanecarboxylate (CAS registration number 1791398-02-1, hereinafter referred to as α8), α- [3- (4-chloro -2-Fluorophenyl) -5- (2,4-difluorophenyl) -4-isoxazolyl] -3-pyridinemethanol (CAS registration number 1229605-96-2, hereinafter referred to as α9)

(A2) Amine-based fungicides aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine (spixamine)

(A3) Benzimidazole fungicide benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl

(A4) Dicarboximide fungicide, clozolinate, iprodione, procymidone, vinclozolin

(A5) Anilinopyrimidine fungicides cyprodinil, mepanipyrim, pyrimethanil
(A6) Phenylpyrrole fungicide fenpiclonil, fludioxonil

(A7) QoI fungicides azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenamidone Robin (fenaminestrobin), fluphenoxystrobin, fluoxastrobin, cresoxime-methyl, mandestrobin, methinostrobin (methominostrobin) Picoxystrobin (picoxystrobin), pyraclostrobin (pyraclostrobin), Pila meth Azoxystrobin (pyrametostrobin), Pila oxy Azoxystrobin (pyraoxystrobin), pyribencarb (pyribencarb), trichloride pyridinium carb (triclopyricarb), trifloxystrobin (trifloxystrobin)

(A8) RNA polymerase I
Benalaxyl, Benalaxyl M or Kiraraxyl, furalaxyl, metalaxyl, metalaxyl M, oxazir, oxazir, oxazir

(A9) Carboxylic acid amide-based fungicides dimethomorph, flumorph, pyrimorph, benthalicarb, benthalicarb-isopropyl, iprovalib, iprovalib mandipropamid), varifenalate

(A10) SDHI fungicides benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopiram, fluopiram (fluolil) Fluxapyroxad, furametopyr, isofetamid, isopyrazam, mepronil, oxycarboxin, pentipyr, pentopyrad ane), thifluzamide, pyraziflumide, pydiflumethofen, CAS Registry Number 1228284-64-7, 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindane) -4-yl) pyrazole-4-carboxamide (racemic or enantiomers, including mixtures of R and S enantiomers in any proportion, denoted α1), 3-difluoromethyl-N- (7 -Fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7, hereinafter referred to as α10), N-cyclopropyl-3- (difluoro Methyl) -5-fluoro-N (5-chloro-2-isopropyl-benzyl) -1-methyl -1H- pyrazole-4-carboxamide (CAS Registry Number 1255734-28-1, hereinafter referred to as alpha 11)

(A11) dithiocarbamate fungicides ferbam, mancozeb or manzeb, manneb, metyram, propineb, thiram, zine, zine )

(A12) MBI-R agent phthalide or fthalide, pyroquilon, tricyclazole

(A13) MBI-D agent carpropamide, diclocymet, phenoxanil

(A14) Microbial material Agrobacterium radiobacter K84 strain, Bacillus pumilus GB34 strain, Bu F-33 strain, QST2808 strain, Bacillus simplex CGF strain 28 Bacillus subtilis QST713 strain, HAI0404 strain and Y1336 strain, Bacillus amyloliquefaciens QST713 strain, FZB24 strain, FZB42 strain, MBI600 strain, D732 strain, D732 strain, D747 strain Variovorax paradoxus) CGF4526 strain, Erwinia carotovora CGE234M403 strain, Pseudomonas fluorescens G7090 strain, Talaromyces flavider trocholine strain SY-Y-94 derko・ Hardianam (Trichoderma harzianum), Chronostachys rosea (Chronostachys rosea) ACM941 strain However, it is known that the above-mentioned Bacillus pumilus, Bacillus subtilis and Bacillus amyloliquefaciens exist besides And other than the above strains Can also be used in the present invention.

(A15) Other fungicides acibenzolar-S-methyl, amethoctrazine, amisulbrom, anilazine, binapacryl, biphenyl-bibyl-bibradine S), bromothalonil, bupirimate, captafol, captan, quinomethionate, chloronebyl, chlorothanemid, chlorothaneil azofamid, cyflufenamide, cymoxanil, diclofluanid, diclomethine, diclolan, dietofencarb, diethofencarb. Dipymetitrone (CAS registry number 16114-35-5), dithianon, dodine, echromezol or etridiazole, edifenphos, etifoki Ethaboxam, ethirimol, fenhexamid, fenpyrazamine, triphenyltin acetate, fentin chloride, fentindehydroxide, fentindehydrox Ferimzone, fluazinam, fluopicolide, fluorimide, flusulfamide, flutianil, Alpet, fosetyl aluminum, osetyl u Hyxazol, iminoctadin, iminoctaine triacetate, iodocarb, iprobenfos, iprobenfos, iprocarb, iprobenfos, iprocarb, iprocarb Ptyldinocap, metasulfocarb, metraphenone, naphthifine, octilinone, oxathiapiproline, oxathiapiprolin Nicklic acid (oxolinic acid), oxytetracycline (pencycuron), phenacacryl, phenamacriz (picarbutrazox), polyoxenpro (p) probazole (ro) , Prothiocarb, pyrazophos, pyributicarb, pyriophenone, quinoxyfen, quintozen, sylthiofamsil Leptomycin, tebufloquin, teclophthalam, technazene, terbinafine, thiadinyl, tolfolfidomethyl, tolclofol , Tolprocarb, triazoxide, validamycin A, zoxamide, basic copper chloride, cupric hydroxide, basic copper sulfate, organic copper, sulfur, 3-chloro -5-phenyl-6-methyl-4- (2,6-diph Fluorophenyl) pyridazine (CAS registration number 1380661-55-8, hereinafter referred to as α12), 3-cyano-5-phenyl-6-methyl-4- (2,6-difluorophenyl) pyridazine (CAS registration number, hereinafter referred to as α13) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline (CAS registration number 86647-84-9, hereinafter referred to as α14), 2,2- Dimethyl-9-fluoro-5- (quinolin-3-yl) -2,3-dihydro-benzo [f] [1,4] oxazepine (CAS registration number 1207749-50-5, hereinafter referred to as α15), 3- (3,4-dichloroisothiazol-5-ylmethoxy) -benzisothiazole 1,1-dioxide (CAS Registry Number 957144-77-3, N ′-[4-({3-[(4-chlorophenyl) methyl] -1,2,4-thiadiazol-5-yl} oxy) -2,5-dimethylphenyl] -N— Ethyl-N-methylmethanimidamide (CAS registration number 1202781-91-6, hereinafter referred to as α17), N ′-(2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylmethanimidamide (CAS registration number 1052688-31-9, hereinafter referred to as α18), N ′-{4-[(4,5-dichlorothiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl- N-methylmethanimidamide (CAS registration number 929908-57-6, hereinafter referred to as α19), 2- {3- [2- (1-{[3,5-bis (difluoromethyl) -1H-pyrazole] -1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl = methanesulfonate ( CAS Registry Number 1360819-11-9, hereinafter referred to as α20), 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole -5-amine (CAS registration number 1362477-26-6, hereinafter referred to as α21), 2- [6- (3-fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline (CAS registration number) 1257056-97-5, hereinafter referred to as α22), 5-fluoro-2-[(4-methylphenyl) methoxy] -4-pyrimidinamine (CAS Registry Number 11) 4376-25-0, hereinafter referred to as α23), 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2 (1H) -one (CAS Registry Number 1616664-98-2) , Hereinafter referred to as α24),
A compound represented by the following formula (a) (CAS registration number 517875-34-2, hereinafter referred to as α25)

The group b in this specification is a group consisting of insecticides, acaricides and nematocides listed in the following (b1) to (b26).
(B1) Organophosphorus acetylcholinesterase inhibitors Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Kazusafos, Chloretoxine, Chloroxyl ), Chlormefos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos (CYAP), Demeton-S-methynon, S-methyone azinon, dichlorvos (DDVP), dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, phlophos Feminafos, fenitrothion (MEP), fenthion (MPP), fothiazate, heptenophos, imicyafos, isofenphos (isofenphos) Phosphoryl) salicylate or isocarbophos (isopropyl-O- (methoxyaminothiophosphoryl) salicylate or isocarbophos), isoxathion (DM), methamide, Monocrotophos, nared (BRP), ometoate, oxydimethon-methyl, parathion, parathion methyl or methyl parathion (par) thion-methyl or methyl parathion), phenate (PAP), folate, fosalone, phosmetone (PMP), phosphamidon, phoxim, pi-miphos (Profenofos), propetamfos, prothiofos, pyraclofos, pyridafenthion, quinalphos, sulfotep, tebupyrifote Host (temephos), terbufos (terbufos), tetra-chloro bottles host (tetrachlorvinphos), thiometon (thiometon), triazophos (triazophos), trichlorfon (trichlorfon: DEP), vamidothion (vamidothion)

(B2) Carbamate-based compound acetylcholinesterase inhibitor Alanycarb, aldicarb, bendiocarb, benfurcarb, butoxycarb, butoxycarboxyl, butoxycarboxyl, butoxycarboxyl NAC), carbofuran, carbosulfan, etiofencarb, fenobucarb: BPMC, formatenate, furothiocarb, prothiocarb, pro PC ), Methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur (PHC), thiodicarbox, thiodicarb , Trimetacarb, XMC, xylylcarb

(B3) sodium channel modulators acrinathrin, allethrin, bifenthrin, bioallethrin, bioresmethrin (fluetrethrin), cycloprotorin (fluclothrin), cycloprotorin (fluclothrin) cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, alpha-methyperthrin Phosphorus (beta-cypermethrin), theta cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empentrin, empentrin Profenproxin, fenpropatrin, fenvalerate, flucitrinate, flumethrinate, flumethrin, fluvalinate, tau-fluvalinate (tau-fluvalinate) Fenprox, heptafluthrin, imiprothrin, kadesthrin, meperfluthrin, monfluorthrin, merfluthrin, permethrin Pyrethrins, resmethrin, silafluofene, tefluthrin, tetramethrin, tetramethylfluthrin, tralomethrin ralmethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, sigma-cypermethrin (flu), thromthrin, flumethrin, flumethrin, flumethrin ), Dimefluthrin, epsilon-methfluthrin, epsilon-monfluorothrin, methoxychlor.

(B4) Nicotinic acetylcholine receptor channel blocker bensultap, cartap, cartap hydrochloride, thiocyclam, thiosultap-disulfate or thiosultapordis-tap-disb-tap Monosodium salt or monosultap (monoisotapum or monosultap)

(B5) Nicotinic Acetylcholine Receptor Competitive Modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nithipyram, Thialopride, i , Flupyradifurone, triflumezopyrim, dichloromesothiaz, cycloxapride, a compound represented by the following formula (b) (CAS registration number 1363400-41) -2, hereinafter referred to as α26)

(B6) Benzoylurea chitin biosynthesis inhibitors bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, flufenoxuron, flufenoxuron, flufenoxuron , Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron

(B7) GABAergic chloride ion channel blocker etiprole, fipronil, flufiprole, chlordane, endosulfan, alpha-endosulfan

(B8) GABAergic chloride ion channel allosteric modulators afoxalaner, fluralaner, brofuranilide, fluxamethamide

(B9) molting hormone (ecdysone) receptor agonists chromafenozide, halofenozide, methoxyphenozide, tebufenozide

(B10) Ryanodine receptor modulators chlorantraniliprole, cyantraniliprole, cyclaniiliprole, fulbendamide, dianiline, trananiprole

(B11) glutamatergic chloride channel allosteric modulators abamectin, emamectin benzoate, lepimectin, milbemectin

(B12) Juvenile hormone analog hydroprene, kinoprene, methoprene, phenoxycarb, pyriproxyfen

(B13) Other non-specific (multi-site) inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, sodium aluminum fluoride, borax , Boric acid, disodium octaborate, sodium borate, sodium metaborate, tartaretic, dazomet, metham )

(B14) Mite growth inhibitor clofentezine, hexythiazox, diflovidazin, etoxazole

(B15) Mitochondrial ATP synthase inhibitor diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifone

(B16) Oxidative phosphorylation uncoupler chlorfenapyr, DNOC, sulfuramide

(B17) benzoylurea chitin biosynthesis inhibitors bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, flufenoxuron, flufenoxuron, flufenoxuron , Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron

(B18) Mitochondrial electron transport system complex III inhibitor hydramethylnon, acequinocyl, fluacrypyrim, bifenazate

(B19) Mitochondrial electron transport system complex I inhibitor fenazaquin, fenpyroximate, pyridaben, pyrimidifene, tebufenpyrad, tolfenpyrad

(B20) Acetyl CoA carboxylase inhibitor Spirodiclofen, Spiromesifen, Spirotetramat

(B21) Mitochondrial electron transport complex IV inhibitor Aluminum phosphide, calcium phosphide, hydrogen phosphine, zinc phosphide, calcium cyanide , Potassium cyanide, sodium cyanide

(B22) Mitochondrial electron transport system complex II inhibitor Cyenopyrafen, cyflumetofen, piflubumide

(B23) Natural insecticide machine oil, nicotine (nicotine), nicotine sulfate (nicotine-sulfate)

(B24) Bacteria thuringiensis, Bacillus thuringiensis subsp. Aizawai, Cristalis thuringiensis, Bacillus thuringiensis, (b24) Microbial-derived insect midgut mesentery (Bacillus thuringiensis), Bacillus thuringiensis subsp. Cis subspecies (Bacillus thuringiensis subsp. Isralensis), Tenebrionis subsp. (Bacillus thuringiensis subsp. Tenebrionis), Bacillus thuringiensis-derived insecticidal protein products (Cry1Ab, Cry1Ac, Cry1Ac, Cry1Ac, A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1, etc.), Bacillus sphaericus

(B25) other microbial materials Beauveria Bashiana (Beauveria bassiana) GHA Ltd., Beauveria Buron'niati (Beauveria brongniartii), Pekiromaisesu-Fumosoroseusu (Paecilomyces fumosoroseus), Pekiromaisesu-Rirashinasu (Paecilomyces lilacinus), Pekiromaisesu tenuipes (Paecilomyces tenuipes), Bertie Sirium lecani, Arthrobotrys dactyroides, Bacillus films I-1582, Bacillus megaterium (Bacillus) megaterium), Hirusutera Rossi Lien cis (Hirsutella rhossiliensis), Hirusutera-Minesotenshisu (Hirsutella minnesotensis), Mona Kurosupo helium-Fimatopagamu (Monacrosporium phymatopagus), Pasutsuria-Nishizawae (Pasteuria nishizawae), Pasutsuria penetrans (Pasteuria penetrans), Pasutsuria-Usugae (Pasteuria usgae), Verticillium chlamydosporium, Harpin protein

(B26) Other insecticides, acaricides, nematicides, spinetoram, spinosad, pymetrozine, pyrifluquinazone, buprofezin, romamizine, romamiz Xoxacarb, metaflumizone, flonicamid, azadirachtin, benzoximate, dibromothiopylate, quinopydithiol pyrylidyl, lime sulfur, sulfur, aphidopyrene, fluazaindolizine, fluensulfodine, flometoxin, flometoxin, flometoxin (Pyriminostrobin), thioxazafen, machine oil, a compound represented by the following formula (c) (CAS registration number 14449021-97-9, hereinafter referred to as α27)

The group c in this specification is a group consisting of the safeners listed below.
Benoxacol, cloquintoset, cloquintocet-mexyl, thiomethrinil, cyprosulfonide, dichlormidol, dichlormidol , Fenchlorazole, fenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, furilazole, isoxadifen ), Isoxadifen-ethyl (isoxadifen-ethyl), mefenpyr (Mefenpyr), mefenpyr-diethyl (mefenpyr-diethyl), Mefenato (Mephenate), naphthalate Rick polyanhydride (naphthalic anhydride), oxabetrinil (Oxabetrinil)

Group d in this specification is a group consisting of plant growth regulators listed below.
Chlormequat-chloride, etephon, gibberellins, gibberellin A3 (gibberellin A3, etc.), hymexazole, i-bendemede, iquade, p methylcyclopropylene, paclobutrazol, prohexadione, prohexadione-calcium, trinexapac, trinexapac-ethyl, trinexapacol conazole), uniconazole P (uniconazole-P), mycorrhizal fungi (Mycorrhiza Fungi)
As the mycorrhizal fungi, Arbuscular mycorrhizal fungus is preferable, and in particular, bacteria belonging to the genus Glomus, such as Glomus intraradices, Glomus mossae. Glomus aggregatum and Glomus etunicatum are preferred. Moreover, these bacterium of the genus Gromas may be used alone, or may be used as a mixture of two or more bacteria.

  The composition of the present invention may further contain a compound such as anthraquinone used as a bird repellent.

  Each of the above-mentioned compounds included in the above-mentioned groups a to d is a known compound. For example, in “The Pesticide Manual-17th edition (published by BCPC); ISBN 978-1-901396-88-1” Have been described. These compounds are disclosed in the patent literature or non-patent literature cited in “The Pesticide Manual-17th edition (published by BCPC); ISBN 978-1-901396-8-1,” or related production methods. Or can be obtained from commercially available formulations. Microbial materials included in groups a to d can also be obtained from a fungus depository.

The number of one or more kinds of compounds selected from these groups a to d can be 1 to 9 (eg, 1, 2, 3, 4, 5, 6, 7, 8, 9).
The

Examples of combinations of the present bipyridine compound and the present compound in the composition of the present invention will be described below. The abbreviation for SX means “any one of the present bipyridine compounds selected from the compound group SX1 to SX46”.
Azaconazole + SX, Viteltanol + SX, Bromuconazole + SX, Cyproconazole + SX, Difenoconazole + SX, Diniconazole + SX, Diniconazole M + SX, Epoxyconazole + SX, Etaconazole + SX, Fenarimol + SX, Fenbuconazole + SX, Flubuconazole X Flusilazole + SX, flutriazole + SX, hexaconazole + SX, imazalil + SX, imibenconazole + SX, ipconazole + SX, metconazole + SX, microbutanyl + SX, nuarimol + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, pefrazoate + SX , Penconazole + SX, prochloraz + SX, propiconazole + SX, prothioco Zole + SX, Pyrifenox + SX, Pyrioxazole + SX, Cimeconazole + SX, Tebuconazole + SX, Tetraconazole + SX, Triadimephone + SX, Triadimenol + SX, Triflumizole + SX, Triphorine + SX, Triticonazole + SX, α2 + SX, α3S , Α6 + SX, α7 + SX, α8 + SX, α9 + SX,
Aldimorph + SX, Dodemorph + SX, Fenpropimorph + SX, Tridemorph + SX, Fenpropidin + SX, Pipelarin + SX, Spiroxamine + SX,
Benomyl + SX, carbendazim + SX, fuberidazole + SX, thiabendazole + SX, thiophanate + SX, thiophanatemethyl + SX, dietofencarb + SX, zoxamide + SX, ethaboxam + SX,
Clozolinate + SX, Iprodione + SX, Procymidone + SX, Vinclozoline + SX,
Cyprodinil + SX, mepanipyrim + SX, pyrimethanil + SX,
Fenpiclonyl + SX, fludioxonil + SX,
Azoxystrobin + SX, umoxistrobin + SX, dimoxystrobin + SX, enoxastrobin + SX, famoxadone + SX, phenamidon + SX, phenaminestrobin + SX, fluphenoxystrobin + SX, fluoxastrobin + SX, cresoxime-methyl + SX, Mandestrobin + SX, Metominostrobin + SX, Orissatrobin + SX, Picoxystrobin + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyroxystrobin + SX, Pyribencarb + SX, Triclopyricarb + SX, Trifloxystrobin + SX ,
Benalaxyl + SX, Benalaxyl M + SX, Furaraxyl + SX, Metalaxyl + SX, Metalaxyl M + SX, Oxadixyl + SX, Offrace + SX,
Dimethomorph + SX, Flumorph + SX, Pyrimorph + SX, Bench Avaricarb + SX, Bench Avaricarb isopropyl + SX, Iprovaricarb + SX, Varifenalate + SX, Mandipropamide + SX,
Benodanyl + SX, benzobindiflupyr + SX, bixafen + SX, boscalid + SX, carboxin + SX, fenfram + SX, fluopyram + SX, flutolanil + SX, floxapyradod + SX, furametopyl + SX, isophetamide + SX, isopyrazam + SX, propyram + SX, propyram + SX, propyram + SX , Pentiopyrad + SX, penflufen + SX, sedaxane + SX, tifluzamide + SX, pyraziflumide + SX, pidiflumethofen + SX, α1 + SX, α10 + SX, α11 + SX,
Ferbum + SX, Manzeb + SX, Mannebu + SX, Methylam + SX, Propinebu + SX, Thiuram + SX, Dinebu + SX, Zillam + SX,
Fusalide + SX, Pyrochilone + SX, Tricyclazole + SX,
Carpropamide + SX, diclosimet + SX, phenoxanyl + SX,
Agrobacterium radiobacter K84 + SX, Bacillus pumilus + SX, Bacillus pumilus GB34 + SX, Bacillus pumilus Bu F-33 + SX, Bacillus pumilus QST2808 + SX, Bacillus simplex CGF2856 + SX, Bacillus X , Bacillus subtilis QST713 strain + SX, Bacillus subtilis HAI0404 strain + SX, Bacillus subtilis Y1336 strain + SX, Bacillus amyloliquefaciens + SX, Bacillus amyloliquefaciens FZB24 strain + SX, Bacillus amylos Z Bacillus amyloliquefaciens MBI600 strain + SX, Bacillus amyloliquefaciens D747 strain + SX, Bacillus amyloliquefaciens Ciens AT-332 strain + SX, Varioborax paradox CGF4526 strain + SX, Erbinia carotobola CGE234M403 strain + SX, Pseudomonas fluorescens G7090 strain + SX, Talalomyces flavus SAY-Y-94-01 strain + SX, Trichoderma -1 Atrobilide SK Strain + SX, Trichoderma harzianum + SX, chronostakis rosea ACM941 strain + SX,
Acibenzoral S methyl + SX, amethoctrazine + SX, amisulbrom + SX, anilazine + SX, binapacryl + SX, biphenyl + SX, blasticidin S + SX, bromotalonyl + SX, buprimate + SX, captaphor + SX, captan + SX, quinomethionate x SX , Cyflufenamide + SX, Simoxanyl + SX, Diclofluanide + SX, Diclomedin + SX, Dichlorane + SX, Diethofencarb + SX, Diflumetrim + SX, Dimethymol + SX, Dinocup + SX, Dipimetitrone + SX, Dithianone + SX, Dithianone + SX, Dothine + SX , Fe Hexamide + SX, fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, triphenyltin hydroxide + SX, ferrimzone + SX, fluazinam + SX, fluopicolide + SX, fluorimide + SX, flusulfamide + SX, fluthianyl + SX, fosetyl aluminum + SX, fosetyl aluminum + SX Guazatine + SX, Himexazole + SX, Iminocazine + SX, Iminoctagine triacetate + SX, Iodocarb + SX, Iprobenfos + SX, Isoprothiolane + SX, Isotianil + SX, Kasugamycin + SX, Laminarin + SX, Meptyl dinocup + SX, S Octylinone + SX, oxathiapiproline + SX, oxolini Citric acid + SX, Oxytetracycline + SX, Pencyclon + SX, Phenacryl + SX, Picalbutrazox + SX, Polyoxin + SX, Probenazole + SX, Propamocarb + SX, Proquinazide + SX, Prothiocarb + SX, Pyrazophos + SX, Pyributycarb XX Silthiofam + SX, Streptomycin + SX, Tebufloquine + SX, Teclophthalam + SX, Technazen + SX, Terbinafine + SX, Thiazinyl + SX, Torulophosmethyl + SX, Tolfenpyrad + SX, Tolylfluanid + SX, Toluprocarb + SX, Triazoxide + SX, X , Cupric hydroxide + SX, Basic copper sulfate + SX, organic copper + SX, sulfur + SX, α12 + SX, α13 + SX, α14 + SX, α15 + SX, α16 + SX, α17 + SX, α18 + SX, α19 + SX, α20 + SX, α21 + SX, α22 + SX, α23 + SX, α23 + SX, α24 + SX,
Acephate + SX, Azamethiphos + SX, Azinphosethyl + SX, Azinphosmethyl + SX, Kazusafos + SX, Chloretoxyphos + SX, Chlorfenvinphos + SX, Chlormefos + SX, Chlorpyrifos + SX, Chlorpyrifosmethyl + SX, Coumaphos + X, S Dichlorvos + SX, Dicrotophos + SX, Dimethoate + SX, Dimethylvinphos + SX, Disulfoton + SX, EPN + SX, Ethion + SX, Etoprophos + SX, Fanful + SX, Phenamiphos + SX, Fenitrothion + SX, Phosthione + SX, Phosthiate + X + S Isopropyl-O- (methoxyaminothio Phosphoryl) salicylate + SX, isoxathion + SX, malathion + SX, mecarbam + SX, methamidophos + SX, methidathion + SX, mevinphos + SX, monocrotophos + SX, nared + SX, ometoate + SX, oxydimethonemethyl + SX, parathionate + SX, X, parathionate + SX, X , Hosalon + SX, Phosmet + SX, Phosphamidone + SX, Hoxime + SX, Pirimiphos methyl + SX, Profenofos + SX, Propetamphos + SX, Prothiophos + SX, Pyracrofos + SX, Pyridafenthion + SX, Quinalphos + SX, Sulfothep + X, Tebupyrimephos + S + SX, Thiometone + SX, Tria Host + SX, trichlorfon + SX, vamidothion + SX,
Aranicarb + SX, Aldicarb + SX, Bendiocarb + SX, Benfuracarb + SX, Butcarboxyme + SX, Butoxycarboxyme + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Ethiophene carb + SX, Fenthiocarb + SX, Formethanate + carb, SX Methiocarb + SX, Mesomil + SX, Metorcarb + SX, Oxamyl + SX, Pirimicurve + SX, Propoxyl + SX, Thiodicarb + SX, Thiophanox + SX, Triazamate + SX, Trimetacarb + SX, XMC + SX, Xylylcarb + SX,
Acrinatrin + SX, Aresulin + SX, Bifenthrin + SX, Kappa Bifenthrin + SX, Bioaresulin + SX, Bioresmethrin + SX, Cycloproton + SX, Cyfluthrin + SX, Beta-Cyfluthrin + SX, Cyhalothrin + SX, Gamma Cyhalothrin X SX, Gamma Cyhalothrin X SX + SX, alphacypermethrin + SX, betacypermethrin + SX, thetacypermethrin + SX, zetacypermethrin + SX, sigmacipermethrin + SX, ciphenothrin + SX, deltamethrin + SX, empentrin + SX, esfenvalerate + SX, ethofenprofenprox Thrin + SX, fenvalerate + SX, flucitrinate + SX, flumethrin + SX, fluva Nate + SX, Taufulvalinate + SX, Halfenprox + SX, Heptafluthrin + SX, Imiprothrin + SX, Kadeslin + SX, Meperfluthrin + SX, Monfluorotrin + SX, Permethrin + SX, Phetothrin + SX, Praretrin + SX, Pyrethrin + SX, Pyrethrin + SX Tefluthrin + SX, kappatefluthrin + SX, tetramethrin + SX, tetramethylfurthrin + SX, tralomethrin + SX, transfluthrin + SX, benfurthrin + SX, flufenprox + SX, flumethrin + SX, furamethrin + SX, sigma-cypermethrin + SX, furamethrin + SX , Profluthrin + SX, Dimefluthrin + SX, Epsilon - Metofluthrin + SX, epsilon - Mont fluoro Trinh + SX, methoxychlor + SX,
Bensultap + SX, Cartap + SX, Cartap Hydrochloride + SX, Thiocyclam + SX, Thiosultap-2 Sodium Salt + SX, Thiosultap-1 Sodium Salt + SX,
Acetamiprid + SX, clothianidin + SX, dinotefuran + SX, imidacloprid + SX, nitenpyram + SX, thiacloprid + SX, thiamethoxam + SX, flupiradiflon + SX, sulfoxafurol + SX, triflumezopyrim + SX, dichloromethothiaprix + SX, dichloromethothiazole SX
Bistrifluron + SX, Chlorfluazuron + SX, Diflubenzuron + SX, Fluazuron + SX, Fullcycloxuron + SX, Flufenoxuron + SX, Hexaflumuron + SX, Rufenuron + SX, Novallon + SX, Novyflumuron + SX, Trifluzuron + SX, Triflumuron
Ethiprol + SX, fipronil + SX, flufiprol + SX, chlordane + SX, endosulfan + SX, alpha endosulfan + SX,
Afoxolanel + SX, fluralanel + SX, brofuranilide + SX, floxamethamide + SX,
Chromafenozide + SX, halofenozide + SX, methoxyphenozide + SX, tebufenozide + SX,
Chlorantraniliprole + SX, cyantranylprolol + SX, cyclaniliprol + SX, fulvendiamide + SX, tetraniprolol + SX, cyhalodiamide + SX,
Abamectin + SX, Emamectin benzoate + SX, Repimectin + SX, Milbemectin + SX,
Hydroprene + SX, quinoprene + SX, metoprene + SX, phenoxycarb + SX, pyriproxyfen + SX,
Methyl bromide + SX, Chlorpicrin + SX, Sulfuryl fluoride + SX, Sodium aluminum fluoride + SX, Borax + SX, Boric acid + SX, Disodium octaborate + SX, Sodium borate + SX, Sodium metaborate + SX, Tartar + SX, Dazomet + SX, Metam + SX,
Clofentedine + SX, Hexithiazox + SX, Diflovidazine + SX, Etoxazole + SX,
Diafenthiuron + SX, Azocyclotin + SX, Cihexatin + SX, Fenbutatin oxide + SX, Propargit + SX, Tetradiphone + SX,
Chlorfenapyr + SX, DNOC, sulfuramide + SX,
Bistrifluron + SX, Chlorfluazuron + SX, Diflubenzuron + SX, Fluazuron + SX, Fullcycloxuron + SX, Flufenoxuron + SX, Hexaflumuron + SX, Rufenuron + SX, Novallon + SX, Novyflumuron + SX, Trifluzuron + SX, Triflumuron
Hydramethylnon + SX, acequinosyl + SX, fluacrylpyrim (+ SX, bifenazate + SX,
Phenazaquin + SX, fenpyroximate + SX, pyridaben + SX, pyrimidifen + SX, tebufenpyrad + SX, tolfenpyrad + SX, rotenone + SX,
Spirodiclofen + SX, Spiromesifene + SX, Spirotetramat + SX,
Aluminum phosphide + SX, calcium phosphide + SX, hydrogen phosphide + SX, zinc phosphide + SX, calcium cyanide + SX, potassium cyanide + SX, sodium cyanide + SX,
Sienopyrafen + SX, Siflumethofen + SX, Pifulbumide + SX,
Machine oil + SX, nicotine + SX, nicotine sulfate + SX,
Derived from Bacillus thuringiensis + SX, Bacillus thuringiensis Isaiwai subspecies + SX, Bacillus thuringiensis cristalki subsp. + SX, Bacillus thuringiensis isla Ellensis subsp. + SX, Bacillus thuringiensis tenebrionis subsp. + SX, derived from Bacillus thuringiensis Insecticidal protein products (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1, etc.) + SX, Bacillus sphaerics + SX,
Boberia Vasiana GHA strain + SX, Boberia bronniati + SX, Pekir Myces fumotheroseus + SX, Pekir Myces relassinas + SX, Pekir Myces tenuipes + SX, Verticillium regani + SX, Arsrobothris dactylides + S film X SX , Bacillus megaterium + SX, Hilstera rossiliensis + SX, Hilstera minnesotensis + SX, Monacrosporium fimatopagum + SX, Pasteuria nisawae + SX, Pasteuria penetrance + SX, Pasteurium usagae + SX, Verticillium crumidus X Harpin protein + SX,
Spinetram + SX, Spinosad + SX, Pymetrozine + SX, Pyrifluquinazone + SX, Buprofezin + SX, Ciromazine + SX, Amitraz + SX, Indoxacarb + SX, Metaflumizone + SX, Flonicamid + SX, Azadirachtin + SX, Benzoxymate + SX , Pyridalyl + SX, Lime sulfur mixture + SX, Sulfur + SX, Aphidopyropene + SX, Fluazaindolizine + SX, Fluene sulfone + SX, Furometokin + SX, Metoxadiazone + SX, Pyriminostrobin + SX, Thioxazafen + SX, Machine oil + SX, α27 + SX,
Benoxacol + SX, croquinto set + SX, croquinto set mexyl + SX, ciomethrinyl + SX, cyprosulfamide + SX, dichlormide + SX, dicyclonon + SX, dietate + SX, fenchlorazole + SX, fenchlorazole ethyl + SX, fenchlorim + SX, flurazole + SX Fluxophenim + SX, Furirazole + SX, Isoxadifen + SX, Isoxadifen ethyl + SX, Mefenpyr + SX, Mefenpyr diethyl + SX, Mefenate + SX, Naphthalic anhydride + SX, Oxabetrinil + SX
Chlormecote + SX, Ethephon + SX, Gibberellin + SX, Gibberellin A3 + SX, Himexazole + SX, Inabenfide + SX, Mepicoat + SX, 1-Methylcyclopropene + SX, Paclobutrazol + SX, Prohexadione + SX, Prohexadione Calcium + SX, Trinexapac Trinexapacethyl + SX, Uniconazole + SX, Uniconazole P + SX, Mycorrhizal fungus + SX, Arbuscular mycorrhizal fungus + SX, Gross spp. .

In the composition of the present invention, usually, the bipyridine compound and one or more compounds selected from the group a to the group d (hereinafter referred to as the present compound) are separately mixed with an arbitrary solid carrier or liquid carrier. If necessary, a surfactant or other formulation adjuvant is added and the formulated bipyridine compound formulation and this compound formulation are mixed, or the bipyridine compound and this compound are mixed in advance. It is mixed and mixed with an arbitrary solid carrier or liquid carrier, and if necessary, a surfactant or other formulation adjuvant is added to form a single formulation.
The formulation forms include emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poisonous baits, resin preparations, pasty preparations, foams, carbon dioxide preparations And tablets.

Examples of the solid carrier include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acid clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate). , Hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphoric acid, ammonium nitrate, urea, ammonium chloride, etc.), synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Resins, nylon-6, nylon-11, nylon-66, and other nylon resins, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.), and organic substances such as rice husk, bran, wheat flour, peat moss, etc. A fine powder can be mentioned.
Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic Hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, myristic acid) Isopropyl, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate), nitriles (acetonitrile, iso Tyronitrile, etc.), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).
Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
Other formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthesis Water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl) A mixture of -4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
For example, glycerin, ethylene glycol or propylene glycol may be added to the preparation as an antifreeze.
Moreover, you may add a coloring agent to a formulation. Examples of the colorant include a red pigment, a blue pigment, a green pigment, and a yellow pigment. Specific examples include monazole red, cyanine green, Prussian blue, and brilliant blue.

  The total content of the present bipyridine compound and the present compound in the composition of the present invention is usually 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight. is there. Moreover, the ratio of content of this bipyridine compound and this compound is 10,000: 1 to 1: 100 by weight ratio.

The pest control method of the present invention (hereinafter referred to as the present control method) includes a step of applying the bipyridine compound and the compound to a plant or a plant cultivation site.
In the control method of the present invention, the bipyridine compound and the compound are usually formulated and applied as separate formulations, or the composition of the present invention may be applied. When applied as separate formulations, they may be applied simultaneously or separately.
In the control method of the present invention, the bipyridine compound and the compound are applied in an effective amount.
Examples of plant cultivation sites in the present invention include farmland, tea garden, orchard, non-agricultural land, seedling tray and seedling box, seedling culture soil and seedling mat.

Examples of the bipyridine compound and the application method of the compound in the control method of the present invention include foliage treatment, soil treatment, seed treatment, and vegetative propagation organ treatment.
Examples of the foliage treatment include a method of treating the surface of a plant that is cultivated by foliage spraying.
Examples of such soil treatment include soil application, soil mixing, and chemical irrigation into soil.
Examples of such seed treatment and vegetative propagation organ treatment include a method of performing seed treatment or vegetative propagation organ treatment using the composition of the present invention. Specifically, for example, the suspension of the composition of the present invention is atomized. Spraying treatment on the seed surface or the surface of the vegetative propagation organ, wet dressing treatment to wet the seed or vegetative propagation organ whose form is a wettable powder, and its form is hydrated The liquid composition of the present invention, in which water is added to the composition of the present invention, which is an agent, emulsion or flowable, as necessary, is applied to the seed or vegetative propagation organ, and the seed is added to the chemical solution containing the composition of the present invention. Or the soaking process which immerses a vegetative propagation organ for a fixed time, the film coat process to the seed of this invention composition, and a pellet coat process are mentioned.
In the present invention, when simply referred to as a plant, the seed of the plant and the vegetative propagation organ of the plant are also included.
The vegetative propagation organ in the present invention means a plant root, stem, leaf or the like that has the ability to grow when its part is separated from the main body and placed in the soil. Examples of vegetative propagation organs include flower bulbs, tubers of tubers, tubers, bulbs, bulbs, root support bodies, and strawberry runners.

In the control method of the present invention, the application amount of the present bipyridine compound and the present compound is the type of plant to be applied, the type and frequency of occurrence of pests to be controlled, formulation form, application time, application method, application location, weather conditions It also depends on the etc.
In the control method of the present invention, when the bipyridine compound and the compound are applied to the plant foliage or the soil where the plant is cultivated, the application amount of the bipyridine compound is usually 1 to 10,000 g per ha, and the total of the compound The application amount is usually 1 to 10,000 g per ha. The wettable powder, granular wettable powder, etc. are usually diluted with water so that the concentration of the bipyridine compound is 0.01 to 10000 ppm and the total concentration of the compound is usually 0.01 to 10000 ppm. The powder and granule are usually used as they are.

The application amount of the bipyridine compound in seed treatment or vegetative propagation organ treatment is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of seed or vegetative propagation organ. Is usually 0.000001 to 50 g, preferably 0.0001 to 30 g per kg of seed or vegetative propagation organ.
Here, the weight of seeds or vegetative propagation organs means the weight of seeds or vegetative propagation organs before application or application of the present bipyridine compound, before seeding or embedding.
By performing seed treatment or vegetative propagation organ treatment as described above, a seed or vegetative propagation organ that retains the present bipyridine compound and the present compound can be obtained.
In the seed treatment or vegetative propagation organ treatment, the bipyridine compound and the compound may be mixed with an adjuvant as necessary. In addition, the bipyridine compound and the compound may be applied separately, and before or after seeding or seeding with either the bipyridine compound or the compound, the other is applied to the soil. May be.
In the present control method, the weight ratio of the application amount of the bipyridine compound to the application amount of the compound is
For the compounds included in group a, regardless of the presence or absence of other components, (the present bipyridine compound) / (one or more compounds selected from group a) = 1/100 to 10,000 / 1,
For the compounds included in group b, regardless of the presence or absence of other components, (the present bipyridine compound) / (one or more compounds selected from group b) = 1/100 to 100/1,
For the compounds included in group c, (the present bipyridine compound) / (one or more compounds selected from group c) = 1/100 to 100/1, regardless of the presence or absence of other components
Regarding the compounds included in group d, (the present bipyridine compound) / (one or more compounds selected from group d) = 1/100 to 100/1 regardless of the presence or absence of other components.

Examples of plants to which the present invention can be applied include the following.
Agricultural crops: cereals (corn, sorghum, wheat (wheat, barley, rye, oat, etc.), rice, millet, etc.), pseudo cereals (buckwheat, amaranth, quinoa, etc.), cereals (soybean, groundnut, etc.), rapeseed , Sugar beet, cotton, sunflower, tobacco, buckwheat, sugar cane, tobacco, hop etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, potatoes, peppers, peppers), cucumbers (cucumbers, pumpkins, zucchini, watermelons, melons, cucumbers, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American Bow Fu etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (silla, mint, basil etc.), legumes (peas, kidney beans, azuki bean, broad beans, chickpea etc.), strawberries, sweet potatoes, yam, taro , Konjac, ginger, ok Etc..
Fruit trees: fruits (apples, pears, pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, oranges, lemons, limes, grapefruits) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, safflower, Amanas, switchgrass, miscanthus, kusayoshi, dangiku, kenaf, cassava, willow, etc.), houseplants, etc.

  The present invention is preferably applied to cereals or cereals. The present invention is more preferably applied to corn, wheat, sorghum, and soybean.

In the present invention, the plant is not limited as long as it is a variety that is generally cultivated. Such varieties of plants include plants to which one or more useful traits have been imparted by genetic breeding techniques or genetic recombination techniques (genetically modified plants) and stack varieties obtained by crossing them.
Such useful traits include herbicide resistance, pest resistance, disease resistance, stress resistance, and quality improvement of fatty acid residue composition modified crops of fats and oils.

  Examples of such a genetically modified plant include, for example, genetic recombination in an electronic information site (http: // www. Plants listed in the crop registration database (GM APPROVAL DATABASE) are listed. More specifically, plants that have been given environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by genetic recombination techniques, or traits related to growth and yield, product quality, fertility traits, etc. It may be a modified plant.

Plants that have been given herbicide tolerance by genetic recombination technology include protoporphyrinogen oxidase (hereinafter abbreviated as PPO) herbicides such as flumioxazin, 4-hydroxyphenylpyruvate diacids such as isoxaflutol and mesotrione. Oxygenase (hereinafter abbreviated as HPPD) inhibitors, acetolactate synthase (hereinafter abbreviated as ALS) inhibitors such as imazetapyr and thifensulfuronmethyl, 5-enolpyruvylshikimate-3-phosphate synthase such as glyphosate ( (Hereinafter abbreviated as EPSP) inhibitors, glutamine synthetase inhibitors such as glufosinate, auxin-type herbicides such as 2,4-D and dicamba, and plants to which resistance to herbicides such as bromoxynil has been conferred by genetic recombination technology included.
Examples of plants to which herbicide tolerance has been imparted by gene recombination technology include glyphosate-resistant EPSPS gene (CP4 epsps) derived from Agrobacterium tumefaciens strain CP4, glyphosate metabolizing enzyme derived from Bacillus licheniformis (Glyphosate N-acetyl transferase) gene, whose activity is enhanced by shuffling technology, glyphosate metabolic enzyme genes (gat4601, gt6421), glyphosate metabolic enzyme (glyphosate oxidase gene, goxv247) derived from Ochrobacterum strain LBAA Or maize-derived glyphosate tolerance mutation EPSPS gene (mepsps, 2mepsps) having has one or more of the introduced glyphosate tolerant transgenic plants and the like. Maize (Zea mays L.), Soybean (Glycine max L.), Cotton (Gossypium hirsutum L.), Sugar beet (Beta vulgaris), Canola (Brassica napus, Brassica rapa), Alfalfa .), Wheat (Triticum aestivum), creeping bentgrass (Agrossis tolonifera) and other plants, there are glyphosate-resistant genetically modified varieties.
Several glyphosate-tolerant transgenic plants are commercially available. For example, genetically modified plants that express glyphosate-resistant EPSPS derived from Agrobacterium are trade names including Roundup Ready (registered trademark) and express glyphosate-metabolizing enzyme derived from Bacillus with enhanced metabolic activity by shuffling technology Genetically modified plants are trade names such as Optimum (registered trademark) GAT (registered trademark), Optimum (registered trademark) Gly canola, and transgenic plants expressing EPSPS having a glyphosate-resistant mutation derived from corn are GlyTol (registered trademark). ) Is already sold under the product name.
Similarly, as an example of a plant to which herbicide tolerance has been imparted by genetic recombination technology, phosphinothricin N-acetyltransferase, a glufosinate metabolizing enzyme derived from Streptomyces hygroscopicus, Phosphithricin N-acetyltransferase, A gene (bar), a phosphinothricin N-acetyltransferase gene (pat), which is a glufosinate metabolizing enzyme derived from Streptomyces viriochromogenes, or a glufosinate-tolerant transgenic plant introduced with a synthesized pat gene or the like There is. There are glufosinate-resistant transgenic varieties such as corn, soybean, cotton, canola, rice (Oryza sativa L.), sugar beet, chicory (Cichorium intybus) and the like.
Several glufosinate-tolerant transgenic plants are commercially available. Genetically modified plants that express glufosinate metabolizing enzymes (bar, pat) derived from Streptomyces are already sold under trade names including LibertyLink (registered trademark).
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, bromoxynyl-tolerant gene recombination in which a nitrilase gene (bxn), which is a bromoxynyl-metabolizing enzyme derived from Klebsiella pneumoniae subsp. Ozaenae, has been introduced. There are plants. Bromoxinyl-resistant genetically modified varieties are produced in plants such as canola, cotton, tobacco (Nicotiana tabacum L.), and are already sold under trade names including Navigator (registered trademark) canola or BXN (registered trademark) .
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, a genetically modified carnation (Dianthus caryophyllus) into which an ALS herbicide-tolerant ALS gene (surB, S4-HrA) derived from tobacco has been introduced as a selection marker ) In addition, a transgenic flax (Linum usitistisumum L.) into which an ALS herbicide-resistant ALS gene derived from Arabidopsis thaliana has been introduced has been developed under the trade name CDC Trifid Flax. A genetically modified soybean introduced with an ALS herbicide-tolerant ALS gene (csr1-2) derived from Arabidopsis thaliana has been developed under the name of Culture (registered trademark). Furthermore, transgenic corn resistant to sulfonylurea and imidazolinone herbicides introduced with corn-derived ALS herbicide-resistant ALS gene (zm-hr), soybean-derived ALS herbicide-resistant ALS gene (gm- There are genetically modified soybeans that are resistant to sulfonylurea herbicides introduced with fra).
Similarly, as an example of a plant to which herbicide resistance has been imparted by genetic recombination technology, an isoxaflutol resistant gene set into which an HPPD herbicide-resistant HPPD gene (hppdPFW336) derived from Pseudomonas fluorescens strain A32 has been introduced. There are modified soybeans and mesotrione resistant genetically modified soybeans introduced with HPPD gene (avhppd-03) derived from oat (Avena sativa).
Similarly, examples of plants to which herbicide tolerance has been imparted by genetic recombination techniques include allyloxyalkanoate dioxygenase, a 2,4-D metabolic enzyme derived from Sphingobium herbicidovorans. ) 2,4-D resistance into which the gene (aad-1) or the allyloxyalkanoate dioxygenase gene (aad-12), which is a 2,4-D metabolic enzyme derived from Delftia acidovorans, has been introduced GM, GM soybean, GM cotton, etc., some of which have been developed under the trade names of Enlist (registered trademark) Maize and Enlist (registered trademark) Soybean. Further, a dicamba-resistant genetically modified soybean, a recombinant cotton, etc., into which a dicamba monooxygenase gene (dmo), which is a dicamba metabolic enzyme derived from Stenotrophomonas maltophilia strain DI-6, has been introduced. is there.
Similarly, examples of plants that have been rendered tolerant to two or more herbicides by genetic engineering techniques include transgenic cotton that is resistant to both glyphosate and glufosinate, and genetically modified maize that is GlyTol® LibertyLink. (Registered trademark), Round Ready (registered trademark) LibertyLink (registered trademark) Maize is already sold under the trade name. In addition, a genetically modified soybean resistant to both glufosinate and 2,4-D was developed under the trade name Enlist (registered trademark) Soybean, and genetically modified cotton resistant to both glufosinate and 2,4-D. There is also. A genetically modified soybean that is resistant to both glyphosate and dicamba has been developed under the trade name Genuity (R) Roundup Ready (R) 2 Xtend (R). Genetically modified maize, soybean, which is resistant to both glyphosate and ALS inhibitors, has been developed under the trade name Optimum® GAT®. In addition, transgenic cotton resistant to both glufosinate and dicamba, transgenic corn resistant to both glyphosate and 2,4-D, transgenic soybean resistant to both glyphosate and HPPD herbicide Has also been developed. In addition, genetically modified soybeans that are resistant to three herbicides, glyphosate, glufosinate and 2,4-D, have also been developed.

Plants to which pest resistance has been imparted by gene recombination technology include plants to which resistance to lepidopterous insects, Coleoptera insects, multiple order insects, nematodes and the like are imparted.
As an example of a plant imparted with resistance against lepidopteran insects by genetic recombination technology, it encodes delta-endotoxin, which is an insecticidal protein derived from soil bacteria Bacillus thuringiensis (hereinafter abbreviated as Bt) And transgenic plants such as corn, soybean, cotton, rice, Populus (Populus sp.), Tomato (Lycopersicon esculentum) and eggplant (Solanum melongena). Cry1A, Cry1Ab, modified Cry1Ab (partially deleted Cry1Ab), Cry1Ac, Cry1Ab-Ac (a hybrid protein in which Cry1Ab and Cry1Ac are fused), Cry1C, Cry1F , Cry1Fa2 (modified cry1F), moCry1F (modified Cry1F), Cry1A. 105 (a hybrid protein in which Cry1Ab, Cry1Ac, and Cry1F are fused), Cry2Ab2, Cry2Ae, Cry9C, Vip3A, Vip3Aa20, and the like.
Examples of plants that have been given resistance to Coleoptera by genetic recombination technology include genetic recombination of maize, potato, etc., into which a gene encoding delta-endotoxin, an insecticidal protein derived from soil bacteria, Bt bacteria is introduced. There are plants. Examples of delta-endotoxins that confer resistance to Coleoptera insects include Cry3A, mCry3A (modified Cry3A), Cry3Bb1, Cry34Ab1, and Cry35Ab1.
As an example of a plant imparted with resistance to multiple insects by gene recombination technology, a gene set introduced with a synthetic gene encoding a hybrid protein eCry3.1Ab fused with Cry3A and Cry1Ab derived from soil bacteria Bt Transgenic corn, genetically modified cotton introduced with a gene encoding trypsin inhibitor CpTI derived from cowpea (Vigna unguicula), a gene set introduced with a gene encoding API that is protease inhibitor protein A derived from Kwai (Sagitaria sagittifolia) There is a replacement poplar.
Insecticidal proteins that impart pest resistance to plants include hybrid proteins of the above-mentioned insecticidal proteins, partially missing proteins, and modified proteins. The hybrid protein is produced by a combination of different domains of a plurality of insecticidal proteins, using genetic recombination technology, and Cry1Ab-Ac or Cry1A. 105 etc. are known. As a protein lacking a part, Cry1Ab and the like lacking a part of the amino acid sequence are known. Examples of the modified protein include proteins in which one or more amino acids of natural delta-endotoxin are substituted, and Cry1Fa2, moCry1F, mCry3A and the like are known.
In addition, as insecticidal proteins that impart pest resistance to plants by genetic recombination technology, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae, insecticidal protein Vip1 derived from Bt bacteria , Vip2, Vip3, nematode-derived insecticidal protein, scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin-produced toxin, filamentous fungal toxin, plant lectin, agglutinin, trypsin inhibitor, serine Protease inhibitors, protease inhibitors such as patatin, cystatin, papain inhibitor, lysine, corn-RIP, ribosome inactivating protein (RIP) such as abrin, ruffin, saporin, bryodin, 3-hydroxysterloy Oxidase, ecdysteroid-UDP-glucosyltransferase, steroid metabolic enzymes such as cholesterol oxidase, ecdysone inhibitor, ion channel inhibitors such as HMG-CoA reductase, sodium channel, calcium channel inhibitor, juvenile hormone esterase, diuretic hormone receptor Body, stilbene synthase, bibenzyl synthase, chitinase, glucanase and the like.

In addition, transgenic plants imparted with pest resistance by introducing one or two or more insecticidal protein genes are already known, and some genetically modified plants are commercially available.
Examples of transgenic cotton imparted with pest resistance include Bollgard (registered trademark) cotton that expresses the insecticidal protein Cry1Ac derived from Bt bacteria, and Bollgard II (registered trademark) that expresses the insecticidal proteins Cry1Ac and Cry2Ab derived from Bt bacteria. ) Cotton, Bollgard III (registered trademark) expressing insecticidal proteins Cry1Ac, Cry2Ab, Vip3A derived from Bt bacteria, VIPCOT (registered trademark) expressing insecticidal proteins Vip3A and Cry1Ac derived from Bt bacteria, insecticidal properties derived from Bt bacteria Commercially available recombinant cotton with a trade name including WideStrike (registered trademark) that expresses the proteins Cry1Ac and Cry1F is commercially available.
Examples of genetically modified maize imparted with pest resistance include Yieldgard® Rootworm RW that expresses the insecticidal protein Cry3Bb1 derived from Bt bacteria, and YieldGard Plus that expresses the insecticidal proteins Cry1Ab and Cry3Bb1 derived from Bt bacteria. Trademark), insecticidal protein Cry1A. YieldGard (registered trademark) VT Pro (registered trademark) and the like that express 105 and Cry2Ab2 are commercially available. Agrisure (registered trademark) RW expressing insecticidal protein mCry3A derived from Bt bacteria, Agrisure (registered trademark) Viptera expressing insecticidal protein Vip3Aa20 derived from Bt bacteria, Agrisure expressing insecticidal protein eCry3.1 Ab derived from Bt bacteria (Registered trademark) Duracade (registered trademark) and the like are also commercially available.
As examples of genetically modified potatoes imparted with pest resistance, Atlantic NewLeaf (registered trademark) potato, NewLeaf (registered trademark) Russet Burbank poto, etc. that express the insecticidal protein Cry3A derived from Bt bacteria are commercially available.

Plants to which disease resistance has been imparted by gene recombination techniques include common bean (Phaseolus vulgaris), papaya (Carica papaya), plum (Prunus domestica), potato, and Cucurbita pepo. , Sweet pepper (Capsicum annuum), tomato and the like. As a genetically modified plant imparted with resistance to plant viral diseases, specifically, a gene set in which a gene that generates double-stranded RNA of a replica protein of Bean golden mosaic virus is introduced. Recombinant kidney beans, transgenic papaya into which a coat protein gene of Papaya ringspot virus has been introduced, a coat protein gene of Potato virus Y, or a potato leaf roll virus ( Potato leaf roll virus) Recombinant potato introduced with a replication enzyme domain gene, Cucumber mosaic virus coat protein Squeezed gene, watermelon melon mosaic virus coat protein gene, zucchini yellow mosaic virus coat protein gene introduced, recombinant squirt, cucumber mosaic virus There are a genetically modified sweet pepper and a genetically modified tomato introduced with a coat protein gene of (Cucumber mosaic virus).
As an example of a genetically modified potato imparted with resistance to a plant viral disease, a genetically modified potato with a trade name including Newleaf (registered trademark) is commercially available.
Plants imparted with disease resistance also include plants imparted with the ability to produce anti-pathogenic substances having a selective action using genetic engineering techniques. As examples of anti-pathogenic substances, PR proteins and the like are known (PRPs, EP392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP392225, WO199533818, EP353191, and the like. Examples of anti-pathogenic substances include, for example, ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.), stilbene synthase, Microorganisms such as benzyl synthase, chitinase, glucanase, peptide antibiotics, heterocyclic antibiotics, and protein factors involved in plant disease resistance (referred to as plant disease resistance genes and described in WO2003010906) are produced. And anti-pathogenic substances.

For plants whose quality of the product has been modified by genetic recombination technology, modification of lignin production, modification of oil or fatty acid component, production of phytate degrading enzyme, modification of flower color, modification of alpha amylase activity, modification of amino acid Genetically modified plants with modified product quality such as starch or carbohydrate component modification, suppression of acrylamide production, reduction of black spots due to mechanical damage, antiallergic properties, reduction of nicotine production, aging or ripening delay, etc. It is done.
Alfalfa-derived S-adenosyl-L-methionine involved in lignin production: trans-caffeoyl CoA A gene that generates double-stranded RNA of 3-methyltransferase (ccomt) gene was introduced to reduce the lignin content by RNA interference. There is a genetically modified alfalfa.
A transgenic canola whose triacylglyceride content including lauric acid has been increased by introducing a 12: 0 ACP thioesterase gene derived from Laurel (Umbulararia californica) involved in fatty acid synthesis under the trade name Laurical (registered trademark) Canola Has been developed.
A genetically modified canola that enhances the degradation of endogenous phytic acid by introducing a 3-phytase gene (phyA) derived from Aspergillus niger, a plant phytic acid degrading enzyme, is produced by Phytaseed (registered trademark) Canola. Developed under the trade name. Similarly, genetically modified maize has been developed in which degradation of endogenous phytic acid is enhanced by introducing a black mold-derived 3-phytase gene (phyA).
Dihydroflavonol-4-reductase gene from Petunia hybrida, an enzyme that produces the blue pigment delphinidin and its derivatives, and petunia, pansy (Viola wittrockiana), salvia (Salvia splendens), or flavonoids from carnation A genetically modified carnation in which the flower color is controlled to be blue by introducing a -3 ′, 5′-hydroxylase gene is known. Genetically modified carnations in which the flower color is controlled to blue are: It has been developed under trade names such as (registered trademark), Moonpearl (registered trademark), Moonberry (registered trademark), and Moonvelvet (registered trademark). In addition, by introducing an anthocyanin-5-acyltransferase gene derived from Torenia sp., An enzyme that produces the blue pigment delphinidin and its derivatives, and a flavonoid-3 ′, 5′-hydroxylase gene derived from pansy A genetically modified rose whose flower color is controlled to blue has also been developed.
There is a genetically modified maize that has enhanced the production of bioethanol by introducing a thermostable alpha-amylase gene (amy797E) of Thermococcales sp. For starch degradation, under the trade name of Enogen® Has been developed.
Genetically modified maize enhanced lysine production by introducing a dihydrodipicolinate synthase gene (cordapA) from Corynebacterium glutamicum for the production of lysine, an amino acid, includes Mavera® Developed under the trade name.
Genetically modified melons and genetically modified tomatoes that have improved shelf life by introducing the S-adenosylmethion hydrolase gene (sam-K) derived from Escherichia coli bacteriophage T3 relating to ethylene production of plant hormones have been developed. . In addition, a gene lacking a part of the ACC synthase gene derived from tomato involved in ethylene production of plant hormones, an ACC deaminase gene derived from Pseudomonas chlororaphis that degrades ethylene precursor ACC, and pectin on the cell wall Tomato-derived polygalacturonase gene double-stranded RNA or a tomato-derived ACC oxidase gene involved in ethylene production has been introduced to improve genetic shelf tomatoes. ing. A genetically modified tomato improved in shelf life by introducing a gene that generates double-stranded RNA of a polygalacturonase gene derived from tomato has been developed under the trade name FLAVR SAVR (registered trademark).
Genes that generate double-stranded RNA of transcription factor genes that promote starch degradation from potato, genes that generate double-stranded RNA of polyphenol oxidase gene derived from potato, and genes that are involved in asparagine production Products that include Innate (registered trademark), a genetically modified potato that reduces the possibility of starch degradation, black spot formation due to mechanical damage, and generation of carcinogenic substances (acrylamide) by heating Developed by name. In addition, a genetically modified potato having a reduced amylose content by introducing an antisense gene of starch synthase derived from potato has been developed under the trade name of Amflora (registered trademark).
Genetically modified rice has been developed that has an immunotolerant effect and a hay fever alleviating effect by introducing a modified cedar pollen antigen protein gene (7crp).
By introducing a partial gene (gm-fad2-1) of ω-6 desaturase derived from soybean, which is a fatty acid desaturase, genetically modified soybean, which suppresses the expression of the same gene and enhances the oleic acid content, (Registered trademark) or Treus (registered trademark). In addition, a gene that generates double-stranded RNA of soybean-derived acyl-acyl carrier protein thioesterase gene (fatb1-A) and a double-stranded RNA of soybean-derived δ-12 desaturase gene (fad2-1A) Genetically modified soybeans having a reduced saturated fatty acid content by introducing a gene to be produced have been developed under the trade name of Visual Gold (registered trademark). In addition, a genetically modified soybean in which the content of ω3 fatty acid is enhanced by introducing a δ-6 desaturase gene (Pj.D6D) derived from primrose and a δ-12 desaturase gene (Nc.Fad3) derived from red bread fungus has been developed. Yes.
A genetically modified tobacco having a reduced nicotine content by introducing an antisense gene of tobacco-derived quinolinate phosphoribosyltransferase gene (NtQPT1) has been developed.
A phytoene synthase gene (psy) derived from Narcissus pseudonarcissus and a carotene desaturase gene (crt1) derived from a soil bacterium that synthesizes carotenoids (Erwinia uredovora) is introduced into β-endosperm tissue and expressed in the endosperm tissue. -Golden rice, a genetically modified rice that can produce carotene and harvest rice containing vitamin A, has also been developed.

Plants whose fertility traits and the like have been modified by gene recombination techniques include genetically modified plants in which the plants are given male sterility and fertility recovery traits. There are genetically modified maize and genetically modified chicory imparted with male sterility by expressing a ribonuclease gene (barnase) derived from Bacillus amyloliquefaciens in cocoon tapetum cells. In addition, there is a genetically modified maize imparted with male sterility by introducing a DNA adenine methylase gene (dam) derived from E. coli. Further, a gene set in which fertility traits are controlled by introducing an alpha-amylase gene (zm-aa1) derived from corn that gives male sterility traits and an ms45 protein gene (ms45) derived from corn that gives fertility recovery traits There is also a replacement corn.
There is a genetically modified canola imparted with a function of restoring fertility by expressing a ribonuclease-inhibiting protein gene (barstar) derived from Bacillus bacteria in cocoon tapetum cells. Further, a gene set in which fertility traits are controlled by expressing a ribonuclease gene (barnase) derived from Bacillus that gives male sterile traits and a ribonuclease inhibitor protein gene (barstar) derived from Bacillus that gives fertility recovery traits There is also a replacement canola.

  Examples of the plant imparted with environmental stress tolerance by genetic recombination technology include a genetically modified plant imparted with drought tolerance. A drought-tolerant maize introduced with a cold shock protein gene (cspB) derived from Bacillus subtilis has been developed under the trade name of Genuity (R) DraughtGard (R). Furthermore, drought-resistant sugarcane into which a choline dehydrogenase gene (RmBetA) derived from Rhizobium meliloti or Escherichia coli has been developed has also been developed.

  Examples of plants whose growth and yield traits have been modified by genetic recombination techniques include genetically modified plants with enhanced growth ability. For example, genetically modified soybeans and the like into which a gene (bbx32) encoding a transcription factor that controls diurnal properties derived from Arabidopsis thaliana has been developed.

The plant in the present invention may be a plant modified using a technique other than the genetic recombination technique. More specifically, it may be a plant imparted with environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by classical breeding technology, genetic marker breeding technology, genome editing technology, or the like.
Examples of plants to which herbicide tolerance has been imparted by classical or genetic marker breeding techniques include corn, rice, wheat, sunflower (Helianthus annuus), canola, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, Lentils (Lens culinaris) and the like are sold under the trade name of Clearfield (registered trademark). Moreover, STS soybean etc. which are sulfonylurea type | system | group herbicide tolerance soybean are examples of the plant to which tolerance to sulfonyl type | system | group ALS inhibition type herbicides, such as thifensulfuron methyl, was provided by the classic or gene marker breeding technique. Similarly, SR corn, which is cetoxydim-resistant maize, is an example of a plant to which tolerance is imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical or genetic marker breeding techniques. is there.
An example of a plant to which pest resistance is imparted by classical or genetic marker breeding techniques is soybean having a Rag1 (Resistance Aphid Gene 1) gene that is an aphid resistance gene. Moreover, as a plant imparted with nematode tolerance by a classical breeding method, soybean imparted with resistance to cyst nematode, cotton imparted with resistance to root knot nematode, and the like can be mentioned.
As a plant to which disease resistance has been imparted by classical or genetic marker breeding techniques, resistance to corn and gray leaf spot that have been imparted resistance to anthracnose disease is given. Resistant corn, resistant to Goss's wilt, resistant to Fusarium stalk rot, resistant to Asian soybean rust Soybeans, Peptotolerant to Phytophathora, Lettuce tolerant to powdery mildew, Tomato tolerant to Bacterial wilt And tomatoes with resistance to geminivirus, lettuce with resistance against downy mildew, and the like.
As an example of a plant to which drought tolerance has been imparted by classical or gene marker breeding techniques, drought-tolerant maize has been developed under the trade names of Agurisure Artesian (registered trademark) and Optimum AQUAmax (registered trademark). Also,
As an example of a plant to which herbicide resistance has been imparted by genome editing technology, a sulfonylurea herbicide is introduced by a rapid variety development technology that introduces a sulfonylurea herbicide resistance mutation into an ALS gene via a DNA and RNA chimeric oligonucleotide. A canola imparted with resistance has been developed under the trade name SU Canola®.

In addition, for the above-mentioned plants, using genetic recombination technology, classical breeding technology, genetic marker breeding, or genome editing technology, environmental stress resistance, disease resistance, herbicide resistance, pest resistance, Two or more types of properties possessed by the parental line by crossing two or more lines with growth, yield traits, product quality, fertile traits, etc., and genetically modified plants with similar or different properties The assigned line is also included. An example of such a plant is a genetically modified plant imparted with both herbicide resistance and pest resistance.
For example, as a transgenic plant imparted with glyphosate resistance and pest resistance, Round Ready (registered trademark) Bollgard (registered trademark) cotton, Round Ready (registered trademark) Bollgard II (registered trademark) cotton, Round Ready (registered trademark) Trade names of Flex (registered trademark) Bollgard II (registered trademark) cotton, Bollgard (registered trademark) III x Roundup Ready (registered trademark) Flex (registered trademark), VIPCOT (registered trademark) Roundup Ready Flex (registered trademark) Cotton, etc. Genetically modified cotton has been developed. In addition, Agurisure (registered trademark) GT / RW, Round Ready (registered trademark) YieldGuard (registered trademark) maize, Genuity (registered trademark) VT Double Pro (registered trademark), Genuity (registered trademark) VT Triple Pro (registered trademark), YieldGard (R), YieldGard (R) CB + RW, YieldGard (R) VT (R) Rootworm (R) RR2, YieldGard (R) RW + RR, YieldGard (R) VTTriGr (R) A genetically modified corn having a trade name such as Plus with RR has been developed. In addition, genetically modified soybeans such as Intatta (registered trademark) Roundup Ready (registered trademark) 2 Pro have been developed.
For example, as a genetically modified plant imparted with glufosinate resistance and pest resistance, products such as Widestrike (registered trademark) Cotton, Twinlink (registered trademark) Cotton, Fibermax (registered trademark) LibertyLink (registered trademark) Bollgard II (registered trademark) Named genetically modified cotton has been developed. Also, Agriure (registered trademark) CB / LL, Agriure (registered trademark) CB / LL / RW, Agriure (registered trademark) Viptera (registered trademark) 2100, Agriure (registered trademark) Viptera (registered trademark) 3100, Bt Xtra (registered trademark). (Trademark) Maize, NatureGard Knockout (registered trademark), Herculex (registered trademark) RW, Herculex (registered trademark) CB, Herculex (registered trademark) XTRA, Starlink (registered trademark) Maize, Liberty Link (registered trademark) YieldGard registered trademark A genetically modified corn having a trade name such as Maize has been developed.
For example, as a genetically modified plant imparted with glyphosate resistance, glufosinate resistance, and pest resistance, Widestrike (registered trademark) Roundup Ready (registered trademark) Cotton, Widestrike (registered trademark) Roundup Ready Flex (registered trademark) Cotton, Registered trademark x Round Ready Flex (registered trademark) x VIPCOT (registered trademark) Cotton, Glytol (registered trademark) x Twinlink (registered trademark) and the like have been developed. In addition, Agurisure (registered trademark) GT / CB / LL, Agurisure (registered trademark) 3000GT, Agrisure (registered trademark) 3122, Agrisure (registered trademark) Viptera (registered trademark) 3110, Agrisure (registered trademark) Viptera 3111, Registered Trademark) Viptera 3220, Agurisure (registered trademark) Duracade (registered trademark) 5122, Agrisure (registered trademark) Duracade (registered trademark) 5222, Optimum (registered trademark) Intrict, Optimum (registered trademark) TRIsect, Optimum (registered trademark) InTRtrust , Optimum (TM) Intrasect Xtreme, Genuity (R) Sma Genetic recombination of trade names such as rtStax (registered trademark), Power Core (registered trademark), Herculex (registered trademark) I RR, Herculex (registered trademark) RW Roundup Ready (registered trademark) 2, Herculex XTRA (registered trademark) RR Corn is being developed.
For example, a genetically modified cotton having a trade name such as BXN (registered trademark) Plus Bollgard (registered trademark) Cotton has been developed as a genetically modified plant imparted with bromoxynyl resistance and pest resistance.

As an example of a line provided with two or more of the above-mentioned plural traits, there is a genetically modified plant provided with disease resistance and pest resistance. For example, Hi-Lite NewLeaf (registered trademark) Y Potato, NewLeaf (registered trademark) Y Russet Burbank Potato, ShepodyNeed as a genetically modified plant imparted with resistance to potato virus Y (Potato virus Y) and pest resistance. (Trademark) Y Potato, or a genetically modified plant imparted with resistance to potato leaf roll virus and pest resistance, and a gene group with a trade name such as NewLeaf (registered trademark) Plus Russset Burbank Potato Replacement potatoes have been developed.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant provided with herbicide resistance and modified product quality. For example, genetically modified canola and genetically modified maize imparted with glufosinate resistance and fertile traits have been developed under the trade names of InVigor (registered trademark) Canola and InVigor (registered trademark) Maize.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant imparted with pest resistance and modified product quality. For example, genetically modified maize imparted with traits that enhance resistance to lepidopterous pests and lysine production has been developed under the trade name of Mavera (registered trademark) Yieldgard (registered trademark) Maize.
In addition, as an example of a strain provided with two or more of the above-mentioned plural traits, a genetically modified plant provided with herbicide tolerance and a modified fertility trait, a gene provided with herbicide tolerance and environmental stress tolerance Recombinant plants, genetically modified plants with herbicide resistance and modified growth and yield traits, genetically modified plants with herbicide resistance, pest resistance, and modified product quality, herbicides Genetically modified plants imparted with resistance, pest resistance, and environmental stress resistance have been developed.

Specific examples of the pests that can be controlled by the present invention include the following.
Hemiptera (Hemiptera): small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera), corn planthopper (Peregrinus maidis), Kitaunka (Javesella pellucida), Crofts Roh planthoppers (Perkinsiella saccharicida), Tagosodes orizicolus, etc. Delphidaide; Nephotettix cincetics, Nephotettix virescens, Nephotettix nigropict us), Inazuma Dorsalis, Empoasca onukii, Empoasca Fabae, corn leaf hoppers (Dalbulus maidis) Mahanarva posticata, Mahanarva fimbriola, etc. (Cercopidaa); his spiraecola), green peach aphid (Myzus persicae), wheat straw chrysanthemum Omar aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), fake radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae) Potato beetle aphids (Auracorthum solani), lettuce beetle aphids (Nasovia ribisnigri), wheat beetle aphids (Rhopalosiphum padi), corn aphids (Rhop) alosiphum maidis), mandarin orange black aphid (Toxoptera citricidus), Momoko butterbur aphid (Hyalopterus pruni), barnyard Roh aphid (Melanaphis sacchari), Oka Bono black aphid (Tetraneura nigriabdominalis), the sugarcane cotton aphid (Ceratovacuna lanigera), woolly apple aphid (Eriosoma lanigerum) Aphididae, etc .; Grape aphids (Daktosphaira vitifoliae), Pecan phylloxera (Phylloxa devastatrix), Pecan leaf phylloxera (Phylox) Ra notabilis), Southern pecan leaf phylloxera (Phylloxera russellae), and the like. Stink bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coastata), Nezoara tententa (Ezesarcoris Eisarcoris Eisarcoris Eisarcoris, Eysarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris Eisarcoris e s lewisi), Shirahoshi stink bug (Eysarcoris ventralis), purple Shirahoshi stink bug (Eysarcoris annamita), brown marmorated stink bug (Halyomorpha halys), southern green stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii) , Oebalus pugnax, Dichelops melacanthus and other stink bugs (Pentatomidae); Burrower brown bug (Scaptocoris castanea) and other stink bugs (Cydnidap) Destris, Leptocorisa chinensis, Leptocorisa acuta, etc., Alyididae; (Coreidae); Nigrelidae such as Caverelius saccharivorus, Copterella vulgaris (Togo hemopterus), American stag beetle (Blyss leucopterus), and T. um), red streaks Kasumi turtle (Stenotus rubrovittatus), lid thorn wheat Miridae (Stenodema calcarata), rust Gray Kasumi turtle (Lygus lineolaris) Kasumi stink bug family such as (Miridae); greenhouse whitefly (Trialeurodes vaporariorum), sweetpotato whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), Aleurocanthus spiniferus, Chatogekonajirami (Aleurocanthus camelliae), Hida-Kakifumia Aidaeroidae Ramushi (Abgrallaspis cyanophylli), Acamar scale insects (Aonidiella aurantii), no circle scale insects (Diaspidiotus perniciosus), white peach scale (Pseudaulacaspis pentagona), Yano yanonensis (Unaspis yanonensis), false Yano yanonensis (Unaspis citri), circle of equal scale insects Diaspididae; Coccidae such as Ruby worms (Ceroplastes rubens); Icerya purchasi; Icerya seychaelarum Margarodidae; Phenococcus solanipsi, Phenococcus sorenopsis, Placococus kraunhiae, Pocococcus kraunhiae, (Pseudococcus calceolalia), Pseudococcus longispinus, Brevennia rehi, etc .; Pseudococcidae; ), Mandarin orange pointed pheasant Rami (Trioza erytreae), Nashikijirami (Cacopsylla pyrisuga), Chu Ngoc pear pheasant Rami (Cacopsylla chinensis), potatoes kurtosis pheasant Rami (Bactericera cockerelli), Pear psylla (Cacopsylla pyricola) psyllid family, etc. (Psyllidae); sycamore Gun by (Corythucha ciriata), Corythuka marmorata, Nashigunbai (Stephanitis nashii), Stefanitis pyrioides, etc .; (Cimicidae) and Giant Cicada (Quesada gigas) Semi-family, etc. (Cicadidae).

  Lepidoptera (Lepidoptera): rice stem borer (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten giant moth (Scirpophaga incertulas), Rupela albina, leaf roller (Cnaphalocrocis medinalis), Marasmia patnalis, rice Hacasa maiga (Marasmia exigua), Watano maiga (Nottarcha derogata), Awa no maiga (Ostrinia furnacalis), European corn borer (Ostrinia nubil) alis), Hydra dalalis, Herpetogramma luctuosale, Pediasia terterus, rice case worm (Nymphra deptalis), Sugara cerbera (Nymphala deptalis) (Elasmopalpus lignosellus), Plodia interpuntella, etc. (Pyralidae); Spodoptera litura (Spodoptera yotto), Spodoptera imna separata), cabbage armyworm (Mamestra brassicae), Ineyotou (Sesamia inferens), Shironayotou (Spodoptera mauritia), Futaobikoyaga (Naranga aenescens), caterpillars (Spodoptera frugiperda), Africa Sirona armyworm (Spodoptera exempta), black cutworm (Agrotis ipsilon) , Tamanaginuawa (Autographa nigrisigna), Rice walrus (Plusia festukae), Soybean looper (Chrysodeixis inclusions), Trichoplusia genus (Trichoplusia. ), Fake American tobacco budworm (Heliothis virescens), such as Heliothis spp., Cotton bollworm (Helicoverpa armigera), American tobacco budworm (Helicoverpa zea) such as Helicoverpa spp., Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis) Noctuidae; Pieridae, such as Pieris rapae; Grapholita molesta, Grapholita dimorpha, Meshinkuiga (Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses azukivora), apple Coca summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai), Chahamaki (Homona magnanima), Mi someone summer fruit moth (Archips fuscocupreanus), codling moth (Cydia pomonella ), Tetramoera schistaceana, Bean Shot Borer (Epinotia aporema), Citrus fruit borer (Ecdytropha aurantiana), etc. Tortricidae (Tortricidae); Chanohosoga (Caloptilia theivora), apple leaf miner subfraction family (Phyllonorycter ringoniella) (Gracillariidae); peach fruit moth (Carposina sasakii) Shinkuiga family such as (Carposinidae); Coffee Leaf miner (Leucoptera coffeela), Momohamoguriga (Lyonetia clerkella) , Lyonetidae such as Lyonetia prunnifoliella; Lymantria dispar, such as Lymantria dispara, Euproctis pseudoconsper a) Euplottis genus (Lymantriidae); Pterella phylogenata (Plutelliaphia moth); operculella), Tutta absoluta, etc. (Gelechiidae); Hyphantria cunea, etc. (Architidae); Giant Subarcane borer (Telchin licans), etc. idae); Cossidae, such as Cosus insularis; Geometridae, such as Ascotis selenaria; ada, T Statomopodidae, etc .; Sphingidae, such as Acherontia lachesis; Sididae, such as Nokona feralis;

  Thysanoptera pests (Thysanoptera): western flower thrips (Frankliniella occidentalis), Minami thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), green onion thrips (Thrips tabaci), Hirazuhanaazamiuma (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis ), Thripidae such as Echinothrips americanus; Phraeothripidae such as Haplotrips aculeatus.

  Diptera: Anthonyidae such as Delia platera, Delia antiqua; U-zigmae; Tomato leafworm (Liriomyza sativae), leguminous leaffly (Liriomyza trifolii), clawfly flies (Chromatomyia horticola), etc .; a cucurbitae), oriental fruit fly (Bactrocera dorsalis), Nasumibae (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quince Queensland fruit fly (Bactrocera tryoni), Mediterranean fruit fly (Ceratitis capitata) Tephritidae such as (Tephritidae); rice Hime leafminer (Hydrellia griseola ), Hydrelia philippina, Hydrelia sasakii, etc .; Drosophila sect; Frosidae (Phoridae) such as Megaselia spiricularis; Drosophila such as Clogmia orbipuntata; Cecidomyiidae, such as Orseolia oryzae; Diopsidae, such as Diopsis macrophthalma; Tipura anecurafura, Cyprus falcon (Tipula aino) (Tipula paludosa) crane fly family, etc. (Tipulidae).

  Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimanta abir cumber worm), Northern corn root worm (Diabrotica worm) Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Bark beetle (Oulema melanopus), Uri potato beetle (Aulac) phora femoralis), Kisujinomihamushi (Phyllotreta striolata), Cabbage flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Inedorooimushi (Oulema oryzae), grape・ Colaspis brunea, corn flare beetle (Chaetocnema pulicaria), sweet potato beetle (Chaetocnem) confi), potato flare Beetle (Epitrix cucumeris), Inetogehamushi (Dicladispa armigera), Grape Colaspis (Colaspis brunnea), southern corn leaf beetle (Myochrous denticollis), cowpea turtle saw beetle (Laccoptera quadrimacu), tobacco flea beetle (Epitrix hirtipennis), etc. Chrysomelidae; Seedcorn beetle (Stenolophus lecontei), Lender seedcorn beetle (Cliveina imprecitrons), etc. Carabidae ; Cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), Aodougane (Anomala albopilosa), Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), black circle Scarabaeidae (Tomarus gibbosus), Holotrichia genus, June Beetle (Phyllophaga crinita), etc., Phyllophaga genus, Dilobodarus abderus, etc. Sweet potato weevil (Cylas formicarius), Imozoumushi (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white streaks reed weevil (Rhabdoscelus lineatocollis), Watamihana Weevil (Anthonomus grandis), Weevil weevil (Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callusus), Soybeans alk weevil (Sternechus subsignatus), Sgarcane wiivil (Sphenophorus levis), rust gourd weevil (Scepticus griseus), Tobi Gray gourd weevil (Scepticus uniformis), Brazil bean weevil (Zabrotes subfasciatus), pine bark beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), genus Aracanthus such as Aracanthus mourei, and Curculionidae such as cotton root borer (Eutinoboth brasiliensis); Tribium castancidae (Tibriocumincidae), Tribium candidae (Tiboriunidae) (Enechuna vicintocidae) Botrychidae); Leopardidae (Ptinidae); Gray Muna tailed click beetle (Agriotes fuscicollis), Kushikometsuki (Melanotus legatus) Elateridae such as (Agriotes sp. Aelous sp. Anchatus sp. Melanotus sp. Limonius sp. , Conoderus sp. Ctenicera sp. ); Staphylinidae such as Paederus fuscipes.

  Orthoptera pests (Orthoptera): locust (Locusta migratoria), Morocco Tobi grasshopper (Dociostaurus maroccanus), Australian Plague Locust (Chortoicetes terminifera), Akatobibatta (Nomadacris septemfasciata), Brown Locust (Locustana pardalina), Tree Locust (Anacridium melanorhodon), Italian Locust (Calliptamus italicus), Differential glasshopper (Melanoplus differentialis), Two stripped glasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida), desert Watari grasshopper (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust ( Austracris guttulosa, Oxya yezoensis, Oxya japonica, Taiwan chinago (Pat) anga succincta) acrididae such as (Acrididae); mole crickets (Gryllotalpa africana) Kera family, etc. (Gryllotalpidae); house cricket (Acheta domesticus), Enmakoorogi (Teleogryllus emma) cricket family, etc. (Gryllidae); Mormon cricket (Anabrus simplex) Tetigoniidae such as.

  Hymenoptera: Family of Ants such as Firent (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara) and the like.

  Cockroaches (Blattodea), such as the German cockroach (Blattellidae); Family (Blittidae); Yamato termite (Reticulitermes supertus), Termite (Copttotermes formosanus), American termite minor (Incicitermes minor), Cyptotermes domes icus), Taiwan termites (Odontotermes formosanus), Kou Shun termite (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Katan termites (Glyptotermes fuscus), giant termite (Hodotermopsis sjostedti), Kou Shu Ye termite (Coptotermes gangzhouensis), Amphictus reticulitermes amianus, Reticulitermes miyatakei, Reticulitermes ka nmonensis), Takashi termites (Nasuittertermes takasagoensis), Nitobe termites (Pericapritermes nitobei), Musashi termites (Sinocapritemes muschae), and Conittermes citrumes family.

  Nematoda: Aphelenchoids (Aphlenchoides besseyi); Pratyrenchus coffeae; Pratylenchidae such as similis; Javaloid nematode (Meloidogyne javanica), Sweet potato nematode (Meloidogyne incognita), Kitaneko nematode (Meloidopane, Meloidopye) Is cyst nematode (Heterodera glycines), potato cyst nematode (Globodera rostochiensis), potato white cyst nematode (Globodera pallida) Heterodera family such as (Heteroderidae); Rotylenchulus reniformis Hopuroraimusu family such as (Hoplolaimidae); Strawberry main nematode (Nothotylenchus acris), Anguinidae such as Dityrenchus dipsci; Tylenchulidae such as Tylenchus semipenetran; Grapes Oharisen (Xiphinema index) Rongidorusu family, etc. (Longidoridae); Torikodorusu family (Trichodoridae); pine wood nematode (Bursaphelenchus xylophilus) para Sita Affairs Ren box family, etc. (Parasitaphelenchidae) and the like.

The present invention is preferably applied to Hemiptera pests, Lepidoptera pests, Diptera pests, Coleoptera pests, nematodes, and particularly, beetles, corn rootworms, moths, fly flies, aphids, and Application to nematodes is preferred.
The target pests may be pests having reduced drug sensitivity to insecticides / acaricides or developed drug resistance. However, when the drug sensitivity is greatly reduced or the drug resistance is greatly developed, it is desirable to use the composition of the present invention containing an insecticide / acaricide other than the target insecticide / acaricide.

Examples of plant diseases in which the composition of the present invention has a controlling effect include the following.
Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling disease (Gibberella fujikuroi), yellowing rot ), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microchichium nirvale, Yellow rust (Puccinia striformis), Red rust (Puccinia citrus red) ochium nivale, Microdochium majus), small snow mold rot (Typhula incarnata, Typhula ishikariensis), loose smut (Ustilago tritici), fishy smell smut (Tilletia caries, Tilletia controversa), Memonbyo (Pseudocercosporella herpotrichoides), Ha枯Disease (Septoria tritici), blight disease (Stagonospora nodorum), macular disease (Pyrenophora tritici-repentis), Rhizotonia solaniis umniomini gane disease, blight Barley powdery mildew (Blumeria graminis), red mold (Fusarium graminearum), Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, yellow rust (Pucciniamor sick) Small disease (Puccinia hordei), naked scab (Ustilago nuda), cloud disease (Rhynchosporium secalis), reticulum disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Poria olea) Tomato disease (Ramularia collo-cygni), Rhizoctonia solani, maize rust (Puccinia polysora), southern rust (Puccinia polysora), tropical rust Disease (Physopella zeae), sesame leaf blight (Cochliobolus heterotrohus), anthracnose (Colletotrichum graminicola), gray leaf spot disease (Cercospora zeae-maydis), brown spot disease (Kabae leaf disease, Kabati leaf disease) Phaeosphaeria maydis), Stenocar pella maydis, Stenocarpella macrospora, stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); cotton of anthracnose (Colletotrichum gossypii), white mold disease (Ramularia areola), black spot disease (Alternaria macrospora, Alternaria gossypii), Black rot rot disease caused by Thielaviopsis genus (Thieaviopsis basicola); coffee rust (Hemilia vastatrix), leaf spot disease (Cer Ospora caffeicola; Sclerotinia sclerotiarum; Black spot disease (Alternaria brasicae); Rust (Puccinia helianthii), downy mildew (Plasmopara halstedii); citrus black spot (Diaportheit citri), scab (Elsinoe falcitophytitis), fruit rot (Penicillium digithititis) ra parasitica, Phytophthora citrophthora; apple monilia disease, rot ai, enthusiosis (Valsa ceratosperma), powdery mildew (Podosphaera leukotrica), spotted leaf disease (Podosphaera leukotrica) Disease (Glomerella cingula), brown spot disease (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), plague (Phytophthora catacurum); Diseases (Alternaria alternaria Japan pathotype), Red Star Disease (Gymnosporangium haraeanum); Peach Bacterial Pulmonary Disease, Clanosporium rot. ); Grapes black rot (Elsinoe ampelina), late rot (Glomerella gingulata), powdery mildew (Uncinula nelopetor), rust (Phakopsora amplopadidis), black lot illness (Guinardiapia wisdom) Anthracnose of oysters (Gloeosporium kaki), deciduous leaf (Cercospora kaki, Mycosphaerella nawae); anthracnose of cucurbits (Colletotrichum lagenarium), powdery mildew (Sphaerofelecula) Disease (Corynespora case) iicola), vine split disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.), seedling blight (Pythium sp.); tomato ring disease (Alternaria leaf) Cladosporium fulvum), Pseudocercospora fuligena, Phytophthora varieties, Black powdery disease (Levelillacea ursina), Eggplant brown rot (Phomopsis cerevisiae) Disease (Alternaria japonica), vitiligo disease (Cercos) orella brassicae, root-knot disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica); green onion rust (Puccinia alliy), black spot disease (Cercospora kirai disease, black spot) sojae), rust disease (Phakopsora pachyrhizi), brown ring disease (Corynespora caesicola), anthracnose disease (Colletotritum glycines), Colletolithium rot (Colletotritium rot) nes), spot disease (Cercospora sojina), mycorrhizal disease (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), stem rot (Phytophoravorus morsae), downy mildew (Peronospora indigenous disease) Of sclerotia sclerotiorum, rusty disease (Uromyces appendiculatus), horny spot disease (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), aphid ora arachidicola), white silkworm (Sclerotium rolfsii); pea powdery mildew (Erysiphe pisi); potato summer plague (Alternaria solanthia), plague (Phytophthora infestans), phlegm rot (Spongospora subterranean f. sp. subterranea, vermicillium albo-atrum, verticillium dahliae, verticillium nigrescens; strawberry powdery disease (e), and Pestalotipsis sp.), Anthracnose (Colletotrichum thea-sinensis); Red leaf disease of tobacco (Alternaria longipes), Anthracnose (Colletotrichum tabacum), Downy mildew (Peronosporatocota tabacin disease) nae); brown spot of sugar beet (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides), rust disease (Uromyc pneumoniae); ), Powdery mildew (Sphaerotheca pannosa); chrysanthemia-indici of chrysanthemum, white rust (Puccinia isriday rot); (Botrytis alli ), Sclerotia rot (Bottrytis squamosa); gray mold of various crops (Botrytis cinereaa); sclerotia sclerotia (Sclerotinia sclerotiorum); radish black spot (Alternaria brasicicola seros) ), Shiba brown patch disease and Rhizotonia solani; and banana Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
Aspergillus genus, Penicillium genus, Fusarium genus, Gibberella genus, Tricoderder genus, Thielaviopsis genus, Rhizopus genus, Mucor genus, Corticium genus, Poma genus, Rhizoctonia genus Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
Rice seedling bacterial disease (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lacrymans); carotovora) and the like.

  The pathogenic bacterium or pathogenic bacterium causing the disease of interest may be a pathogenic bacterium or pathogenic bacterium having reduced drug sensitivity or developed drug resistance to the bactericides included in group a. However, when the drug sensitivity is greatly reduced or the drug resistance is greatly developed, it is desirable to use the composition of the present invention containing a bactericidal agent other than the bactericidal agent.

  The composition of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses.

  Examples of the insect-borne virus having the control effect of the composition of the present invention include the following.

Rice dwarf virus (Rice tungro spurious virus), Rice tungro bacilliform virus, Rice grassy stunt virus (Rice gurstunt virus) Rice stripe virus, Rice black stroked dwarf virus, Southern rice black-streaked dwarf virus, rice leaf dwarf virus, rice leaf dwarf virus blanka virus Rice yellow virus (Rice yellow bundle virus), rice dwarf virus, rice dwarf virus, northern cerebral virus virus Spotted virus (Barley mild mosaic virus), Barley yellow dwarf virus-PAV, Wheat yellow dwarf virus-RPS, Wheat yellow leaf virus (Wale yellow leaf virus) dwarf virus Wheat streak mosaic virus,
Maize dwarf mosaic virus (Maize dwarf mosaic virus), Maize stripe virus, Maize chlorotic mottle virus, Maize chlorotic dwarf virus, Maize rayado fino virus, sugar cane mosaic virus (Sugarcane mosaic virus), Fiji disease virus, Sugarcane yellow leaf virus soybean fine plaques Mosaic virus (Soybean mild mosaic virus), Cycas necrotic stunt virus, soybean dwarf virus, Milky dwarf virus (Milk vetc) dwarf virus), soybean mosaic virus (Soybean mosaic virus), alfalfa mosaic virus (Alfalfa mosaic virus), bean yellow mosaic virus, southern bean mosaic virus mosaic virus, peanut stunt virus, faba bean virus 1 (Broad bean wilt virus 1), faba bean wilt virus 2 (Broad bean wilt virus 2) necrosis virus), broad bean yellow vein virus, clover leaf yellow virus, peanut mottle virus, striped leaf virus, striped tobacco virus. motor virus, Cowpea chlorotic motor virus, Mung bean yellow mosaic virus, Soybean clinker leaf virus,
Tomato chlorosis virus (Tomato chlorosis virus), tomato spotted wilt virus, tomato yellow leaf curl virus, tomato aspermyvirus (Spomatovirus) Chlorosis virus (Tomato infectious chlorosis virus), potato leaf roll virus (Potato leafroll virus), potato Y virus (Potato virus serovirus), melon yellow velop virus spot ),watermelon Zyk virus (Watermelon mosaic virus), Cucumber mosaic virus (Zucchini yellow mosaic virus), Turnip mosaic virus, Turnip mosaic virus, Turnip mosaic virus Mosaic virus (Cauliflower mosaic virus), Lettuce mosaic virus, Celery mosaic virus, Beet mosaic virus, Cucurbit yellowing virus (Cucurb) it chlorotic yellows virus, capsicum chlorosis virus, beet pseudo yellows virus, leaf yellow stripe virus, Leak yellow stripe virus, Leak yellow stripe virus Sweet potato patchy virus, Sweet potato shrimp mosaic virus, Strawberry violet stripe virus d yellowow virus, Strawberry pseudo yellow mild virus, Strawberry crinkle virus, Strawberry band virus, Strawberry band virus (Straw virus virus) ), Chrysanthemum stem necrosis virus, impatiens necrotic spot virus, iris yellow spot virus (Iris yellow spot virus), and lily spotted virus. ), Lily latent virus (Lilly symptomless virus), tulip mosaic virus, etc. (Tulip mosaic virus) and the like.

  Examples of insect-borne bacteria include the following.

  Rice wilt phytoplasma (Candidatus phytoplasma oryzae), Candidatus phytoplasma asteris, Maize bushy stunt phytoplasma, citrus greening fungus, Candida brilliant disease (Candidas Riverbacter americanus) and the like.

  Hereinafter, the present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified.

First, the specific composition of this invention composition is described below.
In addition, the composition which has the combination as described in [Table A] is attached | subjected and numbered as described in [Table A]. For example, the composition of No. 1 in [Table A] is referred to as the present composition 1.
In [Table A], * described in the column of component 1 represents any one of the bipyridine compounds 1 to 347, and the numbers described in [] in the column of each component are the numbers in the present invention. The amount (part) of each component relative to 100 parts of the composition is meant.

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The present compositions 841-1680
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of tebuconazole instead of 2 parts of metconazole.

The present composition 1681-2520
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of difenoconazole instead of 2 parts of metconazole.

This composition 2521-360
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of triticonazole instead of 2 parts of metconazole.

The present composition 3361-4200
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of prothioconazole instead of 2 parts of metconazole.

This composition 4201-5040
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole instead of 2 parts of metconazole.

This composition 5041-5880
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole M instead of 2 parts of metconazole.

The present composition 5881-6720
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of ipconazole instead of 2 parts of metconazole.

The present composition 6721-7560
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of prochloraz instead of 2 parts of metconazole.

The present composition 7561-8400
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of fluquinconazole instead of 2 parts of metconazole.

This composition 8401-9240
In each of the present compositions 1 to 840 described in [Table A], a composition using 2 parts of triazimenol instead of 2 parts of metconazole.

The present compositions A1 to A9240
A composition further comprising 10 parts of clothianidin and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition B1-B9240
A composition further comprising 10 parts clothianidin and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition C1-C9240
A composition further comprising 10 parts clothianidin and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition D1-D9240
A composition further containing 10 parts imidacloprid and 10 parts chlorantraniliprol in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition E1-E9240
A composition further comprising 10 parts imidacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition F1-F9240
A composition further comprising 10 parts imidacloprid and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition G1-G9240
A composition further comprising 10 parts thiamethoxam and 10 parts chlorantraniliprole in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

  A composition further containing 10 parts thiamethoxam and 10 parts cyantraniliprole in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

The present compositions I1-I9240
A composition further comprising 10 parts thiamethoxam and 10 parts fipronil in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition J1-J9240
A composition comprising 10 parts of thiacloprid and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition K1-K9240
A composition further comprising 10 parts thiacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition L1-L9240
A composition further comprising 10 parts of thiacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition M1-M9240
A composition comprising 10 parts of furpyraziflon and 10 parts of chlorantraniliprol in each combination of the present compositions 1-9240 (provided that the composition is 100 parts)

This composition N1-N9240
A composition further comprising 10 parts of furpyraziflon and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition O1-O9240
A composition further comprising 10 parts of furpyradiflon and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition P1-P9240
A composition further comprising clothianidin 20 parts in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition Q1-Q9240
A composition further comprising 10 parts α26 and 10 parts chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition R1-R9240
A composition further comprising 10 parts α26 and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition S1-S9240
A composition further comprising 10 parts of α26 and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

  Next, formulation examples are shown.

Formulation Example 1
The present compositions 1-9240, A1- A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

Formulation Example 2
This composition 1-9240 obtained by adding 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and synthetic silicon hydrous so that the total amount becomes 100 parts, A1 to A9240, B1 to B9240, C1 C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, N1 to N9240, O1 to O9240, Each wettable powder is obtained by thoroughly pulverizing and mixing any one of P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240.

Formulation Example 3
The present compositions 1-9240, A1 obtained by adding 15 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts. A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by finely pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

  Next, application examples of the composition of the present invention to plant seeds will be shown.

Application example 1
200 kg of any one of the flowable preparations obtained by the method described in Preparation Example 1 or 3 is smeared on 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 180 grams of oxabetalinyl is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 1 or 3, and each treated seed is obtained by a smearing treatment as described above.

Application example 2
200 kg of any one of the flowable preparations obtained by the method described in Preparation Example 1 or 3 is smeared on 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 40 g of flxophenim is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 1 or 3, and each treated seed is obtained by smearing treatment in the same manner as described above.

Application example 3
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 1 or 3 to 10 kg of dried corn seed using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the corn, a genetically modified corn containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application example 4
40 kg of any flowable formulation obtained by the method described in Formulation Example 1 or 3 is applied to 10 kg of dried corn seed using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application example 5
100 kg of any flowable formulation obtained by the method described in Formulation Example 1 or 3 is applied to 10 kg of dried corn seed using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application example 6
Each treated seed is obtained by subjecting 10 kg of dried corn seeds to 50 g of any one of the wettable powders obtained by the method described in Formulation Example 2 as a dressing treatment.

Application example 7
Applying 20 ml of any flowable formulation obtained by the method described in Formulation Example 1 or 3 to 10 kg of dried soybean seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH) Thus, each treated seed is obtained. As the soybean, a genetically modified soybean containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 8
Applying 100 ml of any one of the flowable preparations obtained by the method described in Formulation Example 1 or 3 to 10 kg of dried soybean seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH) Thus, each treated seed is obtained.

Application example 9
50 kg of dry seeds, 50 ml of any one of the flowable preparations obtained by the method described in Formulation Example 1 or 3 is smeared using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the cotton, a genetically modified cotton containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 10
50 kg of dried oilseed rape seeds, 50 ml of any one of the flowable preparations obtained by the method described in Formulation Example 1 or 3, using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) Each treated seed is obtained by treatment. As the oilseed rape, a genetically modified oilseed rape including a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 11
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 1 or 3 to 10 kg of dried oilseed rape seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment.

Application Example 12
Apply 50 ml of any one of the flowable preparations obtained by the method described in Formulation Example 1 or 3 to 10 kg of dried wheat seeds using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). To obtain each treated seed

Hereinafter, the effects of the present invention will be shown by test examples.

Test example 1
By seeding any one of the treated seeds of corn obtained by the method described in Application Example 3 at a depth of 5 cm using a seeder at an interval of 15 cm, Rhizotonia solani and Pythium spp. ), High control effect can be obtained against Negusare nematode. When seeds treated with a preparation containing an insecticide are used, a high control effect can be obtained against pests having the control effect of the insecticide.

Test example 2
By sowing any one of soybean treated seeds obtained by the method described in Application Example 7, high control against Fusarium oxysporum, Rhizoctonia solani, and soybean cyst nematode An effect can be obtained. When seeds treated with a preparation containing an insecticide are used, a high control effect can be obtained against pests having the control effect of the insecticide.

Test example 3
By sowing any one of the oilseed rape treated seeds obtained by the method described in Application Example 10, it is possible to obtain a high control effect against Rhizotonia solani and Negusale nematode. When seeds treated with a preparation containing an insecticide are used, a high control effect can be obtained against pests having the control effect of the insecticide.

Claims (8)

A bipyridine compound represented by the following formula (I) or an N oxide compound thereof;
A pest control composition containing one or more compounds selected from the following group a to the following group d.
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide, acaricide, nematocide group c; safener group d; plant growth regulator   The content ratio of the bipyridine compound represented by the formula (I) or an N oxide compound thereof and one or more compounds selected from the group a to the group d is 10000: 1 to 1: 100 by weight. The composition according to claim 1. A plant seed or vegetative propagation organ comprising a bipyridine compound represented by the following formula (I) or an N oxide compound thereof and one or more compounds selected from the following groups a to d:
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide, acaricide, nematocide group c; safener group d; plant growth regulator   The plant seed or vegetative propagation organ according to claim 3, wherein the amount of the bipyridine compound represented by the formula (I) or its N oxide compound is 0.000001 to 50 g per 1 kg of the plant seed or vegetative propagation organ. . A pest comprising a step of applying a bipyridine compound represented by the following formula (I) or an N oxide compound thereof and one or more compounds selected from the following group a to the following group d to a plant or a plant cultivation site: Control method.
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, a phenyl group which may have one or more substituents selected from group D, 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ^{11 represents} R ¹² , a cyano group, a nitro group, or a halogen atom;
R ⁶ is a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano group, nitro group, Or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a C1-C6 chain hydrocarbon optionally having a hydrogen atom or one or more halogen atoms. Represents a group,
R ¹² is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O). ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R ^11a and R ^12a , together with the nitrogen atom to which they are attached, are a 3-7 membered non-aromatic heterocyclic group (the 3-7 membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. (C3-C6 cycloalkyl) which may have a C1-C3 alkyl group or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D You may do it. },
R ¹⁵ and R ¹⁶ each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, hydroxy group, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group that may have one or more, a C3-C6 alkynyloxy group that may have one or more halogen atoms, a sulfanyl group, or a C1-C6 that may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.
Group F: 1 or more halogen atoms optionally may C1-C6 alkoxy group which may ^{have, NHR 21, NR 21 R 22} , a cyano group, phenyl optionally having one or more substituents selected from the group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group The group which consists of a 3-7 membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one, a C3-C6 alkynyloxy group which may have one or more halogen atoms, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]

Group a; fungicide group b; insecticide, acaricide, nematocide group c; safener group d; plant growth regulator   The plant seed or vegetative propagation organ according to claim 3 or 4, wherein the plant is a genetically modified plant.   The pest control method according to claim 5, wherein the plant is a seed or a vegetative propagation organ.   The pest control method according to claim 5 or 7, wherein the plant is a genetically modified plant.