JP2022071005A - Pyrazine compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pyrazine compound capable of showing excellent pest control activity on various pests; and to provide its salt.

SOLUTION: Embodiments of the inventive pyrazine compounds include 2-(2,2,3,3,3-pentafluoropropoxy)-5-(pyridine-4-yl) pyrazine, 2-(3-chloropyridine-4-yl)-5-(2,2,3,3,3-pentafluoropropoxy) pyrazine, 2-((1,1,1,3,3,3-hexafluoropropane-2-yl)oxy)-5-(pyridine-4-yl) pyrazine.

SELECTED DRAWING: None

COPYRIGHT: (C)2022,JPO&INPIT

Description

The present invention relates to a pyrazine compound, a method for producing the same, and a pest control agent containing the pyrazine compound as an active ingredient.

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. Further, Patent Document 2 discloses a quinoxaline compound having a certain 4-pyridyl group as an insecticide. However, no compound having high pest control activity and high practicality has been found.

WO2017 / 06522 WO2015 / 059088

An object of the present invention is to provide a pyrazine compound or a salt thereof, which exhibits better control activity against various pests.

As a result of diligent research, the present inventors have found that a pyrazine compound having a 4-pyridyl group represented by the formula (1) has a 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
独立して１～４個までの置換基Ｒ_４で置換されるピリジル基
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
炭素原子、硫黄原子によりなる５若しくは６員環のアミノ基（ここで、硫黄原子は酸化され、スルフィニル基、スルホニル基でもよい）
Ｎ，Ｎ－ジメチルアセトイミダミド基
１，１，３，３－テトラメチルグアニジニル基
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、直接結合、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
独立して１～４個までの置換基Ｒ_４で置換されるピリジル基
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、直接結合、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＞
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
独立して１～４個までの置換基Ｒ_４で場合により置換されるピリジル基
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、直接結合である、
＜１＞に記載の化合物又はその塩。
＜６＞
＜１＞～＜５＞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。
＜７＞
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。
＜８＞
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、テトラクロラントラニリプロール、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、オキサゾスルフィル、ニコチン、クロロピクリン、フッ化スルフリル、クリロチエ、クロフェンテジン、ジフロビダジン、ロテノン、インドキサカルブ、ピペロニルブトキシド、クロルジメホルム、ピリダリル、アザジラクチン、ベンゾキシメート、アフィドピロペン、フルヘキサホン、フルエンスルホン、ベンクロチアズ、カルゾール、殺虫性石鹸、ジメヒポ、ニチアジン、ホウ酸塩、メタアルデヒド、リアノジン、スルフルラミド、アシノナピル、ベンズピリモキサン、３－ブロモ－Ｎ－（２，４－ジクロロ－６－（メチルカルバモイル）フェニルイル）－１－（３，５－ジクロロピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボキサミド、メタラキシル、メタラキシルM、オキサジキシル、オフラセ、ベナラキシル、ベナラキシル－Ｍ、キララキシル、オフラース、フララキシル、シプロフラン、ブプリメート、ジメチリモール、エチリモール、ヒメキサゾール、ヒドロキシイソキサゾール、オキサチアピプロリン、オクチリノン、オキソリニック酸、ベノミル、チオファネートメチル、カーベンダジム、フベリダゾール、チアベンダゾール、デバカルブ、ジエトフェンカルブ、ゾキサミド、エタボキサム、ペンシクロン、フルオピコリド、フルオピモミド、ジフルメトリム、ブピリメート、ベノダニル、フルトラニル、メプロニル、イソフェタミド、フェンフラム、オキシカルボキシン、カルボキシン、チフルザミド、フルキサピロキサド、フラメトピル、ペンフルフェン、ペンチオピラド、ベンゾビンジフルピル、ビキサフェン、イソピラザム、セダキサン、インピルフルキサム、フルインダピル、イソフルシプラム、ピラプロポイン、ボスカリド、アゾキシストロビン、コウメトキシストロビン、クレソキシムメチル、トリフロキシストロビン、ピコキシストロビン、ピラクロストロビン、ジモキシストロビン、メトミノストロビン、オリサストロビン、フルオキサストロビン、ピラオキシストロビン、ピラメトストロビン、フルフェノキシストロビン、フェナミンストロビン、エノキサストロビン、クモキシストロビン、マンデストロビン、トリクロピリカルブ、ファモキサドン、フェンアミドン、トリクロピリカルブ、ピリベンカルブ、シアゾファミド、アミスルブロム、ビナパクリル、メプチルジノカルブ、ジノカップ、フルアジナム、フェリムゾン、酢酸－フェンチン、塩化フェンチン、水酸化フェンチン、水酸化トリフェニルスズ、酢酸トリフェニルスズ、オキシン銅、シルチオファム、アメトクトラジン、メパニピリム、ニトラピリン、ピリメサニル、シプロジニル、ブラストサイジンＳ、カスガマイシン、カスガマイシン塩酸塩水和物、ストレプトマイシン、オキシテトラサイクリン、キノキシフェン、プロキナジド、フルジオキソニル、フェンピクロニル、フルオロイミド、プロシミドン、イプロジオン、ビンクロゾリン、エジフェンホス、イプロベンホス、ピラゾホス、イソプロチオラン、プロパモカルブ、プロパモカルブ塩酸塩、ゴセイカユプテ抽出物、トリホリン、ピリフェノックス、ピリソキサゾール、フェナリモル、ヌアリモル、アザコナゾール、ブロムコナゾール、ジニコナゾール、ジニコナゾール－Ｍ、エポキシコナゾール、フルキンコナゾール、オキスポコナゾール、ペフラゾエート、ジフェノコナゾール、フェンブコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、ウニコナゾール、イマザリル、ビテルタノール、トリフルミゾール、エタコナゾール、プロピコナゾール、ペンコナゾール、フルシラゾール、フルトリアホール、ミクロブタニル、パクロブトラゾール、プロチオコナゾール、シプロコナゾール、テブコナゾール、ヘキサコナゾール、プロクロラズ、シメコナゾール、イプフェントリフルコナゾール、アルジモルフ、ドデモルフ、酢酸ドデモルフ、トリデモルフ、フェンプロピモルフ、ジメトモルフ、フルモルフ、ピリモルフ、ピペラリン、フェンプロピディン、スピロキサミン、フェンヘキサミド、フェンピラザミン、フェルバム、メタム、メタスルホカルブ、メチラム、チラム、マンゼブ、マンネブ、ジネブ、ジラム、ポリカーバメート、プロビネブ、チウラム、ピリブチカルブ、バリダマイシン、ミルジオマイシン、ポリオキシン、ベンチアバリカルブ、ベンチアバリカルブイソプロピル、バリフェナレート、イプロバリカルブ、マンジプロパミド、フェンピコキサミド、フロリルピコキサミド、フサライド、ピロキロン、トリシクラゾール、カルプロパミド、ジクロシメット、フェノキサニル、アシベンゾラル－Ｓ－メチル、プロベナゾール、ジクロベンチアゾクス、チアジニル、イソチアニル、シモキサニル、ホセチル、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、シフルフェナミド、メトラフェノン、ピリオフェノン、フルチアニル、テブフロキン、イプフルフェノキン、ホセチルアルミニウム、トルクロホス－メチル、エクロメゾール、トルプロカルブ、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、メチルテトラプロール、ピリダクロメチル、ジピメチトロン、ピカルブトラゾクス、テクナゼン、ニトルタール－イソプロピル、ジシクロメット、アシベンゾラル、プロヘキサジオン－カルシウム、ブロノポール、ジフェニルアミン、フルメトベル、ベントキサジン、ビフェニル、クロロネブ、ＣＮＡ、ヨードカルブ、プロチオカルブ、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、＜７＞に記載の組成物。
＜９＞
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。
＜１０＞
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。
＜１１＞
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。
＜１２＞
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。
＜１３＞
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んでなる、製造方法。
＜１４＞
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んでなる、製造方法。 That is, the present invention
<1>
A compound represented by the formula (1) or a salt thereof.

(In equation (1),
R is
Alkyl groups of hydrogen atoms C1 to C6 (here, C1 to C6 alkyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3);
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3);
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
Phenyl group independently substituted with 1 to 5 substituents _R4 Represents a pyridyl group independently substituted with 1 to ₄ substituents R4.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen atom Alkyl group of halogen atom C1 to C6 (Here, C1 to C6 alkyl group is
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenyloxy groups (where C2-C6 alkenyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynyloxy groups (where C2-C6 alkynyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1-C6 alkylthio groups (where C1-C6 alkylthio groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylthio groups (where, the C2-C6 alkenylthio groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylthio group (where, C2-C6 alkynylthio group is
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylsulfinyl groups (where, the C2-C6 alkenylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylsulfinyl groups (where, C2-C6 alkynylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1 to C6 alkylsulfonyl groups (where C1 to C6 alkylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylsulfonyl groups (where, the C2-C6 alkenylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylsulfonyl groups (where the C2-C6 alkynylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group having two substituents of choice A carbon atom, a 5- or 6-membered amino group consisting of a sulfur atom (where the sulfur atom is oxidized and may be a sulfinyl group or a sulfonyl group).
N, N-dimethylacetoimidazole group 1,1,3,3-tetramethylguanidinyl group Independent of hydrogen atom, alkyl group of C1 to C6 which may be substituted with one or more halogen atoms of the same or different. Aminocarbonyl group having two substituents selected in the group Hydrogen atom, C1 to C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, substituted with one or more identical or different halogen atoms. Hydradino group having three substituents independently selected from the C1-C6 acyl group may be the same, or the C1-C6 alkyl group may be substituted with the same or different one or more halogen atoms. Alternatively, a hydrazinocarbonyl group hydrogen atom having three substituents independently selected from the acyl groups of C1 to C6 which may be substituted with one or more different halogen atoms, substituted with the same or different one or more halogen atoms. A hydroxylamino group having two substituents independently selected from an alkyl group of C1 to C6 which may be substituted, and an acyl group of C1 to C6 which may be substituted with the same or different one or more halogen atoms. Represent,
A is a direct bond, O, S, SO, SO ₂ , NR ₃ , NR ₃ C = O or C = ONR ₃
Represents. )
<2>
R is
Alkyl groups of C1 to C6 (where C1 to C6 alkyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
Phenyl group independently substituted with 1 to 5 substituents _R4 Pyridyl group independently substituted with 1 to ₄ substituents R4.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen Atom Alkyl Group of Halogen Atoms C1 to C6 (Here, the C1 to C6 alkyl group may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynyl groups (where the C2-C6 alkynyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkenyloxy groups (where C2-C6 alkenyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynyloxy groups (where C2-C6 alkynyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylthio groups (where C1 to C6 alkylthio groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkenylthio groups (where C2-C6 alkenylthio groups may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkynylthio groups (where C2-C6 alkynylthio groups may be substituted with one or more halogen atoms of the same or different).
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkenylsulfinyl groups (where the C2-C6 alkenylsulfinyl groups may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkynylsulfinyl groups (where C2-C6 alkynylsulfinyl groups may be substituted with one or more identical or different halogen atoms).
C1 to C6 alkylsulfonyl groups (where the C1 to C6 alkylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkenylsulfonyl groups (where the C2-C6 alkenylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynylsulfonyl groups (where the C2-C6 alkynylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group with two substituents selected Aminocarbonyl with two substituents selected independently of the hydrogen atom, the alkyl group of C1-C6 which may be substituted with one or more identical or different halogen atoms. Is the basis and
A is a direct bond, O, S, SO, SO ₂ , NR ₃ , NR ₃ C = O or C = ONR ₃
Is,
The compound according to <1> or a salt thereof.
<3>
R is
Alkyl groups of C1 to C6 (where, the C1 to C6 alkyl groups are one or more halogen atoms that are the same or different, and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
It is a phenyl group that is independently substituted with 1 to 5 substituents _R4 in some cases.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen Atom Alkyl Group of Halogen Atoms C1 to C6 (Here, the C1 to C6 alkyl group may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynyl groups (where the C2-C6 alkynyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylthio groups (where C1 to C6 alkylthio groups may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylsulfonyl groups (where the C1 to C6 alkylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group with two substituents selected Aminocarbonyl with two substituents selected independently of the hydrogen atom, the alkyl group of C1-C6 which may be substituted with one or more identical or different halogen atoms. Is the basis and
A is an oxygen atom,
The compound according to <1> or a salt thereof.
<4>
R is
Alkyl groups of C1 to C6 (where, the C1 to C6 alkyl groups are one or more halogen atoms that are the same or different, and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
It is a phenyl group that is independently substituted with 1 to 5 substituents _R4 in some cases.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen Atom Alkyl Group of Halogen Atoms C1 to C6 (Here, the C1 to C6 alkyl group may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynyl groups (where the C2-C6 alkynyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylthio groups (where C1 to C6 alkylthio groups may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylsulfonyl groups (where the C1 to C6 alkylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group with two substituents selected Aminocarbonyl with two substituents selected independently of the hydrogen atom, the alkyl group of C1-C6 which may be substituted with one or more identical or different halogen atoms. Is the basis and
A is NR ₃ C = O,
The compound according to <1> or a salt thereof.
<5>
R is
Alkyl groups of C1 to C6 (where, the C1 to C6 alkyl groups are one or more halogen atoms that are the same or different, and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
Phenyl group independently substituted with 1 to 5 substituents _R4 A pyridyl group optionally substituted with 1 to ₄ substituents R4.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen atom Alkyl group of halogen atoms C1 to C6 (here, the C1 to C6 alkyl group may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkynyl groups (where the C2-C6 alkynyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylthio groups (where C1 to C6 alkylthio groups may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylsulfonyl groups (where C1 to C6 alkylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group with two substituents selected Aminocarbonyl with two substituents selected independently of the hydrogen atom, the alkyl group of C1-C6 which may be substituted with one or more identical or different halogen atoms. Is the basis and
A is a direct bond,
The compound according to <1> or a salt thereof.
<6>
An insecticidal composition comprising the compounds according to <1> to <5> and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.
<7>
The insecticidal composition according to <1>, further comprising at least one biologically effective compound or agent.
<8>
The at least one biologically effective compound or agent described above is aranicalve, aldicalve, benziocarb, bendiocarb, benfuracarb, buttocarboxym, butoxycarboxym, carballyl, carbofran, carbosulfan, etiophencarb, phenocarb, formethanate, Frathiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamil, Pyrimicalve, Propoxul, Thiodicarb, Thiophanox, Triazamate, Trimethacarb, XMC, Xylylcarb, Mettlecarb, Phenothiocarb, Phenoxycarb, Acefate, Azamethifos, Azinephos-ethyl, Azine Ethoxyphos, cazusaphos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifosmethyl, kumaphos, cyanophos, demeton-S-methyl, diazinone, dichlorvos, dicrotophos, dimethote, dimethylbinphos, EPN, etion, etoplophos, famfur, phenamiphos , Fenitrothion, fenthion, hostizet, heptenophos, imiciaphos, isofenphos, isopropyl = O- (methoxyaminebothiophosphorylsalicylate, isoxathion, malathion, mecarbam, metamidphos, metidathion, mevinphos, chlorpyrifos, naredo, ometoate, oxydimethoneethyl, Parathion, Parathion-Methyl, PAP, Holate, Hosalon, Hosmet, Phosphamiden, Hoxim, Pyrimiphos-Methyl, Prophenofospropetanphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimiphos, Temephos, Telbuphos, Tetrachlorbinphos, Thiometon, triazophos, trichlorfon, bamidione, chlorpyrifos-ethyl, disulphoton, sulprophos, flupyrazophos, fentate, honophos, tribuphos, endosulfan, alpha-endosulfan, gamma-HCH, dichophor, chlorden, allethrin, methoxychlor, acetoplol, fipronyl, ethiprol. Luprol, piriprol, fulfiprol, brofuranilide, afoxolanel, furlalanel, salolalanel, fluxametamid, acrinathrin, allethrin, d-cis-trans allethrin, d-trans Allethrin, Bifenthrin, Kappa-Bifentrin, Bioallethrin S-Cyclopentenyl, Bioresmethrin, Cycloprothrin, Cypermethrin, Beta-Cypermethrin, Cyhalothrin, Lambda-Cihalothrin, Gamma-Cihalothrin, Cypermethrin, Alpha-Cypermethrin, Beta-Cypermethrin, Theta-cypermethrin, zeta-cypermethrin, cypermethrin, deltamethrin, empentrin, esphenvalerate, etofenprox, phenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadestrin , Permethrin, Fenotrin, Praletrin, Piretrin, Allethrin, Cypermethrin, Tefluthrin, Kappa-tefluthrin, Phthalthrin, Tetramethrin, Tralomethrin, Transfluthrin, Metoxadiazone, Metoflutrin, Profluthrin, Pyretram, Terraletrin, Monfluorothrin Methylfluthrin, dimefluthrin, chloropalalethrin, epsilon-methfurthrin, epsilon-monfluosrin, protrifenbut, acetamipride, clothianidin, dinotefuran, imidacloprid, nitempirum, thiacloprid, thiamethoxam, sulfoxaflor, flupyraziflulone Zu, flupyrimin, spinosad, spinnetram, abamectin, ibermectin, emamectin benzoate, milbemectin, repimectin, hydroprene, quinoprene, diophenolan, metoprene, pyriproxyfen, pimetrodin, fronicamid, ethoxazole, diaphenthirone, azocyclotin, cypermethrin, oxidase. , Propargit, Tetradiphon, Chlorphenapir, Tralopyril, DNOC, Bensultap, Cartap, Thiocyclum, Thiosultap, Thiosultap-Sodium, Bistriflulon, Chlorfluazuron, Diflubenzron, Flucycloxron, Fluphenoxron, Hexaflumuron, Luphenuron, Novallon , Noviflumron, Teflubenzron, Triflumron, Bistrifluron, Buprofezin, Cypermethrin, Chromaphenozide, Harofenozide, methoxyphenozide, Tebufenozide, Amitraz, Hi Doramethylnone, acequinosyl, fluaclipirim, pyriminostrobin, fluphenoxystrobin, phenazakin, phenylpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrado, pifrubmid, spirodiclofen, spirotetramate, spiromethifene, spiropidion, siflumethofen Flubendiamide, chloranthraniliprol, cyantraniliprol, cyclaniliprol, tetraniliprol, sihalodiamide, tetrachlorantraniliprol, quinomethionate, hexithiazox, biphenazeto, fluphenerim, pyrifluquinazone, frometkin, fluopyrum, fluazindrinzine , Amidoflumeth, tyclopyrazoflor, thioxazaphen, oxazosulfyl, nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentedin, difluorovidazine, rotenone, indoxacarb, piperonylbutoxide, chlordimeholm, pyridalyl, azadilactin, benzoximate, Afidopyropen, fluhexafone, flubendisulfone, vencrothias, calcole, insecticidal soap, dimehipo, nithiadin, borate, metaaldehyde, ryanodine, sulfurlfuramide, asinonapill, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-) 6- (Methylcarbamoyl) Phenylyl) -1- (3,5-Dichloropyridin-2-yl) -1H-Pyrazole-5-Carboxamide, Metalaxil, Metalaxil M, Oxadixil, Ofurase, Benalaxil, Benalaxil-M, Kiralaxil, Oflars, flaluxil, cyprofuran, buprimate, dimethyrimol, etilimol, himexazole, hydroxyisoxazole, oxathiapiproline, octylinone, oxolinic acid, benomil, thiophanatemethyl, carbendazim, huberidazole, thiabendazole, debacalve, dietofencarb , Fluopimomid, diflumethrim, bupyrimate, benodanyl, flutranyl, mepronil, isofetamide, phenylfuram, oxycarboxyne, carboxin, thyfluzamide, fluxapyroxado, flametopyl, penflufen, penthiopyrado, benzobindiflupill, bixaphen, isopyrazam, sedaxane, impil Fluxam, fluindapyl, isoflusiplum, pyrapropoin, boscalid, azoxystrobin, kowmethoxystrobin, cresoximemethyl, trifloxystrobin, picoxystrobin, pyracrostrobin, dymoxystrobin, metminostrobin, orysustrobin, full Oxastrobin, pyraoxystrobin, pyrametostrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, spumoxystrobin, mandestrobin, triclopyricalve, famoxadon, fenamiden, triclopyricalve, pyribencarb, Siazofamid, amisulbrom, vinapacryl, meptyldinocarb, dinocup, fluazinum, ferimzone, acetate-fentin, fentin chloride, fentin hydroxide, triphenyltin hydroxide, triphenyltin acetate, oxine copper, silthiofam, amethoctrazine, mepanipirim, nitrapyrin, Pyrimesanyl, cyprodinyl, blastidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyphene, proquinazide, fludioxonyl, fenpicronyl, fluoroimide, procymidone, iprodione, binclozoline, edifenphos, iprobenphos, pyrazophos, isoprobenphos Hydrochloride, Gosei Kayupte Extract, Triphorin, Pyriphenox, Pyrisoxazole, Phenalimol, Nuarimol, Azaconazole, Bromconazole, Diniconazole, Diniconazole-M, Epoxyconazole, Flukinconazole, Oxpoconazole, Pefrazoate, Diphenoconazole, Fen Buconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triazimehon, triazimenol, triticonazole, uniconazole, imazalyl, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutorial, microbutanyl. , Paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, phenpropimorph, dimethomorph, flumorph, pilimorph, piperaline , Fenpropidin, spiroxamine, fenhexamide, fenpyrazamine, fervum, metam, metasulfocarb, methylam, tiram, manzeb, manneb, dineb, dilam, polycarbamate, provineb, thiuram, pyribuchicarb, baridamycin, mildiomycin, polyoxin, Bench Avaricarb, Bench Avaricarb Isopropyl, Variphenalate, Iprovaricarb, Mandipropamide, Fempicoxamide, Florylpicoxamide, Fusalide, Pyrochyron, Tricyclazole, Carpropamide, Diclosimet, Phenoxanyl, Acibenzoral-S-methyl, Provenazole, Diclobenazox, thiazinyl, isothianyl, simoxanyl, Josetil, tecrophthalam, triazoxide, flusulfamide, dichromedin, siflufenamide, metrafenone, pyriophenone, fluthianyl, tebuflokin, ipflufenokin, Josetilaluminum, torquelophos-methyl, ecromezol, tolprocarb. Fluconazole, mefentrifluconazole, quinofumerin, pidiflumethofen, Bordeaux mixture, copper acetate, basic copper sulfate, oxychloride copper, cupric hydroxide, oxyquinolin copper, copper, sulfur, captan, captahole, folpet , Anilazine, chlorotalonyl, dichlorophene, pentachlorophenol and its salts, hexachlorobenzene, quintozen, iminoctadine acetate, iminoctadine albesylate, guanidine, copper, dodine free base, guazatin, guazatin acetate, albesylate, dithianone, quinomethionate, Fluolimide, Trillfluanide, Diclofluanide, Zinobuton, Dazomet, Pyraziflumid, Aminopyriphen, Methyltetraprol, Pyridaclomethyl, Dipimethitron, Picalbutrazox, Technazen, Nitortal-isopropyl, Dicyclomet, Acibenzoral, Prohexadione-Calcium , Bronopol, diphenylamine, flumethbel, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, Bacillus, and the insecticidal proteins, bactericidal proteins, bactericidal proteins produced by Bt crops, bactericidal proteins, Selected from the group consisting of entomopathic bacteria, entomopathic viruses and entomopathic fungi, <7 >.
<9>
A composition comprising the compound according to <1> in an amount effective for parasiticide and at least one carrier, which protects animals and birds from harmful parasitic invertebrates.
<10>
A method for controlling a harmful invertebrate by contacting the harmful invertebrate or its environment with a biologically effective amount of the compound according to <1>.
<11>
A method for enhancing the vitality of a crop, wherein a biologically effective amount of the compound according to <1> is brought into contact with the crop, the seed on which the crop grows, or the placenta of the crop.
<12>
The above-mentioned seed which is a treated seed and contains the compound according to <1> in an amount of about 0.0001 to 1% by weight of the seed before the treatment.
<13>
Equation (2):

{In the formula, R, R ₁ , R ₂ and A are the same as above, and X represents a halogen atom. }
With the compound indicated by
Equation (3):

(In the formula, R _a , R _b , R _c and R _d are the same as above, and M is a boronyl group, a dialkoxyboranyl group, a trifluoroborate, a trialkylstanyl group or zinc halide. Indicates that.)
A production method comprising reacting with a compound represented by.
<14>
Equation (4):

(In the formula, R _a , R _b , R _c and R _d are the same as described above, and X indicates a halogen atom.)
With the compound indicated by
Equation (5):

(In the formula, R, R ₁ , R ₂ and A are the same as above, and M is a boronyl group, a dialkoxyboranyl group, a trifluoroborate, a trialkylstanyl group or zinc halide. show.)
A production method comprising reacting with a compound represented by.

The present invention provides a composition comprising the compound of formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. In embodiments, the present invention controls pests containing a compound of formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. The composition is further comprising at least one biologically effective compound or agent.

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

Formula (1) provides a general definition of a compound according to the invention. The range of suitable substituents and / or substituents given in the compound of formula (1) will be specifically described below.
In the definition of the above formula (1), "halo" means "halogen atom", and chlorine atom,
"N-" means normal, "i-" means iso, "s-" means secondary, "c-" means cyclo, and "t-" means tertiary. , "Me" means a methyl group, "Et" means an ethyl group, "Pr" means a propyl group, "Bu" means a butyl group, "Pen" means a pentyl group, and "Ac" means an acetyl group. Further, the numerical range indicated by using "-" indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.

The "C1 to C6 alkyl groups" are, 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, 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 Linear or branched chain such as 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, and the "C2-C6 alkenyl group" is, for example, a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, or 2-. Linear or branched chains such as methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc. , Or a cyclic alkenyl group having 2 to 6 carbon atoms, and the "C2-C6 alkynyl group" is, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, or a 2-butynyl group. , 3-Butynyl group, 3-Methyl-1-propynyl group, 2-Methyl-3-propynyl group, Pentyl group, 1-Hexynyl group, 3-Methyl-1-Butynyl group, 3,3-dimethyl-1-Butynyl A linear or branched chain such as a group, or a cyclic alkynyl group having 2 to 6 carbon atoms is shown.

Examples of the "C1 to 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 and an isopentyloxy group. Tershary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normalhexyloxy group, isohexyloxy group, 1,1,2- Shows a linear or branched chain such as a trimethylpropyloxy group, a cyclopropoxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclopropylmethyloxy group, or a cyclic alkyloxy group having 1 to 6 carbon atoms. As the "C2-C6 alkenyloxy group", 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 and a hexenyloxy group is shown. As the "(C2-C6) alkynyloxy group", 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 and a hexynyloxy group. Is shown.

Examples of the "C1 to 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 normalpentylthio group and an isopenti. Lucio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normalhexylthio group, isohexylthio group, 1,1 , 2-trimethylpropylthio group, cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, cyclopropylmethylthio group and other linear or branched chains, or cyclic alkylthio with 1 to 6 carbon atoms. Examples of the "C1-C6 alkylsulfinyl group" include a methylsulfinyl group, an ethylsulfinyl group, a normalpropylsulfinyl group, an isopropylsulfinyl group, a normalbutylsulfinyl group, a secondary butylsulfinyl group and a tertiarybutylsulfinyl group. Normalpentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normalhexylsulfinyl group, iso Linear or branched chains such as hexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, cyclopropylsulfinyl group, cyclobutylsulfinyl group, cyclopentylsulfinyl group, cyclohexylsulfinyl group, cyclopropylmethylsulfinyl group, or cyclic carbon Shows an alkylsulfinyl group with 1 to 6 atoms,
Examples of the "C1 to 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, normalhexylsulfonyl group, isohexylsulfonyl group, A linear or branched chain such as a 1,1,2-trimethylpropylsulfonyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, a cyclohexylsulfonyl group, a cyclopropylmethylsulfonyl group, or a cyclic carbon atom number 1 to 1 to Shown are 6 alkylsulfonyl groups.

As the "C2-C6 alkenylthio group", for example, a linear or branched alkenylthio group having 2 to 6 carbon atoms such as a propenylthio group, a butenylthio group, a pentenylthio group and a hexenylthio group is shown. As the "C2-C6 alkynylthio group", for example, a linear or branched alkynylthio group having 2 to 6 carbon atoms such as a propynylthio group, a butynylthio group, a pentynylthio group and a hexynylthio group is shown.

As the "C2-C6 alkenyl sulphinyl group", for example, a linear or branched alkenyl sulphinyl group having 2 to 6 carbon atoms such as a propenyl sulphinyl group, a butenyl sulphinyl group, a pentenyl sulphinyl group, and a hexenyl sulphinyl group can be used. As shown above, the "(C2-C6) alkynylsulfinyl group" includes, for example, a linear or branched carbon atom number 2 to 6 such as a propynylsulfinyl group, a butynylsulfinyl group, a pentynylsulfinyl group, and a hexynylsulfinyl group. Shows an alkynylsulfinyl group.

As the "C2-C6 alkenylsulfonyl group", for example, a linear or branched alkenylsulfonyl group having 2 to 6 carbon atoms such as a propenylsulfonyl group, a butenylsulfonyl group, a pentenylsulfonyl group and a hexenylsulfonyl group may be used. As shown above, the "(C2-C6) alkynylsulfonyl group" includes, for example, a linear or branched carbon atom number 2 to 6 such as a propynylsulfonyl group, a butynylsulfonyl group, a pentynylsulfonyl group, and a hexynylsulfonyl group. Shows an alkynylsulfonyl group.

The above-mentioned "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" "Alkenyl sulfinyl group", "C2-C6 alkynyl sulfinyl group", "C2-C6 alkenylsulfonyl group", "C2-C6 alkynylsulfonyl group", "C1-C6 alkyloxy group", "C2-C6 alkenyloxy group", One or two or more halogen atoms may be substituted at substitutable positions of the "C2-C6 alkynyloxy group", and when the number of substituted halogen atoms is two or more, the halogen atoms may be the same or different. ..

Examples of the "5- or 6-membered ring amino group consisting of a carbon atom and a sulfur atom" include a morpholino group, a thiomorpholino group, a thiomorpholino 1-oxide group, and a thiomorpholino 1,1-dioxide group.

を示し、
「１，１，３，３－テトラメチルグアニジニル基」は

を示す。 "N, N-dimethylacetoimidazole group"

Show,
"1,1,3,3-Tetramethylguanidinyl group"

Is shown.

Expressions such as "(C1 to C6)", "(C2 to C6)", and "(C3 to C6)" indicate the range of carbon atoms of various substituents. Further, the above definition can be shown for a group to which the above substituents are linked. For example, in the case of "(C1 to C6) alkyloxy (C1 to C6) alkyl group", the number of carbon atoms is 1 in a straight chain or a branched chain. It is shown that up to 6 alkyloxy groups are bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the salts of the pyrazine compound represented by the formula (1) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates and oxalates. Examples thereof include organic acid salts such as methane sulfonate, benzene sulfonate and paratoluene sulfonate, 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) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more kinds of optical isomers and diastereomers may be present. In some cases, the invention also includes all optical isomers and mixtures containing them in arbitrary proportions. Further, the compound represented by the general formula (1) of the present invention and salts thereof may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula thereof, but the present invention Also includes all geometric isomers and mixtures containing them in arbitrary proportions.

In the pyrazine compound represented by the formula (1) of the present invention or salts thereof, R is preferably an alkyl group of C1 to C6 which may be substituted with one or more halogen atoms of the same or different, or independently. It is a phenyl group substituted with 1 to 5 substituents R ₄ , and R ₁ , R ₂ , R ₄ , R _a , R _b , R _c , and R _d are independently hydrogen atoms or or. Alkyloxy of C1 to C6 which may be substituted with a halogen atom or one or more identical or different halogen atoms, or alkyloxy of C1 to C6 which may be substituted with one or more identical or different halogen atoms. A group or an alkylthio group of C1 to C6 that may be substituted with one or more halogen atoms of the same or different, or an alkylsulfinyl group of C1 to C6 that may be substituted with one or more halogen atoms of the same or different. , Or the alkylsulfonyl groups of C1 to C6 which may be substituted with one or more identical or different halogen atoms, or (C1 which may be substituted with a hydrogen atom or one or more identical or different halogen atoms. Alkyl group of ~ C6, amino group having two substituents independently selected from the acyl group of C1 ~ C6 which may be substituted with the same or different one or more halogen atoms), (hydrogen atom, or An aminocarbonyl group having two substituents independently selected from the alkyl groups C1 to C6 which may be substituted with the same or different one or more halogen atoms), where A is a direct bond, O, S. , SO, SO ₂ , NR ₃ , NR ₃ C = O or C = ONR ₃ .

The pyrazine compound of the present invention or salts thereof can be produced, for example, by the following production method, but the present invention is not limited thereto. Further, the compound represented by the other group (B) is described in Non-Patent Document 1. These compounds can be obtained from commercially available formulations or synthesized by known methods.

Manufacturing method 1
<Scheme 1>

{In the formula, 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, a dialkoxyboranyl group, and trifluoro. It indicates that it is a borate, a trialkylstanyl group or zinc halide, and A ₁ indicates an oxygen atom or a sulfur atom. }

Production method of step a It is represented by the formula (7) 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. Pyrazine compounds can be produced. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26 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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the formula (6).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (6).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 be proceeded without isolation / purification.

Production method of step b The pyrazine compound represented by the formula (7) and the alcohol compound or the thiol compound represented by the formula (8) are reacted in the presence of a base in an inert solvent according to the formula (1a). The pyrazine compound represented can be produced.

Examples of the bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc .; sodium hydride, potassium hydride, etc. Examples thereof include alkoxides such as alkali metals hydride, sodium methoxydo, sodium ethoxydo, and potassium tertiary butoxide. The amount of the base used is usually in the range of about 1 to 5 times the molar amount of the compound represented by the formula (7).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers; 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. , Nitriles such as acetonitrile; esters such as ethyl acetate, polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone and the like. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 the range of about 1 to 5 times mol with respect to the pyrazine compound represented by the formula (7). The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the desired 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>

{In the formula, R, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as above, X indicates a halogen atom, M indicates boronic acid, boronic acid ester, trifluoroboric acid. It indicates that it is a salt, trialkylstanyl or zinc, and A ₁ indicates an oxygen atom or a sulfur atom. }

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

Method for Producing Step c The pyrazine compound represented by the formula (6) and the alcohol compound or the thiol compound represented by the formula (8) are reacted with the formula (2a) in the presence of a base in an inert solvent. The pyrazine compound represented can be produced.

Examples of the bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc .; sodium hydride, potassium hydride, etc. Examples thereof include alkoxides such as alkali metals hydride, sodium methoxydo, sodium ethoxydo, and potassium tertiary butoxide. The amount of the base used is usually in the range of about 1 to 5 times the molar amount of the compound represented by the formula (6).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers; 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. , Nitriles such as acetonitrile; esters such as ethyl acetate, polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone and the like. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 the range of about 1 to 5 times mol with respect to the pyrazine compound represented by the formula (6). The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the desired 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.

Production method of step d It is represented by the formula (1a) 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. Pyrazine compounds can be produced.

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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the general formula (2a).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the general formula (2a).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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>

{In the formula, 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, a dialkoxyboranyl group, and trifluoro. It indicates that it is a borate, a trialkylstanyl group or zinc halide, and A ₁ indicates an oxygen atom or a sulfur atom. }

Further, the compound of the formula (1a) can be produced as shown in Scheme 3.

Production method of step e To produce the pyrazine compound represented by the formula (5) by reacting it with the pyrazine compound represented by the formula (2a) in the presence of diborane or diboron, a metal catalyst, a base and an inert solvent. Can be done.

Examples of the diboran 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). Diboran such as diboron or diboron can be mentioned. The amount of diborane or diborone used in the present invention may be appropriately selected from the range of usually 0.5 times to 5.0 times by mole 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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the formula (2a).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (2a).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 be proceeded without isolation / purification.

<Manufacturing method of process f>
The pyrazine compound represented by the formula (1a) is obtained by reacting the pyrazine compound represented by the formula (5) with the 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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the formula (5).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (5).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 4
<Scheme 4>

{In the formula, 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, a dialkoxyboranyl group, and trifluoro. It indicates that it is a borate, a trialkylstanyl group or zinc halide, A ₁ indicates an oxygen atom or a sulfur atom, D indicates N or CR ₄ , PG indicates a protective group, and PG indicates a protective group. One or two bonds to an amino group. }

Method for Producing Step g The pyrazine compound represented by the formula (9) is formed by reacting the pyrazine compound represented by the formula (8) with the acidified compound or acid anhydride in the presence of a base, a catalyst and an inert solvent. Can be manufactured. The protecting group binds one or two to the amino group.
Examples of the protecting group that can be used in the present invention include an amide-based protecting group reacted with acetyl chloride, anhydrous acetic acid, anhydrous trifluoroacetic acid, etc., benzyl chlorolate, allyl chloroformate, methyl chlorocarbonate, and chloroglycic acid 2,2,2-. Carbamate-based protecting group reacted with trichloroethyl, fluorenylmethylchloroboroate, N- [2- (trimethylsilyl) ethoxycarbonyloxy] succinimide, di-tert-butyl dicarbonate, etc., benzyl chloride, p-methoxybenzyl chloride, etc. Examples thereof include a benzyl-based protecting group reacted with, a sulfonamide-based protecting group reacted with a 2-nitrobenzenesulfonyl group, and the like, but the protecting group that can be used in this reaction is not limited to this. The amount of the acid chloride or acid anhydride to be used may be appropriately selected in the range of about 1-fold molar to 3-fold molar with respect to the compound represented by the formula (8). Examples of the catalyst for reacting acetic anhydride, trifluoroacetic anhydride, di-tert-butyl dicarbonate with the compound of the formula (8) include 4-dimethylaminopyridine and the like, and the amount used thereof is the formula (8). ), Usually, it may be appropriately selected in the range of about 0.1 times mol to 1 times mol. Examples of the base include triethylamine, N, N-diisopropylethylamine, pyridine and the like, and the amount thereof is appropriately in the range of about 1 to 5 times mol with respect to the compound represented by the formula (8). You can select it.

Production method of step h The pyrazine compound represented by the formula (9) and the compound represented by the formula (4) are represented by the formula (10) by reacting in the presence of a metal catalyst, a base and an inert solvent. Pyrazine compounds can be produced. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26 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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the formula (9).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (9).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 be proceeded without isolation / purification.

Production method of step i The pyrazine compound represented by the formula (10) is an acid or a base, or an oxidation of 2,3-dichloro-5,6-dicyano-p-benzoquinone, ammonium hexanitratocerium (IV) or the like. It is represented by the formula (11) by reacting with an agent or an acid and metallic zinc powder or tetrabutylammonium fluoride in the presence of an inert solvent, or by hydrogenating in the presence of a catalyst such as palladium and an inert solvent. A pyrazine compound can be produced.

The reaction temperature in this reaction may be usually in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 24 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 be proceeded without isolation / purification.

Examples of the bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc .; sodium hydride, potassium hydride, etc. Alkoxides such as alkali metals hydride, sodium methoxydo, sodium ethoxydo, and potassium tertiary butoxide; organic bases such as piperidine, pyrrolidine, morpholin, and pyridine can be mentioned. The amount of the base used is usually in the range of about 1 to 5 times the molar amount of the compound represented by the formula (10).

Examples of the acid that can be used in this reaction include hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid and the like. The amount of the acid used is usually in the range of about 1 to 10 times the molar amount of the compound represented by the formula (10).

Examples of the palladium catalyst that can be used in this reaction include palladium, palladium hydroxide and the like. The amount used is usually in the range of about 0.05 times mol to 1 times mol with respect to the compound represented by the formula (10).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers; 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. , Nitriles such as acetonitrile; esters such as ethyl acetate, polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone and the like. , These inert solvents can be used alone or in admixture of two or more.

The compound represented by the production method (11) in step j is a pyrazine compound represented by the formula (10) in step h, in which the amino group of the compound represented by (8) is protected by a protective group in step g. Then, the compound (11) can be synthesized by deprotection in step i, but by reacting the compound represented by (8) with the compound represented by (4) under the same conditions as in step h. , (11) can also be directly produced.

Production method of step k The pyrazine compound represented by the formula (7) is produced by reacting the pyrazine compound represented by the formula (11) in the presence of a diazotizing reagent, a halide, an acid and an inert solvent. Can be done. Depending on the reaction, it is not necessary to add acid. This reaction can be carried out according to the method described in the literature (WO2013 / 053690A1).

Examples of the acid that can be used in this reaction include hydrochloric acid, hydrobromic acid, hydrogen iodide acid, tetrafluoroboric acid, and sulfuric acid. The amount used is usually about 1 times or more the molar amount of the diazotizing reagent, and an acid can also be used as a solvent.

Examples of the halides that can be used in this reaction include hydrochloric acid, hydrobromic acid, hydroiodic acid, bromine, iodine, diiodomethane, copper (I) chloride, copper (I) iodide, and copper (II) iodide. Examples thereof include sodium iodide (I), potassium iodide (I), cesium iodide (I), copper bromide (II), and tetrafluoroboric acid. The amount used is usually in the range of about 1 to 5 times mol with respect to the compound represented by the formula (11).

Examples of the diazotizing reagent that can be used in this reaction include sodium nitrite, isoamyl nitrite, tert-butyl nitrite and the like. The amount used is usually in the range of about 1 to 5 times mol with respect to the compound represented by the formula (11).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers; 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. , Nitriles such as acetonitrile; esters such as ethyl acetate, polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone and the like. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .. The reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the desired 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.

Production method of step l The pyrazine compound represented by the formula (7) and the compound represented by the formula (12) are reacted in the presence of a metal catalyst, a base and an inert solvent to be represented by the formula (13). Pyrazine compounds can be produced. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26 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, [1,1'-bis (diphenylphosphino) butane] Palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) and other zero-valent palladium compounds , Palladium acetate (II), Palladium chloride (II), Bis (acetase) Palladium (II) dichloride, Bis (benzonitrile) palladium (II) dichloride, Allylpalladium (II) chloride dimer, Cyclopentadienylallylpalladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as needed. The amount of the palladium catalyst used in the present invention may be appropriately selected in the range of about 0.001 times mol to 0.1 times mol with respect to the compound represented by the formula (7).

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (7).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The reaction temperature in this reaction may be usually in the range of 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 be proceeded without isolation / purification.
Manufacturing method 5
<Scheme 5>

Production method of step m H- in which the Ra part of the compound represented by the formula (10) or (11) is _a halogen atom (10-a) or (11-a) and has a hydroxyl group, an amino group or a mercapto group. The pyrazine compound represented by the formula (10) or the formula (11) can be produced by reacting with Ra in the presence of _a base and an inert solvent.

Bases that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and potassium hydrogencarbonate. , Calcium carbonate, carbonates such as magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, alcoholite such as potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picolin, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base used may be appropriately selected from the range of 0.5 times mol to 5.0 times mol with respect to the compound represented by the formula (10-a) or the formula (11-a).

The inert solvent that can be used in this reaction may be any solvent as long as it does not significantly inhibit this reaction. For example, alcohols such as water, methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran, dioxane and the like. Chain or cyclic ethers, 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. Examples include nitriles such as acetonitrile, esters such as ethyl acetate, and polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone. , These inert solvents can be used alone or in admixture of two or more.

The present invention provides a composition comprising the compound of formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. In embodiments, the present invention controls pests containing a compound of formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. The composition may further comprise at least one biologically effective compound or agent.

The compound represented by the formula (1) exhibits excellent control activity against agricultural and horticultural pests, as shown in the following examples. Therefore, according to the present invention, there is provided a pest control agent containing the compound represented by the formula (1) or a salt thereof as an active ingredient. Further, the pest control agent according to the present invention may contain an acid addition salt of these compounds as an active ingredient, which is acceptable for horticulture.
Specific examples of the acid addition salt include inorganic acids such as hydrochloride, sulfate, nitrate, and phosphate, formate, acetate, oxalate, citrate, succinate, and maleate. , Fumarate, tartrate, lactate, benzoate, phthalate, and other carboxylates, mesylate, tosilate, benzenesulfonate, and other sulfonates, and the like.

The insect species to be controlled in the present invention (insect species in which the compound represented by the formula (1) exhibits a control effect) are not particularly limited, and can be used for controlling harmful pests in a wide range of agriculture and horticulture. can. Preferred insect control target insect species include, for example, the following. Lepidoptera {eg, Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten Omeiga (Scirpophaga incertulas), Rupela albina, Cobnomeiga (Cnaphalocrocis) , Ineha Casino Meiga (Marasmia exigua), Watanomeiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Hymadalanomeiga (Hellula undalis), Monkikuronomeiga (Herpetogramma) ), Rice case worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis) and other Pyraloid moths (Crambidae); litura), Shiroichimojiyoto (Spodoptera exigua), Awayoto (Mythimna separata), Yotoga (Mamestra brassicae), Ineyoto (Sesamia inferens), Shironayoto (Spodoptera mauritia), Futaobikoyaga (Naranga aenesc) Yoto (Spodoptera exempta), Pyraloid moth (Agrotis ipsilon), Pyraloid moth (Autographa nigrisigna), Pyraloid moth (Plusia festucae), Soybean looper (Chrysodeixis includens), Tricoprusia (Trichoplu) sia spp.), Heliothis spp. Such as Helliothis virescens, Helicoverpa armigera, Helicoverpa zea and other Helicoverpa spp., Velvetbean caterpillar (Anticarsia gemmata) , Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc., Noctuidae; Monshirocho (Pieris rapae), etc. , Leguminivora glycinivorella, Azukivoreses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Chahamaki (Homona magnanima), Chahamaki (Homona magnanima) Pomonella, Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), Tortrix moth (Tortricidae); Gracillariidae); Carposinidae such as Carposina sasakii; Coffee Leaf miner (Leucoptera coffeella), Lyonetia clerkella, Lyonetia prunifoliella, etc. Lymantriidae such as moth (Lymantria dispar), Euproctis spp. Such as Chadokuga (Euproctis pseudoconspersa); Lymantriidae such as Konaga (Plutella xylostella); Pluteliidae such as Konaga (Plutella xylostella) ); Momokibaga (Anarsia lineatella), Imokibaga (Helcystogramma triannulella), Watakamimushiga (Pectinophora gossypiella), Potato moth (Phthorimaea operculella), Tuta absoluta, etc. Castniidae such as Giant Sugarcane borer (Telchin licus); Cossidae such as Cossus insularis; Geometridae such as Ascotis selenaria; Lymacodidae, etc .; Lymantria masinissa, etc., Lymantria disparata (Stathmopodidae); Acherontia lachesis, etc., Sphingidae; Nokona feralis, etc. (Hesperiidae) such as (Parnara guttata)}. Hemiptera {For example, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Javesella pellucida Aphidaceae (Delphacidae) such as orizicolus; Tsumaguro Yokobai (Nephotettix cincticeps), Taiwan Tsumaguro Yokobai (Nephotettix virescens), Cross Jitsumaguro Yokobai (Nephotettix nigropictus), Inazuma Yokobai (Recilia dorsalis) Empoasca fabae), corn leaf hopper (Dalbulus maidis), white aphid (Cofana spectra), etc. (Cicadellidae); Mahanarva posticata, Mahanarva fimbriolata, etc. Aphis glycines, Wata aphids (Aphis gossypii), European apple aphids (Aphis pomi), Yukiyanagi aphids (Aphis spiraecola), Momoka aphids (Myzus persicae), Wheat aphids (Brachycaudus) ), Rosy apple aphid (Dysaphis plantaginea), fake aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisgri) hum padi), stink bug (Rhopalosiphum maidis), stink bug (Toxoptera citricida), stink bug (Hyalopterus pruni), stink bug (Melanaphis sacchari), stink bug (Tetraneura nigriabdominalis) , Aphididae such as Eriosoma lanigerum; Daktulosphaira vitifoliae, Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf Family (Phylloxeridae); Adelgidae (Adelgidae) such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae; Scotinophara lurida, Malayan rice black bug (Scotin) Stink bug (Nezara antennata), stink bug (Eysarcoris aeneus), stink bug (Eysarcoris lewisi), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris aneneus) Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus and other stink bugs (Pentatomidae); Burrower brown bug (Scaptoc) Oris castanea) and other scale insects (Cydnidae); scale insects (Riptortus pedestris), spider scale insects (Leptocorisa chinensis), scale insects (Leptocorisa acuta) and other scale insects (Alydidae) Punctiger), scale insects such as Leptoglossus australis (Coreidae); scale insects (Caverelius saccharivorus), scale insects (Togo hemipterus), American scale insects (Blissus) (Lygaeidae); scale insects (Trigonotylus caelestialium), scale insects (Stenotus rubrovittatus), scale insects (Stenodema calcarata), scale insects (Lygus lineolaris), etc. , Tobacco scale insect (Bemisia tabaci), Mikankonajirami (Dialeurodes citri), Mikantogekonajirami (Aleurocanthus spiniferus), Chatgekonajirami (Aleurocanthus camelliae), Hisakakiwatafukikonajirami (Pealius euryae) (Abgrallaspis cyanophylli), red scale insect (Aonidiella aurantii), scale insect (Diaspidiotus perniciosus), scale insect (Pseudaulacaspis pentagona), scale insect (Unaspis yanonensis), scale insect (Unaspis yanonensis) Diaspididae); Ceroplastes rubens and other scale insects (Coccidae); Scale insects (Icerya purchasi), scale insects (Icerya seychellarum) and other scale insects (Margarodidae); Scale insects (Pseudococcus comstocki), scale insects (Planococcus citri), scale insects (Pseudococcus calceolariae), scale insects (Pseudococcus longispinus), tuttle scale insects (Brevennia rehi) Diaphorina citri), scale insect (Trioza erytreae), scale insect (Cacopsylla pyrisuga), scale insect (Cacopsylla chinensis), scale insect (Bactericera cockerelli), scale insect (Bactericera cockerelli), Pear psylla (Cacops) (Corythucha ciliata), Awadachisougunbai (Corythucha marmorata), Nashigunbai (Stephanitis nashi), Tsutsujigunbai (Stephanitis pyrioides), etc. Scale family (Cicadidae). Coleoptera {For example, Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), banded cue. Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Oulema melanopus, Urihamushi (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta) , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa decemlineata), Inedro oyster (Oulema oryzae), Grape Coraspis (Colaspis brunnea) Beetle beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), beetle beetle (Dicladispa armigera), south corn leaf beetle (Myochrous denticollis), beetle beetle (Laccoptera quadrimaculata)
Chrysomelidae such as ipennis; Carabidae such as Seedcorn beetle (Stenolophus lecontei) and Slender seedcorn beetle (Clivina impressifrons); Phylophylla picea, European Chafer (Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., Phyllophaga crinita, etc. , Diloboderus abderus and other Diloboderus genus (Diloboderus spp.) And other beetles (Scarabaeidae); Ground beetle (Sitophilus zeamais), ground beetle (Echinocnemus squameus), ground beetle (Lissorhoptrus oryzophilus), ground beetle (Rhabdoscelus lineatocollis), cotton ground beetle (Anthonomus calle) Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Scepticus griseus, Scepticus uniformis , Brazilian click beetle (Zabrotes subfasciatus), click beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus mourei, etc. Click beetles (Tribolium castaneum), Click beetles (Tribolium confusum) and other click beetles (Tenebrionidae); Bostrychidae); Curculionidae (Ptinidae); Coleoptera (Anoplophora malasiaca), Migdolus fryanus, etc. (Cerambycidae); Click beetles (Melanotus okinawensis) , Click beetles (Anchastus spp.), Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp. Click beetles (Staphylinidae) such as Aoba arigata click beetles (Paederus fuscipes)}. Thrips palmi (Thysanoptera) {For example, Thrips palmi (Frankliniella occidentalis), Thrips palmi, Thrips palmi, Thrips palmi (Scirtothrips dorsalis), Thrips thrips (Thrips tabi) Thripidae (Thripidae) such as Stenchaetothrips biformis), Thrips palmi Karny (Echinothrips americanus); Thripidae (Phlaeothripidae) such as Haplothrips aculeatus}. Diptera {For example, Anthomyiidae such as Delia platura and Delia antiqua; Agromyzidae such as Tetanops myopaeformis; Agromyzidae (Ulidiidae); ), Tomato leafminer (Liriomyza sativae), leafminer (Liriomyza trifolii), leafminer (Chromatomyia horticola) and other leafminers (Agromyzidae); Bactrocera dorsalis), Nasumi fly (Bactrocera latifrons), Olive mibae (Bactrocera oleae), Quisland mibae (Bactrocera tryoni), Chichukai mibae (Ceratitis capitata), etc. Fly (Hydrellia philippina), Agromyzidae (Hydrellia sasakii) and other leafminers (Ephydridae); Agromyzidae (Drosophila suzukii) and other leafminers; Agromyzidae such as (Clogmia albipunctata); Agromyzidae such as Bradysia difformis; Agromyzidae (Mayetiola destructor), Agromyzidae (Orseolia oryzae) and other leafminers (Cecidomyidae) Agromyzidae (Diopsidae); Agromyzidae (Tipula aino), Common cranefly (Tipula oleracea), Eur Crane fly (Tipulidae) such as opean cranefly (Tipula paludosa)}. Hymenoptera {For example, Tenthredinidae such as Athalia rosae and Athalia japonica; Fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara), etc. The ant family (Formicidae), etc.}. Orthoptera {eg, Locusta migratoria, Morocco locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Locust (Nomadacris septemfasciata), Brown Locust (Locustana par) ), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Military grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pelluc) (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Kobane locust (Oxya yezoensis), Hanena locust (Oxya japonica), Taiwan locust (Patanga locust) (Gryllotalpa orientalis) and other Orthoptera (Gryllotalpidae); European locusts (Acheta domestica), Emma locusts (Teleogryllus emma) and other Orthoptera (Gryllidae); Mormon cricket (Anabrus simplex) and other grasshoppers (Tettigoniidae). Termite pests (Blattodea) {For example, termites (Blattella germanica) and other termites (Blattellidae); termites (Periplaneta fuliginosa), termites (Periplaneta americana), termites (Periplaneta brunnea), termites (Periplaneta brunnea), termites (Periplaneta brunnea) Termites (Blattidae) such as Yamato termites (Periplaneta japonica) and Kowamon termites (Periplaneta australasiae); Termites (Odontotermes formosanus), Koshun termites (Neotermes koshunensis), termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Katan termites (Glyptotermes fuscus), termites (Glyptotermes fuscus), termites (Glyptotermes fuscus) Termites (Reticulitermes amamianus), Miyatake termites (Reticulitermes miyatakei), Kanmon termites (Reticulitermes kanmonensis), Takasago termites (Nasutitermes takasagoensis), Nitobe termites (Pericapritermes nitobei), termites (Pericapritermes nitobei), termites (Pericapritermes nitobei) )}. Mite pests (Acari) {For example, Nami spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Mitsuyubi Nami spider mite (Tetranychus evansi), Panonychus citri, Panonychus citri, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi Family (Tetranychidae); Panonychus pelekassi (Aculops pelekassi), Ryukyu Mikansabi tick (Phyllocoptruta citri), Tomato sabi tick (Aculops lycopersici), Chanosabi tick (Calacarus carinatus), Chanonaga sabi tick (Acaphylla theavans) Panonychus ulnaris (Aculus schlechtendali), Aceria diospyri, Aceria tosichella, Shevtchenkella sp. Tenuipalpidae; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, Dermacentor taiwanensis, Dermacentor variis Spider mite (Ixodes persulcatus), black legd tick (Ixodes scapularis), American Kirara tick (Amblyomma americanum), boophilus microplus, Kuriirokoita tick (Rhipicephalus sanguineus) and other ticks (Ixodidae); ae), Dust mite (Tyrophagus similis) and other house dust mites (Acaridae); Dermatophagoides farinae, Dermatophagoides pteronyssinus and other house dust mites (Pyroglyphidae); Cheyletidae (Cheyletus moorei), Cheyletidae (Cheyletiella yasguri) and other itch mite (Cheyletidae); Demodicidae); Cheyletidae (Listrophoridae); House dust mites (Haplochthoniidae); House dust mites (Ornithonyssus bacoti), Dust mites (Ornithonyssus sylviarum) and other house dust mites (Macronyssidae); (Leptotrombidium akamushi), etc. Cheyletidae (Trombiculidae), etc.}. Plant-parasitic nematodes {for example, Aphelenchoides besseyi, 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), tensai cyst nematode (Heterodera schachtii) C. elegans (Meloidogyne arenaria), C. elegans (Meloidogyne hapla), C. elegans (Meloidogyne incognita), C. drenatus), C. elegans (Pratylenchus loosi), C. elegans (Pratylenchus neglectus), C. elegans (Pratylenchus penetrans), C. elegans (Pratylenchus vulnus), C. C. elegans (Tylenchida)} such as Radopholus similis).

In the present invention, the insect species to be controlled (the insect species in which the compound represented by the formula (1) exhibits a control effect) are further harmful to sanitary pests, shell pests, clothing pests, house pests, parasites and the like. It can also be used to control living things. In particular, it has an excellent control effect against ectoparasites that are harmful to humans and beasts. The ectoparasites to be controlled include those that parasitize the back, armpits, lower abdomen, inner crotch, etc. of the host animal and inhabit by obtaining nutrient sources such as blood and fluff from animals and birds, and host animals. It includes those that fly to the back and hips of animals and obtain nutrient sources such as blood and fluff from animals and birds. Examples of ectoparasites include mites, lice and fleas.

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

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

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

When the compound represented by the formula (1) is used as an insecticide for agriculture and gardening, the compound represented by the formula (1) may be used as it is, but an appropriate solid carrier, liquid carrier, gaseous carrier or the like may be used as an interface. A pesticide preparation may be prepared and used by mixing it with an activator, a dispersant, other pharmaceutical aids, and the like. The pesticide preparation is preferably an emulsion, an EW agent, a liquid agent, a suspension agent, a wettable powder, a granule wettable powder, a powder, a DL powder, a powder or granule, a granule, a tablet, an oil, an aerosol, a flowable agent, or a dry agent. Flowable agents, microcapsules, etc. can be mentioned. It can be used as a dosage form arbitrarily selected as these pesticide preparations. The carrier in the present invention refers to a solid carrier, a liquid carrier, a gaseous carrier, or the like.

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

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

When the compound represented by the formula (1) is used as an acaricide for controlling mites parasitizing livestock such as cows and pigs, and pet animals such as dogs and cats, it is applied to 1 kg of host animals. , The active ingredient can be used in an amount of 0.01-1000 mg.
The control acaricide can be applied by known veterinary techniques. As a method for that, for example, for the purpose of systemic suppression, a method of administering to an animal by tablets, capsules, immersion liquid, feed mixture, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). For the purpose of non-systemic suppression, a method of spraying an oily or aqueous liquid agent by spraying, pouring (pour-on), dropping (spot-on), etc., or kneading an acaricide on the resin. Examples thereof include a method of injecting, forming the kneaded material into an appropriate shape such as a collar and an ear tag, and attaching the kneaded material to an animal.

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

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

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

The compound represented by the formula (1) of the present invention or an acid addition salt thereof which is acceptable for horticultural and veterinary medicine can be applied to a plant, soil or animal in an effective amount thereof to obtain a pest of interest. 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 also includes a method in which the compound represented by the formula (1) or an acid addition salt thereof which is acceptable for horticulture is applied by smoke treatment in a closed space.
The compound represented by the formula (1) of the present invention or an horticulturally acceptable acid addition salt thereof is also treated or treated in a biologically effective amount on the crop, the seed on which the crop grows, or the fetal position of the crop. By being in contact, it enhances the vitality of the crop.
When the target of the treatment or contact is a seed, the amount of the compound represented by the formula (1) of the present invention or an acid addition salt thereof which is acceptable for agriculture and horizons is not limited, but about 0. It is preferable that the compound represented by the formula (1) of the present invention or an acid addition salt thereof which is acceptable for agriculture and horizons is contained in an amount of 0001 to about 1% by mass.
The present invention further provides the 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 effective for parasites and does not harm the target animals / birds. In the above use, the compound represented by the formula (1) of the present invention or an acid addition salt thereof is contacted with a harmful invertebrate or a growing environment thereof in a biologically effective amount to control the harmful inverteous organism.

Next, specific examples of the compound of the present invention are shown below. In the table below, 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, and c- Pent represents a cyclopentyl group.

In formula (A-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (A-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (A-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, 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 the combinations shown in Table 1. Compound.

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

In the formula (A-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (A-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (A-1), the compound of the present invention in which 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 shown in Table 1.

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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (A-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

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

In the formula (A-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (A-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (B-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (B-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (B-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (B-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (B-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (B-1), the compound of the present invention in which 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (B-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (B-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (B-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (B-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (C-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (C-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (C-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (C-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (C-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (C-1), the compound of the present invention in which 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (C-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (C-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (C-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (C-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (D-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (D-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (D-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (D-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (D-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (D-1), the compound of the present invention in which 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (D-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (D-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (D-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (D-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (E-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (E-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (E-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (E-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (E-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (E-1), the compound of the present invention in which 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (E-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

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

In the formula (E-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (E-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (F-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (F-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (F-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (F-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (F-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (F-1), the compound of the present invention in which 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 shown in Table 1.

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 the combinations shown in Table 1. The compound of the present invention.

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

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

In the formula (F-1), 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 the combinations shown in Table 1.

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

The compound of the present invention in formula (F-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

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

In the formula (F-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (F-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1 in the formula (G-1). {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (G-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (G-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (G-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (G-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (G-1), the compound of the present invention in which 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 shown in Table 1.

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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (G-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (G-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (G-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (G-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (H-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (H-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (H-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (H-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (H-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (H-1), the compound of the present invention in which 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 shown in Table 1.

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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (H-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (H-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (H-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (H-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (I-1), wherein R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

The compound of the present invention in formula (I-1), wherein R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

The compound of the present invention in formula (I-1), wherein R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (I-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (I-1), the compound of the present invention in which 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 the combinations shown in Table 1.

The compound of the present invention in formula (I-1), wherein 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (I-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (I-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (I-1), wherein R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (I-1), wherein R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In formula (J-1), the compound of the present invention in which R is CF ₃ CF ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (J-1), the compound of the present invention in which R is CF ₃ CH ₂ CH _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (J-1), the compound of the present invention in which R is CF ₃ CH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the present invention, in 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 the combinations shown in Table 1. Compound.

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

In the formula (J-1), the compound of the present invention in which 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 shown in Table 1.

In the formula (J-1), the compound of the present invention in which 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 the combinations shown in Table 1.

In the formula (J-1), the compound of the present invention in which 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 shown in Table 1.

In 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 the combinations shown in Table 1. The compound of the present invention.

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

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

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

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

The compound of the present invention in formula (J-1), wherein R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in formula (J-1), wherein R is 4-PhOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (J-1), the compound of the present invention in which R is 4-CF ₃ PhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

In the formula (J-1), the compound of the present invention in which R is 4-CF ₃ OPhCH _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compound of the present invention in which R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1 in the formula (K-1). {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

The compound of the present invention in which R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1 in the formula (L-1). {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

The compound of the present invention in which R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1 in the formula (M-1). {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (N-1), the compound of the present invention in which R is CF _3- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (N-1), the compound of the present invention in which R is CF ₃ CF _2- and R ₁ , R ₂ , R _a , R _b , _RC and R _d are the combinations shown in Table 1. {In the equation, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as described above. }

In the formula (N-1), the compound of the present invention in which R is CF ₃ CF ₂ CF _2- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are the combinations shown in Table 1.

The compounds of the present invention can exist as one or more conformers due to the restriction of bond rotation caused by steric hindrance. For example, a compound of formula (1) in which the 4-pyridyl group is replaced with a bulky alkyl group (eg, isopropyl) at the ortho position has two types due to limited rotation to the 4-pyridyl group-pyrazinium ring bond. It can exist as a rotational isomer. The present invention comprises a mixture of conformers.

<Synthesis Example>
Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. In the NMR data, "s" is a singlet (single line), "d" is a doublet (double line), "t" is a triplet (triple line), "q" is a quartet (quartet), and "quin" is a quintet. (Five-line), "sext" indicates a sextet (six-fold line), "sep" indicates a septet (septet), and "m" indicates a multiplet (multiplet).

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) in dimethylformamide (2,2,3,3,3-pentafluoropropoxy) It was dissolved in 75 ml), and 2,2,3,3,3-pentafluoropropane-1-ol (3.78 g, 25.19 mmol) was added at room temperature. Then, sodium hydride (1.09 g, 24.98 mmol) was added at 0 ° C., and the mixture was stirred overnight at room temperature. Water was added, the mixture was extracted twice with ethyl acetate, and washed three times with saturated brine. The extracted ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered, and then the ethyl acetate was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography and 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (6.09 g, 94.4%, pale 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 produced 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.57 g, 1.86 mmol) was dissolved in dioxane (60 ml), nitrogen-conditioned, and bis at room temperature. (Triphenylphosphine) Pyrazine (II) dichloride (0.13 g, 0.19 mmol) was added, and the temperature was raised to 60 ° C. Then, 4-pyridylboronic acid (0.27 g, 2.2 mmol) and 2M-sodium hydrogen carbonate aqueous 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 filtration aid to remove solid matter. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to 2- (2,2,3,3,3-pentafluoropropoxy) -5- (pyridin-4-yl) pyrazine (0.39 g, 68.8). %, White solid) was obtained.
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-1,3,2-dioxabolan-2-yl) ) Preparation of pyrazine Dioxane (55 ml) of 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (3.74 g, 12.18 mmol) produced in Synthesis Example 1-1 was added. Dissolved in nitrogen atmosphere, bis (pinacolato) diboron (3.10 g, 12.21 mmol), bis (triphenylphosphine) palladium (II) dichloride (0.50 g, 0.61 mmol), potassium acetate (3) at room temperature. .59 g, 36.58 mmol) were sequentially added, the temperature was raised, and the mixture was stirred under reflux conditions for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered using a filtration aid to remove solids. The filtrate was distilled off under reduced pressure using an evaporator. The obtained crude product 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3,2-dioxabolan-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 Iodipyrazine (0.57 g, 2.381 mmol) is dissolved in dioxane (45 ml), and bis (triphenylphosphine) palladium (II) dichloride (0.17 g, 0.24 mmol) is added at room temperature under a nitrogen atmosphere. The temperature was raised to 60 ° C. Then, 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3) produced in Synthesis Example 2-1 at 60 ° C. , 2Dioxabolan-2-yl) pyrazine (1.1 g, 1.2 mmol) and 2M-sodium hydrogen carbonate aqueous solution (6 ml) were sequentially added, and the mixture was stirred for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and water and filtered using a filtration aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to 2- (3-chloropyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.39 g, 91.6%, brown oil) was obtained.
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 2,5-dibromopyrazine (0.50 g, 2.102 mmol) is dissolved in dioxane (50 ml) under a nitrogen 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. Then, 4-pyridylboronic acid (0.26 g, 2.1 mmol) and a 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, the mixture was diluted with ethyl acetate and water and filtered using a filtration aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and then the filtrate was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain 2-bromo-5- (pyridin-4-yl) pyrazine (0.11 g, 22.2%, pale yellow solid).
¹ H NMR (CDCl ₃ ) δ8.86 (1H, d, J = 1.2Hz), 8.83-8.74 (3H, m), 7.90 (2H, dd, J = 4.5Hz, 1.8Hz)

Synthesis Example 3-2: 2-((1,1,1,3,3,3-hexafluoropropane-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) produced in Synthesis Example 3-1 was dissolved in dimethylformamide (2 ml) and 1,1 at room temperature. , 1,3,3,3-hexafluoropropane-2-ol (0.83 g, 0.4939 mmol), potassium carbonate (0.11 g, 0.82 mmol), 18-crown-6-ether (catalytic amount) They were added sequentially and stirred overnight at room temperature. Water was added, the mixture was extracted twice with ethyl acetate, and washed three times with saturated brine. The extracted ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered, and then the ethyl acetate was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to 2-((1,1,1,3,3,3-hexafluoropropane-2-yl) oxy) -5- (pyridin-4-yl). Pyrazine (0.66 g, 50.2%, light brown solid) was obtained.
¹ H NMR (CDCl ₃ ) δ8.78 (1H, s), 8.76 (1H, s), 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)

Synthesis Example 4-1: tert-butyl N- (5-bromopyrazine-2-yl) -N-[(2-methylpropan-2-yl) oxycarbonyl)] Preparation of carbamate 2-amino-5-bromo Pyrazine (5.00 g, 28.74 mmol), N, N-diisopropylethylamine (14.6 mL, 85.86 mmol) and 4-dimethylaminopyridine (3.51 g, 28.73 mmol) were dissolved in tetrahydrofuran (50 mL). Di-tert-butyl dicarbonate (13.22 g, 60.57 mmol) was added slowly so as not to foam violently. After stirring at room temperature for 2 hours, water was added, the mixture was extracted twice with ethyl acetate, and magnesium sulfate was added for dehydration. Magnesium sulfide was removed by suction filtration and concentrated under reduced pressure to obtain a brown solid composition, which was purified by silica gel chromatography to give the title compound. (7.60 g, yield 70.7%, white individual)
¹ H NMR (CDCl ₃ ) δ 8.54 (1H, s), 8.36 (1H, s), 1.46 (18H, s)

Synthesis Example 4-2: tert-butyl N- (5- (3-fluoropyridin-4-yl) pyrazine-2-yl) -N-[(2-methylpropan-2-yl) oxycarbonyl)] carbamate Adjustment of tert-butyl N- (5-bromopyrazine-2-yl) -N-[(2-methylpropan-2-yl) oxycarbonyl)] carbamate (3.00 g, 8.02 mmol), 3-fluoro- 4-Pyridineboronic acid pinacol ester (2.15 g, 9.64 mmol) is dissolved in 1,4-dioxane (60 mL), potassium carbonate (3.32 g, 24.02 mmol) is added thereto, and the inside of the reactor is nitrogen. Replaced with gas. [1,1'-Bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (0.65 g, 0.80 mmol) was added thereto, and the mixture was stirred under heating under reflux for 5 hours. After allowing to cool, water and ethyl acetate were added in appropriate amounts, and suction filtration was performed using cerite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain the title compound (1.08 g, yield 34.5%, light brown solid).
¹ H NMR (CDCl ₃ ) δ 9.05 (1H, s), 8.77 (1H, d, J = 1.2Hz), 8.64 (1H, d, J = 2.7Hz), 8.58 (1H, d, J = 4.8Hz) , 8.05 (1H, t, J = 5.7Hz), 1.50 (18H, s)

Synthesis Example 4-3: Preparation of 5- (3-fluoropyridin-4-yl) pyrazine-2-amine tert-butyl N- (5- (3-fluoropyridin-4-yl) pyrazine-2-yl) -N-[(2-Methylpropan-2-yl) oxycarbonyl)] carbamate (3.12 g, 7.9 mmol) was dissolved in methanol (50 mL), and with stirring, concentrated hydrochloric acid (25 mL was added and at 50 ° C.). The mixture was stirred for 2 hours. After allowing to cool, an aqueous solution of sodium hydroxide was added to the reaction product to make it basic, and methanol was removed by concentration under reduced pressure. The obtained aqueous layer was extracted 3 times with ethyl acetate to remove the aqueous layer. Magnesium sulfate was added to dehydrate the organic layer. Magnesium sulfide was removed by suction filtration and concentrated under reduced pressure to give the title compound (1.39 g, yield 91.5%, light brown solid).
¹ H NMR (CDCl ₃ ) δ 8.68 (1H, s), 8.54 (1H, d, J = 3.0Hz), 8.48 (1H, d, J = 4.8Hz), 8.12 (1H, s), 7.95 (1H, t, J = 5.7Hz), 4.83 (2H, s)

Synthesis Example 4-4: Preparation of 5- [3- (ethylthio) pyridine-4-yl] pyrazine-2-amine Add ethanethiol (1.12 mL, 15.14 mmol) to N, N-dimethylformamide (13 mL). In addition, sodium hydride (0.70 g, 55%, 16.04 mmol) was added under cooling in an ice bath, and the mixture was stirred at the same temperature for 30 minutes. 5- (3-Fluoropyridin-4-yl) pyrazine-2-amine (1.39 g, 7.309 mmol) dissolved in N, N-dimethylformamide (13 mL) was added thereto, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added, the mixture was extracted twice with ethyl acetate, washed with saturated brine, and magnesium sulfate was added to dehydrate the organic layer. Then, by suction filtration, magnesium sulfide was removed and concentrated under reduced pressure to obtain a composition of a pale yellow solid, which was purified by silica gel chromatography to obtain the title compound. The title compound (1.12 g, yield 66.0%, light brown solid) was obtained.
¹ H NMR (CDCl ₃ ) δ 8.65 (1H, s), 8.48 (1H, d, J = 4.8Hz), 8.43 (1H, s), 8.10 (1H, s), 7.42 (1H, d, J = 5.1) Hz), 4.77 (2H, s), 2.92 (2H, q, J = 7.5Hz), 1.26 (3H, t, J = 7.5Hz)

Synthesis Example 4-5: Preparation of 2- [3- (ethylthio) pyridine-4-yl] -5-iodopyrazine 5- [3- (ethylthio) pyridin-4-yl] pyrazine-2 in tetrahydrofuran (55 mL) -Amine (1.12 g, 4.82 mmol) was added, followed by amyl nitrite (2.1 mL, 15.78 mmnol), diiodomethane (0.43 mL, 5.35 mmol), copper iodide (II) (1.01 g). 5.30 mmol) was added, and the mixture was stirred under heating and reflux for 3 hours. After allowing to cool, water and ethyl acetate were added in appropriate amounts, and suction filtration was performed using cerite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain the title compound (0.97 g, yield 58.6%, brown solid).
¹ H NMR (CDCl ₃ ) δ 8.97 (1H, s), 8.85-8.45 (3H, m), 7.43 (1H, d, J = 4.2Hz), 2.93 (2H, q, 7.5Hz), 1.26 (3H, t, J = 7.5Hz)

Synthesis Example 4-6: Preparation of 2- [3,5-bis (trifluoromethyl) phenyl] -5- [3- (ethylthio) pyridin-4-yl] -pyrazine (Compound No. -88) tetrahydrofuran (55 mL) ) With 2- [3- (ethylthio) pyridin-4-yl] -5-iodopyrazine (0.20 g, 0.58 mmol) and dichlorobis (triphenylphosphine) palladium (II) (42 mg, 0.06 mmol). , 4-Dioxane was dissolved, the inside of the reactor was replaced with nitrogen gas, and the mixture was heated and stirred at 60 ° C. for 10 minutes. After allowing to cool, [3- (trifluoromethyl) phenyl] boronic acid (133 mg, 0.70 mmol) was added, and the mixture was further stirred with heating under reflux for 5 hours. After allowing to cool, water and ethyl acetate were added in appropriate amounts, and suction filtration was performed using cerite to remove insoluble matter. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a composition organism. The obtained crude product was purified by silica gel chromatography to obtain the title compound (173 mg, yield 81.7%, brown solid).
¹ H NMR (CDCl ₃ ) δ 9.24 (1H, s), 9.10 (1H, d, J = 0.9Hz), 8.77 (1H, s), 8.64-8.56 (3H, m), 8.02 (1H, s), 7.53 (1H, d, J = 4.8Hz), 2.96 (2H, q, J = 7.5Hz), 1.27 (3H, t, J = 7.5Hz)

Synthesis Example 4-7: Preparation of 2- [3,5-bis (trifluoromethyl) phenyl] -5- [3- (ethylsulfonyl) pyridin-4-yl] -pyrazine (Compound No. -90) 2- [3- (Ethylthio) Pyridine-4-yl] -5- [3- (Trifluoromethyl) Phenyl] pyrazine (111 mg, 0.31 mmol) was dissolved in dichloromethane (3 mL), and the mixture was subjected to 3-chloropoly under ice-cooling. Pyrazine benzoic acid (about 30% water content, 183 mg, 0.69 mmol) was added, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium hydrogen carbonate solution was added, the mixture was extracted twice with ethyl acetate, dried over magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a composition organism. The obtained crude product was purified by silica gel chromatography to obtain the title compound (87 mg, yield 71.9%, slightly brown amorphous).
¹ H NMR (CDCl ₃ ) δ 9.37 (1H, s), 9.18 (1H, d, J = 1.2Hz), 9.04 (1H, d, J = 4.8Hz), 8.89 (1H, d, J = 1.5Hz) , 8.59 (2H, s), 8.03 (1H, s), 7.51 (1H, d, J = 4.8Hz) 3.61 (2H, q, J = 7.5Hz), 1.39 (3H, t, J = 7.5Hz)

Synthesis Example 5-1: 2- (3-methoxypyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) Preparation of pyrazine (Compound No. -4) Synthesis Example 2-bromo-5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.50 g, 1.63 mmol) according to 1-1 was dissolved in dioxane (50 mL) and dichlorobis (triphenyl). Phosphine) Pyrazine (II) (114 mg, 0.16 mmol) was added, and the mixture was heated and stirred at 60 ° C. for 10 minutes under a nitrogen atmosphere. After allowing to cool, 5 mL of 4-bromo-3-methoxypyridine (0.30 g, 1.97 mmol) and a 2M-sodium carbonate aqueous solution were added, and the mixture was stirred under heating under reflux for 2 hours. After allowing to cool, water and ethyl acetate were added in appropriate amounts, and suction filtration was performed using cerite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. Then, it was extracted twice with ethyl acetate, dried over magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a composition organism. The obtained crude product was purified by silica gel chromatography to obtain the title compound (0.29 g, yield 53.3%, colorless oil).
¹ H NMR (CDCl ₃ ) δ 8.86 (1H, d, J = 1.2Hz), 8.45 (1H, d, J = 1.5Hz), 8.45 (1H, s), 8.39 (1H, d, J = 5.1Hz) , 7.85 (1H, d, J = 4.8Hz), 4.92 (2H, td, J = 12.8, 0.9Hz), 4.04 (3H, s)

Synthesis Example 6-1: Preparation of 2- (3- (ethylthio) pyrazine-4-yl) -5- (perfluoropropyl) pyrazine (Compound No. -83) Copper (I) chloride (0.29 g, 2. 91 mmol), tert-butoxypotassium (0.33 g, 2.91 mmol), 1,10-phenanthroline (0.53 g, 2.91 mmol) dissolved in N, N-dimethylformamide (6 mL), degassed, and then replaced with nitrogen. And stirred at room temperature for 30 minutes. Trimethyl (heptafluoropropyl) silane (0.71 g, 2.91 mmol) was added at room temperature, the inside of the reactor was replaced with nitrogen again, and the mixture was stirred at room temperature for 1 hour. 2- [3- (Ethylthio) Pyridine-4-yl] -5-iodopyrazine (0.50 g, 1.46 mmol) described in Synthesis Example 4-5 was added thereto, and the mixture was stirred at 50 ° C. for 14 hours. Add an appropriate amount of ethyl acetate to the reaction mixture, suction filter using cerite to remove insoluble matter, and add water to the filtrate. Then, it was extracted with ethyl acetate, dried with magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography to obtain the title compound (0.19 g, yield 33.8%, yellow solid).
¹ H NMR (CDCl ₃ ) δ 9.13 (1H, s), 9.06 (1H, s), 8.79 (1H, s), 8.62 (1H, d, J = 4.8Hz), 7.50 (1H, d, J = 5.1) Hz) 2.94 (2H, q, J = 7.2Hz), 1.26 (3H, t, J = 7.2Hz)

Synthesis Example 7-1: Preparation of 5-chloro-N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide 5-chloropyrazine-2-carboxylic acid (1.00 g, 6.31 mmol) , 2,2,2-Trifluoroethylamine (687.52 mg, 6.94 mmol), N, N-diisopropylethylamine (3.56 mL, 20.81 mmol), O- (7-azabenzotriazole-1-yl)- N, N, N', N'-tetramethyluronium hexafluorophosphate was dissolved in methylene chloride (30 mL) and stirred overnight at room temperature under a nitrogen atmosphere. Then, saturated aqueous sodium hydrogen carbonate was added, the mixture was extracted with ethyl acetate, and magnesium sulfate was added for dehydration. Magnesium sulfide was removed by suction filtration, concentrated under reduced pressure, and the composition was purified by silica gel chromatography to obtain the title compound. (1.10 g, yield 72.8%, white individual)
¹ H NMR (CDCl ₃ ) δ9.20 (1H, d, J = 1.5Hz), 8.56 (1H, d, J = 1.5Hz), 7.94 (1H, bs), 4.14 (2H, ddd, J = 15.9Hz) , 9.0Hz, 6.6Hz)

Synthesis Example 7-2: Preparation of 5- (3-fluoropyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -61) 5-chloro -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (2.98 g, 12.44 mmol), 3-fluoro-4-pyridineboronic acid pinacol ester (2.98 g, 21.15 mmol) Was dissolved in acetonitrile (48 mL), potassium acetate (3.66 g, 37.31 mmol) dissolved in water (5 mL) was added thereto, and the inside of the reactor was replaced with nitrogen gas. Dichlorobis [di-t-butyl (p-dimethylaminophenyl) phosphino] palladium (II) (0.88 g, 1.24 mmol) was added thereto, and the mixture was stirred under heating under reflux for 19 hours. After allowing to cool, water and ethyl acetate were added in appropriate amounts, the mixture was extracted with ethyl acetate, and magnesium sulfate was added for dehydration. Magnesium sulfide was removed by suction filtration, concentrated under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain the title compound (1.66 g, yield 44.5%, yellow solid).
¹ H NMR (CDCl ₃ ) δ9.54 (1H, d, J = 1.5Hz), 8.69 (1H, d, J = 2.7Hz), 8.64 (1H, dd, J = 5.1Hz, 0.9Hz), 8.14 ( 1H, s), 8.10 (2H, dd, J = 6.6Hz, 5.1Hz), 4.17 (2H, dtd, J = 17.7Hz, 9.0Hz, 6.6Hz)

Synthesis Example 8-1: Preparation of 5- (3- (ethylthio) pyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -59) 5 -(3-Fluoropyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -61) (0.12 g, 0.40 mmol) was added to methylene chloride (0.12 g, 0.40 mmol). It was dissolved in 10 mL), ethanethiol (73 μL, 0.80 mmol) was added at room temperature, sodium hydride (34.90 mg, 0.80 mmol) was added, and the mixture was stirred as it was overnight. Then, water was added, the mixture was extracted with ethyl acetate, magnesium sulfate was added, and the mixture was dehydrated. Magnesium sulfide was removed by suction filtration, concentrated under reduced pressure, and the composition was purified by silica gel chromatography to obtain the title compound (0.12 g, yield 92.6%, light brown amorphous).
¹ H NMR (CDCl ₃ ) δ9.53 (1H, d, J = 1.5Hz), 8.95 (1H, d, J = 1.5Hz), 7.78 (1H, s), 8.61 (1H, s), 8.12 (1H) , s), 7.50 (1H, d, J = 1.8Hz), 4.18 (2H, tdd, J = 9.0Hz, 9.0Hz, 6.9Hz), 2.92 (2H, td, J = 7.8Hz, 7.8Hz), 1.25 (3H, t, J = 7.8Hz)

Synthesis Example 9-1: Preparation of 5- (3- (ethylsulfonyl) pyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxamide (Compound No. -68)
5- (3- (Ethylthio) Pyridine-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -59) (0.15 g, 0.44 mmol) It was dissolved in methylene chloride (4.5 ml), m-chloroperbenzoic acid (0.26 g, 70%, 0.96 mmol) was added under cooling in an ice bath, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, saturated aqueous sodium hydrogen carbonate was added, the mixture was extracted twice with ethyl acetate, magnesium sulfate was added, and the organic layer was dehydrated. Then, magnesium sulfide was removed by suction filtration and concentrated under reduced pressure to obtain a composition, which was purified by silica gel chromatography to obtain the title compound (0.09 g, yield 56.7%, white amorphous). ..
¹ H NMR (CDCl ₃ ) δ9.45 (1H, s), 9.35 (1H, s), 9.03 (1H, d, J = 5.1Hz), 8.73 (1H, s), 8.12 (1H, m), 7.46 (1H, d, J = 4.8Hz), 4.18 (2H, m), 3.49 (2H, d, J = 7.5Hz), 1.35 (3H, t, J = 7.5Hz)

Synthesis Example 10-1: Preparation of 5- (3- (dimethylamino) pyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxamide (Compound No. -65)
50% of 5- (3-fluoropyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -61) (0.36 g, 1.20 mmol) It was dissolved in an aqueous dimethylamine solution (10 mL), stirred as it was overnight, and then stirred under heating and reflux for 7 hours. After allowing to cool, the mixture was concentrated under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain the title compound (0.35 g, yield 89.7%, yellow solid).
¹ H NMR (CDCl ₃ ) δ9.50 (1H, d, J = 1.2Hz), 9.20 (1H, d, J = 1.2Hz), 8.51 (1H, s), 8.39 (1H, d, J = 5.1Hz) ), 8.11 (1H, t, J = 5.7Hz), 7.53 (1H, d, J = 4.8Hz), 4.17 (2H, dq, J = 9.0Hz, 6.6Hz), 2.72 (6H, s)

Synthesis Example 11-1: 5- (3- (dimethylamino) Pyridine-4-yl) -N-methyl-N- (2,2,2-trifluoroethyl) pyrazine-2-carboxamide (Compound No.- 66) Adjustment
After dissolving 5- (3- (dimethylamino) pyridin-4-yl) -N- (2,2,2-trifluoroethyl) pyrazine-2-carboxyamide (Compound No. -65) in tetrahydrofuran (10 mL), Sodium hydride (0.12 g, 4.80 mmol) and methyl iodide (299.2 μL, 4.80 mmol) were sequentially added at 0 ° C. under a nitrogen atmosphere. After stirring overnight at room temperature, water was added and the mixture was extracted with ethyl acetate. Magnesium sulfate was added and dehydrated, magnesium sulfide was removed by suction filtration, concentrated under reduced pressure, and the obtained composition was purified by silica gel chromatography to obtain the title compound (42.7 mg, yield 13.6%, yellow). Oily) was obtained.
¹ H NMR (CDCl ₃ ) δ9.23 (0.5H, s), 9.19 (0.5H, s), 9.15 (0.5H, s), 9.12 (0.5H, s), 8.49 (1H, s), 8.38 ( 1H, d, J = 4.8Hz), 7.57-7.50 (1H, m), 4.64 (1H, q, J = 8.1Hz), 4.27 (1H, q, J = 8.7Hz), 3.36 (1.5H, s) , 3.30 (1.5H, s), 2.72 (3H, s), 2.71 (3H, s)

The proton NMR spectrum data and melting point of the compound of formula (1) synthesized by the same method as described above are shown in Tables 2 and 3.

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

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

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

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

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

Pharmaceutical example 7 [Granule]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sun extract P252 2% by weight
(Calcium lignin sulfonate: Product name of Nippon Paper Industries, 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 invention against specific pests. "Control efficacy" refers to the inhibition of growth (including mortality) of harmful invertebrates that significantly reduces feeding. The control and protection of pests achieved by the compounds, however, is not limited to these species. Compound numbers refer to the compounds in Table 2.

Biological test example 1: Aphis gossypii control test (leaf spraying treatment)
Cucumber leaves were cut to a diameter of 3.5 cm and placed on cotton wool moistened with water. Two adult cotton aphids were released here and bred for 24 hours, and then the adults were removed. 2 mL of a diluted solution of the test compound diluted to 200 ppm was sprayed on the cucumber leaves using a spraying tower. After air-drying, it was placed in a plastic cup together with absorbent cotton, covered, and bred in a constant greenhouse at 25 ° C. Life and death were observed 5 days after the treatment, and the insect rate (%) was calculated.
As a result, the compounds of the present invention 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, 70, 71, 72, 74, 75, 76, 80, 85, 86, 87, 88, 89, 90, 93, 94 showed a mortality rate of 80% or more.

Biological test example 2: Aphis gossypii control test (root immersion treatment)
One cucumber seedling (cotyledon stage) was fixed with urethane so that the root was immersed in a vial (inner diameter 2.7 cm x 6 cm) containing 10 mL of a chemical solution diluted to 3.1 ppm. One day after soaking, five first-instar larvae of Aphis gossypii were released and bred in a constant greenhouse at 25 ° C. Five to seven days after the release of the insects, the life and death of the insects and abnormalities were investigated.
As a result, the compounds of the present invention 1, 2, 4, 20, 43, 45, 47, 50, 53, 54, 57, 59, 60, 61, 62, 65, 66 showed an insecticidal rate of 80% or more. ..

Biological test example 3: Tobacco whitefly (Bemisia tabaci) control test (leaf spraying treatment)
Adult tobacco whiteflies are released on cucumbers planted in pots and spawned for 6 hours. After that, the adults are removed and kept under sufficient light conditions. After the hatched larvae have settled, cut the leaves into 4 cm squares to contain the larvae and place them on cotton wool 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 spraying tower. After air-drying, it was placed in a plastic cup together with absorbent cotton, covered, and bred in a constant greenhouse at 25 ° C. Life and death were observed 7 days after the treatment, and the insect rate (%) was calculated.
As a result, the compounds 1, 2, 4, 8, 19, 31, 43, 66, 70, 71, 72, 75, 89, 90 and 92 of the present invention showed an insecticidal rate of 80% or more.

Biological test example 4: Diamondback moth (Plutella xylostella) control test (leaf piece immersion treatment)
The cabbage leaves were cut to a diameter of 5.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted to 200 ppm and air-dried. After air-drying, cabbage leaf pieces were placed in a plastic cup, 10 diamondback moth 3rd instar larvae were released, covered, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the death rate (%) was calculated.
As a result, the compounds of the present invention 2, 6, 11, 84, 89, 90 and 94 showed an insecticidal rate of 80% or more.

Biological test example 5: Brown planthopper (Nilaparvata lugens) control test (foliage soaking treatment)
Ten rice seedlings were taken, immersed in 20 mL of a chemical solution of the test compound diluted to 200 ppm, and air-dried. After air-drying, hold it in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane and stand it in a plastic cup containing 40 mL of water. The brown planthopper 3rd instar larvae were released, covered with medicine wrapping paper, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the death rate (%) was calculated.
As a result, the compounds of the present invention 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, 70, 72, 75, 76, 79, 85, 86, 87, 88, 89, 90, 93 and 94 showed a mortality rate of 80% or more.

Biological test example 6: Brown planthopper (Nilaparvata lugens) control test (root immersion treatment)
Take 10 rice seedlings, hold them in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane, and make a plastic cup (90 mL containing 40 mL of chemical solution diluted to 50 ppm) in the center so that the cylinder stands. I put it on the lid). Two days later, 10 brown planthopper 3rd instar larvae were released, covered with medicine wrapping paper, and bred in a constant greenhouse at 25 ° C. Five to seven days after the treatment, the life and death of insects and abnormalities were investigated.
As a result, the compounds 1, 4, 20, 31, 42, 43, 57, 60 and 62 of the present invention showed an insecticidal rate of 80% or more.

Biological test example 7: Nephotettix cincticeps control test (stem and foliage immersion treatment)
Ten rice seedlings were taken, immersed in 20 mL of a chemical solution of the test compound diluted to 200 ppm, and air-dried. After air-drying, hold it in a glass cylinder (inner diameter 4.5 cm x 14 cm) with urethane and stand it in a plastic cup containing 40 mL of water. The third-instar larvae of Nephotettix crab were released, covered with medicine wrapping paper, and bred in a constant greenhouse at 25 ° C. The life and death of the larvae were observed 5 days after the treatment, and the death rate (%) was calculated.
As a result, the compounds 1, 6, 12, 13, 18, and 27 of the present invention showed an insecticidal rate of 80% or more.

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

Biological test example 9: Tetranychus urticae control test (leaf piece immersion treatment)
Put absorbent cotton sufficiently moistened with water in a plastic container (diameter 6 cm x 3 cm), and lay a filter paper on it. Place a 2 cm square bean leaf piece on a filter paper, release 5 adult bean spider mites, and lay eggs for 24 hours. The next day, the green bean leaf pieces excluding 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 bean leaf pieces were returned to the plastic cup, covered, and bred in a constant greenhouse at 25 ° C. Seven days after the treatment, the life and death of the larvae were observed, the number of unhatched eggs was investigated, and the larval rate (%) was calculated.
As a result, the compounds of the present invention 10, 11, 15, 23, 24, 22, 25, 31, 32, 34, 35, 58 and 93 showed an insecticidal rate of 80% or more.

Biological test example 10: Sweet potato root-knot nematode (Meloidogyne incognita) control test (immersion test)
From the egg sac that had settled on the root of the sweet potato, a suspension of the second stage larvae of the sweet potato nematode was obtained by the Bellman method. This nematode-containing liquid was dispensed into a 48-well plate at a rate of 100 μL (about 50 nematodes) per hole. After that, the same amount of reagent solution as the nematode-containing solution was added, and the mixture was allowed to stand at a constant temperature of 26 ° C. for 3 days. The insect rate was calculated.
Corrected insect rate (%) =
{(Death rate in treated area-Death rate in untreated area) / (100-Death rate in untreated area)} x 100
As a result, the compounds 3 and 22 of the present invention showed a corrected insect mortality rate of 80% or more.

Claims (7)

A pest control agent containing the compound represented by the formula (1) or a salt thereof as an active ingredient.

(In equation (1),
R is
Alkyl groups of hydrogen atoms C1 to C6 (here, C1 to C6 alkyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. An amino group with two substituents selected and / or
It may be independently substituted with a phenyl group substituted with 1 to ₅ substituents R3).
Phenyl group independently substituted with 1 to 5 substituents _R4 Represents a pyridyl group independently substituted with 1 to 5 substituents _R4 .
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen atom Alkyl group of halogen atom C1 to C6 (Here, C1 to C6 alkyl group is
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups and / or may be substituted with one or more halogen atoms of the same or different
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenyloxy groups (where C2-C6 alkenyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynyloxy groups (where C2-C6 alkynyloxy groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1-C6 alkylthio groups (where C1-C6 alkylthio groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylthio groups (where, the C2-C6 alkenylthio groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylthio group (where, C2-C6 alkynylthio group is
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylsulfinyl groups (where, the C2-C6 alkenylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylsulfinyl groups (where, C2-C6 alkynylsulfinyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C1 to C6 alkylsulfonyl groups (where C1 to C6 alkylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkenylsulfonyl groups (where, the C2-C6 alkenylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
C2-C6 alkynylsulfonyl groups (where the C2-C6 alkynylsulfonyl groups are
One or more halogen atoms that are the same or different, and / or
C1-C6 alkyloxy groups, which may be substituted with one or more halogen atoms of the same or different, and / or
C1-C6 alkylthio groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfinyl groups and / or may be substituted with one or more halogen atoms of the same or different.
C1-C6 alkylsulfonyl groups, which may be substituted with one or more halogen atoms of the same or different, and / or
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. It may be substituted with an amino group having two substituents selected)
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group having two substituents of choice A carbon atom, a 5- or 6-membered amino group consisting of a sulfur atom (where the sulfur atom is oxidized and may be a sulfinyl group or a sulfonyl group).
N, N-dimethylacetoimidazole group 1,1,3,3-tetramethylguanidinyl group Independent of hydrogen atom, alkyl group of C1 to C6 which may be substituted with one or more halogen atoms of the same or different. Aminocarbonyl group with two substituents selected in the above group Hydrogen atom, C1 to C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, substituted with one or more identical or different halogen atoms. Hydradino group having three substituents independently selected from the C1-C6 acyl group may be the same, or the C1-C6 alkyl group may be substituted with the same or different one or more halogen atoms. Alternatively, a hydrazinocarbonyl group hydrogen atom having three substituents independently selected from the acyl groups of C1 to C6 which may be substituted with one or more different halogen atoms, substituted with the same or different one or more halogen atoms. A hydroxylamino group having two substituents independently selected from an alkyl group of C1 to C6 which may be substituted, and an acyl group of C1 to C6 which may be substituted with the same or different one or more halogen atoms. Represent,
A represents a direct bond. ) R is
Alkyl groups of C1 to C6 (where, the C1 to C6 alkyl groups are one or more halogen atoms that are the same or different, and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
C2-C6 alkynyl groups (where C2-C6 alkynyl groups are the same or different one or more halogen atoms and / or
It may be independently substituted with 1 to ₅ substituents R3 and optionally with a phenyl group).
Phenyl group independently substituted with 1 to 5 substituents _R4 A pyridyl group optionally substituted with 1 to ₄ substituents R4.
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independent,
Hydrogen Atom Alkyl Group of Halogen Atoms C1 to C6 (Here, the C1 to C6 alkyl group may be substituted with one or more halogen atoms of the same or different).
C2-C6 alkenyl groups (where C2-C6 alkenyl groups may be substituted with one or more halogen atoms that are the same or different).
C2-C6 alkynyl groups (where the C2-C6 alkynyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkyloxy groups (where C1 to C6 alkyloxy groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylthio groups (where C1 to C6 alkylthio groups may be substituted with one or more halogen atoms that are the same or different).
C1-C6 alkylsulfinyl groups (where the C1-C6 alkylsulfinyl groups may be substituted with one or more halogen atoms that are the same or different).
C1 to C6 alkylsulfonyl groups (where the C1 to C6 alkylsulfonyl groups may be substituted with one or more halogen atoms that are the same or different).
Independent of hydrogen atoms, C1-C6 alkyl groups optionally substituted with one or more identical or different halogen atoms, and C1-C6 acyl groups optionally substituted with one or more identical or different halogen atoms. Amino group with two substituents selected Aminocarbonyl with two substituents selected independently of the hydrogen atom, the alkyl group of C1-C6 which may be substituted with one or more identical or different halogen atoms. The basis,
The pest control agent according to claim 1. The pest control agent according to claim 1 or 2, which comprises at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. The pest control agent according to any one of claims 1 to 3, further comprising at least one biologically effective compound or agent. The at least one biologically effective compound or agent described above is aranicalve, aldicalve, benziocarb, bendiocarb, benfuracarb, buttocarboxym, butoxycarboxym, carballyl, carbofran, carbosulfan, etiophencarb, phenocarb, formethanate, Frathiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamil, Pyrimicalve, Propoxul, Thiodicarb, Thiophanox, Triazamate, Trimethacarb, XMC, Xylylcarb, Mettlecarb, Phenothiocarb, Phenoxycarb, Acefate, Azamethifos, Azinephos-ethyl, Azine Ethoxyphos, cazusaphos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifosmethyl, kumaphos, cyanophos, demeton-S-methyl, diazinone, dichlorvos, dicrotophos, dimethote, dimethylbinphos, EPN, etion, etoplophos, famfur, phenamiphos , Fenitrothion, fenthion, hostizet, heptenophos, imiciaphos, isofenphos, isopropyl = O- (methoxyaminebothiophosphorylsalicylate, isoxathion, malathion, mecarbam, metamidphos, metidathion, mevinphos, chlorpyrifos, naredo, ometoate, oxydimethoneethyl, Parathion, Parathion-Methyl, PAP, Holate, Hosalon, Hosmet, Phosphamiden, Hoxim, Pyrimiphos-Methyl, Prophenofospropetanphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimiphos, Temephos, Telbuphos, Tetrachlorbinphos, Thiometon, triazophos, trichlorfon, bamidione, chlorpyrifos-ethyl, disulphoton, sulprophos, flupyrazophos, fentate, honophos, tribuphos, endosulfan, alpha-endosulfan, gamma-HCH, dichophor, chlorden, allethrin, methoxychlor, acetoplol, fipronyl, ethiprol. Luprol, piriprol, fulfiprol, brofuranilide, afoxolanel, furlalanel, salolalanel, fluxametamid, acrinathrin, allethrin, d-cis-trans allethrin, d-trans Allethrin, Bifenthrin, Kappa-Bifentrin, Bioallethrin S-Cyclopentenyl, Bioresmethrin, Cycloprothrin, Cypermethrin, Beta-Cypermethrin, Cyhalothrin, Lambda-Cihalothrin, Gamma-Cihalothrin, Cypermethrin, Alpha-Cypermethrin, Beta-Cypermethrin, Theta-cypermethrin, zeta-cypermethrin, cypermethrin, deltamethrin, empentrin, esphenvalerate, etofenprox, phenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadestrin , Permethrin, Fenotrin, Praletrin, Piretrin, Allethrin, Cypermethrin, Tefluthrin, Kappa-tefluthrin, Phthalthrin, Tetramethrin, Tralomethrin, Transfluthrin, Metoxadiazone, Metoflutrin, Profluthrin, Pyretram, Terraletrin, Monfluorothrin Methylfluthrin, dimefluthrin, chloropalalethrin, epsilon-methfurthrin, epsilon-monfluosrin, protrifenbut, acetamipride, clothianidin, dinotefuran, imidacloprid, nitempirum, thiacloprid, thiamethoxam, sulfoxaflor, flupyraziflulone Zu, flupyrimin, spinosad, spinnetram, abamectin, ibermectin, emamectin benzoate, milbemectin, repimectin, hydroprene, quinoprene, diophenolan, metoprene, pyriproxyfen, pimetrodin, fronicamid, ethoxazole, diaphenthirone, azocyclotin, cypermethrin, oxidase. , Propargit, Tetradiphon, Chlorphenapir, Tralopyril, DNOC, Bensultap, Cartap, Thiocyclum, Thiosultap, Thiosultap-Sodium, Bistriflulon, Chlorfluazuron, Diflubenzron, Flucycloxron, Fluphenoxron, Hexaflumuron, Luphenuron, Novallon , Noviflumron, Teflubenzron, Triflumron, Bistrifluron, Buprofezin, Cypermethrin, Chromaphenozide, Harofenozide, methoxyphenozide, Tebufenozide, Amitraz, Hi Doramethylnone, acequinosyl, fluaclipirim, pyriminostrobin, fluphenoxystrobin, phenazakin, phenylpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrado, pifrubmid, spirodiclofen, spirotetramate, spiromethifene, spiropidion, siflumethofen Flubendiamide, chloranthraniliprol, cyantraniliprol, cyclaniliprol, tetraniliprol, sihalodiamide, tetrachlorantraniliprol, quinomethionate, hexithiazox, biphenazeto, fluphenerim, pyrifluquinazone, frometkin, fluopyrum, fluazindrinzine , Amidoflumeth, tyclopyrazoflor, thioxazaphen, oxazosulfyl, nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentedin, difluorovidazine, rotenone, indoxacarb, piperonylbutoxide, chlordimeholm, pyridalyl, azadilactin, benzoximate, Afidopyropen, fluhexaphone, flubendisulfone, bencrothias, carzole, insecticidal soap, dimehipo, nithiadine, borate, metaaldehyde, lianodine, sulfurlfuramide, asinonapill, benzpyrimoxane, 3-bromo-N- (2,4-dichloro-) 6- (Methylcarbamoyl) Phenylyl) -1- (3,5-Dichloropyridin-2-yl) -1H-Pyrazole-5-Carboxamide, Metalaxil, Metalaxil M, Oxadixil, Ophrase, Benalaxil, Benalaxil-M, Kiralaxil, Oflars, flaluxil, cyprofuran, buprimate, dimethyrimol, etilimol, himexazole, hydroxyisoxazole, oxathiapiproline, octylinone, oxolinic acid, benomil, thiophanatemethyl, carbendazim, huberidazole, thiabendazole, debacalve, dietofencarb , Fluopimomid, diflumethrim, bupyrimate, benodanyl, flutranyl, mepronyl, isofetamide, phenylfuram, oxycarboxyn, carboxylon, tyfluzamide, fluxapyroxado, flametopyl, penflufen, penthiopyrado, benzobindiflupill, bixaphen, isopyrazam, sedaxane, impil Fluxam, fluindapyl, isoflusiplum, pyrapropoin, boscalid, azoxystrobin, kowmethoxystrobin, cresoximemethyl, trifloxystrobin, picoxystrobin, pyracrostrobin, dymoxistrobin, metminostrobin, orysustrobin, full Oxastrobin, pyraoxystrobin, pyrametostrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, spumoxystrobin, mandestrobin, triclopyricalve, famoxadon, fenamiden, triclopyricalve, pyribencarb, Siazofamid, amisulbrom, vinapacryl, meptyldinocarb, dinocup, fluazinum, ferimzone, acetate-fentin, fentin chloride, fentin hydroxide, triphenyltin hydroxide, triphenyltin acetate, oxine copper, silthiofam, amethoctrazine, mepanipirim, nitrapyrin, Pyrimesanyl, cyprodinyl, blastidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyphene, proquinazide, fludioxonyl, fenpicronyl, fluoroimide, procymidone, iprodione, binclozoline, edifenphos, iprobenphos, pyrazophos, isoprobenphos Hydrochloride, Gosei Kayupte Extract, Triphorin, Pyriphenox, Pyrisoxazole, Phenalimol, Nuarimol, Azaconazole, Bromconazole, Diniconazole, Diniconazole-M, Epoxyconazole, Flukinconazole, Oxpoconazole, Pefrazoate, Diphenoconazole, Fen Buconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triazimehon, triazimenol, triticonazole, uniconazole, imazalyl, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutorial, microbutanyl. , Paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, phenpropimorph, dimethomorph, flumorph, pilimorph, piperaline , Fenpropidin, spiroxamine, fenhexamide, fenpyrazamine, fervum, metam, metasulfocarb, methylam, tiram, manzeb, manneb, dineb, dilam, polycarbamate, provineb, thiuram, pyribuchicarb, baridamycin, mildiomycin, polyoxin, Bench Avaricarb, Bench Avaricarb Isopropyl, Variphenalate, Iprovaricarb, Mandipropamide, Fempicoxamide, Florylpicoxamide, Fusalide, Pyrochyron, Tricyclazole, Carpropamide, Diclosimet, Phenoxanyl, Acibenzoral-S-methyl, Provenazole, Diclobenazox, thiazinyl, isothianyl, simoxanyl, Josetil, tecrophthalam, triazoxide, flusulfamide, dichromedin, siflufenamide, metrafenone, pyriophenone, fluthianyl, tebuflokin, ipflufenokin, Josetilaluminum, torquelophos-methyl, ecromezol, tolprocarb. Fluconazole, mefentrifluconazole, quinofumerin, pidiflumethofen, Bordeaux mixture, copper acetate, basic copper sulfate, oxychloride copper, cupric hydroxide, oxyquinolin copper, copper, sulfur, captan, captahole, folpet , Anilazine, chlorotalonyl, dichlorophene, pentachlorophenol and its salts, hexachlorobenzene, quintozen, iminoctadine acetate, iminoctadine albesylate, guanidine, copper, dodine free base, guazatin, guazatin acetate, albesylate, dithianone, quinomethionate, Fluolimide, Trillfluanide, Diclofluanide, Zinobuton, Dazomet, Pyraziflumid, Aminopyriphen, Methyltetraprol, Pyridaclomethyl, Dipimethitron, Picalbutrazox, Technazen, Nitortal-isopropyl, Dicyclomet, Acibenzoral, Prohexadione-Calcium , Bronopol, diphenylamine, flumethbel, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, Bacillus, and the insecticidal proteins, bactericidal proteins, bactericidal proteins produced by Bt crops, bactericidal proteins, Claimed, selected from the group consisting of entomopathic bacteria, entomopathic viruses and entomopathic fungi Item 4. The pest control agent according to Item 4. The pest control agent according to any one of claims 1 to 5, wherein the pest is an ectoparasite. The pest control agent according to claim 6, for controlling animal ectoparasites against ectoparasites of animals and birds.