JP7208704B2 - pyrazine compound - Google Patents

Description

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

Various compounds have so far been investigated and put into practical use for the purpose of controlling arthropod pests. 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, a highly practical compound having high pest control activity has not been found.

WO2017/065228 WO2015/059088

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

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

（式（１）中、
Ｒは、
水素原子
Ｃ１～Ｃ６のアルキル基
（ここで、Ｃ１～Ｃ６アルキル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルホニル基、及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１～５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）；
Ｃ２～Ｃ６のアルケニル基
（ここで、Ｃ２～Ｃ６アルケニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１～５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）；
Ｃ２～Ｃ６のアルキニル基
（ここで、Ｃ２～Ｃ６アルキニル基は、
同一もしくは異なる一以上のハロゲン原子、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルオキシ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルチオ基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルフィニル基、及び／または、
同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６アルキルスルホニル基及び／または、
水素原子、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアルキル基、同一もしくは異なる一以上のハロゲン原子により置換されていてもよいＣ１～Ｃ６のアシル基から独立して選択される２つの置換基を有するアミノ基、及び／または、
独立して１～５個までの置換基Ｒ_３で置換されるフェニル基により置換されていてもよい）
独立して１～５個までの置換基Ｒ_４で置換されるフェニル基
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 Formula (1) or a salt thereof.

(In formula (1),
R is
hydrogen atom C1-C6 alkyl group (wherein the C1-C6 alkyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
independently substituted by a phenyl group substituted with up to 1 to 5 substituents R ₃ );
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
independently substituted by a phenyl group substituted with up to 1 to 5 substituents R ₃ );
a C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
a phenyl group independently substituted with up to 1 to 5 substituents R ₄ a pyridyl group independently substituted with up to 1 to 4 substituents R ₄ ,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
A hydrogen atom halogen atom C1-C6 alkyl group (wherein the C1-C6 alkyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkenyloxy group (wherein the C2-C6 alkenyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynyloxy group (wherein the C2-C6 alkynyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylthio group (wherein the C1-C6 alkylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylthio group (wherein the C2-C6 alkenylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylthio group (wherein the C2-C6 alkynylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfinyl group (wherein the C1-C6 alkylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfinyl group (wherein the C2-C6 alkenylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfinyl group (wherein the C2-C6 alkynylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfonyl group (wherein the C2-C6 alkenylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynylsulfonyl group (wherein the C2-C6 alkynylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms 5- or 6-membered ring amino group consisting of amino group carbon atoms and sulfur atoms having two selected substituents (wherein the sulfur atoms are oxidized and may be sulfinyl groups or sulfonyl groups)
N,N-dimethylacetimidamide group 1,1,3,3-tetramethylguanidinyl group independently from hydrogen atoms, C1 to C6 alkyl groups optionally substituted by one or more same or different halogen atoms Aminocarbonyl group hydrogen atom having two substituents selected by, a C1 to C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, substituted by one or more of the same or different halogen atoms a hydrazino group having three substituents independently selected from optionally C1 to C6 acyl groups hydrogen atom, a C1 to C6 alkyl group optionally substituted by one or more halogen atoms which are the same or different, the same Or a hydrazinocarbonyl group hydrogen atom having three substituents independently selected from C1 to C6 acyl groups optionally substituted by one or more different halogen atoms, substituted by one or more same or different halogen atoms a hydroxylamino group having two substituents independently selected from a C1 to C6 alkyl group which may be substituted, a C1 to C6 acyl group which may be substituted by one or more of the same or different halogen atoms; represent,
A is a direct bond, O, S, SO, SO2 _, NR3 _{, NR3C} =O or C= _ONR3
represents )
<2>
R is
C1-C6 alkyl group (here, the C1-C6 alkyl group is the same or different one or more halogen atoms and / or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
a phenyl group independently substituted with up to 1 to 5 substituents R ₄ a pyridyl group independently substituted with up to 1 to 4 substituents R ₄ ,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , and R _d are independently
hydrogen atom halogen atom C1-C6 alkyl group (here, the C1-C6 alkyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyloxy group (wherein the C2-C6 alkenyloxy group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyloxy group (wherein the C2-C6 alkynyloxy group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylthio group (here, the C1-C6 alkylthio group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenylthio group (wherein the C2-C6 alkenylthio group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynylthio group (wherein the C2-C6 alkynylthio group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfinyl group (here, the C1-C6 alkylsulfinyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenylsulfinyl group (wherein the C2-C6 alkenylsulfinyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynylsulfinyl group (wherein the C2-C6 alkynylsulfinyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfonyl group (here, the C1-C6 alkylsulfonyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenylsulfonyl group (wherein the C2-C6 alkenylsulfonyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynylsulfonyl group (wherein the C2-C6 alkynylsulfonyl group may be substituted with one or more same or different halogen atoms)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms amino group having two selected substituents hydrogen atom, aminocarbonyl having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different is the basis,
A is a direct bond, O, S, SO, SO2 _, NR3 _{, NR3C} =O or C= _ONR3
is
The compound or its salt as described in <1>.
<3>
R is
C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
a phenyl group optionally substituted with up to 1 to ₅ substituents R independently,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , and R _d are independently
hydrogen atom halogen atom C1-C6 alkyl group (here, the C1-C6 alkyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylthio group (here, the C1-C6 alkylthio group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfinyl group (here, the C1-C6 alkylsulfinyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfonyl group (here, the C1-C6 alkylsulfonyl group may be substituted with one or more same or different halogen atoms)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms amino group having two selected substituents hydrogen atom, aminocarbonyl having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different is the basis,
A is an oxygen atom,
The compound or its salt as described in <1>.
<4>
R is
C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
a phenyl group optionally substituted with up to 1 to ₅ substituents R independently,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , and R _d are independently
hydrogen atom halogen atom C1-C6 alkyl group (here, the C1-C6 alkyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylthio group (here, the C1-C6 alkylthio group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfinyl group (here, the C1-C6 alkylsulfinyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfonyl group (here, the C1-C6 alkylsulfonyl group may be substituted with one or more same or different halogen atoms)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms amino group having two selected substituents hydrogen atom, aminocarbonyl having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different is the basis,
A is NR ₃ C=O
The compound or its salt as described in <1>.
<5>
R is
C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
a phenyl group independently optionally substituted with up to 1 to 5 substituents R ₄ a pyridyl group independently optionally substituted with up to 1 to 4 substituents R ₄ ,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , and R _d are independently
hydrogen atom halogen atom C1-C6 alkyl group (here, the C1-C6 alkyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylthio group (here, the C1-C6 alkylthio group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfinyl group (here, the C1-C6 alkylsulfinyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfonyl group (here, the C1-C6 alkylsulfonyl group may be substituted with one or more same or different halogen atoms)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms amino group having two selected substituents hydrogen atom, aminocarbonyl having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different is the basis,
A is a direct bond;
The compound or its salt as described in <1>.
<6>
An insecticidal composition comprising the compound according to <1> to <5> and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
<7>
The insecticidal composition according to <1>, further comprising at least one biologically effective compound or agent.
<8>
said at least one biologically active compound or agent is alanicarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocaboxime, butoxycarboxime, carbaryl, carbofuran, carbosulphane, ethiophenecarb, fenocarb, formetanate, Furatiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, metolcarb, phenothiocarb, fenoxycarb, acephate, azamethifos, azinphos-ethyl, azinphos-methyl, ethylthiomethone, chloride Ethoxyphos, caszaphos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethione, etoprophos, famfur, fenamiphos , Fenitrothion, Fenthion, Hostthiazate, Heptenophos, Imisiaphos, Isofenphos, Isopropyl O-(Methoxyaminebothiophosphoryl salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxymetone-ethyl, parathion, parathion-methyl, PAP, folate, fosalone, phosmet, phosphamidone, phoxime, pirimiphos-methyl, propenofos-propetanphos, prothiophos, pyraclophos, pyridafenthion, quinarphos, sulfotep, tebpyrimifos, temefos, terbufos, tetrachlorbinphos, Thiometone, triazophos, trichlorfon, vamidothione, chlorpyrifos-ethyl, disulfotone, sulprophos, flupyrazophos, phenthate, honophos, tribufos, endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor, acetoprol, fipronil, ethiprole, pilaf luprole, pyriprol, flufiprole, brofuranilide, afoxolaner, fluralaner, sarolalaner, fluxametamide, acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin , permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, metofruthrin, profluthrin, pyrethrin, terarethrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethrin Methylfluthrin, Dimefluthrin, Chlorparathrin, Epsilon-Metofluthrin, Epsilon-Monfluothrin, Protrifenbut, Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam, Sulfoxaflor, Flupyradifuron, Triflumezopyrim, Dichloromesotia flupyrimine, spinosad, spinetoram, abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, hydroprene, quinoprene, diphenolane, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide , propargite, tetradifone, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, thiosultap-sodium, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron , noviflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezin, cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz, hi Doramethylnon, acequinosyl, fluacrypyrim, pyriminostrobin, flufenoxystrobin, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, piflubumide, spirodiclofen, spirotetramat, spiromesifen, spiropidion, cyflumetofen, cyenopyrafen, flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole, quinomethionate, hexythiazox, bifenazate, flufenerim, pyrifluquinazone, flometoquine, fluopyram, fluazaindolizine , amidoflumet, ticlopyrazofrole, thioxazaphene, oxazosulfyl, nicotine, chloropicrin, sulfuryl fluoride, chrylotie, clofentezine, diflovidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, Aphidopyropene, fluhexafone, fluenesulfone, benclotiaz, calsol, insecticidal soap, dimehypo, nitiazine, borate, metaldehyde, ryanodine, sulfluramide, acinonapyr, benzpyrimoxane, 3-bromo-N-(2,4-dichloro- 6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide, metalaxyl, metalaxyl M, oxadixyl, ofrace, benalaxyl, benalaxyl-M, chiralaxyl, Oflas, Furaxil, Cyprofuran, Buprimate, Dimethylmol, Ethymol, Hymexazole, Hydroxyisoxazole, Oxathiapiproline, Octilinone, Oxolinic Acid, Benomyl, Thiophanate-methyl, Carbendazim, Fuberidazole, Thiabendazole, Devacarb, Diethofencarb, Zoxamide, Ethaboxam, Penciclon, Fluopicolide , fluopimimide, diflumetrim, bupirimate, benodanil, flutolanil, mepronil, isofetamide, fenfuram, oxycarboxin, carboxin, thifluzamide, fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpil Fluxam, Fluindapyr, Isoflurcipram, Pyrapropoin, Boscalid, Azoxystrobin, Coumethoxystrobin, Cresoxime methyl, Trifloxystrobin, Picoxystrobin, Pyraclostrobin, Dimoxistrobin, Metominostrobin, Orysastrobin, Flu oxastrobin, pyraoxystrobin, pyrametostrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, comoxistrobin, mandestrobin, triclopiricarb, famoxadone, fenamidone, triclopiricarb, pyribencarb, Cyazofamid, Amisulbrom, Binapacryl, Meptyldinocarb, Dinocap, Fluazinam, Ferimzone, Acetate-Fentin, Fentin Chloride, Fentin Hydroxide, Triphenyltin Hydroxide, Triphenyltin Acetate, Copper Oxine, Silthiofam, Amethoctrazine, Mepanipyrim, Nitrapyrin, pyrimesanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxifene, proquinazid, fludioxonil, fenpicronil, fluoroimide, procymidone, iprodione, vinclozoline, edifenphos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb Hydrochloride, Gosseikajupte Extract, Trifoline, Pyrifenox, Pyrisoxazole, Fenarimol, Nuarimol, Azaconazole, Bromuconazole, Diniconazole, Diniconazole-M, Epoxiconazole, Fluquinconazole, Oxpoconazole, Pefurazoate, Difenoconazole, Fen buconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flucilazole, flutriafol, microbutanil , paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pirimorph, piperaline , fenpropidin, spiroxamine, fenhexamide, fenpyrazamine, ferbum, metam, metasulfocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate, provineb, thiuram, piributicarb, validamycin, mildiomycin, polyoxin, Benthiavalicarb, Benthiavalicarb Isopropyl, Valifenalate, Iprovalicarb, Mandipropamide, Fenpicoxamide, Florylpicoxamide, Fthalide, Pyroquilone, Tricyclazole, Carpropamide, Diclocimet, Fenoxanyl, Acibenzolar-S-methyl, Probenazole, Diclobenchiazox, thiazinyl, isotianil, cymoxanil, fosetyl, tecloftalam, triazoxide, fursulfamide, diclomedine, cyflufenamide, metrafenone, pyriophenone, flutianil, tebufloquine, ipflufenoquine, fosetyl aluminum, tolclofos-methyl, eclomezole, tolprocarb, ipfentri fluconazole, mefentrifluconazole, quinofumeline, pydiflumetofen, Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, cupric hydroxide, copper oxyquinoline, copper, sulfur, captan, captafol, folpet , anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctazine acetate, iminoctazine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate, albesylate, dithianone, quinomethionate, Fluorimide, tolylfluanid, diclofluanid, dinobutone, dazomet, pyraziflumide, aminopyrifene, methyltetraprole, pyridaclomethyl, dipimethitrone, picarbutrazox, technazen, nitrtar-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium , bronopol, diphenylamine, flumetovel, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, Bacillus genus and insecticidal and fungicidal proteins produced by them, insecticidal and fungicidal proteins produced by Bt crops, <7 selected from the group consisting of entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi >.
<9>
A composition for protecting animals and birds from harmful parasitic invertebrate organisms, comprising a parasiticidally effective amount of the compound according to <1> and at least one carrier.
<10>
A method for controlling harmful invertebrate organisms, comprising contacting the harmful invertebrate organisms or their environment with a biologically effective amount of the compound according to <1>.
<11>
A method for enhancing the vitality of crops, wherein the crops, the seeds in which the crops grow, or the placenta of the crops are brought into contact with a biologically effective amount of the compound according to <1>.
<12>
Treated seeds, which contain the compound according to <1> in an amount of about 0.0001 to 1% by weight of the seeds before treatment.
<13>
Formula (2):

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

(Wherein, R _a , R _b , R _c and R _d are the same as above, and M is a boronyl group, a dialkoxyboranyl group, a trifluoroborate, a trialkylstannyl group, or a zinc halide. indicates that.)
A production method comprising obtaining by reacting a compound represented by
<14>
Formula (4):

(Wherein, R _a , R _b , R _c and R _d are the same as above, and X represents a halogen atom.)
A compound represented by
Formula (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 trialkylstannyl group, or a zinc halide. show.)
A production method comprising obtaining by reacting a compound represented by

The present invention provides compositions comprising a 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 provides a compound for controlling harmful invertebrate organisms comprising a compound of formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. wherein said composition further comprises at least one biologically active compound or agent.

INDUSTRIAL APPLICABILITY The pyrazine compound having a 4-pyridyl group represented by 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 the compounds according to the invention. Preferred substituents and/or ranges of substituents that can be mentioned in the compound of formula (1) are specifically described below.
In the definition of the above formula (1), "halo" means "halogen atom", chlorine atom,
means a bromine atom, an iodine atom or a fluorine 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, a numerical range indicated using "-" indicates a range including the numerical values described before and after "-" as the minimum and maximum values, respectively.

"C1-C6 alkyl group" means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, 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 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopropylmethyl group, etc. straight or branched chain , or a cyclic alkyl group having 1 to 6 carbon atoms. Linear or branched chain such as methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group , or a cyclic alkenyl group having 2 to 6 carbon atoms, and "C2-C6 alkynyl group" includes, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group , 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl represents a linear or branched chain or cyclic alkynyl group having 2 to 6 carbon atoms, such as a group.

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

The "C1-C6 alkylthio group" includes, for example, methylthio, ethylthio, normal-propylthio, isopropylthio, normal-butylthio, secondary-butylthio, tertiary-butylthio, normal-pentylthio, isopentylthio luthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group, 1,1 , 2-trimethylpropylthio group, cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, cyclopropylmethylthio group or other linear or branched chain or cyclic alkylthio having 1 to 6 carbon atoms The "C1-C6 alkylsulfinyl group" includes, for example, a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso Linear or branched chain such as hexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, cyclopropylsulfinyl group, cyclobutylsulfinyl group, cyclopentylsulfinyl group, cyclohexylsulfinyl group, cyclopropylmethylsulfinyl group, or cyclic carbon represents an alkylsulfinyl group having 1 to 6 atoms,
"C1-C6 alkylsulfonyl group" includes, for example, methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group , an isopentylsulfonyl group, a tertiary pentylsulfonyl group, a neopentylsulfonyl group, a 2,3-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, a 1-methylbutylsulfonyl group, a normal hexylsulfonyl group, an isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, cyclopropylmethylsulfonyl group, etc. Linear or branched chain or cyclic C 1 to 6 alkylsulfonyl groups are shown.

Examples of the "C2-C6 alkenylthio group" include linear or branched alkenylthio groups having 2 to 6 carbon atoms such as propenylthio, butenylthio, pentenylthio, and hexenylthio, The "C2-C6 alkynylthio group" is, 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.

Examples of the "C2-C6 alkenylsulfinyl group" include linear or branched alkenylsulfinyl groups having 2 to 6 carbon atoms such as propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group and hexenylsulfinyl group. The "(C2-C6) alkynylsulfinyl group" includes, for example, a linear or branched chain having 2 to 6 carbon atoms such as a propynylsulfinyl group, a butynylsulfinyl group, a pentynylsulfinyl group, a hexynylsulfinyl group, etc. represents an alkynylsulfinyl group.

Examples of the "C2-C6 alkenylsulfonyl group" include linear or branched alkenylsulfonyl groups having 2 to 6 carbon atoms such as propenylsulfonyl group, butenylsulfonyl group, pentenylsulfonyl group and hexenylsulfonyl group. The "(C2-C6) alkynylsulfonyl group" includes, for example, a linear or branched chain having 2 to 6 carbon atoms such as a propynylsulfonyl group, a butynylsulfonyl group, a pentynylsulfonyl group, a hexynylsulfonyl group, etc. represents an alkynylsulfonyl group.

The above "C1-C6 alkyl group", "C2-C6 alkenyl group", "C2-C6 alkynyl group", "C1-C6 alkyloxy group", "C2-C6 alkenyloxy group", "C2-C6 alkynyloxy group ", "C1-C6 alkylthio group", "C1-C6 alkylsulfinyl group", "C1-C6 alkylsulfonyl group", "C2-C6 alkenylthio group", "C2-C6 alkynylthio group", "C2-C6 alkenylsulfinyl group", "C2-C6 alkynylsulfinyl group", "C2-C6 alkenylsulfonyl group", "C2-C6 alkynylsulfonyl group", "C1-C6 alkyloxy group", "C2-C6 alkenyloxy group", The substitutable position of the "C2-C6 alkynyloxy group" may be substituted with 1 or 2 or more halogen atoms, and when the substituted halogen atoms are 2 or more, the halogen atoms may be the same or different. .

The "5- or 6-membered amino group consisting of carbon atoms and sulfur atoms" includes, for example, 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-dimethylacetimidamide group" is

shows
"1,1,3,3-tetramethylguanidinyl group" is

indicates

Expressions such as “(C1-C6)”, “(C2-C6)”, “(C3-C6)” indicate the range of the number of carbon atoms of various substituents. Furthermore, the above definitions can also be shown for groups to which the above substituents are linked, for example, in the case of "(C1-C6) alkyloxy (C1-C6) alkyl group" ~6 alkyloxy groups are attached to a linear or branched C1-C6 alkyl group.

Salts of the pyrazine compound represented by formula (1) of the present invention include, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate; acetates, fumarates, maleates, oxalates; Organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium can be exemplified.
The pyrazine compound represented by formula (1) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers are may exist, and the present invention includes all individual optical isomers and mixtures thereof in any proportion. In addition, the compound represented by the general formula (1) of the present invention and its salts may have two geometric isomers derived from a carbon-carbon double bond in the structural formula. includes all geometric isomers and mixtures thereof in any proportion.

In the pyrazine compound represented by formula (1) of the present invention or a salt thereof, preferably R is a C1 to C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, or independently a phenyl group substituted with 1 to 5 substituents R ₄ , wherein R ₁ , R ₂ , R ₄ , R _a , R _b , R _c , and R _d are each independently a hydrogen atom, or a halogen atom, or a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, or a C1-C6 alkyloxy optionally substituted by one or more of the same or different halogen atoms or a C1-C6 alkylthio group optionally substituted by one or more halogen atoms which are the same or different, or a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms which are the same or different , or a C1 to C6 alkylsulfonyl group optionally substituted by one or more of the same or different halogen atoms, or (hydrogen atom, or C1 optionally substituted by one or more of the same or different halogen atoms C6 alkyl group, amino group having two substituents independently selected from C1 to C6 acyl groups optionally substituted by one or more halogen atoms which may be the same or different), (hydrogen atom, or an aminocarbonyl group having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different), A is a direct bond, O, S , SO, SO2 _, NR3 _{, NR3C} =O or C= _ONR3 .

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

Manufacturing method 1
<Scheme 1>

_{ Wherein, R, R ₁ , R ₂ , Ra, 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, a trifluoro It represents a borate, trialkylstannyl group or zinc halide, and A1 represents _an oxygen atom or a sulfur atom. }

Production method of step a The pyrazine compound represented by formula (6) and the compound represented by formula (3) are reacted in the presence of a metal catalyst, a base and an inert solvent to obtain a compound represented by formula (7). It is possible to produce a pyrazine compound that This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26, p. 9392-9396).

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as necessary. The amount of the palladium catalyst to be used in the present invention may be appropriately selected in the range of usually about 0.001 to 0.1 mol per mol of 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by formula (6).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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. Alternatively, the next step may proceed without isolation and purification.

Production method of step b By reacting a pyrazine compound represented by formula (7) with an alcohol compound or a thiol compound represented by formula (8) in the presence of a base in an inert solvent, the formula (1a) is obtained. The represented pyrazine compound can be prepared.

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

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene , nitriles such as acetonitrile; esters such as ethyl acetate; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. . The compound represented by the formula (8) is generally used in an amount of about 1 to 5 times the molar amount of the pyrazine compound represented by the formula (7). This reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.

Manufacturing method 2
<Scheme 2>

_{ Wherein, R, R ₁ , R ₂ , Ra, R _b , R _c and R _d are the same as above, X represents a halogen atom, M represents boronic acid, boronic acid ester, trifluoroboric acid It represents a salt, trialkylstannyl or zinc, and A1 represents _an oxygen atom or a sulfur atom. }

Alternatively, compounds of general formula (1a) can be prepared as shown in Scheme 2.

Production method of step c The pyrazine compound represented by formula (6) and the alcohol compound or thiol compound represented by formula (8) are reacted in the presence of a base in an inert solvent to obtain formula (2a). The represented pyrazine compound can be prepared.

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

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene , nitriles such as acetonitrile; esters such as ethyl acetate; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. . The compound represented by formula (8) is generally used in an amount of about 1 to 5 times the molar amount of the pyrazine compound represented by formula (6). This reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.

Production method of step d The pyrazine compound represented by formula (2a) and the compound represented by formula (3) are reacted in the presence of a metal catalyst, a base and an inert solvent to obtain a compound represented by formula (1a). It is possible to produce a pyrazine compound that

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium 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 to be used in the present invention may be appropriately selected in the range of usually about 0.001-fold mol to 0.1-fold mol relative 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by the general formula (2a).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. . After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.

Manufacturing method 3
<Scheme 3>

_{ Wherein, R, R ₁ , R ₂ , Ra, 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, a trifluoro It represents a borate, trialkylstannyl group or zinc halide, and A1 represents _an oxygen atom or a sulfur atom. }

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

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

Examples of diborane or diboron that can be used in the present invention include tetrahydroxydiborane, tetrakis(dimethylamino)diboron, bis(pinacolato)diboron, bis(neopentylglycolate)diboron, bis(hexylene glycolato)diboron, and bis(catecholato)diboron. Diborane such as diboron or diboron may be mentioned. The amount of diborane or diboron to be used in the present invention may be appropriately selected from the range of usually 0.5 to 5.0 mol per mol of the compound represented by formula (2a).

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium 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 to be used in the present invention may be appropriately selected in the range of usually about 0.001-fold mol to 0.1-fold mol relative to the compound represented by formula (2a).

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

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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. Alternatively, the next step may proceed without isolation and purification.

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

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium 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 to be used in the present invention may be appropriately selected in the range of usually about 0.001 to 0.1 mol per mol of 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by formula (5).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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>

_{ Wherein, R, R ₁ , R ₂ , Ra, 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, a trifluoro borate, trialkylstannyl group or zinc halide, A ₁ represents an oxygen atom or a sulfur atom, D represents N or C—R ₄ , PG represents a protecting group, and PG represents One or two are bound to the amino group. }

Production method of step g A pyrazine compound represented by formula (9) is prepared by reacting a pyrazine compound represented by formula (8) with an acid chloride or an acid anhydride in the presence of a base, a catalyst and an inert solvent. can be manufactured. One or two protecting groups are attached to the amino group.
Examples of protecting groups that can be used in the present invention include amide-based protecting groups reacted with acetyl chloride, acetic anhydride, trifluoroacetic anhydride, etc., benzyl chloroformate, allyl chloroformate, methyl chlorocarbonate, 2,2,2-chloroformate, trichloroethyl, fluorenylmethyl chloroformate, N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide, carbamate-based protecting groups reacted with di-tert-butyl dicarbonate, etc., benzyl chloride, p-methoxybenzyl chloride, etc. and a sulfonamide protecting group reacted with a 2-nitrobenzenesulfonyl group. However, the protecting group that can be used in this reaction is not limited to these. The amount of the acid chloride or acid anhydride to be used may be appropriately selected in the range of about 1 to 3 times the molar amount of the compound represented by the formula (8). 4-dimethylaminopyridine and the like can be mentioned as a catalyst for reacting acetic anhydride, trifluoroacetic anhydride, di-tert-butyl dicarbonate and the compound of formula (8), and the amount thereof used is defined by formula (8 ) may be appropriately selected in the range of about 0.1 to 1 mol per mol of the compound represented by ). Examples of the base include triethylamine, N,N-diisopropylethylamine, pyridine, and the like. The amount of the base to be used is appropriately in the range of usually about 1-fold mol to 5-fold mol relative to the compound represented by formula (8). You can choose.

Production method of step h The pyrazine compound represented by formula (9) and the compound represented by formula (4) are reacted in the presence of a metal catalyst, a base and an inert solvent to obtain a compound represented by formula (10). It is possible to produce a pyrazine compound that This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26, p. 9392-9396).

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium 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 to be used in the present invention may be appropriately selected in the range of generally about 0.001 to 0.1 mol per mol of 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by formula (9).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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. Alternatively, the next step may proceed without isolation and purification.

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

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the scale of the reaction, the reaction temperature, etc., but may be appropriately selected within 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. Alternatively, the next step may proceed without isolation and purification.

Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; alkoxides such as alkali metal hydride, sodium methoxide, sodium ethoxide and potassium tertiary butoxide; organic bases such as piperidine, pyrrolidine, molpoline and pyridine; The amount of the base to be used is generally in the range of about 1 to 5 times the molar amount of the compound represented by formula (10).

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

Palladium catalysts that can be used in this reaction include, for example, palladium and palladium hydroxide. The amount used is usually in the range of about 0.05 to 1 mol per mol of the compound represented by formula (10).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene , nitriles such as acetonitrile; esters such as ethyl acetate; , these inert solvents can be used alone or in combination of two or more.

The compound represented by the production method (11) of step j is obtained by protecting the amino group of the compound represented by (8) with a protecting group in step g, and the pyrazine compound represented by formula (10) in step h. After that, compound (11) can be synthesized by deprotection in step i. 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 prepared directly.

Production method of step k A pyrazine compound represented by formula (11) is reacted in the presence of a diazotizing reagent, a halide, an acid and an inert solvent to produce a pyrazine compound represented by formula (7). can be done. Acid may not be added depending on the reaction. This reaction can be carried out according to the method described in literature (WO2013/053690A1).

Acids that can be used in this reaction include, for example, hydrochloric acid, hydrobromic acid, hydroiodic acid, tetrafluoroboric acid, and sulfuric acid. The amount used is usually about 1 mol or more per diazotizing reagent, and an acid can also be used as a solvent.

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

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene , nitriles such as acetonitrile; esters such as ethyl acetate; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. . This reaction can also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.

Production method of step 1 The pyrazine compound represented by formula (7) and the compound represented by formula (12) are reacted in the presence of a metal catalyst, a base and an inert solvent to obtain a compound represented by formula (13). It is possible to produce a pyrazine compound that This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry (2002), vol67, Issue26, p. 9392-9396).

Metal catalysts 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, Zerovalent palladium compounds such as [1,1′-bis(diphenylphosphino)butane]palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and , palladium(II) acetate, palladium(II) chloride, bis(acetonitrile)palladium(II) dichloride, bis(benzonitrile)palladium(II) dichloride, allylpalladium(II) chloride dimer, cyclopentadienylallyl palladium Known palladium catalysts such as (II) can be mentioned. Moreover, two or more of them can be used as necessary. The amount of the palladium catalyst to be used in the present invention may be appropriately selected in the range of usually about 0.001 to 0.1 mol per mol of 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by formula (7).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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. Alternatively, the next step may proceed without isolation and purification.
Manufacturing method 5
<Scheme 5>

Production method of step m (10-a) or (11- _a ) in which the R part of the compound represented by formula (10) or (11) is a halogen atom and H- having a hydroxyl group, an amino group or a mercapto group A pyrazine compound represented by Formula (10) or Formula (11) can be produced by reacting R _a 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, calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. , carbonates such as calcium carbonate and magnesium carbonate, acetates such as lithium acetate, sodium acetate and potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide and potassium tertiary butoxide, hydrogenation Examples include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine. The amount of the base to be used may be appropriately selected from the range of 0.5 to 5.0 times the molar amount of the compound represented by formula (10-a) or formula (11-a).

The inert solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. chain or cyclic ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene polar solvents such as nitriles such as acetonitrile, esters such as ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; , these inert solvents can be used alone or in combination of two or more.

The present invention provides compositions comprising a 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 provides a compound for controlling invertebrate pests comprising a compound of Formula (1) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. is provided, wherein said composition may further comprise at least one biologically active compound or agent.

The compound represented by formula (1) exhibits excellent control activity against agricultural and horticultural harmful pests, as shown in the following examples. Therefore, according to the present invention, there is provided a pest control agent comprising the compound represented by formula (1) or a salt thereof as an active ingredient. Moreover, the pest control agent according to the present invention may contain an agriculturally and horticulturally acceptable acid addition salt of these compounds as an active ingredient.
Acid addition salts specifically include inorganic acids such as hydrochlorides, sulfates, nitrates, phosphates, formates, acetates, oxalates, citrates, succinates, and maleates. , fumarate, tartrate, lactate, benzoate, phthalate and other carboxylic acid salts, mesylate, tosylate, benzenesulfonate and other sulfonic acid salts, and the like.

Insect species to be controlled in the present invention (insect species for which the compound represented by formula (1) exhibits a control effect) are not particularly limited, and can be used to control harmful pests in a wide range of agricultural and horticultural applications. can. Preferred insect species to be controlled include, for example, the following. Lepidoptera {e.g. Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis , Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Hellula undalis, Herpetogramma luctuosale, Pediasia teterrellus ), Rice case worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. Crambidae; litura), Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, African white Spodoptera exempta, Agrotis ipsilon, Autographa nigrisigna, Plusia festucae, Soybean looper (Chrysodeixis includens), Trichoplu sia spp.), Heliothis spp. such as Heliothis virescens, Helicoverpa armigera, Helicoverpa spp. such as Helicoverpa zea, Velvetbean caterpillar (Anticarsia gemmatalis) , Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc. Noctuidae; Pieridae, such as Pieris rapae; Grapholita molesta, Grapholita dimorpha , Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia Pomonella), Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc.; Gracillariidae); Carposinidae such as Carposina sasakii; Lyonetiidae such as Coffee Leaf miner (Leucoptera coffeella), Lyonetia clerkella, Lyonetia prunifoliella; Lymantria spp. such as Lymantria dispar, Lymantriidae such as Euproctis spp. such as Euproctis pseudoconspersa; Pluteliidae such as Plutella xylostella ); Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Tuta absoluta and other Gelechiidae; Arctiidae such as Hyphantria cunea Giant Sugarcane borer (Telchin licus), etc. Castniidae (Castniidae); Cossus insularis, etc. Cossidae; Geometridae, such as Ascotis selenaria; Limacodidae, such as; Stathmopoda masinissa, etc.; Sphingidae, such as Acherontia lachesis; Sesiidae, such as Nokona feralis; (Parnara guttata), etc. (Hesperiidae)}. Hemiptera pests {e.g. Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus (Delphacidae); Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Empoasca onukii), Potato leafhopper ( Empoasca fabae), corn leaf hopper (Dalbulus maidis), white leafhopper (Cofana spectra), etc. Leafhopper (Cicadelidae); Mahanarva posticata, Mahanarva fimbriolata, etc. Soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), Aphis spiraecola, green peach aphid (Myzus persicae), wheat wart aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae) ), Rosy apple aphid (Dysaphis plantaginea), Lipaphis erysimi (Lipaphis erysimi), Tulip aphid (Macrosiphum euphorbiae), Potato aphid (Aulacorthum solani), Lettuce aphid (Nasonovia ribisnigri), Rhopalosip aphid (Rhopalosip hum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hienoaphis (Melanaphis sacchari), black black aphid (Tetraneura nigriabdominalis), corn aphid (Ceratovacuna lanigera) Aphididae such as Eriosoma lanigerum; Family (Phylloxeridae); Adelgidae, such as Adelges tsugae, Adelges piceae, and Aphrastasia pectinatae; Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Southern stink bug ( Nezara viridula), Brown stink bug (Euschistus heroes), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, etc. (Pentatomidae); Burrower brown bug (Scaptoc oris castanea); Cydnidae, such as Riptortus pedestris; punctiger), Leptoglossus australis, etc.; Lygaeidae; Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris, etc. Miridae; Trialeurodes vaporariorum , Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Pealius euryae, etc. Aleyrodidae; (Abgrallaspis cyanophylli), Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, etc. Diaspididae); Coccidae, such as Ceroplastes rubens Margarodidae, such as Icerya purchasi and Icerya seychellarum; Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcidae, such as Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, and Brevennia rehi; Diaphorina citri), Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Pear psylla (Cacopsylla pyricola); (Corythucha ciliata), Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc.; Cicadidae. Coleoptera pests {e.g. Western Corn Rootworm (Diabrotica virgifera virgifera), Southern Corn Rootworm (Diabrotica undecimpunctata howardi), Northern Corn Rootworm (Diabrotica barberi), Mexican Corn Rootworm (Diabrotica virgifera zeae), Banded Cucumber Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Oulema melanopus, Aulacophora femoralis, Phyllotreta striolata, Cabbage flea beetle (Phyllotreta cruciferae) , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Rice beetle (Oulema oryzae), Grape colaspis (Colaspis brunnea), Corn flare beetle (Chaetocnema pulicaria), Sweet potato Longhorn beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), yellow beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirt)
ipennis), etc.; Carabidae, such as Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Phyllophaga spp. such as Popillia japonica, Heptophylla picea, European Chafer (Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., June beetle (Phyllophaga crinita) , Scarabaeidae such as Diloboderus genus (Diloboderus spp.) such as Diloboderus abderus (Scarabaeidae); Sitophilus zeamais, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineatocollis, Anthonomus grandis, Sphenophorus venatus, Southern Billbug (Sphenophorus callus) Soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rusty gourd weevil (Scepticus griseus), brown gourd weevil (Scepticus uniformis) , Brazilian bean weevil (Zabrotes subfasciatus), pine bark beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus spp. Tenebrionidae, such as Tribolium castaneum and Tribolium confusum; Coccinellidae, such as Epilachna vigintioctopunctata; Lyctus brunneus, etc. Bostrychidae); Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus; Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus , Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp. Elateridae, etc.; Staphylinidae, such as Paederus fuscipes. Thysanoptera {e.g., Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Rice thrips ( Stenchaetothrips biformis, Echinothrips americanus, and other Thripidae; Haplothrips aculeatus, and other Phlaeothripidae}. Diptera {e.g., Anthomyiidae such as Delia platura and Delia antiqua; Ulidiidae such as Tetanops myopaeformis; Agromyza oryzae ), Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola, etc.; Agromyzidae; Chloropidae, such as Chlorops oryzae; Tephritidae such as Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata; Ephydridae, such as Hydrellia philippina and Hydrellia sasakii; Drosophila, such as Drosophila suzukii; Phoridae, such as Megaselia spiracularis; (Clogmia albipunctata), etc.; Sciaridae, such as Bradysia difformis; Mayetiola destructor, Cecidomyiidae, such as Orseolia oryzae; Diopsis macrophthalma Diopsidae, such as; Tipula aino, Common cranefly (Tipula oleracea), Eur (Tipulidae) such as opean cranefly (Tipula paludosa)}. Hymenoptera (Hymenoptera) {for example, Athalia rosae, Athalia japonica, etc., Tenthredinidae; Fire Ant (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara), etc. etc.}. Orthoptera pests {e.g., Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Brown Locust (Locustana pardalina), Tree Locust (Anacridium melanorhodon ), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida), Desert locust (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Oxya yezoensis, Oxya japonica, Patanga succincta, etc. Acrididae; Gryllotalpidae, such as (Gryllotalpa orientalis); Gryllidae, such as European house cricket (Acheta domestica) and Emma cricket (Teleogryllus emma); Tettigoniidae, such as Mormon cricket (Anabrus simplex)}. Cockroach pests (Blattodea) {for example, Blattellidae family such as Blattella germanica; Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis, Blattidae such as Periplaneta japonica and Periplaneta australasiae; Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Taiwan Termites (Odontotermes formosanus), Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Amami termites Termitidae such as Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans )}. Acarina pests (Acari) {for example, spider mites such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp. Family (Tetranychidae); Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Eriophyidae, such as Aculus schlechtendali, Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Brevipalpus phoenicis Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, Dermacentor variabilis, Ixodes ovatus, Schultz Ixodidae such as Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Amblyomma americanum, Boophilus microplus, Rhipicephalus sanguineus; Tyrophagus putrescenti ae), Acaridae such as Tyrophagus similis; Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Cheyletidae such as Cheyletus moorei and Cheyletiella yasguri; Sarcoptidae such as Otodectes cynotis and Sarcoptes scabiei; Demodex canis such as Demodex canis ( Demodicidae); Listrophoridae; Haplochthoniidae; Ornithonyssus bacoti, Macronyssidae such as Ornithonyssus sylviarum; Trombiculidae such as (Leptotrombidium akamushi), etc.}. Plant parasitic nematodes {e.g., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, Bursaphelenchus xylophilus, and other leaf nematodes (Aphelenchida) nematodes, Potato cyst nematode (Globodera pallida), potato cyst nematode (Globodera rostochiensis), wheat cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii), Arena Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne mali, Pratylenchus coffeae, Pralenty drenatus), Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus vulnus, Radopholus citrophilus, Banana nematode ( Radopholus similis), etc. (Tylenchida)}.

Insect species targeted for control in the present invention (insect species for which the compound represented by formula (1) exhibits a control effect) include harmful insect pests such as sanitary pests, storage pests, clothing pests, house pests, and parasites. It can also be used to control organisms. It is particularly effective in controlling ectoparasites, which are harmful to humans and animals. Ectoparasites that are subject to control include parasites that live on the back, armpits, lower abdomen, inner thighs, etc. of host animals and obtain nutrients such as blood and dander from animals and birds, and host animals. Includes those that fly to the back and buttocks of animals and obtain nutrients such as blood and dander from animals and birds. Ectoparasites include mites, lice, fleas, and the like.

Host animals for which the control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; pet birds (e.g., pigeons, parrots, mynahs, Java sparrows, parakeets, marigolds, and canaries). cattle, horses, pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); honeybees (eg, European honey bees, Japanese honey bees);

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

The target mites (Acari) include the following pests. Mites of Mesostigmata {for example, Dermanyssidae such as Dermanyssus gallinae; Ornithonyssus sylviarum of Ornithonyssus spp., Ornithonyssus bursa ticks of the family Macronyssidae, including Ornithonyssus bacoti; Laelapidae, including Laelaps echidninus, Laelaps jettmari, and Tropilelaps clarae of the genus Laelaps spp. ); mites of the family Varroidae including Varroa spp. Varroa destructor, Varroa jacobsoni, Varroa underwoodi. Ticks of the order Metastigmata {e.g., Argas persicus of Argas spp., Argas reflexus, Ornithodoras of Ornithodoros spp. Ticks of the family Argasidae, including Ornithodoros moubata; Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis cinnabarina of Haemaphysalis spp. Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Haemaphysalis yeni, Haemaphysalis campanulata, Haemaphysalis penagital tick Haemaphysalis flava, Haemaphysalis megaspinosa, Haemaphysalis japonica, Haemaphysalis douglasi, Amblyomma spp. Amblyomma americanum, Amblyomma variegatum , Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinarium, Ixodes ricinus, Ixodes spp. Hexagonus ( Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis, Rhipicephalus (Boophilus) microplus of Boophilus spp., Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) decoloratus Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Rhipicephalus spp. ) of Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus (Rhipicephalus turanicus), Rhipicephalus zambeziensis, Dermacentor marginatus of Dermacentor spp., Dermacentor reticulatus, Dermacentor pictus ), Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis}. Acaridida of the order Astigmata {e.g. Psoroptes ovis of Psoroptidae spp., Psoroptes cuniculi, Psoroptes equi, Mites of the family Psoroptidae, including Chorioptes bovis of Chorioptes spp. and Otodectes cynotis of Otodectes spp.; spp.), Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes equi mites of the family Sarcoptidae, including , Sarcoptes suis, and Notoedres cati of the spp. Notoedres spp.; Knemidokoptes spp. Mites of the family Knemidokoptidae, including (Knemidokoptes mutans). Actinedida of the order Prostigmata {e.g. Demodex canis of Demodex spp., Demodex bovis, Demodex ovis, Demodex caprae ), Demodex equi, Demodex caballi, Demodex suis, and Demodex cati; Trombiculidae including Trombicula alfreddugesi and Trombicula akamushi}. Lice (Phthiraptera) include the following pests. Louses of the suborder Anoplura (louses of the family Haematopinidae, including, for example, Haematopinus asini, Haematopinus eurysternus, and Haematopinus suis of the genus Haematopinus spp.; Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis , lice of the family Linognathidae, including Solenopotes capillatus of Solenopotes spp.}. Biting louses of the suborder Amblycera {e.g. Menacanthus stramineus, Menacanthus cornutus, Menacanthus pallidulus, Menacanthus spp. of the family Menoponidae, including, for example, Menopon gallinae of the genus Menopon spp.}. Biting louses of the suborder Ischnocera {e.g. Columbicola columbae of the spp.Columbicola spp., Cuclotogaster spp. heterographus), Goniodes dissimilis, Goniodes gigas, Goniodes gallinae, and Lipeurus caponis of Lipeus spp. Lice of the family Philopteridae; Bovicola bovis of the spp. Bovicola spp., Bovicola ovis, Bovicola limbata, Bovicola caprae, Bovicola equi ), Trichodectes canis of Trichodectes spp., and Felicola subrostrata of Felicola spp.}. Fleas (Siphonaptera) include the following pests: Fleas of the family Tungidae, including e.g. Tunga spp. Tunga penetrans; Ctenocephalides canis, Ctenocephalides felis, Archaeopsilla spp. Archaeopsylla erinacei, Xenopsylla spp., Xenopsylla cheopis, Pulex spp., Pulex irritans, Echidnophaga spp. Fleas of the family Pulicidae including Echidnophaga gallinacea of ); Ceratophyllus gallinae of Ceratophyllus spp., Ceratophyllus anisus, Nosopsyllus spp. fleas of the family Ceratophyllidae, including the European rat flea (Nosopsyllus fasciatus) of A.; Other ectoparasites of interest include Hemiptera pests. Hemiptera pests include the following pests. Insects of the family Cimicidae, including, for example, Cimex spp. Cimex lectularius; Panstrongylus spp., Rhodnius spp. prolixus), insects of the family Reduviidae, including Triatoma infestans of the genus Triatoma spp. It is also effective against Diptera pests, which are biting insects (chewing flies, blood-sucking adult flies, migratory dipteran larvae, parasitic fly maggots). Pests of flies (Diptera) include the following pests. Nematocera {e.g. (a) Culex spp. Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres subalbatus of Armigeres spp., Anopheles gambiae of Anopheles spp., Anopheles maculipennis, Anopheles sinensis, Anopheles lesteri, Aedes aegypti of Aedes spp., Aedes albopictus, Aedes taeniorhynchus, Aedes taeniorhynchus Aedes togoi, Aedes vexans nipponii; (b) Simulium reptans of Simulium spp., Simulium ornatum, Aedes vexans nipponii; blackflies of the family Simuliidae, including Simulium venustum, Simulium salopiense, Prosimulium yezoense of Prosimulium spp.; Culicoides arakawae of Culiodes spp. Culicoides pictimargo, Culicoides kibunensis, Culicoides homotomus, Culicoides oxystoma, The biting midges of the family Ceratopogonidae, including Culicoides nipponensis, Culicoides punctatus, Culicoides maculatus, and Culicoides matsuzawai. }. Suborder Brachycera {e.g. (a) Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, e.g. Tabanus spp. ), Tabanus trigonus, Tabanus chrysurus, Tabanus trigeminus, Tabanus fulvimedioides, Tabanus iyoensis, Chrysops caecutiens of Chrysops spp., Chrysops Tabanidae, including Chrysops relictus, Chrysops suavis, Chrysops japonicus; Musca domestica, Musca bezzii, Neue fly of Muscina spp. (Musca hervei), Musca conducens, Musca stabulans, Stomoxys calcitrans, Haematobia spp. Haematobia irritans, Haematobia Flies of the family Muscidae, including Haematobia irritans exigua, Haematobia stimulans, and Fannia canisularis of the Fannia spp.; Glossina spp. flies of the family Glossinidae, including Melophagus spp.; flies of the family Hippoboscidae, including Melophagus ovinus; Lata);, Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) sericata, Lucilia illustris, Chrysomyia, Chrysomyia spp. flies of the Calliphoridae family, including Chrysomya chloropyga, Chrysomya bezziana; Cuterebrinae, Cuterebra spp. ), Hypoderma bovis of Hypodermatinae and Hypoderma spp., Hypoderma lineatum, Gasterophilinae and Gasterophilus spp. Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Oestrinae ) and also flies of the family Oestridae, including Oestrus ovis of the genus Oestrus spp.

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

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, silica sand, silica stone, zeolite, perlite, attapulgite, 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, kerosene and kerosene. , Toluene, xylene, aromatic hydrocarbons such as methylnaphthalene, ethers such as diethyl ether, dioxane, tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamide, dimethylacetamide, etc. acid amides, vegetable oils such as soybean oil and cottonseed oil, dimethylsulfoxide, water and the like.
Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide, dimethyl ether, and the like.
Examples of the surfactant and the dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, and alkyl sulfosuccinates. Salts, formalin condensates of alkylnaphthalene sulfonates, polycarboxylates, POE polystyrylphenyl ether sulfates and phosphates, POE/POP block polymers, and the like.
Further, the formulation adjuvant includes, for example, carboxymethylcellulose, hydroxypropylcellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, polyethylene glycol, liquid paraffin, calcium stearate, antifoaming agents, preservatives and the like.
The various carriers, surfactants, dispersants, and formulation aids described above can be used alone or in combination, if necessary.

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

When the compound represented by formula (1) is used as an acaricide for controlling mites parasitic on domestic animals such as cattle and pigs, and pet animals such as dogs and cats, , the active ingredient can be used in an amount of 0.01 to 1000 mg.
Acaricides for control can be applied by known veterinary techniques. For example, for the purpose of systemic suppression, administration to animals is by tablets, capsules, immersion solutions, mixed feed, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). For the purpose of non-systemic control, there are methods such as spraying, pour-on, and spot-on of oily or aqueous solutions, and kneading miticides into resins. and forming the kneaded product into a suitable shape such as a collar or ear tag, which is then worn on the animal.

The pesticide according to the invention can be used as is or diluted. Moreover, the pest control agent according to the present invention can be mixed or used together with other insecticides, nematicides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like. Drugs that can be mixed or used together include, for example, Pesticide Manual (17th edition, published by The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 17th edition, published by SHIBUYA INDEX RESEARCH GROUP in 2014) and eye Mode of Action Classification Scheme Version 8.2, published by IRAC, FRAC Code List 2017: Fungicides sorted by mode of action, 2017 edition, published by FRAC Examples include those described and those whose structures can be identified on the Internet (http://www.alanwood.net/pesticides/sitemap.html).

More specifically, insecticides include, for example, alanycarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim ( butoxycarbboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb, metolcarb carbamate compounds such as (metolcarb), phenothiocarb, fenoxycarb;
acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon (diazinon), dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenitrothion ( fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion (isoxathion), malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, dioxydemeton ethyl), parathion, parathion-methyl, PAP, forate, phosalone, phosalone phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinarphos (quinalphos), sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion ), chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazophos, phenthoate, phonofos, tribufos and other organic phosphate compounds,
organochlorine compounds such as endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor;
phenylpyrazole compounds such as acetoprole, fipronil, ethiprole, pyrafluprole, pyriprole, flufiprole;
metadiamide compounds such as broflanilide,
isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, and fluxametamide;
acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl (bioallethrin S-cyclopentenyl), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin (gamma-cyhalothrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin ), cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate ), flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prallethrin, pyrethrin (pyrethrin), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin tramethrin, tralomethrin, transfluthrin, metoxadiazone, metofluthrin, profluthrin, pyrethrum, terallethrin, momfluorothrin, heptafluthrin 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, dichloromezotiaz,
2-aminopyridine compounds spinosad such as flupyrimin, spinosyn compounds such as spinetoram,
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,
pyridine azomethine 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 insecticidal proteins produced by them,
an insecticidal protein produced by a Bt crop that corresponds to the above;
thiourea-based compounds such as diafenthiuron;
organometallic compounds such as azocyclotin, cyhexatin, fenbutatin oxide;
sulfite and diphenyl ether compounds such as propargite;
diphenylsulfone compounds such as tetradifon,
pyrrole compounds such as chlorfenapyr and tralopyril, dinitro compounds such as DNOC,
nereistoxin analogues such as bensultap, cartap, thiocyclam, thiosultap, thiosultap sodium;
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), noviflumuron, teflubenzuron, triflumuron, benzoyl urea compounds such as bistrifluron,
Thiadiazine-based compounds such as buprofezin,
triazole compounds such as cyromazine,
diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
Amidine compounds such as amitraz,
Amidinohydrazone compounds such as hydramethylnon,
Naphthoquinone compounds such as acequinocyl,
strobilurin compounds such as fluacrypyrim, pyriminostrobin, flufenoxystrobin;
quinazoline compounds such as fenazaquin,
phenoxypyrazole compounds such as fenpyroxymate;
Phenoxyethylamine compounds such as pyrimidifen,
Pyridazinone compounds such as pyridaben,
pyrazole carboxamide compounds such as tebufenpyrad, tolfenpyrad, pyflubumide;
hydrazine carboxamide compounds such as metaflumizone,
tetronic and tetramic acid compounds such as spirodiclofen, spirotetaramat, spiromesifen, spiropidion;
beta-ketonitriles such as cyflumetofen, cyenopyrafen,
Phthalamide compounds such as flubendiamide,
anthraniliprole, such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole acid amide compounds,
Quinoxaline compounds such as quinomethionates,
Thiazolidinone compounds such as hexythiazox,
hydrazine compounds such as bifenazate,
pyridinamine compounds such as flufenerim,
Aminoquinazoline compounds such as pyrifluquinazon,
6-phenoxyquinoline compounds such as flometoquin,
pyridinylethylbenzamide compounds such as fluopyram,
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 insecticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, Indian indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, aphidopyropen, fluhexafon, fluensulfone, benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate salt, metaaldehyde, ryanodine, sulfluramid, acinonapyr acynonapyr), benzpyrimoxan, 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H -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 entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

Bactericides used are, for example, metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, kiralaxyl , ofurace, furalaxyl, phenylamide compounds such as cyprofuram,
Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, ethilimol,
isoxazole compounds such as hymexazole and 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-phenyl carbamate compounds such as diethofencarb,
Toluamide compounds such as zoxamide,
Ethylaminothiazole carboxamide compounds such as ethaboxam,
Phenylurea compounds such as pencycuron,
pyridinylmethylbenzamide compounds such as fluopicolide, fluopimomide;
pyrimidine amine compounds such as diflumetorim, bupirimate,
Benzanilide compounds such as benodanil, flutolanil, mepronil,
Phenyloxoethylthiophenamide compounds such as isofetamide,
pyridinylethylbenzamide compounds such as fluopyram,
Furancarboxamide compounds such as fenfuram,
oxathiin carboxamide compounds such as oxycarboxin, carboxin,
Thiazole carboxamide compounds such as thifluzamide,
Fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, impylfluxam pyrazole-4-carboxamide compounds such as (inpyrfluxam), fluindapyr, isoflucypram, pyrapropoyne;
pyridinecarboxamide compounds such as boscalid,
azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin (dimoxystrobin), metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, flufenoxystrobin, phenaminestrobin strobilurin compounds such as (fenaminstrobin), enoxastrobin, coumoxystrobin, mandestrobin, triclopyricarb;
oxazolidinedione compounds such as famoxadone;
imidazolinone compounds such as fenamidone,
benzylcarbamate compounds such as triclopyricarb, pyribencarb;
Cyanoimidazole compounds such as cyazofamid,
sulfamoyltriazole 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,
acetic acid-fentin-acetate, fentin chloride, fentin hydroxide, fenthin hydroxide, fenthin acetate, oxine copper organic and inorganic metal compounds such as
Thiophenecarboxamide compounds such as silthiofam,
triazolopyrimidine amine compounds such as ametoctradin;
Anilinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimethanil, cyprodinil, enopyranuronic acid antibiotics such as blasticidin-S,
hexopyranosyl antibiotics such as kasugamycin, kasugamycin hydrochloride hydrate,
Glucopyranosyl antibiotics such as streptomycin,
tetracycline antibiotics such as oxytetracycline, allyloxyquinoline compounds such as quinoxyfen,
quinazoline compounds such as proquinazid;
Cyanopyrrole compounds such as fludioxonil, fenpiclonil,
dicarboximide compounds such as fluoroimid, procymidone, iprodione, vinchlozolin;
phosphorothiolate compounds such as edifenphos, iprobenfos, pyrazophos;
Dithiolane compounds such as isoprothiolane,
propyl carbamate compounds such as propamocarb, propamocarb hydrochloride;
Bacillus genus and produced bactericidal proteins such as Bacillus subtilis (QST713, FZB24, MBI600, D747 strains), and
fungicidal proteins produced by the Bt crops;
terpene hydrocarbons and terpene alcohols, such as extracts of Gosseikajupt;
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, pefurazoate ( pefurazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol , 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 and pyrimorph ,
Piperidine compounds such as piperalin, fenpropidin,
Spiroketalamine compounds such as spiroxamine,
hydroxyanilide compounds such as fenhexamid,
aminopyrazolinone compounds such as fenpyrazamine;
ferbam, metam, metasulphocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamates ( thiocarbamate/dithiocarbamate compounds such as polycarbamate, propineb, thiuram, and pyributicarb;
glucopyranosyl antibiotics such as validamycin,
Nucleoside antibiotics such as mildiomycin, polyoxin,
valinamide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, iprovalicarb;
Mandelic acid amide compounds such as mandipropamid,
Picolinamide compounds such as fenpicoxamid, florylpicoxamid,
Isobenzofuranone compounds such as fthalides,
Pyrroloquinolinone compounds such as pyroquilone,
triazolobenzothiazole compounds such as tricyclazole;
Cyclopropanecarboxamide compounds such as carpropamid,
Carboxamide compounds such as diclocymet,
Propionamide compounds such as fenoxanil,
benzothiadiazole compounds such as acibenzolar-S-methyl,
benzoisothiazole compounds such as probenazole and dichlobentiazox;
Thiadiazole carboxamide compounds such as tiadinil,
isothiazole carboxamide compounds such as isotianil;
Cyanoacetamide = oxime compounds such as cymoxanil,
Ethylphosphonate compounds such as fosetyl,
phthalamic acid compounds such as techlophthalam,
benzotriazine compounds such as triazoxide,
Benzene sulfonic acid compounds such as flusulfamide,
pyridazinone compounds such as diclomezine,
Phenylacetamide compounds such as cyflufenamide,
benzophenone compounds such as metrafenopne,
Benzoylpyridine compounds such as pyriofenone,
Cyanomethylenethiazolidine compounds such as flutianil,
4-quinolyl acetic acid compounds such as tebufloquin,
3-phenoxyquinoline compounds such as ipflufenoquin,
organophosphorus compounds such as fosetyl-aluminium, tolclofos-methyl;
1,2,4-thiadiazole compounds such as eclomezole,
Trifluoroethyl carbamate compounds such as tolprocarb,
Bordeaux mixture, copper acetate, basic copper sulfate, oxy copper chloride, copper hydroxide, oxine-copper ), copper-based compounds such as
inorganic compounds such as copper, sulfur,
N-halogenothioalkyl compounds such as captan, captafol, folpet,
organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene;
Iminoctadine triacetate salt, iminoctadine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate salt ), guanidine compounds such as albesilates,
Anthraquinone compounds such as dithianon,
Quinoxaline compounds such as quinomethionates,
Maleimide compounds such as fluoroimide,
sulfenic acid compounds such as tolylfluanid and dichlofluanid;
Dinitrophenolic compounds such as dinobuton,
cyclic dithiocarbamate compounds such as dazomet, anilide compounds such as pyraziflumid,
Nicotinic acid ester compounds such as aminopyrifen,
tetrazolinone compounds such as methyltetraprole,
pyridazine-based compounds, such as pyridaclomethyl.
Other fungicides include dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium. (prohexadione-calcium), bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, etc. be done.

By applying an effective amount of the compound represented by the formula (1) of the present invention or its agriculturally and horticulturally and veterinarily acceptable acid addition salt to plants, soil or animals, Can be used for control. Thus, methods for controlling pests in these areas are provided. Here, the control method according to the present invention also includes a method of applying the compound represented by formula (1) or an agriculturally and horticulturally acceptable acid addition salt thereof in a closed space by smoking.
The compound represented by formula (1) of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof may also be applied to crops, seeds for growing crops, or placenta of crops in a biologically effective amount. Increases the vitality of crops by being in contact with them.
When the object to be treated or contacted is seeds, the amount of the compound represented by formula (1) of the present invention or its agriculturally and horticulturally acceptable acid addition salt is not limited, but is about 0.5% of the whole seed after treatment. 0001 to about 1% by weight of the compound represented by formula (1) of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof.
The present invention further provides the use of the compound represented by 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 invertebrate organisms. 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 parasiticidally effective and does not harm target animals and birds. In the above use, the compound represented by the formula (1) of the present invention or an acid addition salt thereof is brought into contact with harmful invertebrate organisms or their growing environment in a biologically effective amount to control harmful invertebrate organisms.

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, c- Pent represents a cyclopentyl group.

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

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

A 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 a combination shown in Table 1 in formula (A-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

A 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 a combination shown in Table 1 in formula (A-1).

A 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 a combination shown in Table 1 in formula (A-1).

A 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 combinations shown in Table 1 in formula (A-1).

A 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 a combination shown in Table 1 in formula (A-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (A-1).

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

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

A 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 a combination shown in Table 1 in formula (A-1).

A 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 a combination shown in Table 1 in formula (A-1).

A 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 a combination shown in Table 1 in formula (A-1).

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

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

A 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 a combination shown in Table 1 in formula (B-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

A 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 a combination shown in Table 1 in formula (B-1).

A 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 combinations shown in Table 1 in formula (B-1).

A 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 combinations shown in Table 1 in formula (B-1).

A 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 a combination shown in Table 1 in formula (B-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 combinations described in Table 1. Compound of the present invention.

A compound of the present invention represented by 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 a combination shown in Table 1.

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

A 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 a combination shown in Table 1 in formula (B-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (B-1).

A 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 a combination shown in Table 1 in formula (B-1).

A 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 a combination shown in Table 1 in formula (B-1).

A 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 combinations shown in Table 1 in formula (B-1).

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

A compound of the present invention in which R is CF ₃ CH ₂ CH ₂ — and R ₁ , R ₂ , R _a , R _b , R _C and R _d are a combination shown in Table 1 in formula (C-1). {In the formula, R ₁ , R ₂ , R _a , R _b , R _c and R _d are as defined above. }

A 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 a combination shown in Table 1 in formula (C-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

A 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 a combination shown in Table 1 in formula (C-1).

A 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 combinations shown in Table 1 in formula (C-1).

A 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 combinations shown in Table 1 in formula (C-1).

A 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 a combination shown in Table 1 in formula (C-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (C-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (C-1).

A 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 a combination shown in Table 1 in formula (C-1).

A 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 a combination shown in Table 1 in formula (C-1).

A 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 combinations shown in Table 1 in formula (C-1).

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

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

A 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 a combination shown in Table 1 in formula (D-1).

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

A 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 a combination shown in Table 1 in formula (D-1).

A 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 a combination shown in Table 1 in formula (D-1).

A 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 a combination shown in Table 1 in formula (D-1).

A 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 a combination shown in Table 1 in formula (D-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (D-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (D-1).

A 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 a combination shown in Table 1 in formula (D-1).

A 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 a combination shown in Table 1 in formula (D-1).

A 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 combinations shown in Table 1 in formula (D-1).

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

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

A 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 a combination shown in Table 1 in formula (E-1).

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

A 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 a combination shown in Table 1 in formula (E-1).

A 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 combinations shown in Table 1 in formula (E-1).

A 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 a combination shown in Table 1 in formula (E-1).

A 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 a combination shown in Table 1 in formula (E-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (E-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (E-1).

A 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 a combination shown in Table 1 in formula (E-1).

A 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 a combination shown in Table 1 in formula (E-1).

A 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 combinations shown in Table 1 in formula (E-1).

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

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

A 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 a combination shown in Table 1 in formula (F-1).

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

A 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 a combination shown in Table 1 in formula (F-1).

A 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 combinations shown in Table 1 in formula (F-1).

A 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 a combination shown in Table 1 in formula (F-1).

A 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 a combination shown in Table 1 in formula (F-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 combinations described in Table 1. Compound of the present invention.

A compound of the present invention represented by 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 a combination shown in Table 1.

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

A 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 a combination shown in Table 1 in formula (F-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (F-1).

A 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 a combination shown in Table 1 in formula (F-1).

A 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 combinations shown in Table 1 in formula (F-1).

A 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 a combination shown in Table 1 in formula (F-1).

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

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

A 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 a combination shown in Table 1 in formula (G-1).

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

A 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 a combination shown in Table 1 in formula (G-1).

A 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 a combination shown in Table 1 in formula (G-1).

A 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 a combination shown in Table 1 in formula (G-1).

A 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 a combination shown in Table 1 in formula (G-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 combinations described in Table 1. Compound of the present invention.

A compound of the present invention represented by 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 a combination shown in Table 1.

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

A 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 a combination shown in Table 1 in formula (G-1).

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

A compound of the present invention in which R is 4-tBuOPh- and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (G-1).

A 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 a combination shown in Table 1 in formula (G-1).

A 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 combinations shown in Table 1 in formula (G-1).

A 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 a combination shown in Table 1 in formula (G-1).

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

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

A 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 a combination shown in Table 1 in formula (H-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

A 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 a combination shown in Table 1 in formula (H-1).

A 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 a combination shown in Table 1 in formula (H-1).

A 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 a combination shown in Table 1 in formula (H-1).

A 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 a combination shown in Table 1 in formula (H-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (H-1).

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

A compound of the present invention in which R is 4-tBuOPh— and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (H-1).

A 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 a combination shown in Table 1 in formula (H-1).

A 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 a combination shown in Table 1 in formula (H-1).

A 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 combinations shown in Table 1 in formula (H-1).

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

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

A 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 a combination shown in Table 1 in formula (I-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

A 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 a combination shown in Table 1 in formula (I-1).

A 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 combinations shown in Table 1 in formula (I-1).

A 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 a combination shown in Table 1 in formula (I-1).

A 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 a combination shown in Table 1 in formula (I-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (I-1).

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

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

A 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 a combination shown in Table 1 in formula (I-1).

A 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 a combination shown in Table 1 in formula (I-1).

A 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 a combination shown in Table 1 in formula (I-1).

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

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

A 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 a combination shown in Table 1 in formula (J-1).

The present invention, wherein 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 combinations described in Table 1. Compound.

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

A 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 a combination shown in Table 1 in formula (J-1).

A 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 a combination shown in Table 1 in formula (J-1).

A 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 a combination shown in Table 1 in formula (J-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 combinations described in Table 1. Compound of the present invention.

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

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

A 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 a combination shown in Table 1 in formula (J-1).

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

A compound of the present invention in which R is 4-tBuOPh— and R ₁ , R ₂ , R _a , R _b , R _c and R _d are a combination shown in Table 1 in formula (J-1).

A 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 a combination shown in Table 1 in formula (J-1).

A 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 combinations shown in Table 1 in formula (J-1).

A 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 combinations shown in Table 1 in formula (J-1).

A compound of the present invention wherein R ₁ , R ₂ , R _a , R _b , R _C and R _d are combinations shown in Table 1 in formula (K-1). {In the formula, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as defined above. }

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

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

A compound of the present invention in which R is CF ₃ — and R ₁ , R ₂ , R _a , R _b , R 2 _C and R _d are a combination shown in Table 1 in formula (N-1). {In the formula, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as defined above. }

A compound of the present invention in which R is CF ₃ CF ₂ — and R ₁ , R ₂ , R _a , R _b , R _C and R _d are a combination shown in Table 1 in formula (N-1). {In the formula, R ₁ , R ₂ , R _a , R _b , R _c and R _d are the same as defined above. }

A 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 a combination shown in Table 1 in formula (N-1).

Compounds of the invention can exist as one or more conformational isomers due to restricted rotation of bonds caused by steric hindrance. For example, a compound of formula (1) in which the 4-pyridyl group is substituted at the ortho position with a bulky alkyl group (eg, isopropyl) can be converted into two species by restricted rotation about the 4-pyridyl group-pyrazinium ring bond. It can exist as rotamers. The present invention includes mixtures of conformers.

<Synthesis example>
EXAMPLES The present invention will be specifically described below with reference to Examples, but the present invention is not limited to these Examples. In the NMR data, "s" is a singlet, "d" is a doublet, "t" is a triplet, "q" is a quartet, and "quin" is a quintet. (quintet), "sext" indicates a sectet (sextet), "sep" indicates a septet (seventet), and "m" indicates a multiplet (multiplet).

Synthetic Example 1-1: Preparation of 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine 2,5-dibromopyrazine (5.00 g, 21.02 mmol) was mixed with dimethylformamide ( 75 ml) and 2,2,3,3,3-pentafluoropropan-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 stirred overnight at room temperature. Water was added, and 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 and filtered, and ethyl acetate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (6.09 g, 94.4%, pale yellow oil). got
¹ H NMR (CDCl ₃ ) δ 8.22 (1H, d, J = 2.9Hz), 8.16 (1H, d, J = 2.9Hz), 4.82 (2H, ddd, J = 14.9Hz, 12.0Hz, 3.0Hz)

Synthesis Example 1-2: Preparation of 2-(2,2,3,3,3-pentafluoropropoxy)-5-(pyridin-4-yl)pyrazine (Compound No.-1) In Synthesis Example 1-1 The prepared 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (0.57 g, 1.86 mmol) was dissolved in dioxane (60 ml), and under a nitrogen atmosphere, a bisulfite was added at room temperature. (Triphenylphosphine)palladium (II) dichloride (0.13 g, 0.19 mmol) was added and the temperature was raised to 60°C. After that, 4-pyridylboronic acid (0.27 g, 2.2 mmol) and 2M aqueous sodium hydrogencarbonate solution (6 ml) were sequentially added at 60° C. and stirred for 4 hours. After cooling to room temperature, dioxane was distilled off under reduced pressure using an evaporator, diluted with ethyl acetate and water, and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was distilled off under reduced pressure using an evaporator. The crude product obtained was purified by silica gel chromatography to give 2-(2,2,3,3,3-pentafluoropropoxy)-5-(pyridin-4-yl)pyrazine (0.39 g, 68.8 g). %, white solid).
¹ H NMR (CDCl ₃ ) δ 8.74 (2H, d, J = 6.0 Hz), 8.61 (1H, d, J = 1.5 Hz), 8.46 (1H, d, J = 1.2 Hz), 7.85 (2H, dd , J=4.8Hz, 1.5Hz), 4.92(2H, td, J=12.8, 0.9Hz)

Synthetic Example 2-1: 2-(2,2,3,3,3-pentafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl ) Preparation of pyrazine 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (3.74 g, 12.18 mmol) prepared in Synthesis Example 1-1 was dissolved in dioxane (55 ml). bis(pinacolato)diboron (3.10 g, 12.21 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.50 g, 0.61 mmol), potassium acetate (3 .59 g, 36.58 mmol) were sequentially added, and the mixture was heated and stirred under reflux conditions for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered using a filter aid to remove solids. The filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product 2-(2,2,3,3,3-pentafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) Pyrazine (4.31 g, 100%, brown oil), was used in the next reaction without purification.
¹ H NMR (CDCl ₃ ) δ 8.52 (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)

Synthetic Example 2-2: Preparation of 2-(3-chloropyridin-4-yl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (Compound No.-6) 3-chloro- 4 Iodopyridine (0.57 g, 2.381 mmol) was dissolved in dioxane (45 ml) and bis(triphenylphosphine)palladium(II) dichloride (0.17 g, 0.24 mmol) was added at room temperature under nitrogen atmosphere, The temperature was raised to 60°C. Thereafter, 2-(2,2,3,3,3-pentafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3 prepared in Synthesis Example 2-1 was heated at 60°C. , 2dioxaboran-2-yl)pyrazine (1.1 g, 1.2 mmol) and 2M aqueous sodium hydrogencarbonate solution (6 ml) were sequentially added and stirred for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and water and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was distilled off under reduced pressure using an evaporator. The crude product obtained was purified by silica gel chromatography to give 2-(3-chloropyridin-4-yl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (0.39 g, 91.6%, brown oil).
¹ H NMR (CDCl ₃ ) δ 8.73 (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)

Synthetic Example 3-1: Preparation of 2-bromo-5-(pyridin-4-yl)pyrazine 2,5-dibromopyrazine (0.50 g, 2.102 mmol) was dissolved in dioxane (50 ml) and dissolved under 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. After that, 4-pyridylboronic acid (0.26 g, 2.1 mmol) and 2M aqueous sodium hydrogencarbonate solution (5 ml) were sequentially added at 60° C. and stirred for 3 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and water and filtered using a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-bromo-5-(pyridin-4-yl)pyrazine (0.11 g, 22.2%, pale yellow solid).
1H NMR ( _CDCl3 ) δ 8.86 (1H, d, J= ^1.2Hz ), 8.83-8.74 (3H, m), 7.90 (2H, dd, J=4.5Hz, 1.8Hz)

Synthetic Example 3-2: 2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-5-(pyridin-4-yl)pyrazine (Compound No.-19) Preparation of 2-bromo-5-(pyridin-4-yl)pyrazine (0.96 g, 0.41 mmol) prepared in Synthesis Example 3-1 was dissolved in dimethylformamide (2 ml), and 1,1 , 1,3,3,3-hexafluoropropan-2-ol (0.83 g, 0.4939 mmol), potassium carbonate (0.11 g, 0.82 mmol), 18-crown-6-ether (catalytic amount). It was added sequentially and stirred overnight at room temperature. Water was added, and 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 and filtered, and ethyl acetate was distilled off under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to give 2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-5-(pyridin-4-yl) Pyrazine (0.66 g, 50.2%, light brown solid) was obtained.
¹ H NMR (CDCl ₃ ) δ 8.78 (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)

Synthetic Example 4-1: Preparation of tert-butyl N-(5-bromopyrazin-2-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl)]carbamate 2-amino-5-bromo Dissolve pyrazine (5.00 g, 28.74 mmol), N,N-diisopropylethylamine (14.6 mL, 85.86 mmol), 4-dimethylaminopyridine (3.51 g, 28.73 mmol) in tetrahydrofuran (50 mL), Di-tert-butyl dicarbonate (13.22 g, 60.57 mmol) was added slowly without vigorous effervescence. 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 the residue was concentrated under reduced pressure to obtain a brown solid composition, which was purified by silica gel chromatography to obtain the title compound. (7.60 g, 70.7% yield, white solid)
^1H NMR( _CDCl3 ) δ 8.54(1H, s), 8.36(1H, s), 1.46(18H, s)

Synthetic Example 4-2: tert-butyl N-(5-(3-fluoropyridin-4-yl)pyrazin-2-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl)]carbamate Preparation of tert-butyl N-(5-bromopyrazin-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) was dissolved in 1,4-dioxane (60 mL), potassium carbonate (3.32 g, 24.02 mmol) was added thereto, and the reactor was filled with 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 reflux for 5 hours. After allowing to cool, appropriate amounts of water and ethyl acetate were added, suction filtration was performed using celite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to give the title compound (1.08 g, yield 34.5%, pale brown solid).
1H NMR( _CDCl3 ) 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)

Synthetic Example 4-3: Preparation of 5-(3-fluoropyridin-4-yl)pyrazin-2-amine tert-butyl N-(5-(3-fluoropyridin-4-yl)pyrazin-2-yl) -N-[(2-methylpropan-2-yl)oxycarbonyl)]carbamate (3.12 g, 7.99 mmol) was dissolved in methanol (50 mL), and concentrated hydrochloric acid (25 mL) was added with stirring. After cooling for 2 hours, the reaction mixture was basified with an aqueous sodium hydroxide solution, and concentrated under reduced pressure to remove methanol.The resulting aqueous layer was extracted three 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 the residue was concentrated under reduced pressure to give the title compound (1.39 g, yield 91.5%, pale brown solid).
¹ H NMR(CDCl ₃ ) δ 8.68(1H, s), 8.54(1H, d, J=3.0 Hz), 8.48(1H, d, J=4.8 Hz), 8.12(1H, s), 7.95(1H, t, J=5.7Hz), 4.83(2H, s)

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

Synthetic Example 4-5: Preparation of 2-[3-(ethylthio)pyridin-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 isoamyl nitrite (2.1 mL, 15.78 mmnol), diiodomethane (0.43 mL, 5.35 mmol), copper (II) iodide (1.01 g , 5.30 mmol) was added, and the mixture was stirred under reflux for 3 hours. After allowing to cool, appropriate amounts of water and ethyl acetate were added, suction filtration was performed using celite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to give the title compound (0.97 g, 58.6% yield, 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)

Synthetic Example 4-6: Preparation of 2-[3,5-bis(trifluoromethyl)phenyl]-5-[3-(ethylthio)pyridin-4-yl]-pyrazine (Compound No.-88) Tetrahydrofuran (55 mL) ) was added 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, and after purging the inside of the reactor with nitrogen gas, 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 under reflux with heating for 5 hours. The mixture was allowed to cool, appropriate amounts of water and ethyl acetate were added, and suction filtration was performed using celite 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 resulting crude product was purified by silica gel chromatography to give the title compound (173 mg, 81.7% yield, 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)

Synthetic Example 4-7: Preparation of 2-[3,5-bis(trifluoromethyl)phenyl]-5-[3-(ethylsulfonyl)pyridin-4-yl]-pyrazine (Compound No.-90) 2- [3-(Ethylthio)pyridin-4-yl]-5-[3-(trifluoromethyl)phenyl]pyrazine (111 mg, 0.31 mmol) was dissolved in dichloromethane (3 mL). Benzoic acid (about 30% water content, 183 mg, 0.69 mmol) was added and stirred at room temperature for 2 hours. A saturated sodium bicarbonate aqueous solution was added, extracted twice with ethyl acetate, dried over magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a composition organism. The resulting crude product was purified by silica gel chromatography to give the title compound (87 mg, yield 71.9%, slightly brown amorphous).
1H NMR( _CDCl3 ) 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: Preparation of 2-(3-methoxypyridin-4-yl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (Compound No.-4) Synthesis Example 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (0.50 g, 1.63 mmol) described in 1-1 was dissolved in dioxane (50 mL), and dichlorobis(triphenyl Phosphine)palladium(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, 4-bromo-3-methoxypyridine (0.30 g, 1.97 mmol) and 5 mL of 2M aqueous sodium carbonate solution were added, and the mixture was stirred under reflux for 2 hours. After allowing to cool, appropriate amounts of water and ethyl acetate were added, suction filtration was performed using celite to remove insoluble matter, and the filtrate was concentrated under reduced pressure. Then, it was extracted twice with ethyl acetate, dried with magnesium sulfate, removed by suction filtration, and then concentrated under reduced pressure to obtain a composition organism. The resulting crude product was purified by silica gel chromatography to give the title compound (0.29 g, 53.3% yield, colorless oil).
1H NMR( _CDCl3 ) 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)

Synthetic Example 6-1: Preparation of 2-(3-(ethylthio)pyrazin-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), and 1,10-phenanthroline (0.53 g, 2.91 mmol) dissolved in N,N-dimethylformamide (6 mL), degassed, and then replaced with nitrogen. and stirred for 30 minutes at room temperature. 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)pyridin-4-yl]-5-iodopyrazine (0.50 g, 1.46 mmol) described in Synthesis Example 4-5 was added thereto and stirred at 50° C. for 14 hours. An appropriate amount of ethyl acetate was added to the reaction mixture, suction filtration was performed using celite to remove insoluble matter, and water was added to the filtrate. Then, it was extracted with ethyl acetate, dried over magnesium sulfate, removed by suction filtration, and concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography to give the title compound (0.19 g, 33.8% yield, 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=4.8 Hz), 7.50(1H, d, J=5.1 Hz) 2.94 (2H, q, J=7.2Hz), 1.26 (3H, t, J=7.2Hz)

Synthetic Example 7-1: Preparation of 5-chloro-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide 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-azabenzotriazol-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. After that, a saturated aqueous solution of sodium bicarbonate 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, 72.8% yield, white solid)
1H NMR ( _CDCl3 ) δ 9.20 (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)

Synthetic Example 7-2: Preparation of 5-(3-fluoropyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-61) 5-Chloro -N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (2.98 g, 12.44 mmol), 3-fluoro-4-pyridine boronic 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 reflux with heating for 19 hours. After standing to cool, appropriate amounts of water and ethyl acetate were 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 resulting crude product was purified by silica gel chromatography to give the title compound (1.66 g, 44.5% yield, yellow solid).
¹ H NMR (CDCl ₃ ) δ 9.54 (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)

Synthetic Example 8-1: Preparation of 5-(3-(ethylthio)pyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-59) 5 -(3-fluoropyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-61) (0.12 g, 0.40 mmol) in methylene chloride ( 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 overnight. After that, water 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 (0.12 g, yield 92.6%, pale brown amorphous).
¹ H NMR(CDCl ₃ ) δ 9.53(1H, d, J = 1.5 Hz), 8.95(1H, d, J = 1.5 Hz), 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)

Synthetic 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)pyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-59) (0.15 g, 0.44 mmol) The solution was dissolved in methylene chloride (4.5 ml), m-chloroperbenzoic acid (0.26 g, 70%, 0.96 mmol) was added under cooling with an ice bath, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, saturated aqueous sodium bicarbonate was added, the mixture was extracted twice with ethyl acetate, and magnesium sulfate was added to dehydrate the organic layer. Thereafter, magnesium sulfide was removed by suction filtration, and the product was 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). .
1H NMR( _CDCl3 ) δ 9.45(1H, s), 9.35(1H, s), 9.03(1H, d, J= ^5.1 Hz), 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)

Synthetic Example 10-1: Preparation of 5-(3-(dimethylamino)pyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-65)
5-(3-fluoropyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (Compound No.-61) (0.36 g, 1.20 mmol) at 50% The mixture was dissolved in an aqueous dimethylamine solution (10 mL), stirred overnight, and then stirred under reflux with heating for 7 hours. After allowing to cool, the mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel chromatography to give the title compound (0.35 g, yield 89.7%, yellow solid).
¹ H NMR (CDCl ₃ ) δ 9.50 (1H, d, J = 1.2 Hz), 9.20 (1H, d, J = 1.2 Hz), 8.51 (1H, s), 8.39 (1H, d, J = 5.1 Hz ), 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)

Synthetic Example 11-1: 5-(3-(dimethylamino)pyridin-4-yl)-N-methyl-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (compound number- 66) adjustment
After dissolving 5-(3-(dimethylamino)pyridin-4-yl)-N-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide (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 for dehydration, magnesium sulfide was removed by suction filtration, the composition was concentrated under reduced pressure, and the obtained composition was purified by silica gel chromatography to give the title compound (42.7 mg, yield 13.6%, yellow color). oil) was obtained.
¹ H NMR (CDCl ₃ ) δ 9.23(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)

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

<Formulation example>
Examples of pesticide formulations containing the compound represented by formula (1) according to the present invention as an active ingredient are given below.
Formulation Example 1 [wettable powder]
Compound 30% by weight
Clay 30% by weight
Diatomaceous earth 35% by weight
Sanex P252 4% by weight
(Calcium lignosulfonate: trade name of Nippon Paper Industries Co., Ltd.)
Sorpol 8070 1% by weight
(Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.)
The above ingredients were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 2 [powder]
Compound 2% by weight
Clay 90% by weight
Talc 7% by weight
Calcium stearate 1% by weight
A powder was obtained by uniformly mixing the above components.

Formulation 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 Nippon Oil & Energy Corporation)
Neucalgen CL-H 10% by weight
(POE alkylphenyl ether: product name of Takemoto Oil & Fat Co., Ltd.) The above components were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4 [Emulsion 2]
Compound 5% by weight
Xylene 42.5% by weight
DMSO 42.5% by weight
Nucalgen 2003 10% by weight
(Mixture of POE allyl phenyl ether formaldehyde condensate and metal alkylbenzene sulfonate: product name of Takemoto Oil Co., Ltd.)
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
Formulation Example 5 [granules]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sanex P252 2% by weight
(Calcium lignosulfonate: trade name of Nippon Paper Industries Co., Ltd.)
The above ingredients were uniformly pulverized and mixed, water was added, and the mixture was thoroughly kneaded, then granulated and dried to obtain granules.

Formulation Example 6 [Flowable agent]
Compound 25% by weight
Sorpol 7556 5% by weight
(POE styryl phenyl ether sulfate: product name of Toho Chemical Industry Co., Ltd.)
Propylene glycol 6% by weight
Bentonite 1% by weight
1% xanthan gum aqueous solution 3% by weight
Water 60% by weight
A 1% xanthan gum aqueous solution and the entire amount of the above formulation, excluding an appropriate amount of water, were premixed and then pulverized with a wet pulverizer. Thereafter, a 1% xanthan gum aqueous solution and the remaining water were added to the pulverized product to obtain a 100% by weight flowable agent.

Formulation Example 7 [granules]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sanex P252 2% by weight
(Calcium lignosulfonate: trade name of Nippon Paper Industries Co., Ltd.)
The above ingredients were uniformly pulverized and mixed, water was added, and the mixture was thoroughly kneaded, then granulated and dried to obtain granules.

<Biological test example>
The following tests demonstrate the control efficacy of compounds of this invention against specific pests. "Control efficacy" refers to inhibition of invertebrate pest development (including mortality) that significantly reduces feeding. The pest control protection achieved by the compounds, however, is not limited to these species. Compound numbers refer to compounds in Table 2.

Biological test example 1: Cotton aphid (Aphis gossypii) control test (leaf piece spraying treatment)
Cucumber leaves were cut into 3.5 cm diameter pieces and placed on cotton wool moistened with water. Two adults of Aphis gossypii were released here, and after 24 hours of incubation, the adults were removed. 2 mL of a diluted test compound diluted to 200 ppm was sprayed on the cucumber leaves using a spray tower. After air-drying, they were placed in a plastic cup together with absorbent cotton, covered, and reared in a constant temperature room at 25°C. After 5 days of treatment, live and dead insects were observed, and the mortality rate (%) was calculated.
As a result, 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 part was immersed in a vial bottle (inner diameter: 2.7 cm x 6 cm) containing 10 mL of a chemical solution diluted to 3.1 ppm. One day after the immersion, five 1st instar larvae of Aphis gossypii were released and reared in a constant temperature room at 25°C. 5 to 7 days after release, the insects were examined for survival and abnormalities.
As a result, the compounds 1, 2, 4, 20, 43, 45, 47, 50, 53, 54, 57, 59, 60, 61, 62, 65 and 66 of the present invention showed a mortality rate of 80% or more. .

Biological test example 3: Tobacco whitefly (Bemisia tabaci) control test (leaf piece spraying treatment)
Adult whitefly tabaci are released on cucumbers planted in pots and left to lay eggs for 6 hours. Adults are then removed and kept in sufficient light conditions. After the hatched larvae have settled, the leaves are cut into 4 cm squares containing the larvae and placed upside down on water-moistened cotton wool. 2 mL of a diluted test compound diluted to 200 ppm was sprayed on the cucumber leaves using a spray tower. After air-drying, they were placed in a plastic cup together with absorbent cotton, covered with a lid, and reared in a constant temperature room at 25°C. 7 days after the treatment, life and death were observed, and the mortality 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 a mortality rate of 80% or more.

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

Biological test example 5: Brown planthopper (Nilaparvata lugens) control test (stem and leaf immersion treatment)
Ten seedlings of rice were taken, immersed in 20 mL of a test compound solution diluted to 200 ppm, and air-dried. After air-drying, it is held in a glass cylinder (inner diameter: 4.5 cm x 14 cm) using urethane, and placed in a plastic cup containing 40 mL of water. The 3rd instar larvae of brown planthoppers were released in this, covered with a wrapping paper, and reared in a constant temperature room at 25°C. Five days after the treatment, larvae were observed for life and death, and the mortality rate (%) was calculated.
As a result, 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 put a plastic cup (90 mL) containing 40 mL of a chemical solution diluted to 50 ppm. (with a lid). Two days later, 10 3rd instar larvae of brown planthopper were released, covered with medicine wrapping paper and reared in a constant temperature room at 25°C. 5 to 7 days after the treatment, the insects were examined for survival and abnormalities.
As a result, compounds 1, 4, 20, 31, 42, 43, 57, 60 and 62 of the present invention showed a mortality rate of 80% or more.

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

Biological test example 8: Planococcus citri control test (spraying leaf pieces)
A cucumber leaf was cut into 2 cm squares and placed on absorbent cotton moistened with water. 2 mL of a diluted test compound diluted to 200 ppm was sprayed on the cucumber leaves using a spray tower. After air-drying, 10 citrus mealybug 1st instar larvae were released. After that, they were placed in a plastic cup together with absorbent cotton, covered with a lid, and reared in a constant temperature room at 25°C. 10 days after the treatment, life and death were observed, and the mortality rate (%) was calculated.
As a result, compounds 1, 2 and 6 of the present invention showed a mortality rate of 80% or more.

Biological Test Example 9: Two-spotted spider mite (Tetranychus urticae) control test (leaf piece immersion treatment)
Absorbent cotton sufficiently moistened with water is placed in a plastic container (diameter 6 cm x 3 cm), and filter paper is laid on it. A 2 cm square bean leaf piece is placed on the filter paper, 5 adult two-spotted spider mites are released, and eggs are laid for 24 hours. On the next day, the bean leaf pieces from which the adults have been removed are immersed in 20 mL of a test compound diluted to 200 ppm for 10 seconds. After air-drying, the green bean leaf pieces were returned to the plastic cup, covered, and reared in a constant temperature room at 25°C. Seven days after the treatment, the larvae were observed for life and death, the number of unhatched eggs was investigated, and the mortality rate (%) was calculated.
As a result, compounds 10, 11, 15, 23, 24, 22, 25, 31, 32, 34, 35, 58 and 93 of the present invention showed a mortality rate of 80% or more.

Biological Test Example 10: Meloidogyne incognita control test (liquid immersion test)
A suspension of 2nd stage larvae of Nematode nematode was obtained from egg sacs that had grown on the roots of sweet potato by the Bellman method. This nematode-containing liquid was dispensed into a 48-well plate at a rate of 100 μL (approximately 50 nematodes) per well. After that, add the same amount of nematode-containing liquid and the test reagent solution, leave at 26 ° C. constant temperature conditions for 3 days, investigate the life and death of nematodes under a stereomicroscope, investigate the life and death of nematodes under a stereomicroscope, and correct death. Insect rate was calculated.
Corrected mortality rate (%) =
{(Dead rate in treated area-Dead rate in untreated area)/(100-Dead rate in untreated area)}×100
As a result, compounds 3 and 22 of the present invention showed a corrected mortality rate of 80% or more.

Claims (7)

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

(In formula (1),
R is
hydrogen atom C1-C6 alkyl group (wherein the C1-C6 alkyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, or a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
a C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms an amino group with two selected substituents, and/or
optionally substituted by a phenyl group independently substituted with up to 1 to 5 substituents R ₃ )
a phenyl group independently substituted with up to 1 to 5 substituents R ₄ a pyridyl group independently substituted with up to 1 to 5 substituents R ₄ ,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , R _d are independently
A hydrogen atom halogen atom C1-C6 alkyl group (wherein the C1-C6 alkyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkenyloxy group (wherein the C2-C6 alkenyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynyloxy group (wherein the C2-C6 alkynyloxy group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylthio group (wherein the C1-C6 alkylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylthio group (wherein the C2-C6 alkenylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylthio group (wherein the C2-C6 alkynylthio group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfinyl group (wherein the C1-C6 alkylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfinyl group (wherein the C2-C6 alkenylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkynylsulfinyl group (wherein the C2-C6 alkynylsulfinyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C1-C6 alkylsulfonyl group (wherein the C1-C6 alkylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
C2-C6 alkenylsulfonyl group (wherein the C2-C6 alkenylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
a C2-C6 alkynylsulfonyl group (wherein the C2-C6 alkynylsulfonyl group is
one or more halogen atoms that are the same or different, and/or
a C1-C6 alkyloxy group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylthio group optionally substituted by one or more halogen atoms that are the same or different, and/or
a C1-C6 alkylsulfinyl group optionally substituted by one or more same or different halogen atoms, and/or
a C1-C6 alkylsulfonyl group optionally substituted by one or more identical or different halogen atoms, and/or
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms optionally substituted by an amino group having two selected substituents)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms 5- or 6-membered ring amino group consisting of amino group carbon atoms and sulfur atoms having two selected substituents (wherein the sulfur atoms are oxidized and may be sulfinyl groups or sulfonyl groups)
N,N-dimethylacetimidamide group 1,1,3,3-tetramethylguanidinyl group independently from hydrogen atoms, C1 to C6 alkyl groups optionally substituted by one or more same or different halogen atoms Aminocarbonyl group hydrogen atom having two substituents selected by, a C1 to C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, substituted by one or more of the same or different halogen atoms a hydrazino group having three substituents independently selected from optionally C1 to C6 acyl groups hydrogen atom, a C1 to C6 alkyl group optionally substituted by one or more halogen atoms which are the same or different, the same Or a hydrazinocarbonyl group hydrogen atom having three substituents independently selected from C1 to C6 acyl groups optionally substituted by one or more different halogen atoms, substituted by one or more same or different halogen atoms a hydroxylamino group having two substituents independently selected from a C1 to C6 alkyl group which may be substituted, a C1 to C6 acyl group which may be substituted by one or more of the same or different halogen atoms; represent,
A represents a direct bond. )
However, the compound represented by Formula (1) or a salt thereof excludes 2-(3-(ethylsulfonyl)pyridin-2-yl)-5-(2-(trifluoromethyl)pyridin-4-yl)pyrazine . R is
C1-C6 alkyl group (wherein the C1-C6 alkyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group is the same or different one or more halogen atoms, and/or
independently substituted by a phenyl group optionally substituted with up to 1 to 5 substituents R ₃ )
a phenyl group independently optionally substituted with up to 1 to 5 substituents R ₄ a pyridyl group independently optionally substituted with up to 1 to 4 substituents R ₄ ,
R ₁ , R ₂ , R ₃ , R ₄ , R _a , R _b , R _c , and R _d are independently
hydrogen atom halogen atom C1-C6 alkyl group (here, the C1-C6 alkyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkenyl group (wherein the C2-C6 alkenyl group may be substituted with one or more same or different halogen atoms)
C2-C6 alkynyl group (wherein the C2-C6 alkynyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkyloxy group (wherein the C1-C6 alkyloxy group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylthio group (here, the C1-C6 alkylthio group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfinyl group (here, the C1-C6 alkylsulfinyl group may be substituted with one or more same or different halogen atoms)
C1-C6 alkylsulfonyl group (here, the C1-C6 alkylsulfonyl group may be substituted with one or more same or different halogen atoms)
independently of a hydrogen atom, a C1-C6 alkyl group optionally substituted by one or more of the same or different halogen atoms, and a C1-C6 acyl group optionally substituted by one or more of the same or different halogen atoms amino group having two selected substituents hydrogen atom, aminocarbonyl having two substituents independently selected from C1 to C6 alkyl groups optionally substituted by one or more halogen atoms which may be the same or different is the basis
The pest control agent according to claim 1. 3. A pest control agent according to claim 1 or 2, comprising at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. 4. The pest control agent of any one of claims 1-3, further comprising at least one biologically effective compound or agent. said at least one biologically active compound or agent is alanicarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocaboxime, butoxycarboxime, carbaryl, carbofuran, carbosulphane, ethiophenecarb, fenocarb, formetanate, Furatiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, metolcarb, phenothiocarb, fenoxycarb, acephate, azamethifos, azinphos-ethyl, azinphos-methyl, ethylthiomethone, chloride Ethoxyphos, Cadusaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Dimethyvinphos, EPN, Ethion, Etprophos, Famfur, Fenamiphos , Fenitrothion, Fenthion, Hostthiazate, Heptenophos, Imisiaphos, Isofenphos, Isopropyl O-(Methoxyaminebothiophosphoryl salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxymetone-ethyl, Parathion, parathion-methyl, PAP, folate, fosalone, phosmet, phosphamidone, phoxime, pirimiphos-methyl, propenophos-propetanphos, prothiophos, pyraclophos, pyridafenthion, quinarphos, sulfotep, tebpyrimifos, temefos, terbufos, tetrachlorbinphos, Thiometone, triazophos, trichlorfon, vamidothione, chlorpyrifos-ethyl, disulfotone, sulprophos, flupyrazophos, phenthate, honophos, tribufos, endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor, acetoprol, fipronil, ethiprole, pilaf luprole, pyriprol, flufiprole, brofuranilide, afoxolaner, fluralaner, saroralaner, fluxametamide, acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin , permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, metofruthrin, profluthrin, pyrethrin, terarethrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethrin Methylfluthrin, Dimefluthrin, Chlorparathrin, Epsilon-Metofluthrin, Epsilon-Monfluothrin, Protrifenbut, Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam, Sulfoxaflor, Flupyradifuron, Triflumezopyrim, Dichloromesotia flupyrimine, spinosad, spinetoram, abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, hydroprene, quinoprene, diphenolane, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide , propargite, tetradifone, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, thiosultap-sodium, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron , noviflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezin, cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz, hi Doramethylnon, acequinosyl, fluacrypyrim, pyriminostrobin, flufenoxystrobin, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, piflubumide, spirodiclofen, spirotetramat, spiromesifen, spiropidion, cyflumetofen, cyenopyrafen, flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole, quinomethionate, hexythiazox, bifenazate, flufenerim, pyrifluquinazone, flometoquine, fluopyram, fluazaindolizine , amidoflumet, ticlopyrazofrole, thioxazaphene, oxazosulfyl, nicotine, chloropicrin, sulfuryl fluoride, chrylotie, clofentezine, diflovidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, Aphidopyropene, fluhexafone, fluenesulfone, benclotiaz, calsol, insecticidal soap, dimehypo, nitiazine, borate, metaldehyde, ryanodine, sulfluramide, acinonapyr, benzpyrimoxane, 3-bromo-N-(2,4-dichloro- 6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide, metalaxyl, metalaxyl M, oxadixyl, ofrace, benalaxyl, benalaxyl-M, chiralaxyl, Oflas, Furaxil, Cyprofuran, Buprimate, Dimethylmol, Ethymol, Hymexazole, Hydroxyisoxazole, Oxathiapiproline, Octilinone, Oxolinic Acid, Benomyl, Thiophanate-methyl, Carbendazim, Fuberidazole, Thiabendazole, Devacarb, Diethofencarb, Zoxamide, Ethaboxam, Penciclon, Fluopicolide , fluopimimide, diflumetrim, bupirimate, benodanil, flutolanil, mepronil, isofetamide, fenfuram, oxycarboxin, carboxin, thifluzamide, fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpil Fluxam, Fluindapyr, Isoflurcipram, Pyrapropoin, Boscalid, Azoxystrobin, Coumethoxystrobin, Cresoxime methyl, Trifloxystrobin, Picoxystrobin, Pyraclostrobin, Dimoxistrobin, Metominostrobin, Orysastrobin, Flu oxastrobin, pyraoxystrobin, pyrametostrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, comoxistrobin, mandestrobin, triclopiricarb, famoxadone, fenamidone, triclopiricarb, pyribencarb, Cyazofamid, Amisulbrom, Binapacryl, Meptyldinocarb, Dinocap, Fluazinam, Ferimzone Acetate-Fentin, Fentin Chloride, Fentin Hydroxide, Triphenyltin Hydroxide, Triphenyltin Acetate, Copper Oxine, Silthiopham, Amethoctrazine, Mepanipyrim, Nitrapyrin, pyrimesanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxifene, proquinazid, fludioxonil, fenpicronil, fluoroimide, procymidone, iprodione, vinclozoline, edifenphos, iprobenphos, pyrazophos, isoprothiolane, propamocarb, propamocarb Hydrochloride, Gosseikajupte Extract, Trifoline, Pyrifenox, Pyrisoxazole, Fenarimol, Nuarimol, Azaconazole, Bromuconazole, Diniconazole, Diniconazole-M, Epoxiconazole, Fluquinconazole, Oxpoconazole, Pefurazoate, Difenoconazole, Fen buconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flucilazole, flutriafol, microbutanil , paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pirimorph, piperaline , fenpropidin, spiroxamine, fenhexamide, fenpyrazamine, ferbum, metam, metasulfocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate, provineb, thiuram, piributicarb, validamycin, mildiomycin, polyoxin, Benthiavalicarb, Benthiavalicarb Isopropyl, Valifenalate, Iprovalicarb, Mandipropamide, Fenpicoxamide, Florylpicoxamide, Fthalide, Pyroquilone, Tricyclazole, Carpropamide, Diclocimet, Fenoxanyl, Acibenzolar-S-methyl, Probenazole, Diclobenchiazox, thiazinyl, isotianil, cymoxanil, fosetyl, tecloftalam, triazoxide, fursulfamide, diclomedine, cyflufenamide, metrafenone, pyriophenone, flutianil, tebufloquine, ipflufenoquine, fosetyl aluminum, tolclofos-methyl, eclomezole, tolprocarb, ipfentri fluconazole, mefentrifluconazole, quinofumeline, pydiflumetofen, Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, cupric hydroxide, copper oxyquinoline, copper, sulfur, captan, captafol, folpet , anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctazine acetate, iminoctazine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate, albesylate, dithianone, quinomethionate, Fluorimide, tolylfluanid, diclofluanid, dinobutone, dazomet, pyraziflumide, aminopyrifene, methyltetraprole, pyridaclomethyl, dipimethitrone, picarbutrazox, tecnazen, nitrtar-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium , bronopol, diphenylamine, flumetovel, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, Bacillus genus and insecticidal and fungicidal proteins produced by them, insecticidal and fungicidal proteins produced by Bt crops, Claims selected from the group consisting of entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi Item 5. 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. 7. The pest control agent according to claim 6, which is used for animal ectoparasite control against ectoparasites of animals and birds.