JPWO2020054712A1 - Pest control agent - Google Patents

Abstract

A compound represented by the formula (1), the formula (2) or the formula (3), a salt thereof, or an N-oxide thereof.

Description

The present invention relates to a compound represented by the formula (1), the formula (2), the formula (3) or a salt thereof, an N-oxide thereof, and a pest control agent containing the compound as an active ingredient.

So far, various compounds have been studied and put into practical use for the purpose of controlling harmful arthropods. For example, Patent Documents 1 and 2 disclose condensed heterocyclic compounds as pest control agents. Further, Patent Documents 3 and 4 describe claims including 2- (pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyridine. A compound that has not been actually synthesized and has a certain [1,2,4] triazolo [1,5-a] pyridine ring is disclosed as a pest control agent in Patent Document 5. Further, Patent Document 6 discloses a certain amide compound. However, no compound having high pest control activity and high practicality has been found.

International Publication No. 2009/131237 International Publication No. 2013/180194 International Publication No. 2013/191113 International Publication No. 2015/000715 JP-A-2018-24657 International Publication No. 2015/068719

An object of the present invention is to provide a novel compound exhibiting excellent control activity against various pests and a pest control agent containing the same as an active ingredient.

As a result of intensive studies, the present inventors have found that the compound represented by the formula (1), the formula (2) or the formula (3) has a high pest control activity, and complete the present invention. I arrived.

Ｇ^１は、Ｇ^１−１、Ｇ^１−２、Ｇ^１−３、Ｇ^１−４又はＧ^１−５で表される構造を表し、

Ｇ^２は、Ｇ^２−１、Ｇ^２−２、Ｇ^２−３、Ｇ^２−４又はＧ^２−５で表される構造を表し、

Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は、各々独立して、水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、（Ｃ＝Ｏ）ＮＹ^１Ｙ^２又は−ＮＹ^１Ｙ^２を表し、
Ａ^１は、Ｃ−Ｒ^Ｃ又はＮを表し、
Ａ^２は、Ｃ−Ｒ^Ｅ又はＮを表し、（ここで、Ａ^１、Ａ^２のどちらか一方はＮであり、もう一方はＣ−Ｒ^Ｃ又はＣ−Ｒ^Ｅである。）
Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｃ、Ｒ^Ｄ及びＲ^Ｅは、各々独立して水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_６シクロアルキル、Ｕによって置換された（Ｃ_３〜Ｃ_６）シクロアルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、５個までのＺで置換されても良いフェノキシ基、Ｃ_１〜Ｃ_６アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、（Ｃ＝Ｏ）ＮＹ^３Ｙ^４、−ＮＹ^３Ｙ^４、シアノ、ニトロ、５個までのＺで置換されても良いフェニル基、４個までのＺで置換されても良いピリジル基、３個までのＺで置換されても良いピリミジル基、３個までの置換基で置換されても良いピラジル基、３個までのＺで置換されても良いピリダジル基、３個までのＺで置換されても良いチエニル基、３個までのＺで置換されても良いフラニル基又はＶを表し、
Ｖは、Ｖ−１、Ｖ−２、Ｖ−３、Ｖ−４、Ｖ−５又はＶ−６で表される構造を表し、

Ｚは、各々独立して水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、−ＮＹ^５Ｙ^６、シアノ又はニトロを表し、
Ｑ２、Ｑ３又はＱ４はＺの置換基数を示し、
Ｑ２は、０、１又は２の整数を表し、
Ｑ３は、０、１、２又は３の整数を表し、
Ｑ４は、０、１、２、３又は４の整数を表し、
Ｑ２、Ｑ３又はＱ４が２以上の整数を表す場合には、複数のＺは互いに同一であっても互いに相異なっていても良く、
Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４、Ｙ^５、Ｙ^６は、各々独立して、水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルコキシカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルコキシカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル又はハロ（Ｃ_１〜Ｃ_６）アルキルスルホニルを表し、
Ｕは、シアノ、−Ｃ（Ｏ）ＯＨ又は−Ｃ（Ｏ）ＮＨ_２を表し、
Ｄは水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、Ｃ_３〜Ｃ_６シクロアルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、Ｃ_１〜Ｃ_３アルキルオキシカルボニル、ハロ（Ｃ_１〜Ｃ_３）アルキルオキシカルボニル、５個までのＴで置換されても良いベンゼンカルボニルを表し、
Ｔは各々独立して水素原子、ハロゲン原子、Ｃ_１〜Ｃ_３アルキル、ハロ（Ｃ_１〜Ｃ_３）アルキル、Ｃ_１〜Ｃ_３アルコキシ、ハロ（Ｃ_１〜Ｃ_３）アルコキシを表し、
Ｅは水素原子、Ｃ_１〜Ｃ_６アルキル、シクロプロピルメチル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、Ｃ_３〜Ｃ_６シクロアルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。］
＜２＞
式（１）又は式（２）又は式（３）で表される化合物若しくはその塩又はそれらのＮ−オキシド。
［式（１）、式（２）及び式（３）中、

Ｇ^１は、Ｇ^１−１、Ｇ^１−２、Ｇ^１−３、Ｇ^１−４又はＧ^１−５で表される構造を表し、

Ｇ^２は、Ｇ^２−１、Ｇ^２−２、Ｇ^２−３、Ｇ^２−４又はＧ^２−５で表される構造を表し、

Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は、各々独立して、水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル又はハロ（Ｃ_１〜Ｃ_６）アルキルスルホニルを表し、
Ａ^１は、Ｃ−Ｒ^Ｃ又はＮを表し、
Ａ^２は、Ｃ−Ｒ^Ｅ又はＮを表し、（ここで、Ａ^１、Ａ^２のどちらか一方はＮであり、もう一方はＣ−Ｒ^Ｃ又はＣ−Ｒ^Ｅである。）
Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｃ、Ｒ^Ｄ及びＲ^Ｅは、各々独立して水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_３〜Ｃ_６シクロアルキル、Ｕによって置換された（Ｃ_３〜Ｃ_６）シクロアルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、−ＮＹ^３Ｙ^４、シアノ、ニトロ又はＶを表し、
Ｖは、Ｖ−１、Ｖ−２、Ｖ−３、Ｖ−４、Ｖ−５又はＶ−６で表される構造を表し、

Ｚは、各々独立して水素原子、ハロゲン原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルコキシ、ハロ（Ｃ_１〜Ｃ_６）アルコキシ、Ｃ_１〜Ｃ_６アルキルチオ、ハロ（Ｃ_１〜Ｃ_６）アルキルチオ、Ｃ_１〜Ｃ_６アルキルスルフィニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルフィニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニル、−ＮＹ^５Ｙ^６、シアノ又はニトロを表し、
Ｑ２、Ｑ３又はＱ４はＺの置換基数を示し、
Ｑ２は、０、１又は２の整数を表し、
Ｑ３は、０、１、２又は３の整数を表し、
Ｑ４は、０、１、２、３又は４の整数を表し、
Ｑ２、Ｑ３又はＱ４が２以上の整数を表す場合には、複数のＺは互いに同一であっても互いに相異なっていても良く、
Ｙ^３、Ｙ^４、Ｙ^５、Ｙ^６は、各々独立して、水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルコキシカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルコキシカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル又はハロ（Ｃ_１〜Ｃ_６）アルキルスルホニルを表し、
Ｕは、複数ある場合には各々独立して、シアノ、−Ｃ（Ｏ）ＯＨ又は−Ｃ（Ｏ）ＮＨ_２を表し、
Ｄは水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニルを表し、
Ｅは水素原子、Ｃ_１〜Ｃ_６アルキル、ハロ（Ｃ_１〜Ｃ_６）アルキル、Ｃ_１〜Ｃ_６アルキルカルボニル、ハロ（Ｃ_１〜Ｃ_６）アルキルカルボニル、Ｃ_１〜Ｃ_６アルキルスルホニル、ハロ（Ｃ_１〜Ｃ_６）アルキルスルホニルを表す。］
＜３＞
Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（１）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜４＞
Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（１）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜５＞
Ｇ^１がＧ^１−１であり、Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（１）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜６＞
Ｇ^１がＧ^１−１であり、Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（１）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜７＞
Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（２）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜８＞
Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（２）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜９＞
Ｇ^２がＧ^２−１であり、Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（２）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１０＞
Ｇ^２がＧ^２−１であり、Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（２）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１１＞
Ｇ^２がＧ^２−１であり、Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮであり、Ｒ^ＡがＣ_１〜Ｃ_３アルキルスルホニルであり、Ｒ^Ｂ、Ｒ^Ｄが水素原子であり、Ｒ^Ｃが５個までのＺで置換されても良いフェニル基又はＶである式（２）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１２＞
２−（３−（エチルスルホニル）−５−（１Ｈ−ピラゾール−１−イル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１８０）、
２−（３−（エチルスルホニル）−５−（２Ｈ−１，２，３−トリアゾール−２−イル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１８１）、
２−（３−（エチルスルホニル）−５−（２−（トリフルオロメチル）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１７４）、
２−（３−（エチルスルホニル）−５−（３−（トリフルオロメチル）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１７５）、
２−（３−（エチルスルホニル）−５−（４−（トリフルオロメチル）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１７６）、
２−（５−（２，４−ビス（トリフルオロメチル）フェニル）−３−（エチルスルホニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン、
２−（５−（３，５−ビス（トリフルオロメチル）フェニル）−３−（エチルスルホニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１７８）、
２−（３−（エチルスルホニル）−５−（２−（トリフルオロメトキシ）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン、
２−（３−（エチルスルホニル）−５−（３−（トリフルオロメトキシ）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号２１４）、
２−（３−（エチルスルホニル）−５−（４−（トリフルオロメトキシ）フェニル）ピリジン−２−イル）−６−（トリフルオロメチル）−［１，２，４］トリアゾロ［１，５−ａ］ピリジン（化合物番号１７７）
＜１３＞
Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（３）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１４＞
Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（３）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１５＞
Ｇ^２がＧ^２−１であり、Ａ^１がＮであり、Ａ^２がＣ−Ｒ^Ｅである式（３）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１６＞
Ｇ^２がＧ^２−１であり、Ａ^１がＣ−Ｒ^Ｃであり、Ａ^２がＮである式（３）で表される＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシド。
＜１７＞
＜１＞〜＜１６＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドと、界面活性剤、固体担体及び液体担体からなる群から選択される少なくとも１つの成分を含む有害生物防除組成物。
＜１８＞
少なくとも１つの他の有害生物防除化合物または薬剤をさらに含む、＜１７＞に記載の有害生物防除組成物。
＜１９＞
前記の少なくとも１つの有害生物防除化合物または薬剤が、
アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、オキサミル、ピリミカルブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、ＸＭＣ、キシリルカルブ、メトルカルブ、フェノチオカルブ、フェノキシカルブ、アセフェート、アザメチホス、アジンホス−エチル、アジンホス−メチル、エチルチオメトン、クロルエトキシホス、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、デメトン−Ｓ−メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、ＥＰＮ、エチオン、エトプロホス、ファムフール、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル＝Ｏ−（メトキシアミノチオホスホリルサリチレート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシジメトンエチル、パラチオン、パラチオン−メチル、ＰＡＰ、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス−メチル、プロフェノホス、プロペタンホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリミホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン、クロルピリホス−エチル、ジスルフォトン、スルプロホス、フルピラゾホス、フェントエート、ホノホス、トリブホス、エンドスルファン、アルファ−エンドスルファン、ガンマ−ＨＣＨ、ジコホル、クロルデン、ディルドリン、メトキシクロル、アセトプロール、フィプロニル、エチプロール、ピラフルプロール、ピリプロール、フルフィプロール、ブロフラニリド、アフォキソラネル、フルララネル、サロラネル、フルキサメタミド、ロティラネル、イソシクロシラム、アクリナトリン、アレスリン、ｄ−ｃｉｓ−ｔｒａｎｓアレスリン、ｄ−ｔｒａｎｓアレスリン、ビフェントリン、カッパ−ビフェントリン、ビオアレスリンＳ−シクロペンテニル、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ−シフルトリン、シハロトリン、ラムダ−シハロトリン、ガンマ−シハロトリン、シペルメトリン、アルファ−シペルメトリン、ベータ−シペルメトリン、シータ−シペルメトリン、ゼータ−シペルメトリン、シフェノトリン、デルタメトリン、エンペントリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ−フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、カッパ−テフルトリン、フタルスリン、テトラメトリン、トラロメトリン、トランスフルトリン、メトキサジアゾン、メトフルトリン、プロフルトリン、ピレトラム、テラレトリン、モンフルオロスリン、ヘプタフルトリン、メペルフルスリン、テトラメチルフルスリン、ジメフルトリン、クロロパラレスリン、イプシロン−メトフルスリン、イプシロン−モンフルオスリン、プロトリフェンブト、アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、スルホキサフロル、フルピラジフロン、トリフルメゾピリム、ジクロロメゾチアズ、フルピリミン、スピノサド、スピネトラム、アバメクチン、イベルメクチン、エマメクチン安息香酸塩、ミルベメクチン、レピメクチン、ヒドロプレン、キノプレン、ジオフェノラン、メトプレン、ピリプロキシフェン、ピメトロジン、フロニカミド、エトキサゾール、ジアフェンチウロン、アゾシクロチン、シヘキサチン、酸化フェンブタスズ、プロパルギット、テトラジホン、クロルフェナピル、トラロピリル、ＤＮＯＣ、ベンスルタップ、カルタップ、チオシクラム、チオスルタップ、チオスルタップ−ナトリウム、ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン、ビストリフルロン、ブプロフェジン、シロマジン、クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド、アミトラズ、ヒドラメチルノン、アセキノシル、フルアクリピリム、ピリミノストロビン、フルフェノキシストロビン、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、ピフルブミド、メタフルミゾン、スピロジクロフェン、スピロテトラマト、スピロメシフェン、スピロピディオン、シフルメトフェン、シエノピラフェン、フルベンジアミド、クロラントラニリプロール、シアントラニリプロール、シクラニリプロール、テトラニリプロール、シハロジアミド、テトラクロラントラニリプロール、キノメチオネート、ヘキシチアゾクス、ビフェナゼート、フルフェネリム、ピリフルキナゾン、フロメトキン、フルオピラム、フルアザインドリジン、アミドフルメト、チクロピラゾフロル、チオキサザフェン、オキサゾスルフィル、
ニコチン、クロロピクリン、フッ化スルフリル、クリロチエ、クロフェンテジン、ジフロビダジン、ロテノン、インドキサカルブ、ピペロニルブトキシド、クロルジメホルム、ピリダリル、アザジラクチン、ベンゾキシメート、アフィドピロペン、フルヘキサホン、フルエンスルホン、ベンクロチアズ、カルゾール、殺虫性石鹸、ジメヒポ、ニチアジン、ホウ酸塩、メタアルデヒド、リアノジン、スルフルラミド、アシノナピル、ベンズピリモキサン、３−ブロモ−Ｎ−（２，４−ジクロロ−６−（メチルカルバモイル）フェニルイル）−１−（３，５−ジクロロピリジン−２−イル）−１Ｈ−ピラゾール−５−カルボキサミド、
メタラキシル、メタラキシル−Ｍ、オキサジキシル、オフラセ、ベナラキシル、ベナラキシル−Ｍ、キララキシル、オフラース、フララキシル、シプロフラン、ブプリメート、ジメチリモール、エチリモール、ヒメキサゾール、ヒドロキシイソキサゾール、オキサチアピプロリン、オクチリノン、オキソリニック酸、ベノミル、チオファネートメチル、カーベンダジム、フベリダゾール、チアベンダゾール、デバカルブ、ジエトフェンカルブ、ゾキサミド、エタボキサム、ペンシクロン、フルオピコリド、フルオピモミド、ジフルメトリム、ブピリメート、ベノダニル、フルトラニル、メプロニル、イソフェタミド、フェンフラム、オキシカルボキシン、カルボキシン、チフルザミド、フルキサピロキサド、フラメトピル、ペンフルフェン、ペンチオピラド、ベンゾビンジフルピル、ビキサフェン、イソピラザム、セダキサン、インピルフルキサム、フルインダピル、イソフルシプラム、ピラプロポイン、ボスカリド、アゾキシストロビン、コウメトキシストロビン、クレソキシムメチル、トリフロキシストロビン、ピコキシストロビン、ピラクロストロビン、ジモキシストロビン、メトミノストロビン、オリサストロビン、フルオキサストロビン、ピラオキシストロビン、ピラメトストロビン、フルフェノキシストロビン、フェナミンストロビン、エノキサストロビン、クモキシストロビン、マンデストロビン、トリクロピリカルブ、ファモキサドン、フェンアミドン、トリクロピリカルブ、ピリベンカルブ、シアゾファミド、アミスルブロム、ビナパクリル、メプチルジノカルブ、ジノカップ、フルアジナム、フェリムゾン、酢酸−フェンチン、塩化フェンチン、水酸化フェンチン、水酸化トリフェニルスズ、酢酸トリフェニルスズ、オキシン銅、シルチオファム、アメトクトラジン、メパニピリム、ニトラピリン、ピリメサニル、シプロジニル、ブラストサイジンＳ、カスガマイシン、カスガマイシン塩酸塩水和物、ストレプトマイシン、オキシテトラサイクリン、キノキシフェン、プロキナジド、フルジオキソニル、フェンピクロニル、フルオロイミド、プロシミドン、イプロジオン、ビンクロゾリン、エジフェンホス、イプロベンホス、ピラゾホス、イソプロチオラン、プロパモカルブ、プロパモカルブ塩酸塩、ゴセイカユプテ抽出物、トリホリン、ピリフェノックス、ピリソキサゾール、フェナリモル、ヌアリモル、アザコナゾール、ブロムコナゾール、ジニコナゾール、ジニコナゾール−Ｍ、エポキシコナゾール、フルキンコナゾール、オキスポコナゾール、ペフラゾエート、ジフェノコナゾール、フェンブコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、ウニコナゾール、イマザリル、ビテルタノール、トリフルミゾール、エタコナゾール、プロピコナゾール、ペンコナゾール、フルシラゾール、フルトリアホール、ミクロブタニル、パクロブトラゾール、プロチオコナゾール、シプロコナゾール、テブコナゾール、ヘキサコナゾール、プロクロラズ、シメコナゾール、イプフェントリフルコナゾール、アルジモルフ、ドデモルフ、酢酸ドデモルフ、トリデモルフ、フェンプロピモルフ、ジメトモルフ、フルモルフ、ピリモルフ、ピペラリン、フェンプロピディン、スピロキサミン、フェンヘキサミド、フェンピラザミン、フェルバム、メタム、メタスルホカルブ、メチラム、チラム、マンゼブ、マンネブ、ジネブ、ジラム、ポリカーバメート、プロビネブ、チウラム、ピリブチカルブ、バリダマイシン、ミルジオマイシン、ポリオキシン、ベンチアバリカルブ、ベンチアバリカルブイソプロピル、バリフェナレート、イプロバリカルブ、マンジプロパミド、フェンピコキサミド、フロリルピコキサミド、フサライド、ピロキロン、トリシクラゾール、カルプロパミド、ジクロシメット、フェノキサニル、アシベンゾラル−Ｓ−メチル、プロベナゾール、ジクロベンチアゾクス、チアジニル、イソチアニル、シモキサニル、ホセチル、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、シフルフェナミド、メトラフェノン、ピリオフェノン、フルチアニル、テブフロキン、イプフルフェノキン、ホセチルアルミニウム、トルクロホス−メチル、エクロメゾール、トルプロカルブ、メフェントリフルコナゾール、キノフメリン、ピジフルメトフェン、ボルドー混合液、酢酸銅、塩基性硫酸銅、オキシ塩化銅、水酸化第二銅、オキシキノリン銅、銅、硫黄、キャプタン、カプタホール、フォルペット、アニラジン、クロロタロニル、ジクロロフェン、ペンタクロロフェノール及びその塩、ヘキサクロロベンゼン、キントゼン、イミノクタジン酢酸塩、イミノクタジンアルベシル酸塩、グアニジン、ドジン、ドジン遊離塩基、グアザチン、グアザチン酢酸塩、アルベシレート、ジチアノン、フルオルイミド、トリルフルアニド、ジクロフルアニド、ジノブトン、ダゾメット、ピラジフルミド、アミノピリフェン、メチルテトラプロール、ピリダクロメチル、
ジピメチトロン、ピカルブトラゾクス、テクナゼン、ニトルタール−イソプロピル、ジシクロメット、アシベンゾラル、プロヘキサジオン−カルシウム、ブロノポール、ジフェニルアミン、フルメトベル、ベントキサジン、ビフェニル、クロロネブ、ＣＮＡ、ヨードカルブ、プロチオカルブ、並びに
Ｂａｃｉｌｌｕｓ属、及びそれらにより産生された殺虫性タンパク、殺菌性タンパク、Ｂｔ作物により産生された殺虫性タンパク、殺菌性タンパク、昆虫病原性バクテリア、昆虫病原性ウイルスおよび昆虫病原性菌類
からなる群から選択される、＜１８＞に記載の有害生物防除組成物。
＜２０＞
前記有害生物が動物寄生性害虫であり、動物又は鳥類に投与される＜１８＞に記載の有害生物防除組成物。
＜２１＞
有害生物またはその環境に＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドを有害生物に接触させる、有害生物を防除する方法。
＜２２＞
作物の活力を高める方法であって、作物又は作物の種子に＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドを接触させる、前記方法。
＜２３＞
＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドで処理された種子であって、処理後の種子全体の約０．０００１〜約５０重量％の量の＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドを含む、前記種子。
＜２４＞
＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドで作物の種子を処理する工程を含む、種子の製造方法であって、
処理後の種子が種子全体の約０．０００１〜約５０重量％の量の＜１＞に記載の化合物若しくはその塩又はそれらのＮ−オキシドを含む、
前記方法。That is, the present invention relates to, but is not limited to:
<1>
A compound represented by the formula (1), the formula (2) or the formula (3), a salt thereof, or an N-oxide thereof.
[In equations (1), (2) and (3),

G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by ^G 1 -4 or ^G 1 -5,

G ^{2 is, G 2 -1, G 2 -2} , G 2 -3, represents a structure represented by ^G 2 -4 or ^G 2 -5,

R ¹ , R ² , R ³ and R ⁴ are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo ( C _{1 to} C ₆ ) Alkoxy, halo (C _{1 to} C ₆ ) alkylthio, halo (C _{1 to} C ₆ ) alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, (C = O) NY ¹ Y ² or -Represents NY ¹ Y ²
A ¹ represents C- ^RC or N,
A ² represents a ^{C-R E} or N, (and ^where either of A 1, ^{A 2} is N, and the other is ^{C-R C,} or ^{C-R E.)
R A, R B, R C} , R D and ^{R E} are each independently a hydrogen atom, a halogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C _{6) alkyl,} C 3 -C ₆ cycloalkyl , U substituted (C _{3 to} C ₆ ) cycloalkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, phenoxy groups optionally substituted with up to 5 Z, C ₁ to C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Sulfonyl, (C = O) NY ³ Y ⁴ , -NY ³ Y ⁴ , cyano, nitro, a phenyl group that may be substituted with up to 5 Z, a pyridyl group that may be substituted with up to 4 Z, Pyrimidyl group optionally substituted with up to 3 Zs Pyramidyl group optionally substituted with up to 3 substituents Pyridazyl group optionally substituted with up to 3 Zs substituted with up to 3 Zs Represents a thienyl group that may be substituted, a furanyl group or V that may be substituted with up to 3 Zs,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6.

Z is independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C ₁ to C. C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Represents sulfonyl, -NY ⁵ Y ⁶ , cyano or nitro,
Q2, Q3 or Q4 indicate the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3 and represents
Q4 represents an integer of 0, 1, 2, 3 or 4.
When Q2, Q3 or Q4 represent an integer of 2 or more, the plurality of Zs may be the same as each other or different from each other.
Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ , and Y ⁶ are independent hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, and C _{1 to} C ₆ alkyl, respectively. Carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkoxycarbonyl, halo (C _{1 to} C ₆ ) alkoxy carbonyl, C _{1 to} C ₆ alkyl sulfonyl or halo (C _{1 to} C ₆ ) alkyl sulfonyl Represents
U represents cyano, -C (O) OH or -C (O) NH ₂ .
D is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{3 to} C ₆ cycloalkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, C _{1 to} C ₃ alkyloxycarbonyl, halo (C _{1 to} C ₃ ) alkyloxycarbonyl, even if substituted with up to 5 Ts Represents a good benzenecarbonyl,
T independently represents a hydrogen atom, a halogen atom, C _{1 to} C ₃ alkyl, halo (C _{1 to} C ₃ ) alkyl, C _{1 to} C ₃ alkoxy, and halo (C _{1 to} C ₃ ) alkoxy.
E is a hydrogen atom, C _{1 to} C ₆ alkyl, cyclopropyl methyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{3 to} C ₆ cycloalkyl carbonyl, halo (C _{1 to} C _6). ) Alkylcarbonyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
<2>
A compound represented by the formula (1), the formula (2) or the formula (3), a salt thereof, or an N-oxide thereof.
[In equations (1), (2) and (3),

G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by ^G 1 -4 or ^G 1 -5,

G ^{2 is, G 2 -1, G 2 -2} , G 2 -3, represents a structure represented by ^G 2 -4 or ^G 2 -5,

R ¹ , R ² , R ³ and R ⁴ are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo ( Represents C _{1 to C 6} ) alkoxy, halo (C _{1 to} C ₆ ) alkylthio, halo (C _{1 to} C ₆ ) alkyl sulfinyl or halo (C _{1 to} C ₆ ) alkyl sulfonyl.
A ¹ represents C- ^RC or N,
A ² represents a ^{C-R E} or N, (and ^where either of A 1, ^{A 2} is N, and the other is ^{C-R C,} or ^{C-R E.)
R A, R B, R C} , R D and ^{R E} are each independently a hydrogen atom, a halogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C _{6) alkyl,} C 3 -C ₆ cycloalkyl , U-substituted (C _{3 to} C ₆ ) cycloalkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkyl thio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, -NY ³ Y ⁴ , cyano, nitro or V Represent,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6.

Z is independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C ₁ to C. C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Represents sulfonyl, -NY ⁵ Y ⁶ , cyano or nitro,
Q2, Q3 or Q4 indicate the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3 and represents
Q4 represents an integer of 0, 1, 2, 3 or 4.
When Q2, Q3 or Q4 represent an integer of 2 or more, the plurality of Zs may be the same as each other or different from each other.
Y ³ , Y ⁴ , Y ⁵ , and Y ⁶ are independent hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, and halo (C _1). Represents ~ C ₆ ) alkylcarbonyl, C ₁ ~ C ₆ alkoxycarbonyl, halo (C ₁ ~ C ₆ ) alkoxycarbonyl, C ₁ ~ C ₆ alkyl sulfonyl or halo (C ₁ ~ C ₆ ) alkyl sulfonyl.
U represents cyano, -C (O) OH or -C (O) NH _{2 independently when there are a plurality of U.}
D is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkyl sulfonyl, halo. (C _{1 to} C ₆ ) Represents an alkylsulfonyl,
E is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkyl sulfonyl, halo. (C _{1 to} C ₆ ) Represents an alkylsulfonyl. ]
<3>
The compound according to <1> represented by the formula (1) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.}
<4>
The compound according to <1> represented by the formula (1) in which A ¹ is C- ^RC and A ^{2 is N, a salt thereof, or an N-oxide thereof.}
<5>
G ¹ is a ^G 1 -1, ^{A 1} is N, ^{A 2} is ^{C-R E} Formula (1) represented by <1> according to compounds or their salts or their N- oxide ..
<6>
G ¹ is a ^G 1 -1, ^{A 1} is ^C-R C, ^{A 2} is N Equation (1) represented by <1> according to compounds or their salts or their N- oxide ..
<7>
The compound according to <1> represented by the formula (2) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.}
<8>
The compound according to <1> represented by the formula (2) in which A ¹ is C- ^RC and A ^{2 is N, a salt thereof, or an N-oxide thereof.}
<9>
G ² is ^G 2 -1, ^{A 1} is N, ^{A 2} is ^C-R a ^E represented by the formula (2) <1> according to compounds or their salts or their N- oxide ..
<10>
G ² is ^G 2 -1, ^{A 1} is ^C-R C, ^{A 2} is N Equation (2) is represented by <1> according to compounds or their salts or their N- oxide ..
<11>
G ² is ^G 2 -1, ^{A 1} is ^C-R C, ^{A 2} is N, ^{R A} is _C 1 -C ₃ ^{alkylsulfonyl, R B,} R ^D is hydrogen atom , ^{The compound according to <1> represented by the formula (2), in which RC} is a phenyl group or V which may be substituted with up to 5 Z, or a salt thereof, or an N-oxide thereof.
<12>
2- (3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a ] Pyridine (Compound No. 180),
2- (3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] Pyridine (Compound No. 181),
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 174),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 175),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 176),
2- (5- (2-4-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine,
2- (5- (3,5-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine (Compound No. 178),
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 214),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 177)
<13>
The compound according to <1> represented by the formula (3) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.}
<14>
The compound according to <1> represented by the formula (3) in which A ¹ is C- ^RC and A ^{2 is N, a salt thereof, or an N-oxide thereof.}
<15>
G ² is ^G 2 -1, ^{A 1} is N, ^{A 2} is ^{C-R E} the formula (3) represented by <1> according to compounds or their salts or their N- oxide ..
<16>
G ² is ^G 2 -1, ^{A 1} is ^C-R C, ^{A 2} is N Equation (3) represented by <1> according to compounds or their salts or their N- oxide ..
<17>
A pest control composition containing the compounds according to <1> to <16>, salts thereof, or N-oxides thereof, and at least one component selected from the group consisting of a surfactant, a solid carrier, and a liquid carrier.
<18>
The pest control composition according to <17>, further comprising at least one other pest control compound or agent.
<19>
The at least one pest control compound or agent described above
Aranicarb, Ardicalve, Bendiocarb, Benfracarb, Butocamide, Butoxycarboxym, Carballyl, Carbofuran, Carbosulfan, Ethiophenecarb, Phenocalve, Formethanate, Frathiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamil, Pyrimicalve, Propoxul, Thiodicalbu Knox, triazamate, trimetacarb, XMC, xylylcarb, methylcarb, phenothiocarb, phenoxycarb, acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, ethylthiomethone, chlorethoxyphos, cassaphos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos , Kumaphos, Cyanophos, Demeton-S-Methyl, Diadinone, Dichlorpyrifos, Diclotophos, Dimethate, Dimethylbinphos, EPN, Etion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostiazeto, Heptenophos, Imiciaphos, Isophenphos, Isophenphos, Isophenphos Methoxyaminothiophosphoryl salicylate, isoxathione, malathion, mecarbam, metamidphos, metidation, mevinphos, chlorpyrifos, naredo, ometoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, holate, hosalon, hosmet, phosphamide, hoxim, pyrimiphos -Methyl, Prophenofus, Propetanphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimiphos, Temephos, Telbuphos, Tetrachlorbinphos, Thiometon, Triazophos, Trichlorfon, Bamidethione, Chlorpyrifos-Ethyl, Disulphoton, Sulfrophos, Flupyrazophos, Fent. Tribphos, Endosulfan, Alpha-Endosulfan, Gamma-HCH, Dichoform, Chlorpyrifos, Dildoline, methoxychlor, Acetoprol, Fipronil, Etiprol, Pyrafluprol, Pyriprol, Fulfiprol, Brofuranilide, Afoxolanel, Fluraranel, Salolanel, Fluxamethamide, Rotyranel, Iso , Aclinatrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifentrin, Kappa-Bifen Trin, bioarethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cypermethrin, beta-cypermethrin, cypermethrin, lambda-cypermethrin, gamma-cypermethrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta -Cypermethrin, cypermethrin, deltamethrin, empentrin, esphenothrin, etofenprox, phenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadesrin, permethrin, phenothrin, prarethrin , Pyrethrin, resmethrin, cypermethrin, tefurthrin, kappa-tefurthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, metoxadiazone, metoflutrin, profluthrin, pyrethrum, terraretrin, monfluorothrin, heptafluthrin, mepermethrin, tetra Chloroparalesulin, epsilon-methfurthrin, epsilon-monfluthrin, protrifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitempyram, thiacloprid, thiamethoxam, sulfoxaflor, flupyraziflon, triflumesopyrim, dichloromesopyrim Spinetram, Abamectin, Ibermectin, Emamectin benzoate, Milbemectin, Repimectin, Hydroprene, Kinoprene, Diophenolan, Metoprene, Pyryproxifene, Pymetrodin, Flonicamid, Etoxazole, Diaphenthiron, Azocyclotin, Cypermethrin, Diafenthiron, Azocyclotin, Cypermethrin, Fenbutazin oxide, Propargit , Tralopyrin, DNOC, Bensultap, Cartap, Thiocyclum, Thiosultap, Thiosultap-Sodium, Bistriflulon, Chlorfluazuron, Diflubenzron, Flucycloxuron, Fluphenoxron, Hexaflumron, Ruphenuron, Novalron, Noviflumron, Tefluvenzron, Triflumron , Bistriflulon, buprofezin, cypermethrin, chromaphenozide, halophenothrin, methoxyphenothrin, tebuphenozide, amitraz, hydramethylnone, acequinosyl, fluacripyrethrin Mu, pyriminostrobin, fluphenoxystrobin, phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, pifrubmid, metaflumizone, spirodiclofen, spirotetramato, spiromesifene, spiropidion, siflumethofen, cienopyraffe, flubendiamide , Chlorantraniliprole, Cyantraniliprole, Cycraniliprole, Tetraniliprole, Sihalodiamide, Tetrachlorantraniliprole, Kinomethionate, Hexithiazox, Biphenazate, Fluphenerim, Pyrifluquinazone, Frometkin, Fluopirum, Fluazaindolizine, Amidoflumeth , Tyclopyrazoflor, Thioxazaphen, Oxazosulfyl,
Nicotin, chloropicrin, sulfuryl fluoride, chrylotie, clofentezine, difluorovidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeholm, pyridaryl, azadilactin, benzoximate, afidopyropen, fluhexaphon, fluenesulfone, bencrothias, calcole, insecticidal soap Dimehipo, nithiazine, borate, metaaldehyde, lianodine, sulfurylamide, asinonapill, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3, 5-Dichloropyridin-2-yl) -1H-pyrazole-5-carboxamide,
Metalaxil, Metalaxil-M, Oxadixil, Ophrase, Benalaxil, Benalaxil-M, Kiralaxil, Ophras, Flaluxil, Ciproflan, Buprimate, Dimethyrimol, Etilimol, Himexazole, Hydroxyisoxazole, Oxatiapiproline, Octinone, Oxolinic acid, Benomylic acid , Carbendazim, Huberidazole, Thiabendazole, Devacarb, Dietofencarb, Zoxamide, Etaboxam, Pencyclon, Fluopicolid, Fluopimomid, Diflumethrim, Bupyrimate, Benodanyl, Flutranyl, Mepronil, Isophytamide, Fenfuram, Oxycarboxyn, Carboxone , Penflufen, penthiopyrado, benzobindiflupill, bixaphen, isopyrazam, sedaxane, impilfluxam, fluindapir, isoflusiplum, pyrapropoin, boscalide, azoxystrobin, koumethoxystrobin, cresoximemethyl, trifloxystrobin, picoxy Strobin, Pyracrostrobin, Dimoxystrobin, Metominostrobin, Orisastrobin, Fluoxastrobin, Pyraoxystrobin, Pyrametstrobin, Fluphenoxystrobin, Phenaminestrobin, Enoxastrobin, Spumoxystrobin, Mandestrobin, triclopyricalve, famoxadon, fenamiden, triclopyricalve, pyribenecarb, siazophamid, amisulbrom, vinapacryl, meptyldinocarb, dinocup, fluazinum, ferimzone, acetate-fentin, fentin chloride, fentin hydroxide, trihydroxide Phenyltin, triphenyltin acetate, copper oxine, silthiofam, amethoctrazine, mepanipyrim, nitrapyrin, pyrimesanyl, cyprodinyl, blastsaidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyphene, proquinazide, fludioxonyl, fenpicronyl, fluoro. Imid, procimidone, iprodione, binclozoline, edifenphos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseikayupte extract, triphorin, pyriphenox, pyrisoxazole, phenalimol, nuari Mol, azaconazole, bromconazole, diniconazole, diniconazole-M, epoxyconazole, flukinconazole, oxpoconazole, pefrazoate, diphenoconazole, fembconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triazimephone, tri. Azimenol, triticonazole, uniconazole, imazalyl, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriahole, microbutanyl, paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaco Nazole, Prochloraz, Simeconazole, Ipfentrifluconazole, Aldimorph, Dodemorph, Dodemorph acetate, Tridemorph, Fenpropimorph, Dimethmorph, Fulmorph, Pyrimorph, Piperarin, Fenpropidine, Spiroxamine, Fenhexamide, Fenpyrazamine, Felbam, Metam Calve, Methylam, Tiram, Manzeb, Manneb, Dineb, Diram, Polycarbamate, Provineb, Thiuram, Pyribuchicarb, Varidamycin, Mildiomycin, Polyoxin, Benchavaricarb, Benchavaricarb isopropyl, Variphenalate, Iprovaricarb, Mandipropamide, Fempicoxamide, Florylpicoxamide, Fusalide, Pyrochylone, Tricyclazole, Carpropamide, Diclosimet, Phenoxanyl, Acibenzoral-S-methyl, Provenazole, Diclobenazox, Thiazinyl, Isothianyl, Simoxanyl, Josetil, Teclophthalam, Triazoxide, Flusulfamide, Dichromedin, ciflufenamide, metrafenone, periodofenone, fluthianyl, tebuflokin, ipfluphenokin, Josetylaluminum, turquophos-methyl, ecromezol, tolprocarb, mefentrifluconazole, quinofmerin, pidiflumethofen, Bordeaux mixture, copper acetate, basic sulfate Copper, oxychloride, cupric hydroxide, oxyquinolin copper, copper, sulfur, captan, captahole, forpet, anilazine, chlorotalonyl, dichlorophene, pentachlorophenol and its salts, hexachlorobenzene, quintozen, iminoctadine acetate, Imminoctadine albesilate, guanidine, copper, copper Free base, guazatin, guazatin acetate, albecilate, dithianone, fluoroimide, trillfluanide, diclofluanide, dinobutone, dasomet, pyraziflumid, aminopyriphen, methyltetraprol, pyridaclomethyl,
Produced by dipimethitron, picarbutrazox, technazen, nitrtal-isopropyl, dicyclomet, asibenzoral, prohexadione-calcium, bronopole, diphenylamine, flumethobelle, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, and the genus Bacillus. Described in <18>, selected from the group consisting of insecticidal proteins, bactericidal proteins, insecticidal proteins produced by Bt crops, bactericidal proteins, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi. Pest control composition.
<20>
The pest control composition according to <18>, wherein the pest is an animal parasitic pest and is administered to an animal or a bird.
<21>
A method for controlling a pest by bringing the compound according to <1> or a salt thereof or an N-oxide thereof into contact with the pest or its environment.
<22>
The method for enhancing the vitality of a crop, wherein the crop or the seeds of the crop are brought into contact with the compound according to <1>, a salt thereof, or N-oxides thereof.
<23>
The compound according to <1> or a salt thereof or a seed treated with N-oxide thereof, and the amount of the compound according to <1> is about 0.0001 to about 50% by weight of the whole treated seed. Or the seeds comprising salts thereof or their N-oxides.
<24>
A method for producing seeds, which comprises a step of treating crop seeds with the compound according to <1>, a salt thereof, or N-oxides thereof.
The treated seeds contain an amount of about 0.0001 to about 50% by weight of the total seeds of the compound according to <1> or a salt thereof or N-oxides thereof.
The method.

The compounds represented by the formulas (1), (2) and (3) according to the present invention or salts thereof or their N-oxides show extremely excellent control effects on pests, and are pest control agents. It is useful as.

In the present specification, the definitions and meanings of the following terms are as follows.

In addition, the compounds included in the present invention include optically active substances due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms or axial asymmetry, but the present invention includes all optics. Includes active or racemic forms.

In addition, the compounds included in the present invention may have tautomers depending on the type of substituent, but the present invention is a mixture of all tautomers or tautomers contained in any proportion. It includes.

In addition, the compounds included in the present invention may contain geometric isomers due to imino groups, but the present invention includes all geometric isomers or a mixture of geometric isomers contained in an arbitrary ratio. It is a thing.

The geometric isomer resulting from the imino group is composed of, for example, a bond represented by a wavy line between D represented by the formula (1) and an imino group nitrogen atom, and forms an E-form, a Z-form, or an E-form and a Z-form. Indicates a mixture of isomers contained in any proportion.

Among the compounds included in the present invention, those which can be salted according to a conventional method are, for example, salts of hydrohalogenic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid. Salts of inorganic acids such as nitrate, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, formic acid, Salts of carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, glutamic acid, Amino acid salts such as aspartic acid, alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, aluminum salts, tetramethylammonium salts, tetrabutylammonium salts and benzyltrimethylammonium salts. Etc. are quaternary ammonium salts.

In the compound of the present invention, the N-oxide is a compound in which the nitrogen atom constituting the ring on the heterocycle is oxidized. Examples of the heterocycle capable of forming an N-oxide include a fused ring containing a pyridine ring.

Next, specific examples of each substituent shown in the present specification are shown below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and c- means cyclo.

Examples of the "halogen atom" in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In addition, the notation of "halo" in this specification also represents these halogen atoms.

_{The notation "C a to} C _b alkyl" in the present specification represents a linear or branched hydrocarbon group having a to b carbon atoms, for example, a methyl group, an ethyl group, or n-. Specific examples include propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group and the like. It is listed and selected within the range of each specified number of carbon atoms.

In the present specification, _{the notation of "halo (C a to} C _b ) alkyl" is a direct number of carbon atoms consisting of a to b, in which a hydrogen atom bonded to a carbon atom is replaced by a number of halogen atoms. Representing a chain or branched hydrocarbon group, when substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 1-fluoroethyl group, 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2 2-Trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, 2-chloro- 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2 , 2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2 , 2,2-Trifluoro-1- (methyl) ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (tri Specific examples include fluoromethyl) ethyl group, 2,2,3,4,5,4-hexafluorobutyl group, 2,2,3,3,4,5,4-heptafluorobutyl group, nonafluorobutyl group and the like. It is selected in the range of each specified number of carbon atoms.

The notation "C _{a to} C _b cycloalkyl" represents a cyclic hydrocarbon group having a to b carbon atoms and forms a monocyclic or complex ring structure from a 3-membered ring to a 6-membered ring. Can be done. Further, each ring may be optionally substituted with an alkyl group within a specified number of carbon atoms. For example, a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like are given as specific examples, and each designated carbon atom is given. Selected in a range of numbers.

The notation "C _{a to} C _b alkoxy" represents the above-mentioned alkyl-O-group having a number of carbon atoms consisting of a to b, for example, a methoxy group, an ethoxy group, an n-propyloxy group, or i-. Specific examples include a propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, a 2-ethylhexyloxy group, etc., which are selected within the specified number of carbon atoms. NS.

The notation "halo (C _{a to} C _b ) alkoxy" represents the haloalkyl-O- group having the above-mentioned meaning consisting of a to b carbon atoms, and for example, a difluoromethoxy group, a trifluoromethoxy group, or a chlorodifluoro. Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2,-tetrafluoroethoxy group, 2-chloro-1 , 1,2-Trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like are given as specific examples, and are selected within the range of each designated carbon atom number.

The notation "C _{a to} C _b alkylthio" represents an alkyl-S-group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylthio group, an ethylthio group, an n-propylthio group, or an i-propylthio. Specific examples include a group, an n-butylthio group, an i-butylthio group, an s-butylthio group, a tert-butylthio group and the like, and each group is selected within a specified number of carbon atoms.

The notation of "halo (C _{a to} C _b ) alkylthio" in the present specification represents the haloalkyl-S- group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethylthio group and a trifluoro group. Methylthio group, chlorodifluoromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-tri Fluoroethylthio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (tri) Specific examples thereof include a fluoromethyl) ethylthio group and a nonafluorobutylthio group, which are selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkylsulfinyl" represents the above-mentioned meaning alkyl-S (O) -group consisting of a to b carbon atoms, for example, methylsulfinyl group, ethylsulfinyl group, n-. Specific examples include a propylsulfinyl group, an i-propylsulfinyl group, an n-butylsulfinyl group, an i-butylsulfinyl group, an s-butylsulfinyl group, a tert-butylsulfinyl group, and the like, and each has a specified range of carbon atoms. Is selected with.

The notation of "halo (C _{a to} C _b ) alkylsulfinyl" in the present specification represents the haloalkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethyl. Sulfinyl group, trifluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ) Ethylsulfinyl group, nonafluorobutylsulfinyl group and the like are given as specific examples, and are selected within the range of each specified number of carbon atoms.

The notation "C _{a to} C _b alkylsulfonyl" represents an alkyl-SO ₂ -group having the above meaning consisting of a to b carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, or an n-propylsulfonyl group. Specific examples include groups, i-propylsulfonyl groups, n-butylsulfonyl groups, i-butylsulfonyl groups, s-butylsulfonyl groups, tert-butylsulfonyl groups, etc., which are selected within the specified number of carbon atoms. Will be done.

The notation of "halo (C _{a to} C _{b ) alkylsulfonyl" in the present specification represents the haloalkyl-SO 2} -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethylsulfonyl group. , Trifluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1 , 1,2-Trifluoroethylsulfonyl group and the like are given as specific examples, and are selected within the range of each specified number of carbon atoms.

The notation "C _{a to} C _b alkylcarbonyl" represents the above-mentioned meaning alkyl-C (O) -group having a number of carbon atoms of a to b, for example, an acetyl group, a propionyl group, a butyryl group, and the like. Specific examples thereof include an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a hexanoyl group, and a heptanoyle group, and each group is selected within a specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkylcarbonyl" represents the haloalkyl-C (O) -group having the above meaning consisting of a to b carbon atoms, for example, a fluoroacetyl group and a chloroacetyl group. Group, difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropa A noyl group or the like is given as a specific example, and each is selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkoxycarbonyl" represents the alkyl-OC (O) -group having the above meaning consisting of a to b carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, and the like. Specific examples thereof include n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, s-butoxycarbonyl group, tert-butoxycarbonyl group, 2-ethylhexyloxycarbonyl group and the like. Is selected in the range of each specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkoxycarbonyl" represents the haloalkyl-OC (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a chloromethoxycarbonyl group. , 2-Chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group and the like are given as specific examples, respectively. It is selected in the range of the specified number of carbon atoms in.

_{The notation "(C a to} C _b ) cycloalkyl substituted by U" is described above, wherein the hydrogen atom bonded to the carbon atom is replaced by an arbitrary number of U, and the number of carbon atoms is a to b. Represents the meaning cycloalkyl group and is selected within the range of each specified number of carbon atoms. At this time, _{when there are two or more substituents U on each (C a to} C _b ) cycloalkyl group, each U may be the same as or different from each other.

In the compound or its salts or their N- oxide represented by the formula (1) of the present invention, preferably, ^{G 1 is G 1 -1, R 1, R} 2, R 3 and ^{R 4,} Independently, hydrogen atom, halogen atom, halo (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkylthio, halo (C _{1 to} C ₆ ) alkyl sulfinyl, halo (C _{1 to} C ₆ ) Alkoxysulfonyl, ^RA is C _{1 to} C ₃ alkoxy, halo (C _{1 to} C ₃ ) alkoxy, C _{1 to} C ₃ alkyl thio, halo (C _{1 to} C ₃ ) alkyl thio, C _{1 to} C ₃ alkyl sulfonyl. , halo _(C 1 _{~C 3)} alkylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 1} is ^{C-R C} or N, a ² is a ^{C-R E} or N, ^(wherein either of a 1, ^{a 2} is N, the other is ^{C-R C,} or ^{C-R E.), R} B, ^RC , R ^D and ^RE are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, respectively. each independently may be substituted with Z up to five by phenyl, V-2, V-4 , V-5, a V-6, D is a hydrogen _atom, C 1 -C ₃ alkyl, halo (C _{1 to} C ₃ ) Alkoxy, C _{1 to} C ₆ Alkoxycarbonyl, C _{3 to} C ₆ Cycloalkylcarbonyl, Halo (C _{1 to} C ₆ ) Alkoxycarbonyl, C _{1 to} C ₃ Alkoxysulfonyl, Halo (C _{1 to} C ₃₎ ) _{alkylsulfonyl,} C 1 -C ₃ alkyloxycarbonyl, halo _(C 1 -C ₃₎ alkyloxycarbonyl, are each independently may be substituted with T up to five with benzene carbonyl, T is hydrogen atom, Halogen atom, C _{1 to} C ₃ alkyl, halo (C _{1 to} C ₃ ) alkyl, C _{1 to} C ₃ alkoxy, halo (C _{1 to} C ₃ ) alkoxy, E is hydrogen atom, C _{1 to} C ₆ Alkoxy, cyclopropylmethyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkylcarbonyl, C _{3 to} C ₆ cycloalkylcarbonyl, halo (C _{1 to} C ₆ ) alkylcarbonyl, C _{1 to} C ₆ alkyl Sulfonyl, halo (C _{1 to} C ₆ ) alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

In the compound or its salts or their N- oxide represented by the formula (1) of the present invention, more preferably, ^{G 1 is G 1 -1, R 1, R} 2, R 3 and ^{R 4} hydrogen atom, halo _(C 1 _{~C 3)} alkyl, ^{R a} is, ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 1} is ^{C-R C, a 2} is ^N, R B, ^{R D} is hydrogen atom, ^{R C} is may be substituted by each independently up to two Z-phenyl, 1H -Pyrazole-1-yl, 2H-1,2,3-triazole-2-yl, Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, D is hydrogen atom, acetyl. , E is a hydrogen _atom, C 1 -C ₃ alkyl, cyclopropylmethyl, halo _(C 1 ~C ₃₎ alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

In the compound or its salts or their N- oxide represented by the formula (1) of the present invention, more preferably, ^{G 1 is G 1 -1, R 1, R} 2, R 3 and ^{R 4} hydrogen atom, halo _(C 1 _{~C 3)} alkyl, ^{R a} is, ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 2} is ^{C-R E, a 1} is ^N, R B, ^{R D} is hydrogen atom, ^{R C} is may be substituted by each independently up to two Z-phenyl, 1H -Pyrazole-1-yl, 2H-1,2,3-triazole-2-yl, Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, D is hydrogen atom, acetyl. , E is a hydrogen _atom, C 1 -C ₃ alkyl, cyclopropylmethyl, halo _(C 1 ~C ₃₎ alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

In the compound represented by the formula (1) of the present invention, salts thereof, or N-oxides thereof, ^RA is more preferably ethylthio or ethylsulfonyl.

Particularly preferably, in the compound represented by the formula (1) of the present invention, salts thereof, or N-oxides thereof.
3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 91),
3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) -N- (4- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 100),
N-((3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) ((4- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide (compound) Number 101),
3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 103),
3- (Ethylsulfonyl) -5- (1H-1,2,4-triazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 105),
N-((3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino ) Methylene) acetamide (Compound No. 106),
N-((3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide (compound) Number 108),
3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) -N- (6- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 109),
N-((3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) ((6- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide (compound) Number 110),
N-((3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino) methylene) -2, 2,2-Trifluoroacetamide (Compound No. 111),
3- (Ethylsulfonyl) -5- (1H-1,2,3-triazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 120),
5- (Dimethylamino) -3- (Ethylsulfonyl) -N- (5- (Trifluoromethyl) Pyridine-2-yl) picoline imidazole (Compound No. 125),
3- (Ethylsulfonyl) -5-phenyl-N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 127),
5- (4-Chloromethyl) -3- (ethylsulfonyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 131),
5- (3,5-dichlorophenyl) -3- (ethylsulfonyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 133),
3- (Ethylsulfonyl) -5-(3- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 137),
3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 139),
N-((3- (ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide ( Compound No. 140),
3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 142),
5- (2,4-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 144),
5- (3,5-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 146),
N-((3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) (methyl (5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide ( Compound No. 199),
3- (Ethylsulfonyl) -5-(3- (trifluoromethoxy) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 200),
N-((3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) (methyl (5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide (Compound No. 204),
N-((3- (ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) (methyl (5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide (Compound No. 205),
N-((3- (Ethylsulfonyl) -5-(4- (trifluoromethyl) phenyl) pyridin-2-yl) ((methoxymethyl) (5- (trifluoromethyl) pyridin-2-yl) amino) Methylene) acetamide (Compound No. 207),
N-((3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) ((methoxymethyl) (5- (trifluoromethyl) pyridin-2-yl) amino) Methylene) acetamide (Compound No. 209),
N-(((ethoxymethyl) (5- (trifluoromethyl) pyridin-2-yl) amino) (3- (ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) Methylene) acetamide (Compound No. 211),
N-(((Cyanomethyl) (5- (trifluoromethyl) pyridin-2-yl) amino) (3- (ethylsulfonyl) -5-(4- (trifluoromethyl) phenyl) pyridin-2-yl) methylene ) Acetamide (Compound No. 213),
N-((3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide ( Compound No. 220),
N-((ethyl (5- (trifluoromethyl) pyridin-2-yl) amino) (3- (ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) methylene) acetamide ,
N-((3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) (propyl (5- (trifluoromethoxy) pyridin-2-yl) amino) methylene) acetamide ,
N-(((2-Cyanoethyl) (5- (trifluoromethyl) pyridin-2-yl) amino) (3- (ethylsulfonyl) -5-(4- (trifluoromethoxy) phenyl) pyridin-2-yl) ) Methylene) acetamide,
N-((3- (Ethylsulfonyl) -5-(4- (trifluoromethoxy) phenyl) pyridin-2-yl) (((methylsulfonyl) methyl) (5- (trifluoromethyl) pyridin-2-yl) ) Amino) Methylene) Acetamide,
Is.

In the compound or its salts or their N- oxide represented by the formula (2) of the present invention, preferably, ^{G 2 is G 2 -1, R 1, R} 2, R 3 and ^{R 4,} Independently, hydrogen atom, halogen atom, halo (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl thio, halo (C _{1 to} C ₆ ) alkyl sulfinyl, halo (C _{1 to} C ₆ ) Alkoxysulfonyl, ^RA is C _{1 to} C ₃ alkoxy, halo (C _{1 to} C ₃ ) alkoxy, C _{1 to} C ₃ alkyl thio, halo (C _{1 to} C ₃ ) alkyl thio, C _{1 to} C ₃ alkyl sulfonyl. , halo _(C 1 _{~C 3)} alkylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 1} is ^{C-R C} or N, a ² is a ^{C-R E} or N, ^(wherein either of a 1, ^{a 2} is N, the other is ^{C-R C,} or ^{C-R E.), R} B, ^RC , R ^D and ^RE are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio ,, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, respectively. , V-2, V-4, V-5, V-6, each of which may be independently substituted with up to 5 Zs.

In the compound or its salts or their N- oxide represented by the formula (2) of the present invention, more preferably, ^{G 2 is G 2 -1, R 1, R} 2, R 3 and ^{R 4} hydrogen atom, halo _(C 1 _{~C 3)} alkyl, ^{R a} is, ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 1} is ^{C-R C, a 2} is N, ^{R B} and ^{R D} is a hydrogen atom, ^{R C} is may be substituted by each independently up to two Z-phenyl, 1H -Pyrazole-1-yl, 2H-1,2,3-triazole-2-yl, dimethylamino, where Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.

In the compound represented by the formula (2) of the present invention, salts thereof, or N-oxides thereof, ^RA is more preferably ethylthio or ethylsulfonyl.

Particularly preferably, in the compound represented by the formula (2) of the present invention, salts thereof, or N-oxides thereof.
2- (3- (1H-Pyrazole-1-yl) Pyridine-4-yl) -6- (Trifluoromethyl)-[1,2,4] Triazolo [1,5-a] Pyridine (Compound No. 46) ,
2- (3- (2H-1,2,3-triazolo-2yl) pyridin-4-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No. 48),
2- (3- (2H-1,2,3-triazolo-2-yl) pyridin-4-yl) -7- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] Pyridine (Compound No. 170),
5- (Ethylsulfonyl) -N, N-dimethyl-6- (6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridin-2-yl) Pyridine-3-amine (Compound No. 173),
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 174),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 175),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 176),
2- (5- (2-4-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 214),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 177),
2- (5- (3,5-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine (Compound No. 178),
2- (3- (Ethylsulfonyl) -5- (pyrimidine-5-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No. 179),
2- (3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a ] Pyridine (Compound No. 180),
2- (3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] Pyridine (Compound No. 181)
Is.

Most preferably, in the compound represented by the formula (2) of the present invention, salts thereof, or N-oxides thereof.
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 174),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 175),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 176),
2- (5- (2-4-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 214),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 177),
2- (5- (3,5-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine (Compound No. 178),
2- (3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a ] Pyridine (Compound No. 180),
2- (3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] Pyridine (Compound No. 181)
Is.

In the compound or its salts or their N- oxide represented by the formula (3) of the present invention, preferably, ^{G 2 is G 2 -1, R 1, R} 2, R 3 and ^{R 4,} Independently, hydrogen atom, halogen atom, halo (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl thio, halo (C _{1 to} C ₆ ) alkyl sulfinyl, halo (C _{1 to} C ₆ ) Alkoxysulfonyl, ^RA is C _{1 to} C ₃ alkoxy, halo (C _{1 to} C ₃ ) alkoxy, C _{1 to} C ₃ alkyl thio, halo (C _{1 to} C ₃ ) alkyl thio, C _{1 to} C ₃ alkyl sulfonyl. , halo _(C 1 _{~C 3)} alkylsulfonyl, 1H-pyrazol-1-yl, a 2H-1,2,3-triazol-2-yl, ^{a 1} is ^{C-R C} or N, a ² is a ^{C-R E} or N, ^(wherein either of a 1, ^{a 2} is N, the other is ^{C-R C,} or ^{C-R E.), R} B, ^RC , R ^D and ^RE are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, respectively. Phenyl, V-2, V-4, V-5, V-6, each of which may be independently substituted with up to 5 Zs.

In the compound or its salts or their N- oxide represented by the formula (3) of the present invention, more preferably, ^{G 2 is G 2 -1, R 1, R} 2, R 3 and ^{R 4} Hydrogen atom, halo (C _{1 to} C ₃ ) alkyl, ^RA is C _{1 to} C ₃ alkylthio, C _{1 to} C ₃ alkylsulfonyl, A ¹ is C- ^RC , A ² is is N, ^{R B} and ^{R D} is a hydrogen atom, ^{R C} is may be substituted by each independently up to two Z-phenyl, 1H-pyrazol-1-yl, 2H-1, 2 , 3-Triazole-2-yl, where Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.

In the compound or its salts or their N- oxide represented by the formula (3) of the present invention, more preferably, ^{G 2 is G 2 -1, R 1, R} 2, R 3 and ^{R 4} hydrogen atom, halo _(C 1 ~C ₃₎ alkyl, ^{R a} _is C 1 -C _{3 alkylthio,} a C 1 -C ₃ alkylsulfonyl, ^{a 2} is ^{C-R E, a 1} is is N, ^{R B} and ^{R D} is a hydrogen atom, ^{R C} is may be substituted by each independently up to two Z-phenyl, 1H-pyrazol-1-yl, 2H-1, 2 , 3-Triazole-2-yl, where Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.

In the compound represented by the formula (3) of the present invention, salts thereof, or N-oxides thereof, ^RA is more preferably ethylthio or ethylsulfonyl.

In the compound represented by the formula (3) of the present invention, salts thereof, or N-oxides thereof, more preferably.
2- (3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1,3 , 5] Triazine-4-one (Compound No. 193)
2- (3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2- a] [1,3,5] triazine-4-one (Compound No. 215),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1, 3,5] Triazine-4-one (Compound No. 216),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1, 3,5] Triazine-4-one (Compound No. 217),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1, 3,5] Triazine-4-one (Compound No. 218),
2- (3- (Ethylsulfonyl) -5-(4- (trifluoromethoxytrifluoromethoxytrifluoromethoxy) phenyl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2 -A] [1,3,5] triazine-4-one (Compound No. 219),
Is.

The compound represented by the formula (1), the formula (2), or the formula (3) of the present invention, a salt thereof, or an N-oxide thereof (hereinafter, also referred to as a compound of the present invention) is produced by, for example, the following production method. However, the present invention is not limited thereto.

｛式中、Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｄ、Ａ¹、Ａ^２及びＧ^１は前記と同じであることを示す。｝<Manufacturing method 1>

^{{Wherein, R A, R B, R} D, A 1, A 2 and ^{G 1} indicates the same as defined above. }

Step a
The amidine compound represented by the formula (1-1) is produced by reacting the amine compound represented by the formula (4) with the cyano compound represented by the formula (5) in the presence of a base and an inert solvent. Can be manufactured. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79 (10), p. 4687-4693).

Examples of the bases that can be used in this reaction include alkali metals hydride such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, normal butyl lithium, sodium bis (trimethylsilyl) amide, and lithium bis (trimethylsilyl) amide. , Potassium bis (trimethylsilyl) amide, lithium diisopropylamine and the like, but the reactants that can be used in this reaction are not limited to this. The amount of the base used is usually in the range of about 1 to 3 times the molar amount of the compound represented by the formula (4).

The inert solvent that can be used in this reaction may be any that does not significantly inhibit this reaction. For example, chain or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic carbonization such as benzene, toluene and xylene. Hydrogens; polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and these inert solvents alone or 2 More than seeds can be mixed and used.

The reaction temperature in this reaction may be usually in the range of −78 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .. The cyanide compound represented by the formula (5) is usually used in the range of about 1/3 times mol to 1 times mol or about 1 times mol to 3 times mol with respect to the amino compound represented by the formula (4). .. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Another method of step a Amidine represented by formula (1-1) by reacting an amine compound represented by formula (4) with a cyano compound represented by formula (5) in the presence of Lewis acid. Compounds can be produced. This reaction can be carried out according to the method described in the literature (J. Med. Chem. 2002, 45, 21, 4655-4668).

Examples of the Lewis acid that can be used in this reaction include trimethylaluminum, aluminum chloride, titanium tetrachloride, and the like, but the reactants that can be used in this reaction are not limited to this. The amount of Lewis acid used is usually in the range of about 1 to 3 times the molar amount of the compound represented by the formula (4).

The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene; halogenated solvents such as dichloromethane and 1,2-dichloroethane. These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. The cyanide compound represented by the formula (5) is usually used in the range of about 1 to 3 times the molar amount of the amino compound represented by the formula (4). The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Ｄが水素原子ではない場合、式（１−１）で表されるアミジン化合物を、場合により塩基及び不活性溶媒の存在下、反応剤と反応させることにより式（１−２）で表されるアミジン化合物を製造することができる。
｛式中、Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｄ、Ａ¹、Ａ^２、Ｇ^１及びＤは前記と同じであることを示す。｝Step b

When D is not a hydrogen atom, it is represented by the formula (1-2) by reacting the amidine compound represented by the formula (1-1) with a reactant in the presence of a base and an inert solvent. Amidine compounds can be produced.
^{{Wherein, R A, R B, R} D, A 1, A 2, G 1 and D indicates the same as defined above. }

Examples of the reactants that can be used in the present invention include acetates such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonated products, and trifluoromethanesulfonated products, acetic anhydride, and trifluoroacetic anhydride. Acid anhydrides such as trifluorosulfonic acid anhydride; alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, dimethyl sulfate and the like can be used in this reaction. The reactant is not limited to this. The amount of the reactant to be used may be appropriately selected in the range of about 1 to 3 times the molar amount of the compound represented by the formula (1-1), and an excess amount of the reactant such as acetic anhydride is added. Therefore, the reaction can be carried out without a solvent.

Examples of the bases that can be used in the present invention include alkali metals such as triethylamine, N, N-diisopropylethylamine, pyridine, lithium hydride, sodium hydride, potassium hydride, and calcium hydride, normal butyl lithium, and sodium bis. Examples thereof include (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, lithium diisopropylamine, etc., and the amount used thereof is usually about 1 times that of the compound represented by the formula (8). It may be appropriately selected in the range of mol to 5 times mol.

The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, chain or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic carbides such as benzene, toluene and xylene Polar solvents such as hydrogens, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone can be mentioned, and these inert solvents can be used alone or 2 More than seeds can be mixed and used.

The reaction temperature in this reaction may be usually in the range of about −78 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. good. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Ｅが水素原子ではない場合、式（１−２）で表されるアミジン化合物を、塩基及び不活性溶媒の存在下、反応剤と反応させることにより式（１）で表されるアミジン化合物を製造することができる。
｛式中、Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｄ、Ａ¹、Ａ^２、Ｇ^１、Ｄ及びＥは前記と同じであることを示す。｝Step c

When E is not a hydrogen atom, the amidine compound represented by the formula (1-2) is reacted with the reactant in the presence of a base and an inert solvent to produce the amidine compound represented by the formula (1). can do.
^{{Wherein, R A, R B, R} D, A 1, A 2, G 1, D and E show that the same as above. }

Examples of the reactants that can be used in the present invention include acidified products such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonated products, and trifluoromethanesulfonated products; acetic anhydride, trifluoroacetic anhydride, and the like. Acid anhydrides such as trifluorosulfonic acid anhydride; alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, dimethyl sulfate and the like can be used in this reaction. The agent is not limited to this. The amount of the reactant used may be appropriately selected in the range of about 1 to 3 times the molar amount of the compound represented by the formula (1-2).

Examples of the bases that can be used in the present invention include alkali metals such as triethylamine, N, N-diisopropylethylamine, pyridine, lithium hydride, sodium hydride, potassium hydride, and calcium hydride, normal butyl lithium, and sodium bis. Examples thereof include (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, lithium diisopropylamine, etc., and the amount used thereof is usually about about the compound represented by the formula (1-2). It may be appropriately selected in the range of 1-fold molar to 5-fold molar.

The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, chain or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic carbides such as benzene, toluene and xylene Polar solvents such as hydrogens, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone can be mentioned, and these inert solvents can be used alone or 2 More than seeds can be mixed and used.

The reaction temperature in this reaction may be usually in the range of about −78 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. good. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

式（１−１）で表されるアミジン化合物を、不活性溶媒の存在下、反応剤と反応させることにより式（２）で表されるアミジン化合物を製造することができる。本反応は文献記載の方法（Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693）に準じて行うことができる。
｛式中、Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｄ、Ａ¹、Ａ^２、Ｇ^１及びＧ^２は前記と同じであることを示す。｝<Manufacturing method 2>
Step d

The amidine compound represented by the formula (2) can be produced by reacting the amidine compound represented by the formula (1-1) with a reactant in the presence of an inert solvent. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79 (10), p. 4687-4693).
^{{Wherein, R A, R B, R} D, A 1, A 2, G 1 and ^{G 2} show that the same as above. }

Examples of the reactants that can be used in the present invention include iodobenzene diacetate, (bis (trifluoroacetoxy) iodo) benzene, iodosylbenzene, (hydroxy (tosyloxy) iodo) benzene, 2-iodoxybenzoic acid, and Dess-Martin. Examples thereof include oxidizing agents such as superatozinated iodine compounds such as peryodinan, but the reactants that can be used in this reaction are not limited to this. The amount of the reactant to be used may be appropriately selected in the range of about 1 to 5 times the molar amount of the compound represented by the formula (1-1).

The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, for example, halogenated solvents such as dichloromethane and 1,2-dichloroethane, and aromatic hydrocarbons such as benzene, toluene and xylene. , Methanol, ethanol, propanol, 2,2,2, -trifluoroethanol, hexafluoro-2-propanol and other alcohol solvents, ethyl acetate, acetonitrile and the like, and these inert solvents can be used alone or 2 More than seeds can be mixed and used.

The reaction temperature in this reaction may be usually in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

式（１−１）で表されるアミジン化合物を、塩基及び不活性溶媒の存在下、反応剤と反応させることにより式（３）で表されるアミジン化合物を製造することができる。
｛式中、Ｒ^Ａ、Ｒ^Ｂ、Ｒ^Ｄ、Ａ¹、Ａ^２、Ｇ^１及びＧ^２は前記と同じであることを示す。｝<Manufacturing method 3>
Step e

The amidine compound represented by the formula (3) can be produced by reacting the amidine compound represented by the formula (1-1) with a reactant in the presence of a base and an inert solvent.
^{{Wherein, R A, R B, R} D, A 1, A 2, G 1 and ^{G 2} show that the same as above. }

Examples of the reactants that can be used in the present invention include methyl chlorocarbonate, ethyl chlorocarbonate, phenyl chloroformate, 4-nitrophenyl chloroformate, 4-chlorophenyl chloroformate, phosgene, triphosgene, carbonyldiimidazole and the like. The reactants that can be used in this reaction are not limited to this. The amount of the reactant to be used may be appropriately selected in the range of about 1 to 5 times the molar amount of the compound represented by the formula (1-1).

Examples of the base that can be used in the present invention include triethylamine, N, N-diisopropylethylamine, pyridine and the like, and the amount of the base used is usually about 1 with respect to the compound represented by the formula (1-1). It may be appropriately selected in the range of double molar to five-fold molar.

The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, for example, halogenated solvents such as dichloromethane and 1,2-dichloroethane, and aromatic hydrocarbons such as benzene, toluene and xylene. , Diethyl ether, tetrahydrofuran, chain ethers such as dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3- Polar solvents such as dimethyl-2-imidazolinone, ethyl acetate, acetonitrile and the like can be mentioned, and these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may be usually in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Targets of control The pests to be controlled in the present invention are not particularly limited, and can be used for controlling pests, mites, nematodes, and soil pests in a wide range of horticulture-including killing insects. These pests are defined in the present invention as agricultural and horticultural pests. Preferred insect species to be controlled include, for example, the following.
Lepidoptera {eg, Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten Omeiga (Scirpophaga incertulas), Rupela albina, Cobnomeiga (Cnaphalocrocis) , Ineha Casino Meiga (Marasmia exigua), Watano Meiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Hymadalano Meiga (Hellula undalis), Monki Chronomeiga (Hellula undalis), Monki Chronomeiga (Herpetogramma) ), Rice case worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. Crambidae; litura), Lepidoptera exigua, Awayoto (Mythimna separata), Yotoga (Mamestra brassicae), Inferens, Spodoptera mauritia, Spodoptera mauritia, Futaobikoyaga (Naranga aenesc) Yoto (Spodoptera exempta), Tamanayaga (Agrotis ipsilon), Tamanagin uwaba (Autographa nigrisigna), Inekin uwaba (Plusia festucae), Soybean looper (Chrysodeixis includens), Tricoprusia (Trichoplu) sia spp.), Heliothis spp. Such as Helliothis virescens, Helicoverpa armigera, Helicoverpa zea and other Helicoverpa spp., Velvetbean caterpillar (Anticarsia gemmata) , Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc., Noctuidae; , Mameshiniga (Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses azukivora), Ringo-kokakumonhamaki (Adoxophyes orana fasciata), Chanokokakumonhamaki (Adoxophyes honmai), Chahamaki (Homona magnanima), Chahamaki (Homona magnanima) Pomonella, Tortrix moth (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc. Gracillariidae); Carposinidae such as Carposina sasakii; Coffee Leaf miner (Leucoptera coffeella), Lyonetia clerkella, Lyonetia prunifoliella, etc. Lymantria (Lymantria spp.) Such as moth (Lymantria dispar), Euproctis (Lymantriidae) such as Tea tussock moth (Euproctis pseudoconspersa); ); Momokibaga (Anarsia lineatella), Imokibaga (Helcystogramma triannulella), Watakamimushiga (Pectinophora gossypiella), Potatomoga (Phthorimaea operculella), Tuta absoluta, etc. ; Castniidae such as Giant Sugarcane borer (Telchin licus); Twirler moth (Cossidae) such as Cossus insularis; Tea tussock moth (Geometridae) such as Ascotis selenaria; Limacodidae, etc .; Fake gypsy moth family (Stathmopodidae), such as tussock moth (Stathmopoda masinissa); Sphingidae, such as Acherontia lachesis; (Parnara guttata), etc. Lymantria (Hesperiidae)}.
Hemiptera {For example, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Peregrinus maidis, Javesella pellucida, Javesella pellucida Aphidaceae (Delphacidae) such as orizicolus; Aphid aphid (Nephotettix cincticeps), Aphid aphid (Nephotettix virescens), Aphid aphid (Nephotettix nigropictus), Aphid aphid (Recilia dorsalis) Empoasca fabae), corn leaf hopper (Dalbulus maidis), white aphid (Cofana spectra), etc. (Cicadellidae); Mahanarva posticata, Mahanarva fimbriolata, etc. Aphis glycines, Wata aphids (Aphis gossypii), European apple aphids (Aphis pomi), Yukiyanagi aphids (Aphis spiraecola), Momoka aphids (Myzus persicae), Wheat aphids (Brachycaudus) ), Rosy apple aphid (Dysaphis plantaginea), fake aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisgri) hum padi), corn aphididae (Rhopalosiphum maidis), stink bug (Toxoptera citricida), stink bug (Hyalopterus pruni), stink bug (Melanaphis sacchari), stink bug (Tetraneura nigriabdominalis) , Aphididae such as Eriosoma lanigerum; Daktulosphaira vitifoliae, Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf Family (Phylloxeridae); Adelgidae (Adelgidae) such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae; Scotinophara lurida, Malayan rice black bug (Scotin) Stink bug (Nezara antennata), stink bug (Eysarcoris aeneus), stink bug (Eysarcoris lewisi), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris aeneus) 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 (Scaptoc) Oris castanea (Cydnidae); Whitefly (Riptortus pedestris), Whitefly (Leptocorisa chinensis), Whitefly (Leptocorisa acuta), etc. Punctiger), Diaspididae (Leptoglossus australis) and other whiteflies (Coreidae); Whitefly (Caverelius saccharivorus), Whitefly (Togo hemipterus), American whitefly (Blissus) (Lygaeidae); Diaspididae (Trigonotylus caelestialium), Whitefly (Stenotus rubrovittatus), Whitefly (Stenodema calcarata), Sabiirokasumi turtle (Lygus lineolaris), etc. , Whitefly (Bemisia tabaci), Whitefly (Dialeurodes citri), Whitefly (Aleurocanthus spiniferus), Whitefly (Aleurocanthus camelliae), Diaspididae (Pealius euryae) (Abgrallaspis cyanophylli), Whitefly (Aonidiella aurantii), Whitefly (Diaspidiotus perniciosus), Whitefly (Pseudaulacaspis pentagona), Whitefly (Unaspis yanonensis), Whitefly (Unaspis yanonensis) Diaspididae); Diaspididae (Coccidae) such as the whitefly (Ceroplastes rubens); Psyllidae (Phenacoccus solani), Psyllidae (Phenacoccus solenopsis), Psyllidae (Phenacoccus solenopsis) Psyllidae scale insects (Pseudococcus comstocki), Psyllidae scale insects (Planococcus citri), Gahaniko scale insects (Pseudococcus calceolariae), Psyllidae scale insects (Pseudococcus longispinus), Psyllidae Psyllidae (Brevennia rehi) Diaphorina citri), scale insect (Trioza erytreae), psyllidae (Cacopsylla pyrisuga), scale insect (Cacopsylla chinensis), scale insect (Bactericera cockerelli), Psyllidae (Psyllidae) (Corythucha ciliata), Awadachisougunbai (Corythucha marmorata), Nashigunbai (Stephanitis nashi), Tsutsujigunbai (Stephanitis pyrioides), etc. Psyllidae (Cicadidae)}.
Coleoptera {For example, Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae) Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Oulema melanopus, Aulacophora femoralis, Phyllotreta stri , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa decemlineata), Inedro oyster (Oulema oryzae), Grape colaspis (Colaspis brunnea) Beetle beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), beetle beetle (Dicladispa armigera), south corn leaf beetle (Myochrous denticollis), beetle beetle (Laccoptera quadrimaculata) Family (Chrysomelidae); Coleoptera (Carabidae) such as Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Buoy (Anomala cuprea), Himekogane (Anomala rufocuprea), Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), European Chafer (Rhizotrogus majalis), Cromarcogane (Tomaru) ), Phyllophaga spp. Such as June beetle (Phyllophaga crinita), Diloboderus spp. Such as Diloboderus abderus (Scarabaeidae); Cylas formicarius, Anomala albopilosa (Euscepes postfasciatus), Alfera postica, Sitophilus zeamais, Echinocnemus squameus, Anomala albopilosa (Lissorhoptrus oryzophilus) ), Anomala albopilosa (Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Anomala albopilosa (Scepticus griseus) Aracanthus genus (Araca) such as Brazilian beetle (Zabrotes subfasciatus), pine tree beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus mourei nthus spp.), Cotton root borer (Eutinobothrus brasiliensis), etc. Curculionidae; Click beetle (Tribolium castaneum), Click beetle (Tribolium confusum), etc. Coccinellidae such as Coccinellidae; Longhorn beetle (Lyctus brunneus) and other longhorn beetles (Bostrychidae); (Melanotus okinawensis), Click beetle (Agriotes fuscicollis), Longhorn beetle (Melanotus legatus), Click beetle (Anchastus spp.), Conoderus spp. Limonius spp.), Aeolus spp., Etc. Click beetle (Elateridae); Aoba Arigata honeybee (Paederus fuscipes), etc. Click beetle (Staphylinidae)}.
Thrips palmi (Thysanoptera) {For example, Thrips palmi (Frankliniella occidentalis), Thrips palmi, Thrips palmi, Thrips palmi (Scirtothrips dorsalis), Thrips thrips (Thrips tabaci) Thripidae (Thripidae) such as Stenchaetothrips biformis), Thrips palmi Karny (Echinothrips americanus); Thripidae (Phlaeothripidae) such as Haplothrips aculeatus}.
Diptera {For example, Agromyzidae (Anthomyiidae) such as Delia platura and Delia antiqua; Agromyzidae (Ulidiidae) such as Sugar beetroot maggot (Tetanops myopaeformis); ), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza trifolii), Agromyzidae (Chromatomyia horticola) and other leafminers (Agromyzidae); Bactrocera dorsalis), Nasumi fly (Bactrocera latifrons), Olive mibae (Bactrocera oleae), Quisland mibae (Bactrocera tryoni), Chichukai mibae (Ceratitis capitata), etc. Agromyzidae such as fly (Hydrellia philippina) and Agromyzidae (Hydrellia sasakii); Agromyzidae such as Drosophila suzukii; Agromyzidae (Megaselia spiracularis) Agromyzidae (Clogmia albipunctata) and other leafminers; Agromyzidae (Bradysia difformis) and other leafminers (Sciaridae); Agromyzidae (Diopsidae); Agromyzidae (Tipula aino), Common cranefly (Tipula oleracea), Eur Crane fly (Tipulidae) such as opean cranefly (Tipula paludosa)}.
Hymenoptera {For example, Tenthredinidae such as turnip bee (Athalia rosae) and Japanese turnip bee (Athalia japonica); Fire ant (Solenopsis spp.) Family, Brown leaf-cutting ant (Atta capiguara), etc. The ant family (Formicidae), etc.}.
Orthoptera {eg, Locusta migratoria, Morocco locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Locust (Nomadacris septemfasciata), Brown Locust (Locustana par) ), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pelluc) (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Kobane locust (Oxya yezoensis), Hanena locust (Oxya japonica), Taiwan locust (Patanga locust) (Gryllotalpa orientalis) and other Orthoptera (Gryllotalpidae); European locusts (Acheta domestica), Emma locusts (Teleogryllus emma) and other Orthoptera (Gryllidae); Mormon cricket (Anabrus simplex) and other grasshoppers (Tettigoniidae).
Termite pests (Blattodea) {For example, termites (Blattella germanica) and other termites (Blattellidae); termites (Periplaneta fuliginosa), termites (Periplaneta americana), termites (Periplaneta brunnea), termites (Periplaneta brunnea), termites (Periplaneta brunnea) Termites (Blattidae) such as Yamato termites (Periplaneta japonica) and Kowamon termites (Periplaneta australasiae); Termites (Odontotermes formosanus), Koshun termites (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Catan termites (Glyptotermes fuscus), termites (Glyptotermes fuscus), termites (Glyptotermes fuscus) Termites (Reticulitermes amamianus), Miyatake termites (Reticulitermes miyatakei), termites (Reticulitermes kanmonensis), Takasago termites (Nasutitermes takasagoensis), nitobe termites (Pericapritermes nitobei), termites (Pericapritermes nitobei), termites (Pericapritermes nitobei) )}.
Acari {eg, Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus citri, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi Family (Tetranychidae); Panonychus pelekassi (Aculops pelekassi), Ryukyu Panonychus ulta (Phyllocoptruta citri), Tomato sabi tick (Aculops lycopersici), Chanosabi tick (Calacarus carinatus), Chanonaga sabi tick (Acaphylla theavans) Panonychus ulciflora (Aculus schlechtendali), Aceria diospyri, Aceria tosichella, Shevtchenkella sp. Et al. (Tenuipalpidae); Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, American Inukakumadani Spider mite (Ixodes persulcatus), black legd tick (Ixodes scapularis), American mite (Amblyomma americanum), boophilus microplus, spider mite (Rhipicephalus sanguineus) and other spider mite (Ixodidae); ae), Dust mites (Tyrophagus similis) and other house dust mites (Acaridae); Dermatophagoides farinae, Dermatophagoides pteronyssinus and other house dust mites (Pyroglyphidae); Cheyletidae such as Cheyletus moorei and Cheyletiella yasguri; Cheyletidae; Otodectes cynotis, Sarcoptes scabiei and other house dust mites (Sarcoptidae); Demodex canis Demodicidae); Dust mites (Listrophoridae); House dust mites (Haplochthoniidae); Dust mites (Ornithonyssus bacoti), Dust mites (Ornithonyssus sylviarum) and other house dust mites (Macronyssidae); (Leptotrombidium akamushi), etc. Cheyletidae (Trombiculidae), etc.}.
Plant-parasitic nematodes {for example, root-knot nematodes (Aphelenchoides besseyi), strawberry nematodes (Aphelenchoides fragariae), hagare nematodes (Aphelenchoides ritzemabosi), pine wood nematodes (Bursaphelenchus xylophilus), etc. Potato cyst nematode (Globodera pallida), potato cyst nematode (Globodera rostochiensis), wheat cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), tensai cyst nematode (Heterodera schachtii) tri Root-knot nematode (Meloidogyne arenaria), root-knot nematode (Meloidogyne hapla), root-knot nematode (Meloidogyne incognita), root-knot nematode (Meloidogyne javanica), apple root-knot nematode (Meloidogyne mali) drenatus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus vulnus, Pratylenchus vulnus, Kankitsunemogrisenchu Radopholus similis) and other root-knots (Tylenchida)}.

The compound of the present invention can also be used for controlling harmful organisms such as sanitary pests, shell storage pests, clothing pests, house pests and parasites. In particular, it has an excellent control effect on harmful invertebrates that are harmful to humans and animals, and these pests are defined as animal parasitic pests in the present invention. Animal parasitic pests to be controlled include those that parasitize the back, armpits, lower abdomen, inner crotch, etc. of the host animal and inhabit by obtaining nutrient sources such as blood and fluff from animals and birds, and the host. It includes those that fly to the back and buttocks of animals and inhabit them by obtaining nutrient sources such as blood and fluff from animals and birds. Examples of animal parasitic pests include mites, lice and fleas.

Host animals for which the control agent of the present invention is effective include humans, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferret; pet birds (eg pigeons, parrots, myna birds, Java sparrows, parakeets, Bengalese finch, etc.) Canary); cows, horses, pigs, sheep, goats; poultry (eg, duck, chicken, quail, geese); honeybees (eg, bees, Japanese bees); and the like.

That is, the pest control agent of the present invention is effective as an animal parasitic pest control agent for the above-mentioned animals and birds.

The target mites (Acari) include the following pests.
Mesostigmata mites (mite) {For example, Dermanyssidae such as Dermanyssus gallinae; Ornithonyssus spp. Ornithonyssus sylviarum, Ornithonyssus bur , Ornithonyssus bacoti, Macronyssidae mites; Laelaps spp., Laelaps echidninus, Laelaps jettmari, Laelaps jettmari, Laelaaps clarae ) Mites; Dermanyssidae (Varroidae) mites, including the genus Ornithonyssus (Varroa spp.), Varroa destructor, Varroa jacobsoni, and Varroa underwoodi}.
Tick of the order Metastigmata {for example, Argas persicus of Argas spp., Argas reflexus, Ornithodoros spp. Argasidae ticks, including Ornithodoros moubata; Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis punctata・ Otophila (Haemaphysalis otophila), Hemaphysalis leachi (Haemaphysalis leachi), Futatogechi tick (Haemaphysalis longicornis), Magesimachi tick (Haemaphysalis mageshimaensis), Yenchi tick (Haemaphysalis yeni) (Haemaphysalis flava), Argasidae (Haemaphysalis megaspinosa), Argasidae (Haemaphysalis japonica), Douglasi, Argasidae (Amblyomma spp.) , Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinarium, Amblyomma testudinarium, Ixodes spp. Hexagonus ( Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes scapularis, Ixodes holocyclus, Ixodes holocyclus, Ixodes holocyclus Ixodes persulcatus, Ixodes nipponensis, Boophilus spp., Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus (Boophilus) decolor・ Anuratus (Rhipicephalus (Boophilus) annulatus), Lipicephalus (Boophilus) calceratas (Rhipicephalus (Boophilus) calceratus), Ixodes ovatus (Rhipicephalus spp. ) Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus (Rhipicephalus turanicus), Lipicephalus zambeziensis, Dermacentor spp. Dermacentor marginatus, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor reticulatus ), Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Rhipicephalus (Ixodidae) ticks}.
Acaridida of the order Astigmata {for example, the genus Psoroptidae spp., Psoroptes ovis, Psoroptes cuniculi, Psoroptes cuniculi, Psoroptes equi Psoroptidae ticks including Chorioptes bovis of the genus Chorioptes spp. And Otodectes cynotis of the genus Otodectes spp. spp.) Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes rupicaprae, Sarcoptes rupicaprae , Sarcoptes suis, Notoedres spp. Cati, Parajulis cati, Sarcoptidae mites; Knemidokoptes spp. (Knemidokoptes mutans), itch mite (Knemidokoptidae) ticks}.
Prostigmata Prostigmata Actinedida {For example, Demodex spp. Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae ), Demodex equi, Demodex caballi, Demodex suis, Demodex cati, Demodexidae mites; Trombicula spp. Demodex family (Trombiculidae) including Trombicula alfreddugesi and Trombicula akamushi}.
Examples of lice (Phthiraptera) include the following pests.
Louse of the suborder Anoplura {for example, Haematopinus asini of the genus Haematopinus spp., Haematopinus eurysternus, Haematopinus suis) Linognathus spp. Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus ovillus, Linognathus oviformis, Linognathus oviformis , Lice of the family Linognathidae, including the lice of the genus Solenopotes (Solenopotes spp.) (Solenopotes capillatus)}.
Paraphyletic chewing (Amblycera) biting louse {for example, chicken body louse (Menacanthus spp.), Chicken body louse (Menacanthus stramineus), chicken body louse (Menacanthus cornutus), Usuiro niwatori For example, the Paraphyletic chewing (Menoponidae) including the chicken body louse (Menopon gallinae) of the genus Menopon (Menopon spp.)}.
Paraphyletic chewing (biting louse) of the suborder Ischnocera {For example, the paraphyletic chewing (Columbicola columbae) of the genus Columbicola (Columbicola spp.), The paraphyletic chewing (Cuclotogaster spp.) heterographus), Goniodes spp. Kakuagohajirami (Goniodes dissimilis), Maruhajirami (Goniodes gigas), Himeniwatorihajirami (Goniodes gallinae), Lipeurus spp. Paraphyletic chewing (Philopteridae); Bovicola spp. Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola capra, Bovicola capra ), Paraphyletic chewing (Trichodectes canis) of the genus Paraphyletic chewing (Trichodectes spp.), Paraphyletic chewing (Trichodectidae) including the cat of the genus Felicola (Felicola spp.)}.
Examples of fleas (Siphonaptera) include the following pests.
For example, Chigoe flea (Tungidae) fleas including Chigoe flea (Tunga penetrans) of the genus Chigoe (Tunga spp.); Dog fleas (Ctenocephalides canis) of the genus Ctenocephalides spp. Archaeopsylla spp.) Chigoe flea (Archaeopsylla erinacei), Chigoe flea (Xenopsylla spp.) Oriental chigoe flea (Xenopsylla cheopis), Chigoe flea (Pulex spp.) Chigoe flea (Echidnophaga gallinacea), Chigoe flea (Pulicidae) fleas; Chigoe flea (Ceratophyllus spp.) Chigoe flea (Ceratophyllidae) fleas, including the European chigoe flea (Nosopsyllus fasciatus); Chigoe flea (Leptopsyllidae) fleas, including the genus Leptopsylla spp.
Other target animal parasitic pests include Hemiptera pests. Hemiptera pests include the following pests. For example, insects of the Bed Bug family (Cimicidae), including Bed Bugs (Cimex lectularius) of the genus Sysmex (Cimex spp.); Prolixus), Bed Bugs (Reduviidae) insects, including Bed Bugs (Triatoma infestans) of the genus Bed Bug (Triatoma spp.).
It is also effective against diptera pests, which are biting insects (chewing flies, blood-sucking adult flies, mobile dipteran larvae, parasitic maggots). The following pests are listed as pests of flies (Diptera). Nematocera {For example, (a) Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres spp., Armigeres subalbatus, Anopheles spp. maculipennis), Culex pipiens (Anopheles sinensis), Culex pipiens (Anopheles lesteri), Culex pipiens (Aedes spp.) Culex pipiens (Culicidae) including Culex pipiens (Aedes vexans nipponii); (b) Simulium reptans (Simulium reptans), Culex pipiens (Simulium ornatum) (Simulium venustum), Umabuyu (Simulium salopiense), Culex pipiens (Culiodes spp.) Culex pipiens (Culiodes spp.) Culex pipiens (Culiodes spp.) Culex pipiens (Culicoides pictimargo), Culex pipiens (Culicoides kibunensis), Culex pipiens (Culicoides homotomus), Culex pipiens (Culicoides oxystoma), Ceratopogonidae, including Culicoides nipponensis, Culicoides punctatus, Culicoides maculatus, and Culicoides matsuzawai. }. Brachycera {For example, (a) Tabanus spp. Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus ), Tabanus trigonus, Tabanus chrysurus, Tabanus trigeminus, Tabanus fulvimedioides, Tabanus iyoensis, Chrysops spp. Tabanidae tabanus, including Chrysops relictus, Chrysops suavis, and Chrysops japonicus; Muscina spp. (Musca hervei), Musca conducens, Oye fly (Musca stabulans), Stomoxys spp. Stomoxys calcitrans, Tabanus calcitrans, Haematobia spp. Tabanus tabanus exigua, Haematobia stimulans, Tabanus spp. Fannia canisularis, Muscidae tabanus spi; Flies of the family Glossinidae including.); Flies of the family Tabanus (Hippoboscidae) including the species of the genus Melophagus (Melophagus spp.); lata;, Green bottle fly (Lucilia spp.) Green bottle fly (Lucilia (Phaenicia) cuprina) Green bottle fly (Lucilia (Phaenicia) sericata), Green bottle fly (Lucilia illustris), Chrysomya chrysomya (Chrysomyia. Spp.) Hominivorax), Chrysomya chloropyga, Chrysomya bezziana, Calliphoridae flies; Cuterebrinae, Green bottle fly species (Cuterebra spp. ), Warble fly (Hypodermatinae), Warble fly (Hypoderma spp.), Warble fly (Hypoderma bovis), Horse bot (Gasterophilinae), and Botfly (Gasterophilus spp.) Horse bot (Gasterophilus intestinalis), Atoa kauma fly (Gasterophilus haemorroidalis), Gasterophilus inermis, Munea kauma fly (Gasterophilus nasalis), Gasterophilus niglycolnis (Gasterophilus nigricornis), Gasterophilus nigricornis ), And the botfly family (Oestridae) including the botfly (Oestrus ovis) of the genus Warble fly (Oestrus spp.)).

When the compound of the present invention is used as an agricultural and horticultural pest control agent, the compound of the present invention may be used as it is, but a suitable solid carrier, liquid carrier, gaseous carrier, etc., surfactant, dispersant, and other preparations. A pesticide preparation may be prepared and used by mixing it with an auxiliary agent or the like. The pesticide preparation is preferably an emulsion, an EW agent, a liquid agent, a suspension agent, a wettable powder, a granule wettable powder, a powder, a DL powder, a powder or granule, a granule, a tablet, an oil, an aerosol, a flowable agent, or a dry agent. Flowable agents, microcapsules, etc. can be mentioned. It can be used as a dosage form arbitrarily selected as these pesticide preparations. The carrier in the present invention refers to a solid carrier, a liquid carrier, a gaseous carrier, or the like.

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acidic white clay, silica sand, silica stone, zeolite, pearlite, attapulsite, pumice stone, ammonium sulfate, sodium sulfate, urea and the like. Be done.
Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol and propylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, and aliphatic hydrocarbons such as n-hexane, kerosine and kerosene. , Aromatic hydrocarbons such as toluene, xylene, methylnaphthalene, ethers such as diethyl ether, dioxane, tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamide, dimethylacetamide and the like. Acid amides, vegetable oils such as soybean oil and cottonseed oil, dimethylsulfoxide, water and the like can be mentioned.
Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.
Examples of the surfactant and the dispersant include alkyl sulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, and alkyl sulfosuccinic acids. Examples thereof include salts, formalin condensates of alkylnaphthalene sulfonates, polycarboxylates, POE polystyrylphenyl ether sulfates and phosphates, POE / POP block polymers and the like.
Further, as the auxiliary agent for the preparation, for example, carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, arabic gum, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, etc. Examples thereof include polyethylene glycol, liquid paraffin, calcium stearate, antifoaming agent, preservative and the like.
The various carriers, surfactants, dispersants, and pharmaceutical auxiliary agents described above can be used alone or in combination, if necessary.

The content of the compound of the present invention as an active ingredient in the pesticide preparation is not particularly limited, but is preferably 1 to 75% by weight for an emulsion, 0.3 to 25% by weight for a powder, and 1 to 1 for a wettable powder. 90% by weight, 0.1 to 10% by weight for granules.

When the compound of the present invention is used as a control agent for mites parasitizing livestock such as cattle and pigs and pet animals such as dogs and cats, the amount used is not particularly limited, but for example, 1 kg of a host animal. On the other hand, the active ingredient can be used in an amount of 0.01 to 1000 mg.
The compounds of the present invention can be applied to host animals by known veterinary techniques. As a method, for example, for the purpose of systemic suppression, a method of administering to an animal by tablets, capsules, immersion liquid, feed mixture, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) For the purpose of non-systemic suppression, a method of spraying, pouring (pour-on), dropping (spot-on), etc., an oily or aqueous liquid agent, or kneading this compound into a resin. , A method of molding the kneaded product into an appropriate shape such as a collar or an ear tag and attaching it to an animal can be mentioned.

The pest control agent according to the present invention can be used as it is or after being diluted. In addition, the pest control agent according to the present invention can be mixed or used in combination with other insecticides, nematodes, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like. Drugs that can be mixed or used in combination include, for example, Pesticide Manual (17th edition, published by The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP) and i. FRAC Code List (c) * 2017: Fungicides sorted by mode of action, 2017 version, FRAC Code List (c) * 2017: Fungicides sorted by mode of action, Examples include those described in FRAC) and those whose structure can be specified on the Internet (http://www.alanwood.net/pesticides/sitemap.html).

More specifically, the pesticides include, for example, alanicalb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxim, carbyl ( carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, mesomil, Oxamyl, pyrimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, metolcarb Carbamate compounds such as (fenothiocarb), fenoxycarb,
Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, Chlorpyrifos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diadinone (diazinon), dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenamifos fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothiophosphoryl) salicylate [isopropyl O- (methoxyaminothiophosphoryl) salicylate] (isoxathion), malathion, mecarbam, methamidophos, methidathion, mevinphos, chlorpyrifos, naled, omethoate, oxydimeton ethyl ethyl), parathion, parathion-methyl, PAP, phorate, phosalone, e Phosmet, phosphamidon, phoxim, pyrimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridafenthion, pyridafenthion (quinalphos), sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, bamidion ), Chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazophos, phenthoate, fonofos, tribufos and other organic phosphate compounds,
Organic chlorine compounds such as endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxyclor,
Phenylpyrazole compounds such as acetoprole, fipronil, ethiprole, pyrafluprole, pyriprole, flufiprole,
Metadiamide compounds, such as broflanilide,
Isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, fluxametamide, lotilaner, isoxazoline,
Acrinathrin, allethrin, d-cis-trans alesrin, d-cis-trans allethrin, bifenthrin, kappa-bifenthrin, bioaresrin S-cyclopentenyl (bioallethrin S-cyclopentenyl), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, ramda-cyhalothrin, gamma-cyhalothrin (gamma-cyhalothrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin ), Cypermethrin, deltamethrin, empentrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate ), Flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prallethrin, pyrethrin (pyrethrin), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin (te) tramethrin, tralomethrin, transfluthrin, metoxadiazone, metoflutrin, profluthrin, pyrethrum, terallethrin, monfluorothrin, momfluorothrin (heptafluthrin), meperfluthrin, tetramethylfluthrin, dimefluthrin, chloroprallethrin, ipsilon-metofluthrin, ipsilon-metofluthrin, ipsilon-monfluthrin Pyrethroid compounds, such as protrifenbut,
Neonicotinoid compounds such as acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam,
Sulfoxamine compounds, such as sulfoxaflor,
Butenolide compounds, such as flupyradifurone,
Mesoionic compounds such as triflumezopyrim and dichloromethane,
2-Aminopyridine compounds such as flupyrimin Spinosad, spinosin compounds such as spine toram,
Macrolide compounds such as abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin,
Juvenile hormone-like compounds such as hydroprene, quinoprene, Diofenolan, methoprene,
4-Phenoxyphenoxy compounds, such as pyriproxyfene,
Pyridineazomethine compounds, such as pymetrozine,
Pyridinecarboxamide compounds, such as flonicamid,
Oxazole compounds, such as ethoxazole,
Bacillus thuringiensis and Bacillus sphaericus agents such as Bt subsp. Israelensis, Bt subsp. Aizawai, Bt subsp. Kurstaki, Bt subsp. Tenebrionis and the insecticidal proteins they produce.
An insecticidal protein produced by a Bt crop (a genetically modified crop in which a gene that produces a Bacillus thuringiensis toxin is incorporated to have pest resistance) corresponding to the above.
Thiourea compounds, such as diafenthiuron,
Organometallic compounds such as azocyclotin, cyhexatin, fenbutatin oxide,
Sulfurous acid ester-based / diphenyl ether-based compounds such as propargite,
Diphenyl sulfone compounds, such as tetradifon,
Pyrrole compounds such as chlorfenapyr, tralopyril,
Dinitro compounds such as DNOC,
Nereistoxin analogs such as bensultap, cartap, thiocyclam, thiosultap, thiosultap sodium,
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), Noviflumuron, teflubenzuron, triflumuron, benzoylurea compounds such as bistrifluron,
Thiasiazine compounds, such as buprofezin,
Triazole compounds, such as cyromazine,
Diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide,
Amidine compounds, such as amitraz,
Amidino hydrazone compounds, such as hydramethylnon,
Naphthoquinone compounds, such as acequinocyl,
Strobilurin compounds such as fluacrypyrim, pyriminostrobin, Flufenoxystrobin,
Quinazoline compounds, such as fenazaquin,
Phenoxypyrazole compounds, such as fenpyroxymate,
Phenoxyethylamine compounds, such as pyrimidifen,
Pyridadinone compounds, such as pyridaben,
Pyrazole carboxamide compounds such as tebufenpyrad, tolfenpyrad, pyflubumide,
Hydrazinecarboxamide compounds, such as metaflumizone,
Tetrolic acid and tetramic acid compounds such as spirodiclofen, spirotetaramat, spiromesifen, spiropidion,
Beta-ketonitrile compounds such as cyflumetofen, cyenopyrafen,
Phtalic acid amide compounds, such as flubendiamide,
Anthranilic acids such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole Acid amide compounds,
Quinoxaline compounds, such as quinomethionate,
Thiazoridinone compounds, such as hexythiazox,
Hydrazine compounds, such as bifenazate,
Pyridinamine compounds, such as flufenerim,
Aminoquinazoline compounds, such as pyrifluquinazon,
6-Phenoxyquinoline compounds, such as flometokin,
Pyridinyl ethylbenzamide compounds, such as fluopyram,
Sulfonamide compounds such as fluazaindolizine, amidoflumet Pyridylpyrazole compounds such as tyclopyrazoflor Oxadiazole compounds such as tioxazafen,
It can be a benzoxazole-based compound such as oxazosulfyl.
Other pesticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, India. Indoxacarb, piperonyl butoxide, clofentimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, afidopyropen, fluhexafon, fluhexafon, fluhexafon Benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate salt, metaaldehyde, ryanodine, sulfluramid, asinonapill ( acynonapyr), benzpyrimoxan, 3-bromo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3,5-dichloropyridine-2-yl) -1H Examples include compounds such as -pyrazole-5-carboxamide. Furthermore, the pest control agent according to the present invention can also be mixed or used in combination with microbial pesticides such as insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi.

The fungicides used are, for example, metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, kiralaxyl. , Phenylamide compounds such as ofurace, furalaxyl, cyprofuram,
Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, ethilimol,
Isoxazole compounds such as hymexazole, hydroxyisoxazole,
Piperidinyl thiazole isooxazoline compounds, such as oxathia piprolin,
Isothiazolone compounds, such as octhilinone,
Carboxylic acid compounds, such as oxolinic acid,
Benzimidazole-thiophanate compounds such as benomyl, thiophanate-methyl, carbendazole, fuberidazole, thiabendazole, debacarb,
N-Phenylcarbamate compounds, such as diethofencarb,
Truamide compounds, such as zoxamide,
Ethylaminothiazole carboxamide compounds, such as ethaboxam,
Phenylurea compounds, such as peniccuron,
Pyridinyl methylbenzamide compounds, such as fluopicolide, fluopimomide,
Pyrimidine amine compounds, such as diflumetorim, bupirimate,
Benzanilide compounds such as benodanil, flutolanil, mepronil,
Phenyloxoethylthiophene amide compounds, such as isofetamid,
Pyridinyl ethylbenzamide compounds, such as fluopyram,
Francarboxamide compounds, such as fenfuram,
Oxycarboxin, oxatiin carboxamide compounds such as carboxin,
Thiazole carboxamide compounds, such as thifluzamide,
Fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, impilfluxane Pyrazole-4-carboxamide compounds such as (inpyrfluxam), fluindapyr, isoflucypram, pyrapropoyne,
Pyridinecarboxamide compounds, such as boscalid,
Azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dymoxystrobin (dimoxystrobin), metaminostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, flufenoxystrobin, phenaminestrobin Strobilurin compounds such as (fenaminstrobin), enoxastrobin, coumoxystrobin, mandestrobin, triclopyricarb,
Oxazolidinedione compounds, such as famoxadon,
Imidazolinone compounds, such as fenamidone,
Benzyl carbamate compounds such as trilopyricarab, pyribencarb,
Cyanoimidazole compounds, such as cyazofamid,
Sulfamoyltriazole-based compounds, such as amisulbrom,
Dinitrophenyl croton compounds such as binapacryl, meptyldinocap, dinocap,
2,6-dinitroaniline compounds, such as fluazinam,
Pyrimidinone hydrazone compounds, such as ferimzone,
Fentin-acetate, fentin chloride, fentin hydroxide, triphenyltin hydroxide (fenthin hydroxide), triphenyltin acetate (fenthin acetate), oxine copper Organic / inorganic metal compounds, such as
Thiophene carboxamide compounds, such as silthiofam,
Triazolopyrimidine amine compounds, such as ametoctradin,
Anilinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimesanil, cyprodinil, enopyranulonic acid antibiotics such as blasticidin-S,
Hexopyranosyl antibiotics, such as kasugamycin, kasugamycin hydrochloride hydrate,
Glucopyranosyl antibiotics, such as streptomycin,
Tetracycline antibiotics such as oxytetracycline, allyloxyquinoline compounds such as quinoxyfen,
Quinazoline compounds, such as proquinazid,
Cyanopyrrole compounds such as fludioxonil, fenpiclonil,
Dicarboxyimide compounds such as fluoroimid, procymidone, iprodione, vinchlozolin,
Phosphorothiolate compounds such as edifenphos, iprobenfos, pyrazophos,
Dithiolane compounds, such as isoprothiolane,
Propylcarbamate compounds such as propamocarb, propamocarb hydrochloride,
Bacillus and bactericidal proteins produced, such as Bacillus subtilis (QST713, FZB24, MBI600, D747 strains), and
Bactericidal proteins produced by the Bt crop,
Terpene hydrocarbons and terpene alcohols, such as the extract of Gosei Kayupte,
Piperazine compounds, such as triforine,
Pyridine compounds such as pyrifenox, pyrisoxazole,
Pyrimidine compounds such as fenarimol, nuarimol,
Azaconazole, bromuconazole, diniconazole, diniconazole-M, epoxyconazole, fluquinconazole, oxpoconazole, pefrazoate () pefurazoate, diphenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimefon, triadimefon, triadimefon , Triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole ), Flutriafol, myclobutanil, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz () Azole compounds such as prochloraz), simeconazole, ipfentrifluconazole, mefentrifluconazole,
Morpholine compounds such as aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pyrimorph ,
Piperidine compounds such as piperalin, fenpropidin,
Spiroketal amine compounds, such as spiroxamine,
Hydroxyanilide compounds, such as fenhexamid,
Aminopyrazolinone compounds, such as fenpyrazamine,
Ferbam, metam, metasulphocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate (ziram) Thiocarbamate / dithiocarbamate compounds such as polycarbamate), propineb, thiuram, pyributicarb,
Glucopyranosyl antibiotics, such as validamycin,
Nucleoside antibiotics, such as mildiomycin and polyoxin,
Valine amide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, iprovalicarb,
Mandelic acid amide compounds, such as mandipropamid,
Picolinamide compounds such as fenpicoxamid, florylpicoxamid,
Isobenzofuranone compounds such as fthalide,
Pyrroloquinolinone compounds, such as pyroquilone,
Triazolobenzothiazole compounds, such as tricyclazole,
Cyclopropanecarboxamide compounds, such as carpropamid,
Carboxamide compounds, such as diclocymet,
Propionamide compounds, such as fenoxanil,
Benthiadiazole compounds such as acibenzolar-S-methyl,
Benisothiazole compounds such as probenazole, dichlobentiazox,
Thiadiazole carboxamide compounds, such as tiadinil,
Isothiazole carboxamide compounds, such as isotianil,
Cyanoacetamide = oxime compounds, such as cymoxanil,
Ethylphosphonate compounds, such as fosetyl,
Phtalamic acid compounds such as techlophthalam,
Bentotriazine compounds, such as triazoxide,
Benzene sulfonic acid compounds, such as flusulfamide,
Pyridadinone compounds, such as diclomezine,
Phenylacetamide compounds, such as cyflufenamide,
Benzophenone compounds, such as metrafenopne,
Benzoylpyridine compounds, such as pyriofenone,
Cyamethylene thiazolidine-based compounds, such as flutianil,
4-quinolyl acetic acid compounds, such as tebufloquin,
3-Phenoxyquinoline compounds, such as ipflufenoquin,
Organophosphorus compounds such as fosetyl-aluminium and tolclofos-methyl,
1,2,4-thiadiazole compounds, such as echlomezole,
Trifluoroethyl carbamate compounds, such as tolprocarb,
Pyrazole carboxamide compounds, such as pydiflumetofen,
Bordeaux mixture, copper acetate, basic copper sulfate, oxy copper chloride, cupper hydroxide, oxine-copper ) Like copper-based compounds,
Inorganic compounds such as copper and sulfur,
N-halogenothioalkyl compounds such as captan, captafol, folpet,
Organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene,
Iminoctadine triacetate salt, iminoctadine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate salt ), Guanidine compounds such as albesilate,
Anthraquinone compounds, such as dithianon,
Quinoxaline compounds, such as quinomethionate,
Maleimide-based compounds such as fluoroimide,
Sulfenic acid compounds such as tolylfluanid, dichlofluanid,
Dinitrophenolic compounds, such as dinobuton,
Cyclic dithiocarbamate compounds such as dazomet Anilides compounds such as pyraziflumid,
Nicotinic acid ester compounds, such as aminopyrifen,
Tetrazolinone compounds, such as methyltetraprole,
There may be pyridazine compounds such as pyridachlometyl.
Other fungicides include quinofumelin, dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, Prohexadione-calcium, bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodcarb, prothiocarb prothiocarb) and the like.

The compound of the present invention or an acid addition salt thereof that is horticulturally acceptable can be used for controlling pests of interest by applying an effective amount thereof to plants and soil. The amount of the active ingredient in the formulation is 0.01 to 90% by weight. Wettable powders, emulsions, suspensions, flowables, aqueous solvents, and granule wettable powders are diluted with water to the desired concentration and powdered / granulated in the form of a solution, suspension, or emulsion. Can be applied as is to plants or soil. When the compound of the present invention or an acid addition salt thereof that is acceptable for agriculture and horticulture is used for epidemic prevention, the emulsion, wettable powder, flowable agent, etc. may be diluted with water to a desired concentration before application. The oil, aerosol, fumes, poison bait, tick-proof sheet, etc. can be used as they are.
In the specification of the present application, "crop" refers to all cultivated plants, specifically edible crops, forage crops, green fertilizer crops, horticultural crops (including ornamental plants), and industrial crops.
The present invention also includes a method of enhancing the vitality of a crop, which method comprises contacting the compound of the present invention with the crop or the seeds of the crop. The present invention also includes a method for producing crop seeds, which method comprises treating the compounds of the present invention with crop seeds.
When the target of the treatment or contact is a seed, the amount of the compound of the present invention or an acid addition salt thereof that is acceptable for agriculture and horizons is not limited, but the amount of the active ingredient is about 0.0001 to the amount of the seed after the treatment. It is preferable that the compound of the present invention or an acid addition salt thereof which is acceptable for horticultural use is contained in an amount of about 50% by weight.
The present invention further provides the use of the compound of the present invention or an acid addition salt thereof as an active ingredient of a composition for protecting animals and birds from animal parasitic pests. The composition contains the compound of the present invention or an acid addition salt thereof in an amount that is parasitically effective and does not harm the target animal / bird. The compound of the present invention or an acid addition salt thereof is contacted with a pest or its growing environment-for example, animals / birds, crops, seeds of crops, soil, etc.-in a biologically effective amount to control harmful invertebrates. do.

Next, specific examples of the compound of the present invention are shown below.

^{G 1} of the formula (1) is ^G 1 -1 in the formula ^{(1-3), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1, D is a substituent described in Table 2, E is a substituent described in Table 3, R ^a is a substituent described in Table ^{4, R} B, R D, is R ^E in Table 5 The compound of the present invention in a combination that is a substituent of.

^{G 1} of the formula (1) is ^G 1 -1 in the formula ^{(1-3), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6, D is a substituent described in Table 2, E is a substituent described in Table 3, R ^a is a substituent described in Table ^{4, R B, R C,} R D is described in Table 7 The compound of the present invention in a combination that is a substituent of.

^{G 2} of formula (2) is ^G 2 -1 In the formula ^{(2-1), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1, R ^a is a substituent described in Table ^{4, R B, R D,} R E is a compound of the invention or a substituted group described in Table 5.

^{G 2} of formula (2) is ^G 2 -1 In the formula ^{(2-1), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6, R ^a is a substituent described in Table ^{4, R B, R C,} R D is a compound of the invention or a substituted group described in Table 7.

In the formula (3-1) ^{G 2} is ^G 2 -1 of the formula ^{(3), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1, R ^a is a substituent described in Table ^{4, R B, R D,} R E is a compound of the invention or a substituted group described in Table 5.

In the formula (3-1) ^{G 2} is ^G 2 -1 of the formula ^{(3), R 1, R} 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6, R ^a is a substituent described in Table ^{4, R B, R C,} R D is a compound of the invention or a substituted group described in Table 7.

<Synthesis Example>
Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to these Examples. In the NMR data, "s" is a singlet (single line), "d" is a doublet (double line), "t" is a triplet (triple line), "q" is a quartet (quadruple line), and "m" is a multi. A triplet (multiple line) and "road" indicate a broad (wide line), and J indicates a coupling constant.

Synthesis Example 1-1-1: 3- (1H-pyrazole-1-yl) Preparation of isonicotinonitrile 3-Chloroisonicotinonitrile (1.00 g, 7.22 mmol), 1H-pyrazole (0.52 g) , 7.94 m mmol) was dissolved in N, N-dimethylformamide (10 ml), cooled in an ice bath, sodium hydride (0.35 g, 7.94 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. .. Water was added, and the mixture was extracted 3 times with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.79 g, 64.2%, white solid).
1H NMR (CDCl ₃ ) δ9.17 (1H, s), 8.71 (1H, s, J = 5.1Hz), 8.17 (1H, d, J = 2.7Hz), 7.88 (1H, d, J = 1.5Hz) , 7.65 (1H, dd, J = 5.1, 0.6Hz), 6.62 (1H, dd, J = 2.7, 0.6Hz)

Synthesis Example 1-1-2: Preparation of 3- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotine imidazole (Compound No. 5) 5- (Trifluoromethyl) Pyridine-2-amine (0.52 g, 3.23 mmol) is dissolved in N, N-dimethylformamide (15 mL) and sodium hydride (content 55%, 0.14 g, 3.23 mmol) is added. In addition, it was stirred at room temperature for 30 minutes. 3- (1H-Pyrazole-1-yl) isonicotinonitrile (0.50 g, 2.94 mmol) prepared in Synthesis Example 1-1-1 was added thereto, and the mixture was stirred at the same temperature for 1 hour and then hydrogen. Sodium hydride (content 55%, 0.05 g, 1.15 mmol) was added and stirred at the same temperature for an additional 17 hours. Water was added, and the mixture was extracted 3 times with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.57 g, 58.6%, white solid).
1H NMR (CDCl ₃ ) δ10.36 (1H, broad), 8.90-8.70 (2H, m), 8.55 (1H, s), 7.95-7.81 (2H, m), 7.81-7.70 (2H, m), 7.24 (1H, d, J = 9.0Hz), 6.49 (1H, broad), 6.53 (1H, t, J = 2.1Hz)

Synthesis Example 1-1-3: N-((3- (1H-pyrazole-1-yl) pyridin-4-yl) ((5- (trifluoromethyl) pyridin-2-yl) amino) methylene) acetamide Preparation of (Compound No. 14) Synthesis 3- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotine imidazole prepared in Example 1-1-2 Acetic anhydride (6 mL) was added to (0.30 g, 0.90 mmol), and the mixture was stirred under reflux for 15 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 76.9%, white viscous product).
1H NMR (CDCl ₃ ) δ12.90 (1H, s), 8.77 (1H, s), 8.77-8.63 (2H, m), 7.99 (1H, d, J = 7.8Hz), 7.76 (1H, d, J) = 1.8Hz), 7.69 (1H, s), 7.53 (1H, d, J = 4.8Hz), 7.38 (1H, d, J = 8.4Hz), 6.44 (1H, s), 1.96 (3H, s)

Synthesis Example 1-1-4: N-((3- (1H-pyrazole-1-yl) pyridin-4-yl) (methyl (5- (trifluoromethyl) pyridin-2-yl) amino) methylene) Preparation of acetamide (Compound No. 17) N-((3- (1H-pyrazole-1-yl) pyridine-4-yl) ((5- (trifluoromethyl) pyridine) prepared in Synthesis Example 1-1-3) -2-yl) Amino) Methylene) acetamide (0.13 g, 0.35 mmol) was dissolved in N, N-dimethylformamide (2.6 mL) and sodium hydride (content 55%, 0.02 g, 0.41 mmol). ) Was added, and the mixture was stirred at room temperature for 10 minutes. Methyl iodide (25 μL, 0.40 mmol) was added thereto, and the mixture was stirred at the same temperature for 3 hours, water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered. , Distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (8.8 mg, 6.5%, yellow viscous product).
1H NMR (CDCl ₃ ) δ8.70 (1H, s), 8.56 (1H, s), 8.43 (1H, s), 7.30-7.20 (2H, m), 7.91 (1H, d, J = 2.7Hz), 7.74 (1H, d, J = 1.5Hz), 7.67 (1H, dd, J = 8.7, 2.4Hz), 6.49 (1H, t, J = 2.4Hz), 3.44 (3H, s), 1.89 (3H, s) )

Synthesis Example 1-1-5: N, N'-dimethyl-3- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotine imidazole (compound) Preparation of No. 20) N-((3- (1H-pyrazole-1-yl) pyridin-4-yl) ((5- (trifluoromethyl) pyridin-2-yl) prepared in Synthesis Example 1-1-2) Il) amino) methylene) acetamide (0.15 g, 0.45 mmol) is dissolved in N, N-dimethylformamide (3 mL), sodium hydride (content 55%, 22 mg, 0.50 mmol) is added, and 10 at room temperature. After stirring for 1 minute, methyl iodide (30 μL, 0.40 mmol) was added, and the mixture was stirred at the same temperature for 30 minutes. Further, sodium hydride (content 55%, 22 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 10 minutes, methyl iodide (30 μL, 0.40 mmol) was added, and the mixture was stirred at the same temperature for 2.5 hours. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (31 mg, 18.8%, white solid).
8.90 (1H, s), 8.45 (1H, d, J = 4.8Hz), 8.29 (1H, d, J = 2.4Hz), 8.16 (1H, s), 7.78 (1H, d, J = 1.5Hz), 1H NMR (CDCl ₃ ) δ7.59 (1H, dd, J = 8.4, 2.4Hz), 7.03 (1H, d, J = 4.8Hz), 6.78 (1H, d, J = 8.4Hz), 6.48 (1H, 1H, t, J = 2.1Hz), 3.12 (3H, s), 2.57 (3H, s)

Synthesis Example 1-1-6: Preparation of 3- (2H-1,2,3-triazole-2-yl) isonicotinonitrile 3-Chloroisonicotinonitrile (1.50 g, 7.22 mmol), 1H -1,2,3-triazole (1.50 g, 14.44 mmol) is dissolved in dimethyl sulfoxide (20 mL), cooled in a water bath, sodium hydride (0.98 g, 21.77 mmol) is added, and then 100. The mixture was stirred at ° C. for 2 hours. Water was added, and the mixture was extracted 4 times with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain 3- (2H-1,2,3-triazole-2-yl) isonicolinonitrile (0.92 g, 49.8%) and 3- (1H). -1,2,3-triazole-1-yl) isonicotinonitrile (0.92 g, 9.6%) was obtained.
3- (2H-1,2,3-triazole-2-yl) isonicolinonitrile
1H NMR (CDCl ₃ ) δ9.50 (1H, s), 8.77 (1H, d, J = 4.8Hz), 8.00 (2H, s), 7.71 (1H, d, J = 5.1Hz)
3- (1H-1,2,3-triazole-1-yl) isonicotinonitrile
1H NMR (CDCl ₃ ) δ9.25 (1H, s), 8.92 (1H, d, J = 5.1Hz), 8.29 (1H, d, J = 1.2Hz), 7.98 (1H, d, J = 1.2Hz) , 7,76 (1H, d, 5,1Hz)

Synthesis Example 1-1-7: 3- (2H-1,2,3-triazole-2-yl) -N- (5-trifluoromethyl) pyridin-2-yl) isonicotine imidazole (Compound No. 7) ) Preparation 5- (trifluoromethyl) pyridin-2-amine (0.57 g, 3.51 mmol) was dissolved in N, N-dimethylformamide (12 mL) and sodium hydride (content 55%, 0.17 g, 3.86 mmol) was added, and the mixture was stirred at room temperature for 1 hour. 3- (2H-1,2,3-triazole-2-yl) isonicotinonitrile (0.60 g, 3.51 mmol) prepared in Synthesis Example 1-1-6 was added thereto for 13 hours at room temperature. Stirred. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.74 g, 63.3%).
1H NMR (CDCl ₃ ) δ10.34 (1H, broad), 9.08 (1H, s), 8.80 (1H, d, J = 4.8Hz), 8.57 (1H, s), 7.86 (2H, s), 7.81 ( 1H, dd, J = 8.4, 2.4Hz), 7.54 (1H, d, J = 5.1Hz), 7.14 (1H, d, J = 8.7Hz), 6.23 (1H, broad)

Synthesis Examples 1-1-8: N-((3- (2H-1,2,3-triazole-2-yl) pyridin-4-yl) ((5- (trifluoromethyl) pyridin-2-yl) ) Preparation of amino) methylene) acetamide (Compound No. 16) 3- (2H-1,2,3-triazole-2-yl) -N- (5-trifluoromethyl) prepared in Synthesis Example 1-1-7 ) Pyridine-2-yl) Acetic anhydride (7 mL) was added to isonicotine imidazole (0.36 g, 1.08 mmol), and the mixture was stirred under reflux for 20 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 63.6%, white solid).
1H NMR (CDCl ₃ ) δ13.33 (1H, s), 9.34 (1H, s), 8.76 (1H, s), 8.71 (1H, d, J = 5.1Hz), 7.97 (1H, d, J = 6.9) Hz), 7.78 (2H, s), 7.43 (1H, d, J = 5.1Hz), 7.32 (1H, d, J = 8.4Hz), 2.09 (3H, s)

Synthesis Example 1-21: 2- (3- (1H-pyrazole-1-yl) pyridin-4-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5] -A] Preparation of pyridine (Compound No. 46) 3- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) prepared in Synthesis Example 1-1-2. Isonicotin imidazole (0.20 g, 0.60 mmol) was dissolved in dichloromethane (10 mL), iodobenzenediacetate (0.23 g, 0.72 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Iodobenzene diacetate (0.23 g, 0.72 mmol) was further added, and the mixture was stirred at room temperature for 5 hours. Dichloromethane was distilled off under reduced pressure with an evaporator, and the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.12 g, 61.3%, white solid).
1H NMR (CDCl ₃ ) δ8.88 (1H, s), 8.86-8.77 (2H, m), 8.07 (1H, d, J = 4.8Hz), 7.84 (1H, d, J = 9.3Hz), 7.75- 7.64 (3H, m), 6.49 (1H, t, J = 2.4Hz)

Synthesis Example 1-2-2: 2- (3- (2H-1,2,3-triazole-2-yl) pyridin-4-yl) -6- (trifluoromethyl)-[1,2,4 ] Preparation of triazolo [1,5-a] pyridine (Compound No. 48) 3- (2H-1,2,3-triazole-2-yl) -N- (5) prepared in Synthesis Example 1-1-7 -Trifluoromethyl) Pyridine-2-yl) Isonicotin imidazole (0.14 g, 0.75 mmol) is dissolved in dichloromethane (7 mL), iodobenzenediacetate (0.16 g, 0.49 mmol) is added, and room temperature Was stirred for 45 minutes. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.10 g, 74.1%).
1H NMR (CDCl ₃ ) δ9.03 (1H, s), 8.89 (1H, d, J = 5.1Hz), 8.80 (1H, s), 8.10 (1H, d, J = 5.1Hz), 7.85 (2H, s), 7.82 (1H, d, J = 9.3Hz), 7.69 (1H, dd, J = 9.3, 1.8Hz)

Synthesis Examples 1-3-1: 2- (3- (1H-pyrazole-1-yl) pyridin-4-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1 , 3, 5] Preparation of triazine-4-one (Compound No. 61) 3- (1H-pyrazole-1-yl) -N- (5- (trifluoromethyl) prepared in Synthesis Example 1-1-2 Pyridine-2-yl) isonicotine imidazole (0.18 g, 0.54 mmol) dissolved in dichloromethane (8 mL), 4-chlorophenyl chloroformate (200 μL, 1.45 mmol), followed by triethylamine (400 μL, 5.42 mmol). ) Was added, and the mixture was stirred at room temperature for 1 hour. Then, dichloromethane was distilled off by an evaporator, ethyl acetate (10 mL) was added, and the mixture was stirred under heating under reflux for 4 hours. Ethyl acetate was distilled off under reduced pressure with an evaporator, and the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.16 g, 84.6%, white solid).
1H NMR (CDCl ₃ ) δ9.37 (1H, s), 8.87 (1H, s), 8.11 (1H, d, J = 4.8Hz), 8.10 (1H, dd, J = 9.0, 2.4Hz), 7.94 ( 1H, d, J = 5.1Hz), 7.80 (1H, d, J = 2.4Hz), 7.58 (1H, d, J = 1.8Hz), 7.52 (1H, d, J = 9.3Hz), 6.46 (1H, 1H, t, J = 2.1Hz)

Synthesis Example 1-3-2: 2- (3- (2H-1,2,3-triazole-2-yl) pyridin-4-yl) -7- (trifluoromethyl) -4H-pyrido [1, 2-a] [1,3,5] Preparation of triazine-4-one (Compound No. 62) 3- (2H-1,2,3-triazole-2-yl) prepared in Synthesis Example 1-1-7 ) -N- (5-trifluoromethyl) pyridin-2-yl) isonicotine imidazole (0.16 g, 0.49 mmol) dissolved in dichloromethane (10 mL) and 4-chlorophenyl chloroformate (150 μL, 1.09 mmol). ), Subsequently, triethylamine (300 μL, 2.16 mL) was added, and the mixture was stirred at room temperature for 12 hours. Then, dichloromethane was distilled off by an evaporator, ethyl acetate (15 mL) was added, and the mixture was stirred under heating under reflux for 2 hours. Ethyl acetate was distilled off under reduced pressure with an evaporator, and the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.13 g, 74.0%).
1H NMR (CDCl ₃ ) δ9.39 (1H, s), 9.19 (1H, s), 8.85 (1H, d, J = 4.8Hz), 8.12 (1H, dd, J = 9.3, 2.4Hz), 7.92 ( 1H, d, J = 5.1Hz), 7.78 (2H, s), 7.53 (1H, d, J = 9.0Hz)

Synthesis Example 2-1-1: 3- (Ethylthio) Preparation of picorinonitrile 3-Chloropicorinonitrile (1.00 g, 7.22 mmol) and ethyl mercaptan (0.59 mL, 7.98 m mmol) were added in N, N. -It was dissolved in dimethylformamide (10 mL), cooled in an ice bath, sodium hydride (0.35 g, 8.02 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. Water was added, and the mixture was extracted 3 times with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (1.11 g, 93.6%, pale yellow oil).
1H NMR (CDCl ₃ ) δ8.49 (1H, dd, J = 4.5, 1.2Hz), 7.75 (1H, dd, J = 8.4, 1.5Hz), 7.43 (1H, dd, J = 8.1, 4.5Hz), 3.06 (2H, q, J = 7.5Hz), 1.38 (1H, t, J = 7.5Hz)

Synthesis Example 2-1-2: Preparation of 3- (ethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 36) 5- (trifluoromethyl) pyridine- 2-Amine (1.09 g, 6.72 mmol) is dissolved in N, N-dimethylformamide (16 mL), sodium hydride (content 55%, 0.33 g, 7.56 mmol) is added, and the mixture is stirred at room temperature for 15 minutes. bottom. 3- (Ethylthio) picorinonitrile (1.11 g, 6.76 mol) prepared in Synthesis Example 2-1-1 was added thereto, and the mixture was stirred at the same temperature for 5 hours, water was added, and 2 was added with ethyl acetate. Extraction was performed once, and the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled off under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.90 g, 41.0%, white solid).
1H NMR (CDCl ₃ ) δ10.04 (1H, broad), 8.63 (1H, s), 8.35 (1H, dd, J = 4.5, 1.2Hz), 7.91 (1H, broad), 7.84 (1H, dd, J) = 8.4, 2.4Hz), 7.71 (1H, dd, J = 8.4, 1.2Hz), 7.43 (1H, d, J = 8.7Hz), 7.32 (1H, dd, J = 8.1, 4.5Hz), 2.92 (2H) , q, J = 7.5Hz), 1.41 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-3: Preparation of 3- (ethylthio) -5- (4- (trifluoromethyl) phenyl) picolinonitrile 5-bromo-3- (ethylthio) prepared by the method described in WO2017016922, p57. ) Picolinonitrile (0.48 g, 1.97 mmol) was dissolved in 1,4-dioxane (25 mL), the inside of the system was degassed with a pump, and then replaced with nitrogen to dichlorobis (triphenylphosphine) palladium (II). (0.14 g, 0.20 mmol) was added, and the mixture was heated and stirred at 60 ° C. for 10 minutes under a nitrogen atmosphere. Then, (4- (trifluoromethyl) phenyl) boronic acid (0.45 g, 2.37 mmol) and 2M aqueous sodium carbonate solution (5 mL) were added, degassed again, replaced with nitrogen, and stirred under reflux for 2 hours. .. After allowing to cool, ethyl acetate and water were added, and unnecessary substances were removed by filtration using a filtration aid. Water was further added to the filtrate, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.60 g, 98.6%).
1H NMR (CDCl ₃ ) δ8.69 (1H, d, J = 1.8Hz), 7.87 (1H, d, J = 2.1Hz), 7.80 (2H, d, J = 8.4Hz), 7.70 (2H, d, J = 8.4Hz), 3.13 (1H, q, J = 7.5Hz), 1.43 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-4: Preparation of 3- (ethylthio) -5- (4- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole ( Compound No. 138)
5- (Trifluoromethyl) pyridine-2-amine (106 mg, 0.65 mmol) was dissolved in N, N-dimethylformamide (4 mL), sodium hydride (content 55%, 31 mg, 0.71 mmol) was added. The mixture was stirred at room temperature for 15 minutes. 3- (Ethylthio) -5-(4- (trifluoromethyl) picolinonitrile (200 mg, 6.49 mol) prepared in Synthesis Example 2-1-3 was added thereto, and the mixture was stirred at room temperature for 16 hours, and then the mixture was stirred. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography and then acetate. The product was suspended in a mixed solution of ethyl and hexane and filtered to obtain the desired product.
1H NMR (CDCl ₃ ) δ10.07 (1H, broad), 8.65 (1H, s), 8.55 (1H, d, J = 1.8Hz), 7.86 (1H, dd, J = 8.4Hz, 2.4Hz), 7.84 (1H, d, J = 2.1Hz), 7.78 (2H, d, J = 8.1Hz), 7.72 (2H, d, J = 8.1Hz), 7.46 (1H, d, J = 8.4Hz), 2.97 (2H) , q, J = 7.5Hz), 1.46 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-5: Preparation of 3- (ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 139)
Synthesis 3- (ethylthio) -5-(4- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole prepared in Example 2-1-4 ( 0.27 g, 0.57 mmol) was dissolved in dichloromethane (5.5 mL), 3-chloroperbenzoic acid (65%, 0.31 g, 1.15 mmol) was added, and the mixture was stirred at room temperature for 18 hours. An aqueous sodium hydrogen carbonate solution was added, the mixture was extracted with ethyl acetate, the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 91.5%).
1H NMR (CDCl ₃ ) δ10.17 (1H, broad), 9.05 (1H, d, J = 2.1Hz), 8.71 (1H, d, J = 1.5Hz), 8.69 (1H, s), 7.95-7.75 ( 6H, m), 7.20 (1H, d, J = 2.4Hz), 4.05 (2H, q, J = 7.5Hz), 1.42 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-6: 3- (ethylthio) -5- (2H-1,2,3-triazole-2-yl) preparation of picorinonitrile 5-bromo prepared by the method described in WO2017016222, p57. -3- (Ethylthio) picorinonitrile (1.00 g, 4.11 mmol) is dissolved in N, N-dimethylformamide (10 mL) and 1H-1,2,3-triazole (0.31 g, 4.49 mmol) is dissolved. , Potassium carbonate (0.85 g, 6.15 mmol) was added, and the mixture was stirred at 80 ° C. for 5 hours. After allowing to cool, water was added, the mixture was extracted twice with ethyl acetate, washed with saturated brine, the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.49 g, 51.5%).
1H NMR (CDCl ₃ ) δ9.21 (1H, d, J = 2.4Hz), 8.36 (1H, d, J = 2.1Hz), 7.93 (2H, s), 3.17 (2H, q, J = 7.5Hz) , 1.47 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-7: 3- (ethylthio) -5- (2H-1,2,3-triazole-2-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline Preparation of imidazole (Compound No. 102)
5- (Trifluoromethyl) pyridine-2-amine (130 mg, 0.80 mmol) is dissolved in N, N-dimethylformamide (4 mL), sodium hydride (content 55%, 35 mg, 0.89 mmol) is added. The mixture was stirred at room temperature for 15 minutes. 3- (Ethylthio) -5- (2H-1,2,3-triazole-2-yl) picolinonitrile (186 mg, 0.80 mol) prepared in Synthesis Example 2-1-6 was added thereto, and the temperature was changed to room temperature. Was stirred for 4 hours. Water was added to the reaction product, the mixture was extracted with ethyl acetate, washed with saturated brine, the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography, and then the product was suspended in a mixed solution of ethyl acetate and hexane, and filtered to obtain the desired product (92 mg, 29.1%).
1H NMR (CDCl ₃ ) δ10.06 (1H, broad), 9.08 (1H, d, J = 2.1Hz), 8.65 (1H, s), 8.40 (1H, d, J = 2.1Hz), 7.90 (2H, s), 7.86 (1H, dd, J = 8.7, 2.7Hz), 7.45 (1H, d, J = 8.4Hz), 3.02 (2H, q, J = 7.5Hz), 1.48 (3H, t, J = 7.5) Hz)

Synthesis Example 2-1-8: 3- (ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) Preparation of picoline imidazole (Compound No. 103)
Synthesis Example 3- (ethylthio) -5- (2H-1,2,3-triazole-2-yl) -N- (5- (trifluoromethyl) pyridin-2-yl prepared in Example 2-1-7 ) Picoline imidazole (62 mg, 0.16 mmol) was dissolved in dichloromethane (2.5 mL), 3-chloroperbenzoic acid (65%, 86 g, 0.32 mmol) was added, and the mixture was stirred at room temperature for 2 hours. An aqueous sodium hydrogen carbonate solution was added, the mixture was extracted with ethyl acetate, the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (45 mg, 67.1%).
1H NMR (CDCl ₃ ) δ9.55 (1H, d, J = 2.4Hz), 9.18 (1H, d, J = 1.8Hz), 8.68 (1H, s), 8.05-7.92 (3H, m), 7.88 ( 1H, dd, J = 8.7Hz, 2.1Hz), 7.20 (1H, d, J = 8.7Hz), 4.07 (2H, q, J = 7.5Hz), 1.44 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-9: Preparation of 3-chloro-5- (dimethylamino) picolinonitrile 3,5-dichloropicorinonitrile (1.00 g, 5.78 mmol) was added to N, N-dimethylformamide (10 mL). ), A 50% aqueous dimethylamine solution (1.21 mL, 11.56 mmol) was added, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction product, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.70 g, 66.7%).
1H NMR (CDCl ₃ ) δ8.01 (1H, d, J = 2.7Hz), 6.88 (1H, d, J = 2.7Hz), 3.10 (3H, s)

Synthesis Example 2-1-10: Preparation of 5- (dimethylamino) -3- (ethylthio) picolinonitrile 3-Chloro-5- (dimethylamino) picolinonitrile prepared in Synthesis Example 2-1-9 (0.70 g, 3.85 mmol) is dissolved in N, N-dimethylformamide (14 mL), ethyl mercaptan (0.92 mL, 3.92 mmol) is added, and sodium hydride (55%, 0.19 g) is added under ice-cooling. 4.29 mmol) was added and stirred. After returning to room temperature and stirring at the same temperature for 3 hours, water was added to the reaction product, the mixture was extracted twice with ethyl acetate, the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator. A crude product (0.81 g) was obtained.
1H NMR (CDCl ₃ ) δ7.94 (1H, d, J = 2.7Hz), 6.81 (1H, d, J = 3.0Hz), 3.09 (6H, s), 3.03 (2H, q, J = 7.5Hz) , 1.35 (3H, t, J = 7.5Hz)

Synthesis Example 2-1-11: Preparation of 5- (dimethylamino) -3- (ethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (Compound No. 124)
Synthesis Example 5- (dimethylamino) -3- (ethylthio) picolinonitrile (0.20 g, 0.96 mmol) prepared in Example 2-1-10 is dissolved in toluene (10 mL), and trimethylaluminum is cooled under ice. (1.8 M toluene solution, 1.0 mL, 3.92 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Then, 5- (trifluoromethyl) pyridine-2-amine (0.16 g, 0.96 mmol) was added, and the mixture was stirred at 70 ° C. for 6 hours. Water was added to the reaction product, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure with an evaporator to obtain the desired product (73 mg, 21%).
1H NMR (CDCl ₃ ) δ9.98 (1H, broad), 8.58 (1H, s), 7.89 (1H, d, J = 1.8Hz), 7.80 (1H, dd, J = 8.4Hz, 2.4Hz), 7.42 (1H, broad), 6.82 (1H, d, J = 2.4Hz), 3.09 (6H, s), 2.89 (2H, q, J = 7.5Hz), 1.44 (3H, t, J = 7.5Hz)

Synthesis Example 2-2-1: 2- (3- (Ethylthio) Pyridine-2-yl) -6- (Trifluoromethyl)-[1,2,4] Triazolo [1,5-a] Pyridine (Compound) Preparation of No. 53) 3- (ethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole (0.38 g, 1.16 mmol) prepared in Synthesis Example 2-1-2. Was dissolved in dichloromethane (12 ml), iodobenzenediacetate (0.39 g, 1.22 mmol) was added, and the mixture was stirred at room temperature for 10 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.19 g, 49.1%).
1H NMR (CDCl ₃ ) δ9.06 (1H, s), 8.60 (1H, dd, J = 4.5, 1.2Hz), 7.98 (1H, d, J = 9.3Hz), 7.76 (1H., D, J = 8.1, 1.5Hz), 7.72 (1H, dd, J = 9.3, 1.8Hz), 7.37 (1H, dd, J = 8.1, 4.5Hz), 3.02 (2H, q, J = 7.5Hz), 1.40 (3H, 3H, t, J = 7.5Hz)

Synthesis Example 2-2-2: 2- (3- (ethylsulfinyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine ( Compound No. 54) and 2- (3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No. 55) 2- (3- (Ethylthio) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] prepared in Synthesis Example 2-2-1. ] Pyridine (0.13 g, 0.40 mmol) was dissolved in dichloromethane (10 mL), 3-chloroperbenzoic acid (65%, 0.16 g, 0.60 mmol) was added, and the mixture was stirred at room temperature for 20 minutes. After distilling dichloromethane under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to 2- (3- (ethylsulfinyl) pyridin-2-yl) -6- (trifluoromethyl)-[1, 2,4] Triazolo [1,5-a] pyridine (6.4 mg, 4.7%) and 2- (3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1 , 2,4] Triazolo [1,5-a] pyridine (95 mg, 66.5%) was obtained.
Compound 54
1H NMR (CDCl ₃ ) δ9.04 (1H, s), 8.93 (1H, s), 8.63 (1H, dd, J = 8.1, 1.5Hz), 7.98 (1H, d, J = 9.3Hz), 7.79 ( 1H, dd, J = 9.3, 1.8Hz), 7.70 (1H, dd, J = 8.1, 4.8Hz), 3.46 (1H, m), 3.00 (1H, m), 1.39 (3H, t, J = 7.5Hz) )
Compound 55
1H NMR (CDCl ₃ ) δ9.07-8.98 (2H, m), 8.55 (1H, dd, J = 8.1, 1.8Hz), 7.94 (1H, d, J = 9.6Hz), 7.76 (1H, dd, J) = 9.6, 1.8Hz), 7.68 (1H, dd, J = 7.8, 4.5Hz), 3.96 (2H, q, J = 7.5Hz), 1.41 (3H, t, J = 7.5Hz)

Synthesis Example 2-2-3: 2- (3- (ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2 , 4] Preparation of triazolo [1,5-a] pyridine (Compound No. 176)
Synthesis Example 3- (ethylsulfonyl) -5-(4- (trifluoromethyl) phenyl) -N- (5- (trifluoromethyl) pyridin-2-yl) picoline imidazole prepared in Example 2-1-5 (51 mg, 0.10 mmol) was dissolved in dichloromethane (2.5 mL), iodobenzenediacetate (98 mg, 0.30 mmol) was added, and the mixture was stirred at room temperature for 18 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (37 mg, 72.8%).
1H NMR (CDCl ₃ ) δ9.23 (1H, d, J = 2.1Hz), 9.02 (1H, s), 8.74 (1H, d, J = 2.1Hz), 7.96 (1H, d, J = 9.3Hz) , 7.89-7.79 (4H, m), 7.78 (1H, dd, J = 9.3Hz, 1.5Hz), 4.05 (2H, q, J = 7.5Hz), 1.46 (3H, t, J = 7.5Hz)

Synthesis Example 2-2-4: 2- (3- (ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -6- (trifluoromethyl) -Preparation of [1,2,4] triazolo [1,5-a] pyridine (Compound No. 181)
Synthesis Example 3- (ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) prepared in Example 2-1-8 Il) Picoline imidazole (0.10 g, 0.24 mmol) was dissolved in dichloromethane (3 mL), iodobenzenediacetate (0.23 g, 0.71 mmol) was added, and the mixture was stirred at room temperature for 16 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (72 mg, 72.4%).
1H NMR (CDCl ₃ ) δ9.74 (1H, d, J = 2.1Hz), 9.20 (1H, d, J = 2.1Hz), 9.02 (1H, s), 8.01-7.92 (3H, m), 7.78 ( 1H, dd, J = 9.3Hz, 1.5Hz), 4.06 (2H, q, J = 7.5Hz), 1.47 (3H, t, J = 7.5Hz)

The compound of the present invention of the formula (1-3) shown in Table 8, the main compound of the formula (1-4) shown in Table 9, and the book of the formula (2-2) shown in Table 10 synthesized by the same method as described above. originating compounds, the onset compound of formula (2-3) shown in Table 11, the onset compound of formula (3-2) shown in Table 12, ¹ H of the onset compound of formula (3-3) shown in Table 13 -NMR data and melting point are shown in Table 14. In some NMR data, amidine protons were not detected.

<Formulation example>
In addition, examples of pesticide preparations containing the compound of the present invention as an active ingredient are listed below.
Pharmaceutical example 1 [wettable powder]
Compound 30% by weight
Clay 30% by weight
Diatomaceous earth 35% by weight
Sun extract P252 4% by weight
(Calcium lignin sulfonate: Trade name of Nippon Paper Industries, Ltd.)
Solpole 8070 1% by weight
(Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.)
The components were uniformly mixed and pulverized to obtain a wettable powder.

Pharmaceutical example 2 [powder]
Compound 2% by weight
Clay 90% by weight
Talc 7% by weight
Calcium stearate 1% by weight
The above components were uniformly mixed to obtain a powder.

Pharmaceutical example 3 [Emulsion]
Compound 20% by weight
N, N-dimethylformamide 20% by weight
T-SOL 150 50% by weight
(Aromatic solvent: Product name of JXTG Energy Co., Ltd.)
New Calgen CL-H 10% by weight
(POE alkyl phenyl ether: product name of Takemoto Oil & Fat Co., Ltd.)
The components were uniformly mixed and dissolved to obtain an emulsion.

Pharmaceutical Example 4 [Emulsion 2]
Compound 5% by weight
Xylene 42.5% by weight
DMSO 42.5% by weight
New Calgen 2003 10% by weight
(Mixing of POE allylphenyl ether formaldehyde condensate and alkylbenzene sulfonic acid metal salt: Product name of Takemoto Oil & Fat Co., Ltd.)
The components were uniformly mixed and dissolved to obtain an emulsion.
Pharmaceutical example 5 [Granule]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sun extract P252 2% by weight
(Calcium lignin sulfonate: Trade name of Nippon Paper Industries, Ltd.)
The components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain granules.

Pharmaceutical example 6 [Flowable agent]
Compound 25% by weight
Solpole 7556 5% by weight
(POE styrylphenyl ether sulfate: product name of Toho Chemical Industry Co., Ltd.)
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
60% by weight of water
After premixing the entire amount of the above formulation excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water, the mixture was pulverized with a wet pulverizer. Then, a 1% aqueous solution of xanthan gum and the remaining water were added to the obtained pulverized product to obtain a 100% by weight flowable agent.

Pharmaceutical example 7 [Granule]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sun extract P252 2% by weight
(Calcium lignin sulfonate: Trade name of Nippon Paper Industries, Ltd.)
The components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain granules.

<Biological test example>
The following tests demonstrate the control efficacy of the compounds of the invention against specific pests. "Control efficacy" refers to inhibition of growth (including mortality) of harmful invertebrates that significantly reduces feeding. The pest control protection achieved by the compounds, however, is not limited to these species. Compound numbers refer to the compounds in Tables 8-13.

Biological test example 1: Aphis gossypii control test (leaf spraying treatment)
Cucumber leaves were cut to a diameter of 3.5 cm and placed on cotton wool moistened with water. Two adult Aphis gossypii were released here and laid for 24 hours, after which the adults were removed. 2 mL of a diluted solution of the test compound diluted with water so as to be 200 ppm was sprayed on the cucumber leaves using a spraying tower. After air-drying, it was placed in a plastic cup together with absorbent cotton, covered, and bred in a constant greenhouse at 25 ° C. Life and death were observed 5 days after the treatment, and the mortality rate was calculated.
As a result, the compounds of the present invention 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 14, 17, 18, 19, 20, 26, 27, 28, 29, 30, 31, 42, 43, 45, 46, 48, 49, 50, 51, 53, 54, 55, 59, 61, 62, 66, 80, 85, 86, 87, 91, 103, 105, 106, 108, 110, 111, 112, 114, 120, 123, 125, 127, 135, 148, 150, 152, 156, 160, 170, 173, 174, 175, 177, 180, 181, 199, 201, 204, 207, 209, 215 and 220 showed a mortality rate of 80% or more.

Biological test example 2: Aphis gossypii control test (root immersion treatment)
One cucumber seedling (cotyledon stage) was fixed with urethane so that the root was immersed in a vial (inner diameter 2.7 cm x 6 cm) containing 10 mL of a chemical solution diluted with water at 3.1 ppm. One day after soaking, five first-instar larvae of Aphis gossypii were released and bred in a constant greenhouse at 25 ° C. Five to seven days after the release of the insects, the life and death of the insects and abnormalities were investigated.
As a result, the compounds of the present invention 2, 3, 7, 14, 20, 29, 45, 46, 48, 51, 53, 55, 62, 85, 91, 103, 105, 106, 108, 111, 120, 170, 173, 180 and 199 showed a mortality rate of 80% or more.

Biological test example 3: Bemisia tabaci control test (spraying of foliage)
Cucumber leaves were cut to a diameter of 6.0 cm and placed on cotton wool moistened with water. 2 mL of a diluted solution of the test compound diluted with water so as to be 200 ppm was sprayed on the cucumber leaves using a spraying tower. After air-drying, the cucumber leaves were placed in a plastic cup, 20 adult Bemisia tabaci were released, covered, and bred in a constant temperature room at 25 ° C. Life and death were observed 5 days after the treatment, and the mortality rate was calculated.
As a result, the compounds of 13, 156, 196, 204, 209, and 215 showed an insecticidal rate of 80% or more.

Biological test example 4: Diamondback moth (Plutella xylostella) control test (leaf piece immersion treatment)
The cabbage leaves were cut to a diameter of 7.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water so as to have a diameter of 200 ppm, and air-dried. After air-drying, cabbage leaf pieces were placed in a plastic cup, 10 diamondback moth 3rd instar larvae were released, covered, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the larval death rate was calculated.
As a result, the compounds of the present invention 7, 8, 37, 46, 48, 55, 61, 69, 78, 91, 100, 101, 103, 105, 106, 108, 109, 110, 111, 112, 113, 114, 120, 125, 127, 128, 129, 131, 137, 139, 140, 142, 152, 158, 161, 175, 176, 177, 178, 180, 181, 188, 191, 195, 199, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 218, 219 and 220 showed a mortality rate of 80% or more.

Biological test example 5: Brown planthopper (Nilaparvata lugens) control test (stem and leaf immersion treatment)
Ten rice seedlings were taken, immersed in 20 mL of a chemical solution of the test compound diluted with water to 200 ppm, and air-dried. After air-drying, hold it in a glass cylinder (inner diameter 4.5 cm x 14 cm) with urethane and stand it in a plastic cup containing 40 mL of water. The brown planthopper 3rd instar larvae were released, covered with a medicine wrapping paper, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the larval death rate was calculated.
As a result, the compounds of the present invention 1, 2, 3, 4, 5, 7, 10, 11, 14, 16, 18, 19, 20, 26, 29, 31, 42, 43, 44, 45, 46, 48, 49, 50, 51, 53, 55, 59, 61, 85, 86, 90, 91, 98, 103, 106, 152, 170, 176, 181 and 215 showed a mortality rate of 80% or more.

Biological test example 6: Segatella furcifera control test (root immersion treatment)
Take 10 rice seedlings, hold them in a glass cylinder (inner diameter 4.5 cm x 14 cm) with urethane, and stand them in a plastic cup containing 40 mL of a chemical solution diluted with water to a concentration of 3.1 ppm. Two days later, 10 Sedirounka 3rd instar larvae were released in this glass cylinder, covered with a medicine wrapping paper, and bred in a constant temperature room at 25 ° C. The life and death of the larvae were observed 7 days after the treatment, and the larval death rate was calculated.
As a result, the compounds of the present invention 2, 3, 4, 16, 20, 29, 42, 47, 48, 53 and 55 showed an insecticidal rate of 80% or more.

Biological test example 7: Spodoptera litura control test (sprouting treatment)
The cabbage leaves were cut to a diameter of 5.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water so as to have a diameter of 200 ppm, and air-dried. After air-drying, cabbage leaf pieces were placed in a plastic cup, and five Spodoptera litura 2nd instar larvae were released, covered, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the larval death rate was calculated.
As a result, the compounds of the present invention 91, 100, 103, 106, 120, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 178, 180, 181, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 219 and 220 showed a mortality rate of 80% or more.

Biological test example 8: Phyllotreta striolata control test (stem and leaf immersion treatment)
The cabbage leaves were cut to a diameter of 2.8 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water so as to have a diameter of 200 ppm, and air-dried. After air-drying, the cabbage leaf pieces were placed in a plastic cup, and five adult cabbage beetles were released, covered, and bred in a constant greenhouse at 25 ° C. Two days after the treatment, the life and death of the adults were observed, and the death rate and the degree of feeding damage were calculated.
As a result, compounds 91, 100, 101, 103, 106, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 181 and 205 were 80% or more dead insects. The rate or the degree of feeding damage of 10% or less was shown.

Claims (24)

A compound represented by the formula (1), the formula (2) or the formula (3), a salt thereof, or an N-oxide thereof.
[In equations (1), (2) and (3),

G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by ^G 1 -4 or ^G 1 -5,

G ^{2 is, G 2 -1, G 2 -2} , G 2 -3, represents a structure represented by ^G 2 -4 or ^G 2 -5,

R ¹ , R ² , R ³ and R ⁴ are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo ( C _{1 to} C ₆ ) Alkoxy, halo (C _{1 to} C ₆ ) alkylthio, halo (C _{1 to} C ₆ ) alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, (C = O) NY ¹ Y ² or -Represents NY ¹ Y ²
A ¹ represents C- ^RC or N,
A ² represents a ^{C-R E} or N, (and ^where either of A 1, ^{A 2} is N, and the other is ^{C-R C,} or ^{C-R E.)
R A, R B, R C} , R D and ^{R E} are each independently a hydrogen atom, a halogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C _{6) alkyl,} C 3 -C ₆ cycloalkyl , U substituted (C _{3 to} C ₆ ) cycloalkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, phenoxy groups optionally substituted with up to 5 Z, C ₁ to C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Sulfonyl, (C = O) NY ³ Y ⁴ , -NY ³ Y ⁴ , cyano, nitro, a phenyl group that may be substituted with up to 5 Z, a pyridyl group that may be substituted with up to 4 Z, Pyrimidyl group optionally substituted with up to 3 Zs Pyramidyl group optionally substituted with up to 3 substituents Pyridazyl group optionally substituted with up to 3 Zs substituted with up to 3 Zs Represents a thienyl group that may be substituted, a furanyl group or V that may be substituted with up to 3 Zs,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6.

Z is independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C ₁ to C. C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Represents sulfonyl, -NY ⁵ Y ⁶ , cyano or nitro,
Q2, Q3 or Q4 indicate the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3 and represents
Q4 represents an integer of 0, 1, 2, 3 or 4.
When Q2, Q3 or Q4 represent an integer of 2 or more, the plurality of Zs may be the same as each other or different from each other.
Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ , and Y ⁶ are independent hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, and C _{1 to} C ₆ alkyl, respectively. Carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkoxycarbonyl, halo (C _{1 to} C ₆ ) alkoxy carbonyl, C _{1 to} C ₆ alkyl sulfonyl or halo (C _{1 to} C ₆ ) alkyl sulfonyl Represents
U represents cyano, -C (O) OH or -C (O) NH ₂ .
D is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{3 to} C ₆ cycloalkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, C _{1 to} C ₃ alkyloxycarbonyl, halo (C _{1 to} C ₃ ) alkyloxycarbonyl, even if substituted with up to 5 Ts Represents a good benzenecarbonyl,
T independently represents a hydrogen atom, a halogen atom, C _{1 to} C ₃ alkyl, halo (C _{1 to} C ₃ ) alkyl, C _{1 to} C ₃ alkoxy, and halo (C _{1 to} C ₃ ) alkoxy.
E is a hydrogen atom, C _{1 to} C ₆ alkyl, cyclopropyl methyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{3 to} C ₆ cycloalkyl carbonyl, halo (C _{1 to} C _6). ) Alkylcarbonyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ] A compound represented by the formula (1), the formula (2) or the formula (3), a salt thereof, or an N-oxide thereof.
[In equations (1), (2) and (3),

G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by ^G 1 -4 or ^G 1 -5,

G ^{2 is, G 2 -1, G 2 -2} , G 2 -3, represents a structure represented by ^G 2 -4 or ^G 2 -5,

R ¹ , R ² , R ³ and R ⁴ are independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo ( Represents C _{1 to C 6} ) alkoxy, halo (C _{1 to} C ₆ ) alkylthio, halo (C _{1 to} C ₆ ) alkyl sulfinyl or halo (C _{1 to} C ₆ ) alkyl sulfonyl.
A ¹ represents C- ^RC or N,
A ² represents a ^{C-R E} or N, (and ^where either of A 1, ^{A 2} is N, and the other is ^{C-R C,} or ^{C-R E.)
R A, R B, R C} , R D and ^{R E} are each independently a hydrogen atom, a halogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C _{6) alkyl,} C 3 -C ₆ cycloalkyl , U-substituted (C _{3 to} C ₆ ) cycloalkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkyl thio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, -NY ³ Y ⁴ , cyano, nitro or V Represent,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6.

Z is independently hydrogen atom, halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C ₁ to C. C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkylsulfonyl, halo (C _{1 to} C ₆ ) alkyl Represents sulfonyl, -NY ⁵ Y ⁶ , cyano or nitro,
Q2, Q3 or Q4 indicate the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3 and represents
Q4 represents an integer of 0, 1, 2, 3 or 4.
When Q2, Q3 or Q4 represent an integer of 2 or more, the plurality of Zs may be the same as each other or different from each other.
Y ³ , Y ⁴ , Y ⁵ , and Y ⁶ are independent hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, and halo (C _1). Represents ~ C ₆ ) alkylcarbonyl, C ₁ ~ C ₆ alkoxycarbonyl, halo (C ₁ ~ C ₆ ) alkoxycarbonyl, C ₁ ~ C ₆ alkyl sulfonyl or halo (C ₁ ~ C ₆ ) alkyl sulfonyl.
U represents cyano, -C (O) OH or -C (O) NH _{2 independently when there are a plurality of U.}
D is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkyl sulfonyl, halo. (C _{1 to} C ₆ ) Represents an alkylsulfonyl,
E is a hydrogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, halo (C _{1 to} C ₆ ) alkyl carbonyl, C _{1 to} C ₆ alkyl sulfonyl, halo. (C _{1 to} C ₆ ) Represents an alkylsulfonyl. ] The compound according to claim 1 represented by the formula (1) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.} The compound according to claim 1 represented by the formula (1) in which A ¹ is C- ^RC and A ^{2 is N, a salt thereof, or an N-oxide thereof.} G ¹ is a ^G 1 -1, ^{A 1} is N, compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by the formula (1) is a ^{C-R E} .. G ¹ is a ^G 1 -1, ^{A 1} is ^{C-R C,} compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by the formula (1) is N .. The compound according to claim 1 represented by the formula (2) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.} The compound according to the formula (2) in which A ¹ is C- ^RC and A ² is N, a salt thereof, or an N-oxide thereof. G ² is ^G 2 -1, ^{A 1} is N, compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by formula (2) is a ^{C-R E} .. G ² is ^G 2 -1, ^{A 1} is ^{C-R C,} compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by formula (2) is N .. G ² is ^G 2 -1, ^{A 1} is ^C-R C, ^{A 2} is N, ^{R A} is _C 1 -C ₃ ^{alkylsulfonyl, R B,} R ^D is hydrogen atom The compound according to claim 1 represented by the formula (2) or a salt thereof, or an N-oxide thereof, wherein ^{RC is a phenyl group or V which may be substituted with up to 5 Z.} 2- (3- (Ethylsulfonyl) -5- (1H-pyrazole-1-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a ] Pyridine (Compound No. 180),
2- (3- (Ethylsulfonyl) -5- (2H-1,2,3-triazole-2-yl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] Pyridine (Compound No. 181),
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 174),
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 175),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 176),
2- (5- (2-4-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine,
2- (5- (3,5-bis (trifluoromethyl) phenyl) -3- (ethylsulfonyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1 , 5-a] Pyridine (Compound No. 178),
2- (3- (Ethylsulfonyl) -5- (2- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine,
2- (3- (Ethylsulfonyl) -5- (3- (trifluoromethoxy) phenyl) Pyridine-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 214),
2- (3- (Ethylsulfonyl) -5- (4- (trifluoromethoxy) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] Pyridine (Compound No. 177) The compound according to claim 1 represented by the formula (3) in which A ¹ is N and A ² is C- ^{RE, a salt thereof, or an N-oxide thereof.} The compound according to claim 1 represented by the formula (3) in which A ¹ is C- ^RC and A ^{2 is N, a salt thereof, or an N-oxide thereof.} G ² is ^G 2 -1, ^{A 1} is N, compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by the formula (3) is a ^{C-R E} .. G ² is ^G 2 -1, ^{A 1} is ^{C-R C,} compound or a salt thereof or a N- oxide according to claim ^{1, A 2} is represented by the formula (3) N .. A pest control composition comprising the compound according to claims 1 to 16, a salt thereof, or an N-oxide thereof, and at least one component selected from the group consisting of a surfactant, a solid carrier, and a liquid carrier. The pest control composition according to claim 17, further comprising at least one other pest control compound or agent. The at least one pest control compound or agent described above
Aranicarb, Ardicalve, Bendiocarb, Benfracarb, Butocamide, Butoxycarboxym, Carballyl, Carbofuran, Carbosulfan, Ethiophenecarb, Phenocalve, Formethanate, Frathiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamil, Pyrimicalve, Propoxul, Thiodicalbu Knox, triazamate, trimetacarb, XMC, xylylcarb, methylcarb, phenothiocarb, phenoxycarb, acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, ethylthiomethone, chlorethoxyphos, cassaphos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos , Kumaphos, Cyanophos, Demeton-S-Methyl, Diadinone, Dichlorpyrifos, Diclotophos, Dimethate, Dimethylbinphos, EPN, Etion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostiazeto, Heptenophos, Imiciaphos, Isophenphos, Isophenphos, Isophenphos Methoxyaminothiophosphoryl salicylate, isoxathione, malathion, mecarbam, metamidphos, metidation, mevinphos, chlorpyrifos, naredo, ometoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, holate, hosalon, hosmet, phosphamide, hoxim, pyrimiphos -Methyl, Prophenofus, Propetanphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimiphos, Temephos, Telbuphos, Tetrachlorbinphos, Thiometon, Triazophos, Trichlorfon, Bamidethione, Chlorpyrifos-Ethyl, Disulphoton, Sulfrophos, Flupyrazophos, Fent. Tribphos, Endosulfan, Alpha-Endosulfan, Gamma-HCH, Dichoform, Chlorpyrifos, Dildoline, methoxychlor, Acetoprol, Fipronil, Etiprol, Pyrafluprol, Pyriprol, Fulfiprol, Brofuranilide, Afoxolanel, Fluraranel, Salolanel, Fluxamethamide, Rotyranel, Iso , Aclinatrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifentrin, Kappa-Bifen Trin, bioarethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cypermethrin, beta-cypermethrin, cypermethrin, lambda-cypermethrin, gamma-cypermethrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta -Cypermethrin, cypermethrin, deltamethrin, empentrin, esphenothrin, etofenprox, phenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadesrin, permethrin, phenothrin, prarethrin , Pyrethrin, resmethrin, cypermethrin, tefurthrin, kappa-tefurthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, metoxadiazone, metoflutrin, profluthrin, pyrethrum, terraretrin, monfluorothrin, heptafluthrin, mepermethrin, tetra Chloroparalesulin, epsilon-methfurthrin, epsilon-monfluthrin, protrifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitempyram, thiacloprid, thiamethoxam, sulfoxaflor, flupyraziflon, triflumesopyrim, dichloromesopyrim Spinetram, Abamectin, Ibermectin, Emamectin benzoate, Milbemectin, Repimectin, Hydroprene, Kinoprene, Diophenolan, Metoprene, Pyryproxifene, Pymetrodin, Flonicamid, Etoxazole, Diaphenthiron, Azocyclotin, Cypermethrin, Diafenthiron, Azocyclotin, Cypermethrin, Fenbutazin oxide, Propargit , Tralopyrin, DNOC, Bensultap, Cartap, Thiocyclum, Thiosultap, Thiosultap-Sodium, Bistriflulon, Chlorfluazuron, Diflubenzron, Flucycloxuron, Fluphenoxron, Hexaflumron, Ruphenuron, Novalron, Noviflumron, Tefluvenzron, Triflumron , Bistriflulon, buprofezin, cypermethrin, chromaphenozide, halophenothrin, methoxyphenothrin, tebuphenozide, amitraz, hydramethylnone, acequinosyl, fluacripyrethrin Mu, pyriminostrobin, fluphenoxystrobin, phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, pifrubmid, metaflumizone, spirodiclofen, spirotetramato, spiromesifene, spiropidion, siflumethofen, cienopyraffe, flubendiamide , Chlorantraniliprole, Cyantraniliprole, Cycraniliprole, Tetraniliprole, Sihalodiamide, Tetrachlorantraniliprole, Kinomethionate, Hexithiazox, Biphenazate, Fluphenerim, Pyrifluquinazone, Frometkin, Fluopirum, Fluazaindolizine, Amidoflumeth , Tyclopyrazoflor, Thioxazaphen, Oxazosulfyl,
Nicotin, chloropicrin, sulfuryl fluoride, chrylotie, clofentezine, difluorovidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeholm, pyridaryl, azadilactin, benzoximate, afidopyropen, fluhexaphon, fluenesulfone, bencrothias, calcole, insecticidal soap Dimehipo, nithiazine, borate, metaaldehyde, lianodine, sulfurylamide, asinonapill, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3, 5-Dichloropyridin-2-yl) -1H-pyrazole-5-carboxamide,
Metalaxil, Metalaxil-M, Oxadixil, Ophrase, Benalaxil, Benalaxil-M, Kiralaxil, Ophras, Flaluxil, Ciproflan, Buprimate, Dimethyrimol, Etilimol, Himexazole, Hydroxyisoxazole, Oxatiapiproline, Octinone, Oxolinic acid, Benomylic acid , Carbendazim, Huberidazole, Thiabendazole, Devacarb, Dietofencarb, Zoxamide, Etaboxam, Pencyclon, Fluopicolid, Fluopimomid, Diflumethrim, Bupyrimate, Benodanyl, Flutranyl, Mepronil, Isophytamide, Fenfuram, Oxycarboxyn, Carboxone , Penflufen, penthiopyrado, benzobindiflupill, bixaphen, isopyrazam, sedaxane, impilfluxam, fluindapir, isoflusiplum, pyrapropoin, boscalide, azoxystrobin, koumethoxystrobin, cresoximemethyl, trifloxystrobin, picoxy Strobin, Pyracrostrobin, Dimoxystrobin, Metominostrobin, Orisastrobin, Fluoxastrobin, Pyraoxystrobin, Pyrametstrobin, Fluphenoxystrobin, Phenaminestrobin, Enoxastrobin, Spumoxystrobin, Mandestrobin, triclopyricalve, famoxadon, fenamiden, triclopyricalve, pyribenecarb, siazophamid, amisulbrom, vinapacryl, meptyldinocarb, dinocup, fluazinum, ferimzone, acetate-fentin, fentin chloride, fentin hydroxide, trihydroxide Phenyltin, triphenyltin acetate, copper oxine, silthiofam, amethoctrazine, mepanipyrim, nitrapyrin, pyrimesanyl, cyprodinyl, blastsaidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyphene, proquinazide, fludioxonyl, fenpicronyl, fluoro. Imid, procimidone, iprodione, binclozoline, edifenphos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseikayupte extract, triphorin, pyriphenox, pyrisoxazole, phenalimol, nuari Mol, azaconazole, bromconazole, diniconazole, diniconazole-M, epoxyconazole, flukinconazole, oxpoconazole, pefrazoate, diphenoconazole, fembconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triazimephone, tri. Azimenol, triticonazole, uniconazole, imazalyl, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriahole, microbutanyl, paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaco Nazole, Prochloraz, Simeconazole, Ipfentrifluconazole, Aldimorph, Dodemorph, Dodemorph acetate, Tridemorph, Fenpropimorph, Dimethmorph, Fulmorph, Pyrimorph, Piperarin, Fenpropidine, Spiroxamine, Fenhexamide, Fenpyrazamine, Felbam, Metam Calve, Methylam, Tiram, Manzeb, Manneb, Dineb, Diram, Polycarbamate, Provineb, Thiuram, Pyribuchicarb, Varidamycin, Mildiomycin, Polyoxin, Benchavaricarb, Benchavaricarb isopropyl, Variphenalate, Iprovaricarb, Mandipropamide, Fempicoxamide, Florylpicoxamide, Fusalide, Pyrochylone, Tricyclazole, Carpropamide, Diclosimet, Phenoxanyl, Acibenzoral-S-methyl, Provenazole, Diclobenazox, Thiazinyl, Isothianyl, Simoxanyl, Josetil, Teclophthalam, Triazoxide, Flusulfamide, Dichromedin, ciflufenamide, metrafenone, periodofenone, fluthianyl, tebuflokin, ipfluphenokin, Josetylaluminum, turquophos-methyl, ecromezol, tolprocarb, mefentrifluconazole, quinofmerin, pidiflumethofen, Bordeaux mixture, copper acetate, basic sulfate Copper, oxychloride, cupric hydroxide, oxyquinolin copper, copper, sulfur, captan, captahole, forpet, anilazine, chlorotalonyl, dichlorophene, pentachlorophenol and its salts, hexachlorobenzene, quintozen, iminoctadine acetate, Imminoctadine albesilate, guanidine, copper, copper Free base, guazatin, guazatin acetate, albecilate, dithianone, fluoroimide, trillfluanide, diclofluanide, dinobutone, dasomet, pyraziflumid, aminopyriphen, methyltetraprol, pyridaclomethyl,
Produced by dipimethitron, picarbutrazox, technazen, nitrtal-isopropyl, dicyclomet, asibenzoral, prohexadione-calcium, bronopol, diphenylamine, flumethobelle, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, and the genus Bacillus. 28. Claim 18 selected from the group consisting of insecticidal proteins, bactericidal proteins, insecticidal proteins produced by Bt crops, bactericidal proteins, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi. Pest control composition. The pest control composition according to claim 18, wherein the pest is an animal parasitic pest and is administered to an animal or a bird. A method for controlling a pest by bringing the compound according to claim 1 or a salt thereof or an N-oxide thereof into contact with the pest or the environment thereof. The method for enhancing the vitality of a crop, wherein the crop or the seeds of the crop are brought into contact with the compound according to claim 1, a salt thereof, or an N-oxide thereof. A compound according to claim 1, which is a seed treated with the compound according to claim 1, a salt thereof, or an N-oxide thereof, and in an amount of about 0.0001 to about 50% by weight of the whole treated seed. Or the seeds comprising salts thereof or their N-oxides. A method for producing seeds, which comprises a step of treating crop seeds with the compound according to claim 1, a salt thereof, or N-oxides thereof.
The treated seeds contain an amount of about 0.0001 to about 50% by weight of the total seeds of the compound according to claim 1 or a salt thereof or N-oxides thereof.
The method.