JP2018199664A - Pyrazine compound - Google Patents

Abstract

To provide a pyrazine compound or a salt thereof having excellent control activity against various harmful organisms.SOLUTION: There is provided a derivative of a compound represented by formula (1a) below and obtained by directly combining pyrazine and pyridine.SELECTED DRAWING: None

Description

  The present invention relates to a pyrazine compound, a process for producing the same, and a pest control agent containing the same 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 Document 1 discloses a pyrazine compound having a certain 2-pyridyl group as an insecticide. Patent Document 2 discloses a quinoxaline compound having a certain 4-pyridyl group as an insecticide. However, no highly practical compound having high pest control activity has been found.

International Publication No. 2017/065228 International Publication No. 2015/059088

  This invention makes it a subject to provide the pyrazine compound or its salt which shows the more excellent control activity with respect to various pests.

  As a result of intensive studies, the present inventors have found that a pyrazine compound having a 4-pyridyl group represented by the formula (1) has high pest control activity, and have completed the present invention.

（式（１）中、
Ｒは、
水素原子
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）；
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）；
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）
独立して１〜５個までの置換基Ｒ_４で置換されるフェニル基
を表し、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄは独立して、
水素原子
ハロゲン原子
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルオキシ基
（ここで、Ｃ１〜Ｃ６アルキルオキシ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルオキシ基
（ここで、Ｃ２〜Ｃ６アルケニルオキシ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルオキシ基
（ここで、Ｃ２〜Ｃ６アルキニルオキシ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルチオ基
（ここで、Ｃ１〜Ｃ６アルキルチオ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルチオ基
（ここで、Ｃ２〜Ｃ６アルケニルチオ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていても良いＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルチオ基
（ここで、Ｃ２〜Ｃ６アルキニルチオ基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルフィニル基
（ここで、Ｃ１〜Ｃ６アルキルスルフィニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルスルフィニル基
（ここで、Ｃ２〜Ｃ６アルケニルスルフィニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルスルフィニル基
（ここで、Ｃ２〜Ｃ６アルキニルスルフィニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルホニル基
（ここで、Ｃ１〜Ｃ６アルキルスルホニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルスルホニル基
（ここで、Ｃ２〜Ｃ６アルケニルスルホニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルスルホニル基
（ここで、Ｃ２〜Ｃ６アルキニルスルホニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基により置換されていてもよい）
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基から独立して選択される２つの置換基を有するアミノカルボニル基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される３つの置換基を有するヒドラジノ基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される３つの置換基を有するヒドラジノカルボニル基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するヒドロキシルアミノ基
を表し、
Ａは、Ｏ、Ｓ、ＳＯ、ＳＯ_２、ＮＲ_３、ＮＲ_３Ｃ＝Ｏ又はＣ＝ＯＮＲ_３
を表す。）
＜２＞
Ｒが、
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）
独立して１〜５個までの置換基Ｒ_４で置換されるフェニル基
であり、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄが独立して、
水素原子
ハロゲン原子
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルオキシ基
（ここで、Ｃ１〜Ｃ６アルキルオキシ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルオキシ基
（ここで、Ｃ２〜Ｃ６アルケニルオキシ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルオキシ基
（ここで、Ｃ２〜Ｃ６アルキニルオキシ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルチオ基
（ここで、Ｃ１〜Ｃ６アルキルチオ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルチオ基
（ここで、Ｃ２〜Ｃ６アルケニルチオ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルチオ基
（ここで、Ｃ２〜Ｃ６アルキニルチオ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルフィニル基
（ここで、Ｃ１〜Ｃ６アルキルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルスルフィニル基
（ここで、Ｃ２〜Ｃ６アルケニルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルスルフィニル基
（ここで、Ｃ２〜Ｃ６アルキニルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルホニル基
（ここで、Ｃ１〜Ｃ６アルキルスルホニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニルスルホニル基
（ここで、Ｃ２〜Ｃ６アルケニルスルホニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニルスルホニル基
（ここで、Ｃ２〜Ｃ６アルキニルスルホニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基から独立して選択される２つの置換基を有するアミノカルボニル基
であり、
Ａが、Ｏ、Ｓ、ＳＯ、ＳＯ_２、ＮＲ_３、ＮＲ_３Ｃ＝Ｏ又はＣ＝ＯＮＲ_３
である、
＜１＞に記載の化合物又はその塩。
＜３＞
Ｒが、
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
独立して１〜５個までの置換基Ｒ_４で場合により置換されるフェニル基
であり、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄが独立して、
水素原子
ハロゲン原子
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルオキシ基
（ここで、Ｃ１〜Ｃ６アルキルオキシ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルチオ基
（ここで、Ｃ１〜Ｃ６アルキルチオ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルフィニル基
（ここで、Ｃ１〜Ｃ６アルキルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルホニル基
（ここで、Ｃ１〜Ｃ６アルキルスルホニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基から独立して選択される２つの置換基を有するアミノカルボニル基
であり、
Ａが、酸素原子である、
＜１＞に記載の化合物又はその塩。
＜４＞
Ｒが、
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子、及び／または、
独立して１〜５個までの置換基Ｒ_３で場合により置換されていてもよいフェニル基により置換されていてもよい）
独立して１〜５個までの置換基Ｒ_４で場合により置換されるフェニル基
であり、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄが独立して、
水素原子
ハロゲン原子
Ｃ１〜Ｃ６のアルキル基
（ここで、Ｃ１〜Ｃ６アルキル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルケニル基
（ここで、Ｃ２〜Ｃ６アルケニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ２〜Ｃ６のアルキニル基
（ここで、Ｃ２〜Ｃ６アルキニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルオキシ基
（ここで、Ｃ１〜Ｃ６アルキルオキシ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルチオ基
（ここで、Ｃ１〜Ｃ６アルキルチオ基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルフィニル基
（ここで、Ｃ１〜Ｃ６アルキルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
Ｃ１〜Ｃ６のアルキルスルホニル基
（ここで、Ｃ１〜Ｃ６アルキルスルホニル基は、同一もしくは異なる一以上のハロゲン原子により置換されていてもよい）
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１〜Ｃ６のアルキル基から独立して選択される２つの置換基を有するアミノカルボニル基
であり、
Ａが、ＮＲ_３Ｃ＝Ｏである、
＜１＞に記載の化合物又はその塩。
＜５＞
＜１＞乃至＜４＞のいずれか一項に記載の化合物と、界面活性剤、固体希釈剤および液体希釈剤からなる群から選択される少なくとも１つの成分を含む殺虫組成物。
＜６＞
少なくとも１つの生物学的に有効な化合物または薬剤をさらに含む、＜１＞に記載の殺虫組成物。
＜７＞
前記の少なくとも１つの生物学的に有効な化合物または薬剤が、アラニカルブ、アルジカルブ、ベンジオカルブ、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−（メトキシアミンボチオホスホリルサリチラート、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、サロララネル、フルキサメタミド、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、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、キノメチオナート、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、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、２−［３−（エタンスルホニル）ピリジン−２−イル］−５−（トリフルオロメタンスルホニル）ベンゾキサゾール、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、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、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、イプフェントリフルコナゾール、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、キノメチオネート、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、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、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、＜５＞に記載の組成物。
＜８＞
殺寄生虫的に有効な量の＜１＞に記載の化合物と、少なくとも１つの担体を含む、動物・鳥類を有害寄生性無脊椎生物から保護する組成物。
＜９＞
有害無脊椎生物またはその環境に生物学的に有効な量の＜１＞に記載の化合物を接触させる、有害無脊椎生物を防除する方法。
＜１０＞
作物の活力を高める方法であって、作物、作物が成長する種子、または作物の胎座に、生物学的に有効な量の＜１＞に記載の化合物を接触させる、上記方法。
＜１１＞
処理された種子であって、処理前に、種子の約０．０００１〜１重量％の量の＜１＞に記載の化合物を含む、上記種子。
＜１２＞
式（２）：

｛式中、Ｒ、Ｒ₁、Ｒ₂及びＡは前記と同じであり、Ｘはハロゲン原子を示す。｝
で示される化合物と、
式（３）：

（式中、Ｒ_a、Ｒ_b、Ｒ_c及びＲ_dは前記と同じであり、Ｍはボロニル基、ジアルコキシボラニル基、トリフルオロホウ酸塩、トリアルキルスタニル基或いはハロゲン化亜鉛であることを示す。）
で示される化合物とを反応させることにより得ることを含む、製造方法。
＜１３＞
式（４）：

（式中、Ｒ_a、Ｒ_b、Ｒ_c及びＲ_dは前記と同じであり、Ｘはハロゲン原子を示す。）
で示される化合物と、
式（５）：

（式中、Ｒ、Ｒ₁、Ｒ₂及びＡは前記と同じであり、Ｍはボロニル基、ジアルコキシボラニル基、 トリフルオロホウ酸塩、トリアルキルスタニル基或いはハロゲン化亜鉛であることを示す。）
で示される化合物とを反応させることにより得ることを含む、製造方法。 That is, the present invention
<1>
A compound represented by formula (1) or a salt thereof.

(In the formula (1),
R is
Hydrogen atom
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms An amino group having two selected substituents, and / or
Independently 1 to 5 substituents R₃Optionally substituted by a phenyl group substituted with
C2-C6 alkenyl group
(Wherein the C2-C6 alkenyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms An amino group having two selected substituents, and / or
Independently 1 to 5 substituents R₃Optionally substituted by a phenyl group substituted with
C2-C6 alkynyl group
(Wherein the C2-C6 alkynyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms An amino group having two selected substituents, and / or
Independently 1 to 5 substituents R₃May be substituted with a phenyl group substituted with
Independently 1 to 5 substituents R₄Phenyl group substituted with
Represents
R₁, R₂, R₃, R₄, R_a, R_b, R_c, R_dIs independent
Hydrogen atom
Halogen atom
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyl group
(Wherein the C2-C6 alkenyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynyl group
(Wherein the C2-C6 alkynyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkyloxy group
(Wherein the C1-C6 alkyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyloxy group
(Here, the C2-C6 alkenyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynyloxy group
(Wherein the C2-C6 alkynyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylthio group
(Wherein the C1-C6 alkylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylthio group
(Wherein the C2-C6 alkenylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group which may be substituted by one or more same or different halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylthio group
(Wherein the C2-C6 alkynylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfinyl group
(Wherein the C1-C6 alkylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfinyl group
(Wherein the C2-C6 alkenylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfinyl group
(Wherein the C2-C6 alkynylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfonyl group
(Wherein the C1-C6 alkylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfonyl group
(Here, the C2-C6 alkenylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfonyl group
(Wherein the C2-C6 alkynylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected
An aminocarbonyl group having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, the same or different
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Hydrazino group having three selected substituents
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Hydrazinocarbonyl group having three selected substituents
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Hydroxylamino group with two selected substituents
Represents
A is O, S, SO, SO₂, NR₃, NR₃C = O or C = ONR₃
Represents. )
<2>
R is
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group is the same or different one or more halogen atoms and / or
Independently 1 to 5 substituents R₃May be substituted with a phenyl group substituted with
C2-C6 alkenyl group
(Wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and / or
Independently 1 to 5 substituents R₃May be substituted with a phenyl group substituted with
C2-C6 alkynyl group
(Wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms and / or
Independently 1 to 5 substituents R₃May be substituted with a phenyl group substituted with
Independently 1 to 5 substituents R₄Phenyl group substituted with
And
R₁, R₂, R₃, R₄, R_a, R_b, R_c, R_dIs independent
Hydrogen atom
Halogen atom
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group may be substituted with one or more halogen atoms which are the same or different)
C2-C6 alkenyl group
(Here, the C2-C6 alkenyl group may be substituted with one or more halogen atoms which are the same or different.)
C2-C6 alkynyl group
(Here, the C2-C6 alkynyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkyloxy group
(Here, the C1-C6 alkyloxy group may be substituted with one or more halogen atoms that are the same or different.)
C2-C6 alkenyloxy group
(Here, the C2-C6 alkenyloxy group may be substituted with one or more halogen atoms which are the same or different).
C2-C6 alkynyloxy group
(Here, the C2-C6 alkynyloxy group may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylthio group
(Wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms which are the same or different)
C2-C6 alkenylthio group
(Here, the C2-C6 alkenylthio group may be substituted with one or more halogen atoms which are the same or different).
C2-C6 alkynylthio group
(Here, the C2-C6 alkynylthio group may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylsulfinyl group
(Here, the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which are the same or different).
C2-C6 alkenylsulfinyl group
(Here, the C2-C6 alkenylsulfinyl group may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynylsulfinyl group
(Here, the C2-C6 alkynylsulfinyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkylsulfonyl group
(Here, the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkenylsulfonyl group
(Here, the C2-C6 alkenylsulfonyl group may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynylsulfonyl group
(Here, the C2-C6 alkynylsulfonyl group may be substituted with one or more halogen atoms that are the same or different).
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected
An aminocarbonyl group having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, the same or different
And
A is O, S, SO, SO₂, NR₃, NR₃C = O or C = ONR₃
Is,
The compound or its salt as described in <1>.
<3>
R is
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
C2-C6 alkenyl group
(Wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
C2-C6 alkynyl group
(Wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
Independently 1 to 5 substituents R₄Optionally substituted phenyl group
And
R₁, R₂, R₃, R₄, R_a, R_b, R_c, R_dIs independent
Hydrogen atom
Halogen atom
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group may be substituted with one or more halogen atoms which are the same or different)
C2-C6 alkenyl group
(Here, the C2-C6 alkenyl group may be substituted with one or more halogen atoms which are the same or different.)
C2-C6 alkynyl group
(Here, the C2-C6 alkynyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkyloxy group
(Here, the C1-C6 alkyloxy group may be substituted with one or more halogen atoms that are the same or different.)
C1-C6 alkylthio group
(Wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms which are the same or different)
C1-C6 alkylsulfinyl group
(Here, the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkylsulfonyl group
(Here, the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms that are the same or different).
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected
An aminocarbonyl group having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, the same or different
And
A is an oxygen atom,
The compound or its salt as described in <1>.
<4>
R is
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
C2-C6 alkenyl group
(Wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
C2-C6 alkynyl group
(Wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms and / or
Independently 1 to 5 substituents R₃And optionally substituted with an optionally substituted phenyl group)
Independently 1 to 5 substituents R₄Optionally substituted phenyl group
And
R₁, R₂, R₃, R₄, R_a, R_b, R_c, R_dIs independent
Hydrogen atom
Halogen atom
C1-C6 alkyl group
(Wherein the C1-C6 alkyl group may be substituted with one or more halogen atoms which are the same or different)
C2-C6 alkenyl group
(Here, the C2-C6 alkenyl group may be substituted with one or more halogen atoms which are the same or different.)
C2-C6 alkynyl group
(Here, the C2-C6 alkynyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkyloxy group
(Here, the C1-C6 alkyloxy group may be substituted with one or more halogen atoms that are the same or different.)
C1-C6 alkylthio group
(Wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms which are the same or different)
C1-C6 alkylsulfinyl group
(Here, the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which are the same or different).
C1-C6 alkylsulfonyl group
(Here, the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms that are the same or different).
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected
An aminocarbonyl group having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, the same or different
And
A is NR₃C = O,
The compound or its salt as described in <1>.
<5>
An insecticidal composition comprising the compound according to any one of <1> to <4> and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.
<6>
The insecticidal composition according to <1>, further comprising at least one biologically active compound or agent.
<7>
The at least one biologically active compound or agent is alanicarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butcarboxyme, butoxycarboxyme, carbaryl, carbofuran, carbosulfan, etiophencarb, fenobucarb, formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxyl, Thiodicarb, Thiophanox, Triazamate, Trimetacarb, XMC, Xylylcarb, Metolcarb, Phenothiocarb, Phenoxycarb, Acephate, Azamethiphos, Azine Phos-ethyl Chlorothone Ethoxyphos, Kazusafos, Chloretoxyphos, Chlorfenvinphos, Lumefos, Chlorpyrifos, Chlorpyrifosmethyl, Coumafos, Cyanophos, Demeton-S-Methyl, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Dimethylvinphos, EPN, Ethion, Etoprophos, Famfur, Fenamiphos, Fenitrothion, Fentione, Phostiazeto, Heptenophos, Imithiaphos , Isopropyl = O- (methoxyaminebothiophosphorylsalicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naredo, ometoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, folate, hosalon, Phosmet, phosphamidon, phoxime, pyrimiphos-methyl, profenophospropetane , Prothiophos, pyraclofos, pyridafenthione, quinalphos, sulfotep, tebupyrimifos, temefos, terbufos, tetrachlorvinfos, thiometon, triazophos, trichlorphone, bamidthione, chlorpyrifos-ethyl, disulfone, sulfophos, flupyrazophos, phenoate, phonophos, tribufos, endosulfos -Endosulfan, gamma-HCH, dicophore, chlordane, dieldrin, methoxychlor, acetoprole, fipronil, etiprole, pyrafluprole, pyriprole, flufiprole, brofuranilide, afoxolanel, fluralanel, saloraranel, floxamethamide, acrinathrin, d-cis-, d-cis- trans allethrin, d-trans Allethrin, bifenthrin, kappa-bifenthrin, bioareslin S-cyclopentenyl, bioresmethrin, cycloproton, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, Theta-Cypermethrin, Zeta-Cypermethrin, Cifenothrin, Deltamethrin, Empentrin, Esfenvalerate, Etofenprox, Fenpropatoline, Fenvalerate, Flucitrinate, Flumetrin, Tau-fulvalinate, Halfenprox, Imiprotorin, Cadethrin Permethrin, phenothrin, praretrin, pyrethrin, resmethrin, silafluophene, tefluthrin, Pep-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, methfluthrin, profluthrin, pyrethrum, teraretrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, chloroparathrin, epsilon-methfluthrin Epsilon-monfluosrine, prototrifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, sulfoxaflor, flupirazifuron, triflumezopyrim, dichloromethozothiaz, flupirmine, spinosad, incense, vernetin Acid salt, milbemectin, lepimectin Hydroprene, quinoprene, diophenolane, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotin, cyhexatin, phenbutasium oxide, propargite, tetradiphone, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclthiol sultap Sodium, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezin, cyromazine, chromafenozide, halofenozide, methoxyphenozide, Tebufenozide, Amitraz, Gi Doramethylnon, acequinosyl, fluacrylpyrim, pyriminostrobin, fluphenoxystrobin, phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, piflubimide, spirodiclofen, spirotetramat, spiromethifene, spiropidion, ciflumethofen Flubendiamide, Chlorantraniliprole, Cyantraniliprole, Cyclaniliprol, Tetraniliprol, Cyhalodiamide, Quinomethionate, Hexithiazox, Bifenazate, Flufenerim, Pyrifluquinazone, Furometokin, Fluopyram, Fluazaindolizine, Amidoflumet, Cyclopyrazofurol , Thixazaphen, nicotine, chloropicrin, fluoride Furyl, crilothie, clofentadine, difluvidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, aphidopyropene, fluhexaphone, fluenesulfone, vencrothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate , Methaldehyde, ryanodine, sulfuramide, asinonapyr, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3,5-dichloropyridine-2- Yl) -1H-pyrazole-5-carboxamide, 2- [3- (ethanesulfonyl) pyridin-2-yl] -5- (trifluoromethanesulfonyl) benzoxazole, metalaxyl, metalaxyl M Oxazixyl, ofrase, benalaxyl, benalaxyl-M, kilaraxyl, oflers, furaxyl, cyprofuran, buprimate, dimethylimole, ethylimol, himexazole, hydroxyisoxazole, oxathiapiproline, octyrinone, oxolinic acid, benomyl, thiophanate methyl, carbendazol, carbendazole , Debacarb, dietofencarb, zoxamide, ethaboxam, pencyclon, fluopicolide, diflumetrim, bupirimate, benodanyl, flutolanil, mepronil, isophetamide, fenflam, oxycarboxyl, carboxin, tifluzamide, floxapyroxad, flametopyr, penflufen, pendipyropido Pills, bixafe , Isopyrazam, sedaxane, impylfluxam, fluindapir, isoflucipram, pyrapropoin, boscalid, azoxystrobin, cumethoxystrobin, cresoximemethyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxist Robin, Metominostrobin, Oryastrostrobin, Fluoxastrobin, Pyroxystrobin, Pyramethostrobin, Fluphenoxystrobin, Phenamine Strobin, Enoxastrobin, Coxoxystrobin, Mandestrobin, Triclopyricarb, Famoxadone, Fenamidon, Triclopyricarb, Pyribencarb, Ciazofamide, Amisulbrom, Vinapacryl, Meptyldinocarb, Dinocup, Fluazinam, Ferimzone, Acetic acid Fentin, fentin chloride, fentin hydroxide, triphenyltin hydroxide, triphenyltin acetate, oxine copper, sylthiofam, amethocrazine, mepanipyrim, nitrapirin, pyrimesanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, Oxytetracycline, quinoxyphene, proquinazide, fludioxonil, fenpicuronyl, fluoroimide, procymidone, iprodione, vinclozolin, edifenephos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseicaupte extract, triphorin, pyrifenomolpyrimolazole , Azaconazole, bromconazole, dinico Sol, diniconazole-M, epoxiconazole, fluquinconazole, oxpoconazole, pefazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimethone, triazimenol, triticonazole, uniconazole , Imazalyl, viteltanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriazole, microbutanyl, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, cimeconazole, ipfen Trifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomol , Fulmorph, Pyrimorph, Piperalin, Fenpropidin, Spiroxamine, Fenhexamide, Fenpyrazamine, Felbam, Metam, Metasulfocarb, Methylam, Tiram, Manzeb, Manneb, Ginebu, Zillam, Polycarbamate, Provineb, Tiuram, Pyributicarb, Validamycin , Mildiomycin, Polyoxin, Bench Avaricarb, Bench Avaricarb Isopropyl, Variphenalate, Iprovaricarb, Mandipropamide, Fenpicoxamide, Fusaride, Pyroxylone, Tricyclazole, Carpropamide, Diclocimet, Phenoxanyl, Acibenzoral-S-methyl, Probenazole , Diclobenchazox, thiazinyl, isothianyl, simoxanyl, fosetyl, teclophthalam, triazol , Sulfulamide, dichromemedin, cyflufenamide, metolaphenone, piophenone, fluthianyl, tebufloquine, fosetyl aluminum, tolcrophos-methyl, eclomezole, tolprocarb, ipfentrifluconazole, mefentrifluconazole, quinofumerin, pidiflumethofene, Bordeaux mixed solution, copper acetate , Basic copper sulfate, copper oxychloride, cupric hydroxide, copper oxyquinoline, copper, sulfur, captan, captahol, phorpet, anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, Iminotadine acetate, iminoctadine albecylate, guanidine, dodin, dodin free base, guazatine, guazatine acetate, albesylate, di Anone, Quinomethionate, Fluorimide, Tolylfluoride, Diclofluanide, Dinobutone, Dazomet, Pyraziflumide, Aminopyrifen, Dipimethitrone, Picalbutrazox, Technazen, Nitortal-isopropyl, Dicyclomet, Acibenzoral, Prohexadione-Calcium, Bronopol, Diphenylamine , Flumetovel, bentoxazine, biphenyl, chloronebu, CNA, iodocarb, prothiocarb, genus Bacillus, and insecticidal proteins produced by them, bactericidal proteins, insecticidal proteins produced by Bt crops, bactericidal proteins, entomopathogenic bacteria The composition according to <5>, selected from the group consisting of an entomopathogenic virus and an entomopathogenic fungus.
<8>
A composition that protects animals and birds from harmful parasitic invertebrates, comprising a parasitically effective amount of the compound according to <1> and at least one carrier.
<9>
A method for controlling a harmful invertebrate, comprising contacting the harmful invertebrate or its environment with a biologically effective amount of the compound according to <1>.
<10>
A method for increasing the vitality of a crop, wherein the crop, the seed on which the crop grows, or the placenta of the crop is contacted with a biologically effective amount of the compound according to <1>.
<11>
A seed that has been treated, comprising the compound according to <1> in an amount of about 0.0001 to 1% by weight of the seed before the treatment.
<12>
  Formula (2):

{Where R, R₁, R₂And A is the same as described above, and X represents a halogen atom. }
A compound represented by
Formula (3):

(Wherein R_a, R_b, R_cAnd R_dIs the same as above, and M represents a boronyl group, dialkoxyboranyl group, trifluoroborate, trialkylstannyl group or zinc halide. )
The manufacturing method including obtaining by making the compound shown by react.
<13>
  Formula (4):

(Wherein R_a, R_b, R_cAnd R_dIs the same as above, and X represents a halogen atom. )
A compound represented by
  Formula (5):

(Where R, R₁, R₂And A is the same as described above, and M represents a boronyl group, dialkoxyboranyl group, trifluoroborate, trialkylstannyl group or zinc halide. )
The manufacturing method including obtaining by making the compound shown by react.

  The present invention provides a composition comprising a compound of formula (1) and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. In an embodiment, the present invention controls a harmful invertebrate comprising a compound of formula (1) and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. Wherein the composition further comprises at least one biologically active compound or agent.

  The pyrazine compound having a 4-pyridyl group represented by the formula (1) according to the present invention exhibits a very excellent control effect against pests and is useful as a pest control agent.

Formula (1) provides a general definition of the compounds according to the invention. Suitable substituents and / or ranges of substituents listed in the compound of formula (1) are specifically described below.
In the definition of the formula (1), “halo” means “halogen atom”, means chlorine atom, bromine atom, iodine atom or fluorine atom, “n-” means normal, and “i-” means iso. , “S-” is secondary, “c-” is cyclo, “t-” is tertiary, “Me” is methyl group, “Et” is ethyl group, “Pr” is propyl group, “Bu” Represents a butyl group, “Pen” represents a pentyl group, and “Ac” represents an acetyl group. Moreover, the numerical range shown using "to" shows the range which includes the numerical value described before and behind "to" as a minimum value and a maximum value, respectively.

  “C1-C6 alkyl group” means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group. Group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl Group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopropylmethyl group, etc. Or a cyclic alkyl group having 1 to 6 carbon atoms, “C2-C6 alkenyl group” means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2- A linear or branched chain or cyclic alkenyl group having 2 to 6 carbon atoms such as a methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, or a 3,3-dimethyl-1-butenyl group; "C2-C6 alkynyl group" means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl -3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, linear or branched chain such as 3,3-dimethyl-1-butynyl group, or cyclic 2 to 6 carbon atoms Pieces Show an alkynyl group.

  Examples of the “C1-C6 alkyloxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, Tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2- A linear or branched chain or cyclic alkyloxy group having 1 to 6 carbon atoms such as trimethylpropyloxy group, cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopropylmethyloxy group, etc. , "C2-C6 alkenyl The “xy group” represents, for example, a linear or branched alkenyloxy group having 2 to 6 carbon atoms such as a propenyloxy group, a butenyloxy group, a pentenyloxy group, a hexenyloxy group, and the like “(C2 to C6)”. The “) alkynyloxy group” is, for example, a linear or branched alkynyloxy group having 2 to 6 carbon atoms such as a propynyloxy group, a butynyloxy group, a pentynyloxy group, or a hexynyloxy group.

Examples of the “C1-C6 alkylthio group” include a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, a normal pentylthio group, and an isopentyl group. Ruthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group, 1,1 , 2-trimethylpropylthio group, cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, cyclopropylmethylthio group, etc., linear or branched chain or cyclic alkylthio having 1 to 6 carbon atoms A group represented by "C1-C6 alkylsulfinyl group" As, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary Pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropyl Sulfinyl, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfur Group, a linear or branched chain, or cyclic alkylsulfinyl group having 1 to 6 carbon atoms, such as cyclopropyl methylsulfinyl group,
Examples of the “C1-C6 alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a normalpropylsulfonyl group, an isopropylsulfonyl group, a normalbutylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, and a normalpentylsulfonyl group. , Isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, Black propyl straight or branched chain, such as methylsulfonyl group, or an alkylsulfonyl group having 1 to 6 carbon atoms in the ring.

  Examples of the “C2 to C6 alkenylthio group” include linear or branched alkenylthio groups having 2 to 6 carbon atoms such as a propenylthio group, a butenylthio group, a pentenylthio group, and a hexenylthio group, Examples of the “C2 to C6 alkynylthio group” include linear or branched alkynylthio groups having 2 to 6 carbon atoms such as propynylthio group, butynylthio group, pentynylthio group, and hexynylthio group.

  Examples of the “C2 to C6 alkenylsulfinyl group” include linear or branched alkenylsulfinyl groups having 2 to 6 carbon atoms such as propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group, hexenylsulfinyl group and the like. As the “(C2-C6) alkynylsulfinyl group”, for example, a linear or branched carbon atom number of 2 to 6 such as propynylsulfinyl group, butynylsulfinyl group, pentynylsulfinyl group, hexynylsulfinyl group, etc. Each alkynylsulfinyl group.

  Examples of the “C2-C6 alkenylsulfonyl group” include linear or branched alkenylsulfonyl groups having 2 to 6 carbon atoms such as propenylsulfonyl group, butenylsulfonyl group, pentenylsulfonyl group, hexenylsulfonyl group and the like. As the “(C2-C6) alkynylsulfonyl group”, for example, a linear or branched carbon atom number of 2 to 6 such as propynylsulfonyl group, butynylsulfonyl group, pentynylsulfonyl group, hexynylsulfonyl group, etc. Each alkynylsulfonyl group.

  "C1-C6 alkyl group", "C2-C6 alkenyl group", "C2-C6 alkynyl group", "C1-C6 alkyloxy group", "C2-C6 alkenyloxy group", "C2-C6 alkynyloxy group" "," C1-C6 alkylthio group "," C1-C6 alkylsulfinyl group "," C1-C6 alkylsulfonyl group "," C2-C6 alkenylthio group "," C2-C6 alkynylthio group "," C2-C6 " “Alkenylsulfinyl group”, “C2 to C6 alkynylsulfinyl group”, “C2 to C6 alkenylsulfonyl group”, “C2 to C6 alkynylsulfonyl group”, “C1 to C6 alkyloxy group”, “C2 to C6 alkenyloxy group”, 1 or 2 or more halogen atoms are substituted at substitutable positions of the “C 2 -C 6 alkynyloxy group”. Is good, in the case of the halogen atom is 2 or more substituted, a halogen atom may be the same or different.

  Expressions such as “(C1 to C6)”, “(C2 to C6)”, and “(C3 to C6)” indicate the range of the number of carbon atoms of various substituents. Furthermore, the above-mentioned definition can be shown also about the group which the said substituent connected, for example, in the case of "(C1-C6) alkyloxy (C1-C6) alkyl group", linear or branched carbon number 1 It indicates that ˜6 alkyloxy groups are bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

  Examples of the salt of the pyrazine compound represented by the formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate, Examples thereof include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium. The pyrazine compound represented by the formula (1) and salts thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers are present. The present invention includes all the optical isomers and a mixture containing them in an arbitrary ratio. Further, the compound represented by the general formula (1) and salts thereof of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. Includes all geometric isomers and mixtures containing them in any proportion.

In the pyrazine compound represented by the formula (1) or a salt thereof of the present invention, preferably, R is a C1-C6 alkyl group which may be substituted with one or more same or different halogen atoms, or independently. R ₁ , R ₂ , R ₄ , R _a , R _b , R _c , R _d are each independently a hydrogen atom, or a phenyl group substituted with 1 to 5 substituents R ₄ A halogen atom, or a C1-C6 alkyl group optionally substituted by one or more same or different halogen atoms, or a C1-C6 alkyloxy optionally substituted by one or more halogen atoms A group, or a C1-C6 alkylthio group optionally substituted by one or more halogen atoms which are the same or different, or one or more halogen atoms which are the same or different An optionally substituted C1-C6 alkylsulfinyl group, or a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, or (a hydrogen atom, or the same or Two independently selected from a C1-C6 alkyl group optionally substituted by one or more different halogen atoms and a C1-C6 acyl group optionally substituted by one or more different halogen atoms An amino group having a substituent), an aminocarbonyl having two substituents independently selected from a hydrogen atom or a C1-C6 alkyl group optionally substituted by one or more halogen atoms, which are the same or different And A is O, S, SO, SO ₂ , NR ₃ , NR ₃ C═O or C═ONR ₃ .

  The pyrazine compound or salts thereof of the present invention can be produced, for example, by the following production method, but the present invention is not limited to these. Non-patent document 1 describes compounds that can be represented by the other group (B). These compounds can be obtained from commercial preparations or synthesized by known methods.

<Manufacturing method 1>
Scheme 1

{Wherein R, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as above, X represents a halogen atom, M represents a boronyl group, dialkoxyboranyl group, trifluoro A borate, a trialkylstannyl group or a zinc halide is shown, and A ₁ represents an oxygen atom or a sulfur atom. }

<Production method of step a>
A pyrazine compound represented by the formula (7) is produced by reacting the pyrazine compound represented by the formula (6) with the compound represented by the formula (3) in the presence of a metal catalyst, a base and an inert solvent. can do. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue 26 p. 9392-9396).

  Examples of the metal catalyst that can be used in the present invention include [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, [1,1′-bis (diphenylphosphino) propane] palladium (II) dichloride, Zero-valent palladium compounds such as [1,1′-bis (diphenylphosphino) butane] palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), , Palladium (II) acetate, palladium (II) chloride, bis (acetonitrile) palladium (II) dichloride, bis (benzonitrile) palladium (II) dichloride, allyl palladium (II) chloride dimer, cyclopentadienylallyl palladium (II) and other known palladium catalysts Rukoto can. Moreover, 2 or more types can also be used as needed. What is necessary is just to select the usage-amount of the palladium catalyst in this invention suitably in the range of about 0.001 time mole-0.1 time mole normally with respect to the compound represented by Formula (6).

  Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. Hydrogenation, carbonates such as calcium carbonate, magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. What is necessary is just to select suitably the usage-amount of a base from the range of 0.5 times mole-5.0 times mole with respect to the compound represented by Formula (6).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the above, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene There may be mentioned polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can also be used in mixtures species or more.

  The reaction temperature in this reaction may usually be 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. . 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. Further, the next step may proceed without isolation / purification.

<Manufacturing method of step b>
A pyrazine compound represented by the formula (1a) by reacting a pyrazine compound represented by the formula (7) with an alcohol compound or thiol compound represented by the formula (8) in the presence of a base in an inert solvent. Can be manufactured.

  Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; sodium hydride, potassium hydride and the like. Alkoxides such as alkali metal hydrides, sodium methoxide, sodium ethoxide, potassium tertiary butoxide and the like can be mentioned. The amount of the base used is usually in the range of about 1 to 5 moles to the compound represented by the formula (7).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the following: aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene Nitrites such as acetonitrile; esters such as ethyl acetate; polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can be used by mixing seeds more.

  The reaction temperature in this reaction may usually be 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 compound represented by the formula (8) is usually used in a range of about 1 to 5 moles relative to the pyrazine compound represented by the formula (7). Moreover, this reaction can also be performed in the atmosphere of inert gas, such as nitrogen gas and argon gas, for example. 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.

<Manufacturing method 2>
Scheme 2

{Wherein R, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as above, X represents a halogen atom, M represents a boronic acid, boronic ester, trifluoroboric acid. It is a salt, trialkylstannyl or zinc, and A ₁ represents an oxygen atom or a sulfur atom. }

  Further, the compound of the general formula (1a) can be produced as shown in Scheme 2.

<Manufacturing method of process c>
The pyrazine compound represented by the formula (2a) is obtained by reacting the pyrazine compound represented by the formula (6) with the alcohol compound or thiol compound represented by the formula (8) in the presence of a base in an inert solvent. Can be manufactured.

  Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; sodium hydride, potassium hydride and the like. Alkoxides such as alkali metal hydrides, sodium methoxide, sodium ethoxide, potassium tertiary butoxide and the like can be mentioned. The amount of the base used is usually in the range of about 1 to 5 moles to the compound represented by formula (6).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the following: aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene Nitrites such as acetonitrile; esters such as ethyl acetate; polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can be used by mixing seeds more.

  The reaction temperature in this reaction may usually be 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 compound represented by the formula (8) is usually used in a range of about 1 to 5 moles relative to the pyrazine compound represented by the formula (6). Moreover, this reaction can also be performed in the atmosphere of inert gas, such as nitrogen gas and argon gas, for example. 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.

<Manufacturing method of step d>
A pyrazine compound represented by the formula (1a) is produced by reacting the pyrazine compound represented by the formula (2a) with the compound represented by the formula (3) in the presence of a metal catalyst, a base and an inert solvent. can do.

  Examples of the metal catalyst that can be used in the present invention include [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, [1,1′-bis (diphenylphosphino) propane] palladium (II) dichloride, Zero-valent palladium compounds such as [1,1′-bis (diphenylphosphino) butane] palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), , Palladium (II) acetate, palladium (II) chloride, bis (acetonitrile) palladium (II) dichloride, bis (benzonitrile) palladium (II) dichloride, allyl palladium (II) chloride dimer, cyclopentadienylallyl palladium A known palladium catalyst such as (II) It can gel. Moreover, 2 or more types can also be used as needed. What is necessary is just to select the usage-amount of the palladium catalyst in this invention suitably in the range of about 0.001 times mole-0.1 times mole normally with respect to the compound represented by General formula (2a).

  Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. Hydrogenation, carbonates such as calcium carbonate, magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. What is necessary is just to select suitably the usage-amount of a base from the range of 0.5 times mole-5.0 times mole with respect to the compound represented by General formula (2a).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the above, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene There may be mentioned polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can also be used in mixtures species or more.

  The reaction temperature in this reaction may usually be 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. . 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.

<Manufacturing method 3>
Scheme 3

{Wherein R, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as above, X represents a halogen atom, M represents a boronyl group, dialkoxyboranyl group, trifluoro A borate, a trialkylstannyl group or a zinc halide is shown, and A ₁ represents an oxygen atom or a sulfur atom. }

  The compound of formula (1a) can also be prepared as shown in Scheme 3.

<Manufacturing method of process e>
The pyrazine compound represented by the formula (5) can be produced by reacting the pyrazine compound represented by the formula (2a) with diborane or diboron, a metal catalyst, a base and an inert solvent.

  Examples of diborane or diboron that can be used in the present invention include tetrahydroxydiborane, tetrakis (dimethylamino) diboron, bis (pinacolato) diboron, bis (neopentylglycolato) diboron, bis (hexyleneglycolato) diboron, and bis (catecholato) Examples include diborane such as diboron or diboron. The amount of diborane or diboron used in the present invention may be appropriately selected from the range of usually 0.5-fold to 5.0-fold mol with respect to the compound represented by the formula (2a).

  Examples of the metal catalyst that can be used in the present invention include [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, [1,1′-bis (diphenylphosphino) propane] palladium (II) dichloride, Zero-valent palladium compounds such as [1,1′-bis (diphenylphosphino) butane] palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), , Palladium (II) acetate, palladium (II) chloride, bis (acetonitrile) palladium (II) dichloride, bis (benzonitrile) palladium (II) dichloride, allyl palladium (II) chloride dimer, cyclopentadienylallyl palladium (II) and other known palladium catalysts Rukoto can. Moreover, 2 or more types can also be used as needed. What is necessary is just to select the usage-amount of the palladium catalyst in this invention suitably in the range of about 0.001 times mole-0.1 times mole normally with respect to the compound represented by Formula (2a).

  Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. Hydrogenation, carbonates such as calcium carbonate, magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. What is necessary is just to select suitably the usage-amount of a base from the range of 0.5 time mole-5.0 times mole with respect to the compound represented by Formula (2a).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the above, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene There may be mentioned polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can also be used in mixtures species or more.

  The reaction temperature in this reaction may usually be 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. . 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. Further, the next step may proceed without isolation / purification.

<Manufacturing method of process f>
A pyrazine compound represented by the formula (1a) is reacted with a compound represented by the formula (5) and a compound represented by the general formula (4) in the presence of a metal catalyst, a base and an inert solvent. Can be manufactured.

  Examples of the metal catalyst that can be used in the present invention include [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, [1,1′-bis (diphenylphosphino) propane] palladium (II) dichloride, Zero-valent palladium compounds such as [1,1′-bis (diphenylphosphino) butane] palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), , Palladium (II) acetate, palladium (II) chloride, bis (acetonitrile) palladium (II) dichloride, bis (benzonitrile) palladium (II) dichloride, allyl palladium (II) chloride dimer, cyclopentadienylallyl palladium (II) and other known palladium catalysts Rukoto can. Moreover, 2 or more types can also be used as needed. What is necessary is just to select the usage-amount of the palladium catalyst in this invention suitably in the range of about 0.001 times mole-0.1 times mole normally with respect to the compound represented by Formula (5).

  Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. Hydrogenation, carbonates such as calcium carbonate, magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. What is necessary is just to select suitably the usage-amount of a base from the range of 0.5 times mole-5.0 times mole with respect to the compound represented by Formula (5).

  The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include water, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, diethyl ether, tetrahydrofuran, and dioxane. Linear or cyclic ethers of the above, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene There may be mentioned polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone These inert solvents can be used alone or It can also be used in mixtures species or more.

  The reaction temperature in this reaction may usually be 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. . 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.

  The present invention provides a composition comprising a compound of formula (1) and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. In an embodiment, the present invention controls a harmful invertebrate comprising a compound of formula (1) and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. Wherein the composition may further comprise at least one biologically active compound or agent.

The compound represented by the formula (1) exhibits excellent control activity against agricultural and horticultural harmful insect pests as shown in the following examples. Therefore, according to this invention, the pest control agent which contains the compound or its salt represented by Formula (1) as an active ingredient is provided. Moreover, the pest control agent according to the present invention may contain, as an active ingredient, an acid-addition salt of these compounds which is acceptable in agriculture and horticulture.
The acid addition salt specifically includes, for example, inorganic acids such as hydrochloride, sulfate, nitrate, phosphate, formate, acetate, oxalate, citrate, succinate, maleate Carboxylic acid salts such as fumarate, tartrate, lactate, benzoate, and phthalate, and sulfonates such as mesylate, tosylate, and benzenesulfonate.

In the present invention, the insect species to be controlled (the insect species in which the compound represented by the formula (1) exhibits a controlling effect) is not particularly limited and may be used for controlling harmful insect pests in a wide range of agricultural and horticultural fields. it can. Examples of preferable insect species to be controlled include the following. Lepidoptera {e.g. Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalopatis medina , Inasha casino maiga (Marasmia exigua), cotton flounder (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), European corn borer (Hellula undalis), Herpetalema rel ), Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Crambidae); litura) Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Spodoptera mauritia, pod Sera exempta), Agrotis ipsilon, Autographa nigrisigna, Inakinawaba (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia spp., Heliothis virescens (Heliothis virescens, etc.) spp.), Helicoverpa armigera, Helicoverpa zea, and other Helicoberpa spp. Noctuidae; Pieris rapae, etc. (Pieridae); (Adoxophyes orana fasciata), Chanokokumonmonaki (Adoxophyes honmai), Chamonaki (Homona magnanima), Midarekakumumonamaki (Archips fuscocupreanus), Kodlinga (Cydia pomonella), Kanshashinihamaki (Tetramoera schistaceer) aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc. Tortricidae; Calophilia theivora, Phyllonorycter ringoniella; nidae); Coffee Leaf miner (Leucoptera coffeella); Euproctis spp., etc., such as pseudoconspersa; Lymantriidae, such as Plutella xylostella; Pluteliidae; ), Potato moth (Phthorimaea operculella), Tuta absoluta, etc. Gelechiidae; Cossus insularis), etc. e); Geometridae, such as Ascotis selenaria; Limacodidae, such as Parasas lepida; lachesis) such as Sphingidae; Nokona feralis such as Sesiidae; Parnara guttata such as Hesperiidae}. Hemiptera {e.g. Laodelphax striatellus, yellow leafhopper (Nilaparvata lugens), white leafhopper (Sogatella furcifera), corn leafhopper (Peregrinus maidis), yellow leafhopper (Javesella pellucella), blackfish Delphacidae, such as orizicolus; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalisoa, Enoca cai Empoasca fabae), corn leaf hopper (Dalbulus maidis), leafhopper family (Cicadellidae) such as Cofana spectra; Mahanarva posticata, mahanarva fimbriolata, etc .; Aphis fabae, soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), european apple aphids (Aphis pomi), snowy aphids (Aphis spiraecola), peach aphids (Myzus persicae), wheat aphids B helichrysi), radish aphids (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), black radish aphids (Lipaphis erysimi), tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum viaga) Barley beetle (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach beetle (Hyalopterus pruni), hyena aphid (Melanaphis sacchari), brown aphid (Tetraneura nigriabdominalis), aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum); Aphididae; Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae), etc. Nephididae (Phylloxeridae); ); Rice stink bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), blue stink bug (Nezara antennata), black spider stink bug (Eysarcoris aeneus), white spider stink bug (Eysarcoris ys) , Eryscalis annamita, Halyomorpha halys, Nezara viridula, Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus p (Pentatomidae); Burrower brown bug (Scaptocoris castanea), etc. (Cydnidae); Alydidae); Cletus punctiger, Leptoglossus australis, etc. (Coreidae); Naga (Blissus leucopterus) Lygaeidae; Trigonotylus caelestialium; Stenotus rubrovittatus; Stenodema calcarata; vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus whitefly (Aleurocanthus spiniferus), chaffed whitefly (Aleurocanthus camelliae), Hisakakifuta (Pealius eleyrodidae); Buprestidae (Abgrallaspis cyanophylli), Buprestidae (Aonidiella aurantii), Buprestidae (Diaspidiotus perniciosus), Scarab scale (Pseudaulacaspis pentagona), Buprestidae (Unaspis yanone) nsis), Species of Diaspididae such as Unaspis citri; Coccidae such as Ceroplastes rubens; Icerya purchasi, Icerya purchasi, Iruma Species of Margarodidae; Phenacoccus solani; Phenacoccus solenopsis; Pterococcus kraunhiae; Pseudococcidae such as Pseudoococcus calceolariae, Pseudococcus longispinus, Brevennia rehi; Diaphorina citri, citrus Miridae (Trioza erytreae), Japanese lice (Cacopsylla pyrisuga), Chinese horned lice (Cacopsylla chinensis), Potato moth (Bactericera cockerelli), Pear psylla (Cacopsylla pyricola), etc. Gumbai (Corythucha marmorata), Nashigumbai (Stephanitis nashi), Azalea Gumbai (Stephanitis pyrioides), etc .; Camidex lectularius, etc .; Coleoptera {eg Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cumber Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), terrestrial beetle (Oulema melanopus), cucumber leaf beetle (Aulacophora femoralis), pheasant leaf beetle (Phyllotreta beltaleleetle potato) , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Rice beetle (Oulema oryzae), Grape colaspis (Colaspis brunnea), Corn corn Beetle (Chaetocnema pulicaria), Sweet potato beetle (Chaetocnema confinis), Potato flare beetle (Epitrix cucumeris), Rice beetle (Dicladispa armigera), Southern corn leaf beetle (Myochrous dentica), opt. (Epitrix hirt
Chrysomelidae such as ipennis; Carabidae such as Seedcorn beetle (Stenolophus lecontei) and Slender seedcorn beetle (Clivina impressifrons); Anomala cuprea; Anomala rufocuprea; Phyllaga spy (Popillia japonica), Heptophylla picea, European Chafer (Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., Phyllophaga crinlloph Scarabaeidae such as Diloboderus spp., Such as Diloboderus abderus; Araecerus coffeae, Cylas formicarius, Ezocepes postfasyp Sweeophilus zeamais ), Weevil (Echinocnemus squameus), rice weevil (Lissorhoptrus oryzophilus), white weevil (Rhabdoscelus lineatocollis), cotton weevil (Anthonomus grandis), Sphenophorus venatus (Sphenophorus venatus), Southern weevil (Sphenophorus venatus), Southern weevil (Sphenophorus venatus) Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), scorpion fly weevil (Scepticus griseus), white fly weevil (Scepticus uniformis), Brazilian weevil (Zabrotes subfasciatus), pine beetle (Tomicus pini) (Tomicus pini) Aracanthus mourei and other genus Aracanthus (Aracanthus spp.), Cotton root borer (Eutinobothrus brasiliensis) and other weevil (Curculionidae); Tricholium castaneum and Tribolium confusum and others Tenebrionidae); Epilachna vigintioctopunctata and other ladybirds (Coccinellidae); Cerambycidae (Cerambycidae); Melanonotus okinawensis, Agriotes fuscicollis, Melanotus legatus, sp. Sphaphyceae (Elateridae) such as Ctenicera spp., Limonius spp., Aeolus spp .; Staphylinidae} such as Paederus fuscipes}. Thysanoptera {e.g., Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabasa, i. Stenchaetothrips biformis), Thripidae such as Echinothrips americanus; Phlaeothripidae} such as Haplothrips aculeatus}. Diptera {e.g., Dela platura, Delia antiqua, etc .; Anthomyiidae; Sugar beet root mygots (Tetanops myopaeformis), etc .; Ulididae; ), Tomato leaf fly (Liriomyza sativae), beetle leaf fly (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafhoppers (Agromyzidae); Bactrocera dorsalis, Bactrocera latifrons, Olive fruit fly (Bactrocera oleae), Quinland fruit fly (Bactrocera tryoni), Ceratitis capitata, etc. (Tephritidae); Hydrellia philippina, Hydrellia sasakii, and other species (Ephydridae); Drosophila suzukii, and other species; ); Drosophila such as Clogmia albipunctata; Bradysia difformis and other species, Sciaridae; ); Diops macrophthalma, etc. (Diopsidae); Cranefish (Tipula aino), Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa), etc. Hymenoptera {For example, Athalia japonica, Tenthredinidae, such as Athalia rosae; Firefly (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara), etc. Formicidae etc.}. Orthoptera {for example, locust migratoria, Moroccan grasshopper (Dociostaurus maroccanus), Australian grasshopper (Chortoicetes terminifera), red locust (Nomadacris septemfasciata), Brown Locust (Crustana pardalina, Locustana pardalina, ), 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 pelican) (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Panax eel (Oxya yezoensis), Red-tailed hawk (Oxya japonica), Thai-winged tiger (Acanthaceae) Gryllotalpa orientalis) Kera family such as (Gryllotalpidae); house cricket (Acheta domestica), Enmakoorogi (Teleogryllus emma) cricket family such as (Gryllidae); Mormon cricket (Anabrus simplex) tettigoniidae such (Tettigoniidae)}. Cockroach (Blattodea) {For example, the German cockroach family (Blattellidae) such as Blattella germanica; Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, ali, Cockroaches (Blattidae) such as the cockroach (Periplaneta japonica) and the cockroach (Periplaneta australasiae); Termites (Odontotermes formosanus), Coleoptera termites (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Buffalo termites (Glyptotermes nakajimai), Caterpillars (Glyptotermes fuscus), Oosi Loite (Hodotermopsis sjostedti), Coleoptera termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Ants (Reticulitermes kanmontisis term) Termites such as termites (Sinocapritermes mushae) and Cornitermes cumulans}. Acari, for example, Tranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oonychus sp. Tetranychidae; Acarops pelekassi, Phyllocoptruta citri, Tomato, Aculops lycopersici, Calacarus carinatus, Acaphylla theensis Acari schlechtendali, Aceria diospyri, Aceria tosichella, Sheevtchenkella sp., Eriophyidae; Typhididae (Tenuipalpidae), such as Brevipalpus phoenicis; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanenxo, Dermacentor taiwanenxo ), Tick (Ixodidae), black legged tick (Ixodes scapularis), black tick (Amblyomma americanum), boophilus microplus, Rhipicephalus sanguineus, etc .; Tyrophagus putrescentiae), Acaridae such as Tyrophagus similis; Pyroglyphiee such as Dermatophagoides farinae and Dermatophagoides pteronyssinus Chicklet mite (Cheyletus eruditus), stag beetle mite (Cheyletus malaccensis), southern tick mite (Cheyletus moorei), crested mite (Cheyletidae); mite mite (Otodectes cynotis) Sarcoptidae; Demodexidae, such as Demodex canis; Listrophoridae; Listrophoridae; Haplochthoniidae; Ornithonyssus bacoti; (Dermanyss gallinae), etc. (Dermanyssidae); Red beetle (Leptotrombidium akamushi), etc.} Plant parasitic nematodes {eg, Aphelenchida lines such as Aphelenchoides besseyi, strawberry nematodes (Aphelenchoides fragariae), Aphelenchoides ritzemabosi, bursaphelenchus xylophilus, etc. Potato cyst nematode (Globodera pallida), potato cyst nematode (Globodera rostochiensis), wheat cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), sugar beet nematode (Heterodera schachtera), trifoliate (Heterodera schachtii), clover Root-knot nematode (Meloidogyne arenaria), Kita-ketsu nematode (Meloidogyne hapla), Sweet Root-knot nematode (Meloidogyne incognita), Java Root-knot nematode (Meloidogyne javanica), Apple-knot nematode Meloidogyne mali), Pratylenchus coffeae, Sawtooth nematode (Pratylenchus drenatus), Chanegusa nematode (Pratylenchus loosi), Muginegus nematode (Pratylenchus neglectus), Penitarne pistula (Pratylenchus vulnus), cynomolgus nematode (Radopholus citrophilus), banana moth nematode (Radopholus similis), etc.

  Insect species to be controlled in the present invention (insect species for which the compound represented by the formula (1) exhibits a controlling effect) are further harmful such as sanitary pests, storage shell pests, clothing pests, house pests, and parasites. Can also be used to control organisms. In particular, it has an excellent control effect against ectoparasites that harm humans. Ectoparasites that are subject to control include those that inhabit the back, underarms, lower abdomen, and inner crotch of the host animal and obtain nutrients such as blood and dandruff from animals and birds, and host animals Including those that fly to the back and buttocks of the sea and obtain nutrients such as blood and dandruff from animals and birds. Examples of ectoparasites include ticks, lice and fleas.

  Examples of host animals in which the control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; pet birds (eg, pigeons, parrots, nine-birds, wild birds, parakeets, duvets, canaries) Cattle, horses, pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); bees (eg, honey bees, Japanese bees);

  That is, the pest control agent of the present invention is effective as an ectoparasite control agent for animals that protects the above animals and birds.

The following pests are listed as target mites (Acari). Mesostigmata mites {e.g. Dermanyssidae, such as Dermanyssus gallinae; Ornithonyssus sylviarum, Ornithonyssus spp., Ornithonyssus bur , Mites of the family mite (Macronyssidae) including house mites (Ornithonyssus bacoti); ) Ticks; Varroa spp. Varroa destructor, Varroa jacobsoni, Varroa underwoodi, Varroa underwoodi} tick. Metastigmata tick (eg, Argas spsi., Argas persicus), Argas reflexus, Ornithodoros spp. Ornithodras・ Tick of the genus Argasidae, including Ornithodoros moubata; Haemaphysalis concinna of Haemaphysalis spp., Haemaphysalis punctata, Haemaphysalis punctata, Haemaphysalis puncta,・ Otophyra (Haemaphysalis otophila), Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Tiger tick (Haemaphysalis yeni), Tani Haema Tick ticks (Haemaphysalis pentalagi), Tick ticks (Haemaphysalis flava), Big tick (Haemaphysalis megaspinosa), Tick ticks (Haemaphysalis japonica), Douglas tick ticks (A. mb) Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, mite spider mite (dess) (Ixodes ricinus), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundu s), Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis, Tick subspice (Boophilus sp. p.) Rhipicephalus (Boophilus) microplus), Lipicephalus (Boophilus) decoloratus (Rhipicephalus (Boophilus) decoloratus), Lipisephalas (Boophilus) annulatus (Rhipicephalus (Boophilus) annulatus), Lipisecephalus (Boophilus) Karratas (Thip) Genus species (Rhipicephalus spp. ) Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Ripeicephalus capicula (Rhipicephalus turanicus), Rhipicephalus zambeziensis, Dermacentor marginatus (Dermacentor marginatus), Dermacentor reticulatus (Dermacentor reticulatus), or Kuta ), Dermacentor albipictus, Dermacentor andersoni, Dermacentor Baribilis (Derma) Tick of Ixodidae containing centor variabilis}. Astigmata (Acaridida) {eg Psoroptidae spp., Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Psoroptes equi Mites of the genus Psoroptidae (Psoroptidae), including the genus Chorioptes spp. (Chorioptes bovis), the genus Otodectes spp. (Otodectes cynotis); spp.) Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes rupicaprae , Butenko Sarcoptes suis, Notoedres spp., Notoedres cati, and other genus Sarcoptidae; Knemidokoptes spp. ) Mites from the family Knemidokoptidae. Prostigmata mites (Actinedida) {e.g., Demodex canp, Demodex bovis, Demodex ovis, Demodex ovis, Demodex caprae ), Mite (Demodex equi), demodex cavali (Demodex caballi), butterfly mite (Demodex suis), cat mite (Demodex cati) mite (Demodixidae) mite; trombicula spp. Trombiculidae including Trombicula alfreddugesi, Trombicula akamushi}. Examples of lice (Phthiraptera) include the following pests. Anoplura louse {eg Haematopinus asini of Haematopinus spp., Haematopinus eurysternus, Haematopinus suis) Linognathus spp., Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus oviformis Linognathus oviformis Linognathus oviformis Linognathus oviformis Linognathidae lice, including Solenopotes capillatus, Solenopotes spp.}. Amblycera subspecies (biting louse) {eg, Menacanthus stramineus, Menacanthus cornutus, pallidus acne, anthracite , For example, Mennopon gallinae, including Menopon gallinae}. Ischnocera subspecies (biting louse) {eg, Columbicola spp., Columbicola columbae, Cuclotogaster spp., Cublotogaster spp. heterographus), Goniodes spp., Goniodes dissimilis, Butterfly (Goniodes gigas), Blueflies (Goniodes gallinae), Ripeurus spp. Philopteridae larvae; Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola capra equi, Bovicola caprae, Bovicola caprae ), Trichodectes sp p.) Trichodectes canis, Felicola spp. Felicola subrostrata, and Trichodectidae's lice}. The fleas (Siphonaptera) include the following pests. For example, fleas from the family Tungidae, including the Tunga spe. (Tunga penetrans); the fleas (Ctenocephalides canis), the cat fleas (Ctenocephalides felis) Archaeopsylla spp.'S hedgehog worm (Archaeopsylla erinacei), murine genus Xenopsylla spp. ) Fleas (Pulicidae) fleas (Echidnophaga gallinacea); chironomid species (Ceratophyllus gallinae); Fleas from the family Ceratophyllidae, including the European murine flea (Nosopsyllus fasciatus); Fleas of the family Leptopsyllidae, including Leptopsylla segnis, from the genus Leptopsylla spp. Other target ectoparasites include Hemiptera pests. Hemiptera pests include the following pests: For example, insects of Cimicidae including Cimex spp. Cimex lectularius; Panstrongylus spp., Rhodnius spp., Venezuelan turtle (Rhodnius) prolixus), Reduviidae insects, including Triatoma infestans of the genus Triatoma spp. In addition, it is also effective against Diptera pests, which are biting insects (chewing flies, blood-sucking adult flies, migratory dipterous larvae, parasitic fly maggots). The following pests can be mentioned as pests of flies (Diptera). Nematocera {e.g. (a) Culex spp. Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Almigeres spal. (Armigeres subalbatus), Anopheles spp. maculipennis), Anopheles sinensis, Anopheles lesteri, Aedes spp. Aedes togoi) Culicidae mosquitoes including Aedes vexans nipponii; (b) Simulium spp. Simulium reptans, Simulium ornatum, Simulium venustum , Simulium salopiense, Prosimulium spp, Prosimulium yezoense, and other species of Simuliidae; Culiodes spp., Culicoides arkawae ), Kibunekaka (
Culicoides kibunensis), Cedaranukaka (Culicoides homotomus), Boonukaka (Culicoides oxystoma), Nipponkakaka (Culicoides nipponensis), Hoshinukaka (Culicoides punctatus), Miyamanukaka (Culicoides maculatus), Matsuzaulka }. Short-horned subtype {e.g., (a) for example Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus (Tabanus sudeticus) ), Bovine Ab (Tabanus trigonus), Red Bull Ab (Tabanus chrysurus), White-footed Ab (Tabanus trigeminus), Kisjiab (Tabanus fulvimedioides), White-faced Bib (Tabanus iyoensis), Chrysops spp.・ Abidae (Tabanidae) including Chrysops relictus, Chrysops suavis, Chrysops japonicus; Musca domestica, Musca bezzi, Musca bezz (Musca hervei), Usiroi fly ( Musca conducens), Musca stabulans, Stomoxys spp., Stomoxys calcitrans, Haematobia spp., Haematobia irritans guati , Haematobia stimulans, Fannia spp., Fannia canisularis, Muscidae flies; Glossina spp., Glossinidae Flies of the genus Melophagus spp. Melophagus ovinus, the flies of the family Hypoboscidae; Calliphora, Calliphora lata ;, Lucilia spp. Of the flies of Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) sericata, The phoridae family of the flies flies (Lucilia illustris), Chrysomya hominivorax (Chrysomya hominivorax), Chrysomya chloropyga, Chrysomya bezziana; (Cuterebrinae) Rabbit Drosophila (Cuterebra spp. ), Hypodermatinae, Hypoderma spp., Hypoderma bovis, Hypoderma lineatum, Gasterophilinae, and Gasterophilus spp. Horseflies (Gasterophilus intestinalis), Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis (Gasterophilus nigricornis), Gumophilus pe ) And Oestridae flies including Oestrus spp. (Oestrus ovis).

  When the compound represented by the formula (1) is used as an agricultural and horticultural insecticide, the compound represented by the formula (1) may be used as it is, but an appropriate solid carrier, liquid carrier, gaseous carrier, etc. An agrochemical formulation may be prepared and used by mixing with an active agent, a dispersant, other formulation adjuvants, and the like. As the agrochemical formulation, preferably, emulsion, EW agent, solution, suspension, wettable powder, wettable powder, powder, DL powder, powder, granule, tablet, oil, aerosol, flowable, dry A flowable agent, a microcapsule agent, etc. can be mentioned. It can be used as a dosage form arbitrarily selected as these agricultural chemical preparations. The carrier in the present invention refers to a solid carrier, a liquid carrier, a gaseous carrier and the like.

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, silica sand, silica, zeolite, perlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, urea, and the like. It is 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, kerosene, and kerosene. , Aromatic hydrocarbons such as toluene, xylene and methylnaphthalene, ethers such as diethyl ether, dioxane and 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, dimethyl sulfoxide, water and the like.
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 sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, and alkyl sulfosuccinic acids. Salt, formalin condensate of alkyl naphthalene sulfonate, polycarboxylate, POE polystyryl phenyl ether sulfate and phosphate, POE / POP block polymer, and the like.
Furthermore, as the above-mentioned adjuvant for preparation, for example, carboxymethylcellulose, hydroxypropylcellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, Examples include polyethylene glycol, liquid paraffin, calcium stearate, and antifoaming agents and preservatives.
The above-mentioned various carriers, surfactants, dispersants, and formulation adjuvants can be used alone or in combination as necessary.

  The content of the compound represented by the formula (1) which is an active ingredient in the agrochemical formulation is not particularly limited, but is preferably 1 to 75% by weight in the emulsion, 0.3 to 25% by weight in the powder, water It is 1 to 90% by weight for a summing agent, and 0.1 to 10% by weight for a granule.

When the compound represented by the formula (1) is used as an acaricide for controlling mites parasitic on livestock such as cattle and pigs, and pet animals such as dogs and cats, The active ingredient can be used in an amount of 0.01 to 1000 mg.
The acaricide for control can be applied by a known veterinary technique. As the method, for example, for the purpose of systemic suppression, it is a method of administering to animals by tablets, capsules, immersion liquid, feed mixing, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) In cases where non-systemic suppression is intended, methods such as spraying, pour-on, or dropping (spot-on) oily or aqueous liquids, kneading miticides into the resin And a method of forming the kneaded product into an appropriate shape such as a collar and an ear tag and mounting it on an animal.

  The pest control agent according to the present invention can be used as it is or after being diluted. The pest control agent according to the present invention can be mixed or used in combination with other insecticides, nematicides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like. Examples of drugs that can be mixed or used in combination include the Pesticide Manual (17th edition, published by The British Crop Protection Council) and Shibuya Index (17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP) and Eye Rack mode of action classification scheme (Mode of Action Classification Scheme Version 8.2, published by IRAC), FRAC Code List 2017: Fungicides sorted by mode of action (2017 edition, published by FRAC) Examples include those listed and those whose structure can be specified on the Internet (http://www.alanwood.net/pesticides/sitemap.html).

More specifically, the insecticides are, for example, alanycarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocarboxim, butoxycarbox ( butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formenanate, furathiocarb, isoprocarb, methiocarb, Methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, metolcarb (metolcarb), Fenothioca Bed (fenothiocarb), carbamate compounds such as fenoxycarb (fenoxycarb),
Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, Chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon (diazinon), dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenitrothion fenitrothion), fenthion, phostiazate (fosthiazate), heptenophos, imiciaphos, isofenphos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, Mecarbam, metamidophos, methidathion, mevinphos, monocrotophos, nared, omethoate, dioxydemeton ethyl, parathion, parathion -Parathion-methyl, PAP, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, profenofos (propetamphos), prothiofos, pyracrofos ( pyraclofos, pyridaphenthion, quinalphos, sulfopep, tebupirimfos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triazophos , Trichlorfon, vamidion, chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazophos, phenthoate, fonofos, tribuhos Organophosphate compounds such as
Organochlorine compounds such as endosulfan, alpha-endosulfan, gamma-HCH, dicohol, chlordane, dieldrin, methoxyclor,
Phenylpyrazole compounds such as acetoprole, fipronil, etiprole, pyrafluprole, pyriprole, flufiprole,
Metadiamide compounds such as broflanilide,
Isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, fluxametamide,
Acrinathrin, allethrin, d-cis-trans allethrin, d-cis-trans allethrin, bifenthrin, kappa-bifenthrin, bioarethrin S-cyclopentenyl (bioallethrin S-cyclopentenyl), violesmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin (gamma-cyhalothrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin ), Cyphenothrin, deltamethrin, Penentrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fulvalinate -fluvalinate), halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prarethrin, pyrethrin, resmethrin, silafluen (silafluen) Tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, metoxadiazone, methfluthrin, fluflurin ), Pyrethrum, terallethrin, monmfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, profenbutbut Pyrethroid compounds such as
Neonicotinoid compounds such as acetamiprid, acanthiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam,
Sulfoxamine compounds such as sulfoxaflor,
Butenolide compounds such as flupyradifurone,
Mesoionic compounds such as triflumezopyrim, dicloromezotiaz,
2-aminopyridine compounds such as fluprimin spinosad, spinosyn compounds such as spinetoram,
Macrolide compounds such as abamectin, ivermectin, ivermectin, emamectin benzoate, milbemectin, lepimectin,
Juvenile hormone-like compounds such as hydroprene, quinoprene, diofenolan, metoprene,
4-phenoxyphenoxy compounds such as pyriproxyfene,
Pyridine azomethine compounds such as pymetrozine,
Pyridine carboxamide 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.
An insecticidal protein produced by a Bt crop corresponding to the above,
Thiourea compounds such as diafenthiuron,
Organometallic compounds such as azocyclotin, cyhexatin, fenbutatin oxide,
Sulfite-based compounds and diphenyl ether-based compounds such as propargite
Diphenylsulfone 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, bistrifluron and other benzoylurea compounds,
Thiadiazine compounds such as buprofezin,
Triazole compounds such as cyromazine,
Diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide,
Amidine-based compounds such as amitraz,
Amidinohydrazone 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,
Pyridazinone compounds such as pyridaben,
Pyrazole carboxamide compounds such as tebufenpyrad, tolfenpyrad, pyflubumide,
Hydrazine carboxamide compounds such as metaflumizone,
Tetronic and tetramic acid compounds such as spirodiclofen, spirotetaramat, spiromesifen, spiropidion,
Beta-ketonitrile compounds such as cyflumetofen, cyenopyrafen,
Phthalic acid amide compounds such as flubendiamide,
Anthranilic amide compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide,
Quinoxaline compounds such as quinomethionate,
Thiazolidinone compounds such as hexythiazox,
Hydrazine compounds such as bifenazate,
Pyridinamine compounds such as flufenerim,
Aminoquinazoline compounds such as pyrifluquinazon,
6-phenoxyquinoline compounds such as flometoquin,
Pyridinylethylbenzamide compounds such as fluopyram,
It may be an oxadiazole compound such as fluazaindolizine, a sulfonamide compound such as amidoflumet, a pyridylpyrazole compound such as tyclopyrazoflor, and tioxazafen.
Other insecticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, India Indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, fluhexafon, fluhexafon, fluone Benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate salt, metaaldehyde, ryanodine, sulfluramid, asinonapill ( acynonapyr), benzpyrimoxan, 3-bu Mo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3,5-dichloropyridin-2-yl) -1H-pyrazole-5-carboxamide, 2- [3- ( And compounds such as ethanesulfonyl) pyridin-2-yl] -5- (trifluoromethanesulfonyl) benzoxazole. Furthermore, the pest control agent according to the present invention can be mixed or used together with microbial pesticides such as entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

The fungicides used are, for example, metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, kiralaxyl , Phenylamide compounds such as ofurace, fluralaxyl, cyprofuram,
Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, ethilimol,
Isoxazole compounds such as hymexazole, hydroxyisoxazole,
Piperidinylthiazole isoxazoline compounds such as oxathiapiprolin,
Isothiazolones such as octhilinone,
Carboxylic acid compounds such as oxolinic acid,
Benzimidazole thiophanate compounds such as benomyl, thiophanate-methyl, carbendazole, fuberidazole, thiabendazole, debacarb,
N-phenyl carbamate compounds such as dietofencarb,
Toluamide compounds such as zoxamide,
Ethylaminothiazole carboxamide compounds such as ethaboxam,
Phenylurea compounds such as pencicuron (pencycuron),
Pyridinylmethylbenzamide compounds such as fluopicolide,
Pyrimidineamine compounds such as diflumetorim, bupirimate,
Benzanilide compounds such as benodanil, flutolanil, mepronil,
Phenyloxoethylthiophenamide compounds such as isofetamid,
Pyridinylethylbenzamide compounds such as fluopyram,
A furan carboxamide compound such as fenfuram,
Oxycarboxin, oxathiin carboxamide compounds such as carboxin (carboxin),
Thiazole carboxamide compounds such as thifluzamide,
Fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpyrufluxam pyrazole-4-carboxamide compounds such as (inpyrfluxam), fluindapyr, isoflucypram, pyrapropoyne,
Pyridinecarboxamide compounds such as boscalid,
Azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin (dimoxystrobin), mettominostrobin, oryastrostrobin, 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 triclopyricarab, pyribencarb,
Cyanoimidazole compounds such as cyazofamid,
Sulfamoyltriazole compounds such as amisulbrom,
Dinitrophenylcroton compounds such as binapacryl, meptyldinocarb, dinocap,
2,6-dinitroaniline compounds such as fluazinam,
Pyrimidinone hydrazone compounds such as ferimzone,
Fentin-acetate, fentin chloride, fentin hydroxide, fenthin hydroxide, fenthin acetate, oxine copper Such as organic and inorganic metal compounds,
Thiophenecarboxamide compounds such as silthiofam,
Triazolopyrimidineamine compounds such as ametoctradin,
Anipinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimethanil, cyprodinil, enopyranuronic 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,
Dicarboximide compounds such as fluoroimid, procymidone, iprodione, vinchlozolin,
Phosphorothiolate compounds such as edifenphos, iprobenfos, pyrazophos,
Dithiolane compounds such as isoprothiolane,
Propyl carbamate compounds such as propamocarb, propamocarb hydrochloride,
Bacillus genus and produced bactericidal proteins such as Bacillus subtilis (QST713, FZB24, MBI600, strain D747), and
Bactericidal proteins produced by the Bt crops,
Terpene hydrocarbons and terpene alcohols, such as Goseika Yupte extract,
Piperazine compounds such as triforine,
Pyridine compounds such as pyrifenox, pyrisoxazole,
Pyrimidine compounds such as fenarimol and nuarimol,
Azaconazole, bromuconazole, diniconazole, diniconazole-M, epoxyconazole, fluquinconazole, oxpoconazole, pefazoate ( pefurazoate), difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol (triadiolon) , Triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole ), Lutriahol, microbutanil, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, cimeconazole (simeconazole), azole compounds such as ipfentrifluconazole,
Morpholine compounds such as aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pyrimorph ,
Piperidine, piperidine compounds such as 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 ( polycarbamate), thiocarbamate and dithiocarbamate compounds such as propineb, thiuram, pyributicarb,
Glucopyranosyl antibiotics such as validamycin,
Nucleoside antibiotics such as mildiomycin, polyoxin,
Valinamide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, iprovalicarb,
Mandelic acid amide compounds such as mandipropamid,
Picolinamide compounds such as fenpicoxamid,
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,
Benzothiadiazole compounds such as acibenzolar-S-methyl,
Benzisothiazole compounds such as probenazole, diclobentiazox,
Thiadiazole carboxamide compounds such as tiadinil,
Isothiazole carboxamide compounds such as isothianil,
Cyanoacetamide oxime compounds such as cymoxanil,
Ethylphosphonate compounds such as fosetyl,
Phthalamic acid compounds such as techlophthalam,
Benzotriazine compounds such as triazoxide,
Benzenesulfonic acid compounds such as flusulfamide,
Pyridazinone compounds such as diclomezine,
Phenylacetamide compounds such as cyflufenamide,
Benzophenone compounds such as metrafenopne,
Benzoylpyridine compounds such as pyriofenone,
Cyanomethylene thiazolidine compounds such as flutianil,
4-quinolyl acetic acid compounds such as tebufloquin,
Organophosphorus compounds such as fosetyl-aluminium, tolclofos-methyl,
1,2,4-thiadiazole compounds such as echlomezole,
Trifluoroethyl carbamate compounds such as tolprocarb,
Bordeaux mixed solution, copper acetate, basic copper sulfate, oxy copper chloride, copper hydroxide, oxine-copper Copper-based compounds such as
Inorganic compounds such as copper and sulfur,
N-halogenothioalkyl compounds such as captan, captafol, folpet,
Organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, 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 compounds such as fluoroimide,
Sulfenic acid-based compounds such as tolylfluanid, dichlorfluanid,
Dinitrophenol compounds such as dinobuton,
There can be cyclic dithiocarbamate compounds such as dazomet, anilide compounds such as pyraziflumid, and nicotinic acid ester compounds such as aminopyrifen.
Other fungicides include dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, and prohexadione-calcium. (prohexadione-calcium), bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, etc. It is done.

By applying an effective amount of the compound represented by the formula (1) of the present invention or the agricultural and horticultural and veterinary pharmaceutically acceptable acid salt to plants, soils or animals, Can be used for control. That is, a method for controlling pests in these fields is provided. Here, the control method according to the present invention includes a method in which the compound represented by the formula (1) or an acid-addition salt acceptable in agriculture and horticulture is applied by smoke treatment in a sealed space.
The compound represented by the formula (1) of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof is also treated or applied to a crop, a seed on which the crop grows, or a crop placenta in a biologically effective amount. Increases the vitality of crops through contact.
When the object to be treated or contacted is a seed, the amount of the compound represented by the formula (1) of the present invention or an acid-addition salt acceptable in agriculture and horticulture is not limited, but about 0. It is preferable that the compound represented by the formula (1) of the present invention or an agricultural and horticulturally acceptable acid addition salt thereof is contained in an amount of 0001 to about 1% by weight.
The present invention further provides use of the compound represented by the formula (1) of the present invention or an acid addition salt thereof as an active ingredient of a composition for protecting animals and birds from harmful parasitic invertebrates. The composition contains the compound represented by the formula (1) of the present invention or an acid addition salt thereof in an amount that is parasitically effective and does not harm the target animal or bird. In the above-mentioned use, the compound represented by the formula (1) of the present invention or an acid addition salt thereof is brought into contact with the harmful invertebrate organism or its growing environment in a biologically effective amount to control the harmful invertebrate organism.

（A−１） Next, specific examples of the compound of the present invention are shown below. In the following table, Me represents a methyl group, Et represents an ethyl group, n-Pr represents a normal propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, c- Pent represents a cyclopentyl group.

(A-1)

In the formula (A-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (A-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (A-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In Formula (A-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (A-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (A-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (A-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (A-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In Formula (A-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c, and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (A-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (A-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

The compound of the present invention in which R is 3-CF ₃ OPh— and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1 in the formula (A-1).

In the formula (A-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (A-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (A-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (A-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (A-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（B−１）

(B-1)

In the formula (B-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (B-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (B-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (B-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (B-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (B-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In Formula (B-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (B-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (B-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (B-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (B-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (B-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (B-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (B-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (B-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (B-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (B-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｃ−１）

(C-1)

In the formula (C-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (C-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (C-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (C-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (C-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (C-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (C-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention as a combination.

In the formula (C-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (C-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (C-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (C-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (C-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (C-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (C-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (C-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (C-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (C-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｄ−１）

(D-1)

In the formula (D-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (D-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (D-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (D-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (D-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (D-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (D-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (D-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (D-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (D-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (D-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (D-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (D-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (D-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (D-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (D-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (D-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｅ−１）

(E-1)

In the formula (E-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (E-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (E-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Invention compounds.

In the formula (E-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (E-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (E-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (E-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (E-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (E-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are represented by Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (E-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (E-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (E-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (E-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (E-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (E-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (E-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (E-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｆ−１）

(F-1)

In the formula (F-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (F-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (F-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (F-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (F-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (F-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In formula (F-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (F-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In Formula (F-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c, and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (F-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (F-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (F-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (F-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (F-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (F-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (F-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (F-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｇ−１）

(G-1)

In the formula (G-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (G-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (G-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Invention compounds.

In the formula (G-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (G-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (G-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (G-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (G-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In Formula (G-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c, and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (G-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (G-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (G-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (G-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (G-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (G-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (G-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (G-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｈ−１）

(H-1)

In the formula (H-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (H-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (H-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (H-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as shown in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (H-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (H-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (H-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (H-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In Formula (H-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c, and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (H-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (H-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (H-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (H-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (H-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (H-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (H-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (H-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｉ−１）

(I-1)

In the formula (I-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (I-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (I-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (I-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as shown in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (I-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (I-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (I-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (I-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (I-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (I-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (I-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (I-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (I-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (I-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (I-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (I-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (I-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

（Ｊ−１）

(J-1)

In the formula (J-1), R is CF ₃ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (J-1), R is CF ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention. {Wherein R ₁ , R ₂ , R _a , R _b , R _c and R _d represent the same as above. }

In the formula (J-1), R is CF ₃ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. Invention compounds.

In the formula (J-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as shown in Table 1-1 and Table 1-2. The compound of the present invention which is a combination described.

In the formula (J-1), R is (CF ₃ ) ₂ CH—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (J-1), R is CH ₃ CH ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (J-1), R is CF ₃ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are as described in Table 1-1 and Table 1-2. The compound of the present invention which is a combination.

In the formula (J-1), R is CF ₂ HCF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations described in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (J-1), R is CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are in Table 1-1 and Table 1- The compound of the present invention which is a combination according to 2.

In the formula (J-1), R is 4-CF ₃ Ph—, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (J-1), R is 4-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (J-1), R is 3-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (J-1), R is 2-CF ₃ OPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2. The compound of the present invention.

In the formula (J-1), R is 4-tBuOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (J-1), R is 4-PhOPh-, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations described in Table 1-1 and Table 1-2 Compound.

In the formula (J-1), R is 4-CF ₃ PhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

In the formula (J-1), R is 4-CF ₃ OPhCH ₂ —, and R ₁ , R ₂ , R _a , R _b , R _c and R _d are combinations shown in Table 1-1 and Table 1-2. A compound of the present invention.

  The compounds of the present invention can exist as one or more conformers due to bond rotation limitations caused by steric hindrance. For example, a compound of formula (1) in which a 4-pyridyl group is substituted with a bulky alkyl group at the ortho position (eg, isopropyl) can result in two species due to limited rotation with respect to the 4-pyridyl group-pyrazinium ring bond. Can exist as rotamers. The present invention includes mixtures of conformers.

<Synthesis Example>
EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples. In the NMR data, “s” is a singlet, “d” is a doublet, “t” is a triplet, “q” is a quartet, and “quin” is a quintet. (Quintet), “sext” indicates a sectet (hexadecimal line), “sep” indicates a septet (seventh line), and “m” indicates a multiplet (multiple line).

Synthesis Example 1-1: Preparation of 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine 2,5-dibromopyrazine (5.00 g, 21.02 mmol) was converted to dimethylformamide ( 75 ml) and 2,2,3,3,3-pentafluoropropan-1-ol (3.78 g, 25.19 mmol) was added at room temperature. Thereafter, sodium hydride (1.09 g, 24.98 mmol) was added at 0 ° C., and the mixture was stirred at room temperature overnight. Water was added, the mixture was extracted twice with ethyl acetate, and washed 3 times with saturated brine. The extracted ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered, and then ethyl acetate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (6.09 g, 94.4%, light yellow oil). Got.
¹ H NMR (CDCl ₃ ) δ8.22 (1H, d, J = 2.9Hz), 8.16 (1H, d, J = 2.9Hz), 4.82 (2H, ddd, J = 14.9Hz, 12.0Hz, 3.0Hz)

Synthesis Example 1-2: Preparation of 2- (2,2,3,3,3-pentafluoropropoxy) -5- (pyridin-4-yl) pyrazine (Compound No. -1) In Synthesis Example 1-1 The prepared 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.57 g, 1.86 mmol) was dissolved in dioxane (60 ml), and the mixture was biscuated at room temperature under nitrogen atmosphere. (Triphenylphosphine) palladium (II) dichloride (0.13 g, 0.19 mmol) was added, and the temperature was raised to 60 ° C. Thereafter, 4-pyridylboronic acid (0.27 g, 2.2 mmol) and 2M-aqueous sodium hydrogen carbonate solution (6 ml) were sequentially added at 60 ° C., and the mixture was stirred for 4 hours. After cooling to room temperature, dioxane was distilled off under reduced pressure with an evaporator, diluted with ethyl acetate and water, and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate and filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2- (2,2,3,3,3-pentafluoropropoxy) -5- (pyridin-4-yl) pyrazine (0.39 g, 68.8). %, White solid).
¹ H NMR (CDCl ₃ ) δ8.74 (2H, d, J = 6.0Hz), 8.61 (1H, d, J = 1.5Hz), 8.46 (1H, d, J = 1.2Hz), 7.85 (2H, dd , J = 4.8Hz, 1.5Hz), 4.92 (2H, td, J = 12.8, 0.9Hz)

Synthesis Example 2-1: 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3,2dioxaboran-2-yl) Preparation of Pyrazine 2-Bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (3.74 g, 12.18 mmol) prepared in Synthesis Example 1-1 was added to dioxane (55 ml). Dissolved and nitrogen atmosphere, at room temperature bis (pinacolato) diboron (3.10 g, 12.21 mmol), bis (triphenylphosphine) palladium (II) dichloride (0.50 g, 0.61 mmol), potassium acetate (3. 59 g, 36.58 mmol) was sequentially added, and the mixture was warmed and stirred for 2 hours under reflux conditions. After cooling to room temperature, it was diluted with ethyl acetate and filtered using a filter aid to remove solids. The filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3,2dioxaboran-2-yl) pyrazine (4.31 g, 100%, brown oil) was used in the next reaction without purification.
¹ H NMR (CDCl ₃ ) δ8.52 (1H, d, J = 2.9Hz), 8.50 (1H, d, J = 2.9Hz), 4.87 (2H, ddd, J = 14.9Hz, 12.0Hz, 3.0Hz) , 1.39 (12H, s)

Synthesis Example 2-2: Preparation of 2- (3-chloropyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (Compound No. 6) 3-Chloro- 4-Iodopyridine (0.57 g, 2.381 mmol) was dissolved in dioxane (45 ml), bis (triphenylphosphine) palladium (II) dichloride (0.17 g, 0.24 mmol) was added at room temperature under a nitrogen atmosphere, The temperature was raised to 60 ° C. Thereafter, 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3, prepared in Synthesis Example 2-1 at 60 ° C. 2Dioxaboran-2-yl) pyrazine (1.1 g, 1.2 mmol) and 2M-aqueous sodium hydrogen carbonate solution (6 ml) were sequentially added and stirred for 2 hours. After cooling to room temperature, it was diluted with ethyl acetate and water and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate and filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2- (3-chloropyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.39 g, 91.6%, brown oil).
¹ H NMR (CDCl ₃ ) δ8.73 (1H, s), 8.65 (1H, d, J = 1.5Hz), 8.61 (1H, d, J = 5.1Hz), 8.49 (1H, d, J = 1.5Hz ), 7.61 (1H, d, J = 5.1Hz), 4.93 (2H, td, J = 12.9Hz, 0.9Hz)

Synthesis Example 3-1 Preparation of 2-bromo-5- (pyridin-4-yl) pyrazine 2-Bromo-5-dibromopyrazine (0.50 g, 2.102 mmol) was dissolved in dioxane (50 ml) and nitrogen was added. Under an atmosphere, bis (triphenylphosphine) palladium (II) dichloride (0.13 g, 0.19 mmol) was added at room temperature, and the temperature was raised to 60 ° C. Thereafter, 4-pyridylboronic acid (0.26 g, 2.1 mmol) and 2M-aqueous sodium hydrogen carbonate solution (5 ml) were sequentially added at 60 ° C., and the mixture was stirred for 3 hours. After cooling to room temperature, it was diluted with ethyl acetate and water and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate and filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-bromo-5- (pyridin-4-yl) pyrazine (0.11 g, 22.2%, light yellow solid).
¹ H NMR (CDCl ₃ ) δ 8.86 (1H, d, J = 3.0Hz), 8.83-4.74 (3H, m), 7.89 (2H, dd, J = 6.0Hz, 3.0Hz), 7.66-7.50 (1H , m), 7.43-7.29 (1H, m)

Synthesis Example 3-2: 2-((1,1,1,3,3,3-hexafluoropropan-2-yl) oxy) -5- (pyridin-4-yl) pyrazine (Compound No. -19) Preparation of 2-Bromo-5- (pyridin-4-yl) pyrazine (0.96 g, 0.41 mmol) prepared in Synthesis Example 3-1 was dissolved in dimethylformamide (2 ml), and 1,1 at room temperature. , 1,3,3,3-hexafluoropropan-2-ol (0.83 g, 0.4939 mmol), potassium carbonate (0.11 g, 0.82 mmol), 18-crown-6-ether (catalytic amount). Sequentially added and stirred at room temperature overnight. Water was added, the mixture was extracted twice with ethyl acetate, and washed 3 times with saturated brine. The extracted ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered, and then ethyl acetate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-((1,1,1,3,3,3-hexafluoropropan-2-yl) oxy) -5- (pyridin-4-yl). Pyrazine (0.66 g, 50.2%, light brown solid) was obtained.
¹ H NMR (CDCl ₃ ) δ8.77 (2H, d, 5.7Hz), 8.63 (1H, d, J = 1.2Hz), 8.58 (1H, d, J = 1.5Hz), 7.87 (1H, d, J = 1.8Hz), 7.85 (1H, d, J = 1.5Hz), 6.50-6.38 (1H, m)

  The proton NMR spectrum data and melting point of the compound of formula (1) synthesized by the same method as above were as shown in Table 2-1, Table 2-2, Table 3-1, and Table 3-2.

<Formulation example>
Moreover, the example of an agrochemical formulation which contains the compound represented by Formula (1) based on this invention as an active ingredient is given below.
Formulation Example 1 [wettable powder]
30% by weight of compound
30% by weight of clay
Diatomaceous earth 35% by weight
Sun extract P252 4% by weight
(Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.)
Solpol 8070 1% by weight
(Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.)
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.

Formulation Example 2 [Dust]
Compound 2% by weight
90% by weight clay
7% by weight of talc
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 3 [Emulsion]
20% by weight of compound
N, N-dimethylformamide 20% by weight
T-SOL 150 50% by weight
(Aromatic solvent: Product name of JXTG Energy Corporation)
New Calgen CL-H 10% by weight
(POE alkylphenyl ether: product name of Takemoto Yushi Co., Ltd.) The above ingredients were mixed uniformly and dissolved to obtain an emulsion.

Formulation Example 4 [Emulsion 2]
5% by weight of compound
Xylene 42.5% by weight
DMSO 42.5 wt%
New Calgen 2003 10% by weight
(POE allyl phenyl ether formaldehyde condensate and alkylbenzene sulfonic acid metal salt mixture: product name of Takemoto Yushi Co., Ltd.)
The above ingredients were mixed uniformly and dissolved to obtain an emulsion.
Formulation Example 5 [Granule]
5% by weight of compound
Bentonite 40% by weight
Talc 10% by weight
43% by weight clay
Sun extract P252 2% by weight
(Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.)
The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain granules.

Formulation Example 6 [Flowable Agent]
25% by weight of compound
Solpol 7556 5% by weight
(POE styryl phenyl 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
The whole amount of the above formulation except for 1% aqueous xanthan gum solution and an appropriate amount of water was premixed and then pulverized with a wet pulverizer. Thereafter, 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.

Formulation Example 7 [Granule]
5% by weight of compound
Bentonite 40% by weight
Talc 10% by weight
43% by weight clay
Sun extract P252 2% by weight
(Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.)
The above 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 present invention against certain pests. “Control efficacy” refers to the inhibition (including mortality) of harmful invertebrate growth 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 2-1 and 2-2.

Biological test example 1: Cotton aphid (Aphis gossypii) control test (foliar spray treatment)
Cucumber leaves were cut to a diameter of 3.5 cm and placed on absorbent cotton moistened with water. Two adult cotton aphids were released here and allowed to lay for 24 hours, and then the adults were removed. 2 mL of a diluted solution of the test compound diluted to 200 ppm on this cucumber leaf was sprayed using a spray tower. After air drying, they were put in a plastic cup together with absorbent cotton, covered and kept in a constant temperature room at 25 ° C. After 5 days of treatment, mortality was observed and the death rate (%) was calculated.
As a result, the present compound 1, 2, 4, 6, 8, 12, 16, 17, 18, 19, 20, 21, 23, 27, 31, 32, 33, 34, 36, 37, 39, 42, 43, 44, 46, 47, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67 are more than 80% dead Showed the rate.

Biological test example 2: Cotton aphid (Aphis gossypii) control test (root soak treatment)
One cucumber seedling (cotyledon stage) was fixed with urethane so that the roots were immersed in a vial (inner diameter 2.7 cm × 6 cm) containing 10 mL of a chemical solution diluted to 3.1 ppm. One day after immersion, 5 cotton aphid first instar larvae were released and raised in a constant temperature room at 25 ° C. Life and death of the insects and abnormalities were investigated 5 to 7 days after the release.
As a result, the compounds 1, 2, 4, 20, 43, 45, 47, 50, 53, 54, 57, 59, 60, 61, and 62 of the present invention showed a death rate of 80% or more.

Biological test example 3: Tobacco whitefly (Bemisia tabaci) control test (leaf spray treatment)
Release the adult whitefly on a potted cucumber and lay eggs for 6 hours. Then remove the adults and keep them in a condition with sufficient light. After the hatched larvae have settled, the leaves are cut into 4 cm squares so as to contain the larvae, and placed on the absorbent cotton moistened with water with the back of the leaves facing up. 2 mL of a diluted solution of the test compound diluted to 200 ppm was sprayed on the cucumber leaves using a spray tower. After air drying, it was placed in a plastic cup together with absorbent cotton, covered and kept in a constant temperature room at 25 ° C. Life and death were observed 7 days after the treatment, and the death rate (%) was calculated.
As a result, the compounds 1, 2, 4, 8, 19, 31, 43 of the present invention showed a death rate of 80% or more.

Biological test example 4: Plutella xylostella control test (leaf dip treatment)
The cabbage leaf was cut to a diameter of 5.0 cm, and the cabbage leaf piece was immersed in 20 mL of a diluted solution of the test compound diluted to 200 ppm and air-dried. After air-drying, the cabbage leaf pieces were placed in a plastic cup, and 10 Kogana 3rd instar larvae were released, covered and kept in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for survival, and the mortality rate (%) was calculated.
As a result, the compounds 2, 6, and 11 of the present invention showed a death rate of 80% or more.

Biological test example 5: Niilaparvata lugens control test (stem and leaf immersion treatment)
Ten rice seedlings were taken and immersed in 20 mL of a chemical solution of a test compound diluted to 200 ppm and air-dried. After air-drying, it is held in a glass cylinder (inner diameter 4.5 cm × 14 cm) using urethane and placed on a plastic cup containing 40 mL of water. To this, the brown planthopper 3rd instar larvae were released, covered with medicine-wrapped paper, and bred in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for survival, and the mortality rate (%) was calculated.
As a result, the compounds 1, 2, 4, 6, 10, 11, 14, 15, 16, 17, 18, 20, 21, 30, 31, 33, 34, 37, 40, 42, 43, 46, 49, 51, 52, 53, 54, 55, 56, 57, 59, 60, 61, 62, 63, 64, 65, 66 showed a death rate of 80% or more.

Biological Test Example 6: Nilaparvata lugens control test (root soaking treatment)
Take 10 rice seedlings, hold them in a glass cylinder (inner diameter 4.5cm x 14cm) using urethane, and make a plastic cup (90mL containing chemical solution diluted to 50ppm) with a hole in the center so that the cylinder stands. (With a lid on it). Two days later, 10 third-instar larvae were released, covered with medicine-wrapped paper, and raised in a constant temperature room at 25 ° C. Life and death of the insects and abnormalities were investigated 5 to 7 days after the treatment.
As a result, the compounds 1, 4, 20, 31, 42, 43, 57, 60 and 62 of the present invention showed a death rate of 80% or more.

Biological Test Example 7: Nephotettix cincticeps control test (stem and leaf immersion treatment)
Ten rice seedlings were taken and immersed in 20 mL of a chemical solution of a test compound diluted to 200 ppm and air-dried. After air-drying, it is held in a glass cylinder (inner diameter 4.5 cm × 14 cm) using urethane and placed on a plastic cup containing 40 mL of water. The leafhopper leafhopper 3rd instar larvae were released, covered with medicine wrapping paper, and raised in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for survival, and the mortality rate (%) was calculated.
As a result, the compounds 1, 6, 12, 13, 18, and 27 of the present invention showed a death rate of 80% or more.

Biological test example 8: Planococcus citri control test (foliar spray treatment)
Cucumber leaves were cut into 2 cm squares and placed on absorbent cotton moistened with water. 2 mL of a diluted solution of the test compound diluted to 200 ppm on this cucumber leaf was sprayed using a spray tower. After air-drying, 10 first-infested larvae were released. Then, it put into a plastic cup with absorbent cotton, covered and raised in a constant temperature room at 25 ° C. Life and death were observed 10 days after the treatment, and the death rate (%) was calculated.
As a result, the compounds 1, 2, and 6 of the present invention showed a death rate of 80% or more.

Biological Test Example 9: Tick spider mite (Tetranychus urticae) control test (leaf soak treatment)
Put absorbent cotton sufficiently dampened with water in a plastic container (diameter 6 cm x 3 cm), and spread filter paper on it. Place 2 cm square kidney beans on the filter paper, release 5 adult spider mites, and lay eggs for 24 hours. The next day, the bean leaf pieces excluding the adults are immersed in 20 mL of a diluted solution of the test compound diluted to 200 ppm for 10 seconds. After air-drying, the kidney beans were put back into the plastic cups, covered and kept in a constant temperature room at 25 ° C. Seven days after the treatment, larvae were observed for survival, the number of unhatched eggs was examined, and the mortality rate (%) was calculated.
As a result, the compounds 10, 11, 15, 23, 24, 22, 25, 31, 32, 34, 35 and 58 of the present invention showed a death rate of 80% or more.

Biological test example 10: Meloidogyne incognita control test (immersion test)
A suspension of sweet potato root nematode stage 2 larvae was obtained from the eggplant grown on the root of the sweet potato by the Bellman method. This nematode-containing solution was dispensed into a 48-well plate by 100 μL per well (approximately 50 nematodes). After that, add the same amount of reagent solution as the nematode-containing solution and let stand at 26 ° C. for 3 days, investigate nematode life and death under a stereomicroscope, investigate nematode life and death under a stereomicroscope, correct death The insect rate was calculated.
Corrected death rate (%) =
{(Treatment area mortality-untreated area mortality) / (100-untreated area mortality)} × 100
As a result, the compounds 3 and 22 of the present invention showed a corrected death rate of 80% or more.

Claims (13)

A compound represented by formula (1) or a salt thereof.

(In the formula (1),
R is
An alkyl group of hydrogen atoms C1 to C6 (wherein the C1 to C6 alkyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms. An amino group having two selected substituents, and / or
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein C2-C6 alkenyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms An amino group having two selected substituents, and / or
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (where C2-C6 alkynyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms An amino group having two selected substituents, and / or
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
Independently represents a phenyl group substituted with 1 to 5 substituents R ₄ ;
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
Alkyl group of hydrogen atom halogen atom C1 to C6 (wherein C1 to C6 alkyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyl group (wherein C2-C6 alkenyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynyl group (where C2-C6 alkynyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms which are the same or different and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyloxy group (wherein C2-C6 alkenyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynyloxy group (wherein C2-C6 alkynyloxy group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylthio group (wherein C1-C6 alkylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylthio group (wherein C2-C6 alkenylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylthio group (wherein C2-C6 alkynylthio group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfinyl group (wherein C1-C6 alkylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfinyl group (wherein C2-C6 alkenylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfinyl group (wherein C2-C6 alkynylsulfinyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfonyl group (wherein C2-C6 alkenylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfonyl group (wherein C2-C6 alkynylsulfonyl group is
One or more of the same or different halogen atoms and / or
A C1-C6 alkyloxy group optionally substituted by one or more same or different halogen atoms, and / or
A C1-C6 alkylthio group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, and / or
A C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, and / or
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Optionally substituted by an amino group having two selected substituents)
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected, Aminocarbonyl having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more same or different halogen atoms Independently of a group hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and a C1-C6 acyl group optionally substituted by one or more halogen atoms. A hydrazino group having three substituents selected from the above, one or more halogens that are the same or different A hydra having three substituents independently selected from a C1-C6 alkyl group optionally substituted by an atom and a C1-C6 acyl group optionally substituted by one or more halogen atoms. A dinocarbonyl group from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and a C1-C6 acyl group optionally substituted by one or more halogen atoms Represents a hydroxylamino group having two independently selected substituents;
A is O, S, SO, SO ₂ , NR ₃ , NR ₃ C═O or C═ONR ₃
Represents. ) R is
A C1-C6 alkyl group (wherein the C1-C6 alkyl group is one or more halogen atoms and / or different
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
A C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
A C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted by a phenyl group substituted by 1 to 5 substituents R ₃ )
Independently a phenyl group substituted by 1 to 5 substituents R ₄ ;
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
Alkyl group of hydrogen atom halogen atom C1 to C6 (wherein the C1 to C6 alkyl group may be substituted by one or more halogen atoms which are the same or different)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted by one or more halogen atoms which may be the same or different)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted by one or more halogen atoms which are the same or different)
C2-C6 alkenyloxy group (wherein the C2-C6 alkenyloxy group may be substituted by one or more halogen atoms which may be the same or different)
C2-C6 alkynyloxy group (wherein the C2-C6 alkynyloxy group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkylthio group (wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms, which may be the same or different)
C2-C6 alkenylthio group (wherein the C2-C6 alkenylthio group may be substituted with one or more halogen atoms which may be the same or different)
C2-C6 alkynylthio group (wherein the C2-C6 alkynylthio group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkylsulfinyl group (wherein the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which may be the same or different)
C2-C6 alkenylsulfinyl group (wherein the C2-C6 alkenylsulfinyl group may be substituted with one or more halogen atoms which may be the same or different)
C2-C6 alkynylsulfinyl group (wherein C2-C6 alkynylsulfinyl group may be substituted with one or more halogen atoms, which may be the same or different)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms, which may be the same or different)
C2-C6 alkenylsulfonyl group (wherein the C2-C6 alkenylsulfonyl group may be substituted with one or more halogen atoms, which may be the same or different)
C2-C6 alkynylsulfonyl group (wherein the C2-C6 alkynylsulfonyl group may be substituted with one or more halogen atoms which may be the same or different)
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected, Aminocarbonyl having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more same or different halogen atoms Group,
A is O, S, SO, SO ₂ , NR ₃ , NR ₃ C═O or C = ONR ₃
Is,
The compound according to claim 1 or a salt thereof. R is
A C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
A C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
A C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
Independently a phenyl group optionally substituted with 1 to 5 substituents R ₄ ;
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
Alkyl group of hydrogen atom halogen atom C1 to C6 (wherein the C1 to C6 alkyl group may be substituted by one or more halogen atoms which are the same or different)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted by one or more halogen atoms which may be the same or different)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted by one or more halogen atoms which are the same or different)
C1-C6 alkylthio group (wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms, which may be the same or different)
C1-C6 alkylsulfinyl group (wherein the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms, which may be the same or different)
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected, Aminocarbonyl having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more same or different halogen atoms Group,
A is an oxygen atom,
The compound according to claim 1 or a salt thereof. R is
A C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
A C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
A C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is one or more halogen atoms which are the same or different, and / or
Independently may be substituted with up to 1 to 5 substituents R ₃ optionally substituted with phenyl.
Independently a phenyl group optionally substituted with 1 to 5 substituents R ₄ ;
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
Alkyl group of hydrogen atom halogen atom C1 to C6 (wherein the C1 to C6 alkyl group may be substituted by one or more halogen atoms which are the same or different)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted by one or more halogen atoms which may be the same or different)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted by one or more halogen atoms which are the same or different)
C1-C6 alkylthio group (wherein the C1-C6 alkylthio group may be substituted with one or more halogen atoms, which may be the same or different)
C1-C6 alkylsulfinyl group (wherein the C1-C6 alkylsulfinyl group may be substituted with one or more halogen atoms which may be the same or different)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms, which may be the same or different)
Independently from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or different halogen atoms Amino group having two substituents selected, Aminocarbonyl having two substituents independently selected from a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more same or different halogen atoms Group,
A is NR ₃ C═O,
The compound according to claim 1 or a salt thereof. An insecticidal composition comprising the compound according to any one of claims 1 to 4 and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. The insecticidal composition according to claim 1, further comprising at least one biologically active compound or agent. The at least one biologically active compound or agent is alanicarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butcarboxyme, butoxycarboxyme, carbaryl, carbofuran, carbosulfan, etiophencarb, fenobucarb, formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxyl, Thiodicarb, Thiophanox, Triazamate, Trimetacarb, XMC, Xylylcarb, Metolcarb, Fenothiocarb, Phenoxycarb, Acephate, Azamethiphos, Azine Phos-ethyl Chlorothone Ethoxyphos, Kazusafos, Chloretoxyphos, Chlorfenvinphos, Chloro Mefos, Chlorpyrifos, Chlorpyrifosmethyl, Coumafos, Cyanophos, Demeton-S-Methyl, Diazinon, Dichlorvos, Dicrotofos, Dimethoate, Dimethylvinphos, EPN, Ethion, Etoprophos, Famfur, Phenamifos, Fenitrothion, Fenthione, Phostiazeto, Heptenofos, Imiciaphos Isopropyl = O- (methoxyaminebothiophosphorylsalicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naredo, ometoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, folate, hosalon Phosmet, Phosphamidone, Hoxime, Pirimiphos-methyl, Profenofospropetanephos, Proti Phos, pyraclofos, pyridafenthion, quinalphos, sulfotep, tebupyrimifos, temefos, terbufos, tetrachlorbinphos, thiomethone, triazophos, trichlorfone, bamidthione, chlorpyrifos-ethyl, disulfone, sulprophos, flupirazophos, phentoate, phonophos, trisulfos, endosulfan, endosulfan , Gamma-HCH, dicophore, chlordane, dieldrin, methoxychlor, acetoprole, fipronil, etiprole, pyrafluprole, pyriprole, flufiprolol, brofuranilide, afoxolanel, fluralanel, saloraranel, floxamethamide, acrinatrin, allethrin, d-cis-trans-trans , D-trans allethrin, biphen Thrin, kappa-bifenthrin, bioaresulin S-cyclopentenyl, violesmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta Cypermethrin, zeta-cypermethrin, ciphenothrin, deltamethrin, enpentrin, esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, tau-fulvalinate, halfenprox, imiprotrin, cadresin, permethrin , Phenothrin, praretrin, pyrethrin, resmethrin, silafluophene, tefluthrin, kappa-tefluthrin, phthalthrin Tetramethrin, tralomethrin, transfluthrin, methoxadiazone, methfluthrin, profluthrin, pyrethrum, teraretrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimeflutrin, chloropararesin, epsilon-methfluthrin, epsilon-monflurusline Trifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, suloxafurol, flupiradiflon, triflumezopyrim, dichloromezothiaz, flupirimine, spinosad, spinetoram, abamectin, evelmectin, emirmectin, ecuminbectin Hydroprene, quinoprene, geopheno , Metoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotin, cyhexatin, fenbutane oxide, propargite, tetradiphone, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, sodium bistriflu Ron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Rufenuron, Novallon, Nobiflumuron, Teflubenzuron, Triflumuron, Bistrifluron, Buprofezin, Ciromazine, Chromafenozide, Halofenozide, Methoxyphenozide, Tebutrazide Hydramethylnon, acequinosyl, fluor Lipilim, pyriminostrobin, fluphenoxystrobin, phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, pifluvide, spirodiclofen, spirotetramat, spiromesifen, spiropidion, cyflumethofen, sienopyrafen, flubendiamide, cloben Lantraniprolol, Cyantraniliprole, Cyclaniliprol, Tetaniliprolol, Cyhalodiamide, Quinomethionate, Hexithiazox, Bifenazate, Flufenelim, Pyrifluquinazone, Furometokin, Fluopyram, Fluazaindolizine, Amidoflumet, Cyclopyrazofurol, Thioxazafen, Nicotine , Chloropicrin, sulfuryl fluoride, chlorothie, clofentezin , Diflovidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, aphidopyropen, fluhexaphone, fluenesulfone, bencrothiaz, carsol, insecticidal soap, dimethylhopo, nithiazine, borate, metaaldehyde, ryanodine, sulfuramide , Acinonapyr, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-6- (methylcarbamoyl) phenylyl) -1- (3,5-dichloropyridin-2-yl) -1H-pyrazole- 5-carboxamide, 2- [3- (ethanesulfonyl) pyridin-2-yl] -5- (trifluoromethanesulfonyl) benzoxazole, metalaxyl, metalaxyl M, oxadixyl, oflase, benarax , Benalaxyl-M, Kiraraxil, Offlath, Flaxil, Cyprofuran, Buprimate, Dimethylylmol, Ethymol, Himexazole, Hydroxyisoxazole, Oxathiapiproline, Octyrinone, Oxolinic acid, Benomyl, Thiophanatomethyl, Carbendazim, Fuberidazole, Thiabendazole, Devacarb Zoxamide, ethaboxam, pencyclon, flupicolide, diflumetrim, buprimate, benodanyl, flutolanil, mepronil, isophetamide, fenflam, oxycarboxyl, carboxin, tifluzamide, floxapyroxad, flametopir, penflufen, pentiopyrado, benzovindiflupyr , Sedaxane, impi Fluxam, fluindapyr, isoflucipram, pyrapropoin, boscalid, azoxystrobin, kwmethoxystrobin, cresoximemethyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, methinostrobin, orisatrobin Oxastrobin, pyroxystrobin, pyramethostrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, umoxystrobin, mandestrobin, triclopyricarb, famoxadone, fenamidone, triclopyricarb, pyribencarb, Cyazofamide, Amisulbrom, Vinapacryl, Meptyldinocarb, Dinocup, Fluazinam, Ferimzone, Acetic acid-fentin, Fentin chloride, Hydroxyl hydroxide Yentin, triphenyltin hydroxide, triphenyltin acetate, oxine copper, silthiofam, amethoctrazine, mepanipyrim, nitrapiline, pyrimethanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyphene, proquinazide, Fludioxonil, fenpicuronyl, fluoroimide, procymidone, iprodione, vinclozolin, edifenphos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseicaupte extract, trifolin, pyrifenox, pyrisoxazole, fenarimol, nuarimol, azaconazole, Diniconazole, diniconazole-M, epoxy Nazole, fluquinconazole, oxpoconazole, pefazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimethone, triadimenol, triticonazole, uniconazole, imazalyl, viteltanol, triflumizole , Ethaconazole, propiconazole, penconazole, flusilazole, flutriazole, microbutanyl, paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, acetic acid Dodemorph, tridemorph, fenpropimorph, dimethomorph, fullmorph, pyrimorph, piperari , Fenpropidin, Spiroxamine, Fenhexamide, Fenpyrazamine, Felbum, Metam, Metasulfocarb, Methylam, Tiram, Manzeb, Manneb, Dinebu, Diram, Polycarbamate, Provineb, Thiuram, Pyributicarb, Validamycin, Mildiomycin, Polyoxin, Bench Avaricarb, Bench Avaricarb Isopropyl, Varifenalate, Iprovaricarb, Mandipropamide, Fenpicoxamide, Fusaride, Pyroxylone, Tricyclazole, Carpropamide, Diclocimet, Phenoxanyl, Acibenzoral-S-methyl, Probenazole, Diclobeneazox, Thiazinyl , Isotianil, simoxanyl, fosetyl, teclophthalam, triazoxide, fursulfamide, dichromedin, Ciflufenamide, metolaphenone, pyriophenone, fluthianyl, tebufloquine, fosetyl aluminum, tolcrofos-methyl, eclomezole, tolprocarb, ipfen trifluconazole, mefentrifluconazole, quinofumerine, pidiflumethofene, Bordeaux mixture, copper acetate, basic copper sulfate, Copper oxychloride, cupric hydroxide, copper oxyquinoline, copper, sulfur, captan, captahol, phorpet, anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctadine acetate, iminotadine albe Silates, guanidine, dodin, dodin free base, guazatine, guazatine acetate, albesylate, dithianone, quinomethionate, fluori , Tolylfluoride, dicloflurane, dinobutone, dazomet, pyraziflumide, aminopyrifen, dipimethrone, picalbutrazox, technazen, nitortal-isopropyl, dicyclomet, acibenzoral, prohexadione-calcium, bronopol, diphenylamine, flumetobell, bentoxazine , Biphenyl, chloronebu, CNA, iodocarb, prothiocarb, genus Bacillus, and insecticidal proteins produced by them, bactericidal proteins, insecticidal proteins produced by Bt crops, bactericidal proteins, entomopathogenic bacteria, entomopathogenicity 6. A composition according to claim 5 selected from the group consisting of viruses and entomopathogenic fungi. A composition for protecting animals and birds from harmful parasitic invertebrates comprising a parasitically effective amount of the compound of claim 1 and at least one carrier. A method for controlling a harmful invertebrate, comprising contacting the harmful invertebrate or its environment with a biologically effective amount of the compound of claim 1. A method of treating a crop, wherein the growing seed of the crop, or placenta, is contacted with a biologically effective amount of the compound of claim 1. A seed that has been treated, comprising the compound of claim 1 or a salt thereof in an amount of about 0.0001 to 1% by weight of the seed. Formula (2):

(In the formula, R, R ₁ , R ₂ and A are the same as described above, and X represents a halogen atom.)
A compound represented by
Formula (3):

Wherein R _a , R _b , R _c and R _d are the same as above, and M is a boronyl group, dialkoxyboranyl group, trifluoroborate, trialkylstannyl group or zinc halide. Indicates that.)
The manufacturing method including obtaining by making the compound shown by react.
Formula (4):

(In the formula, R _a , R _b , R _c and R _d are the same as described above, and X represents a halogen atom.)
A compound represented by
Formula (5):

(Wherein R, R ₁ , R ₂ and A are the same as defined above, and M is a boronyl group, dialkoxyboranyl group, trifluoroborate, trialkylstannyl group or zinc halide). Show.)
The manufacturing method including obtaining by making the compound shown by react.