JP2023007504A - Imine compound or salt thereof, pest control agent containing that compound as active ingredient, and pest control method - Google Patents

Abstract

To provide a novel agricultural and horticultural insect pest control agent, or a novel parasite control agent for animals.SOLUTION: The invention provides a compound represented by the general formula (I) or a salt thereof (R1 to R5, X, Y, Q1 and Q2 are as defined in the specification).

Description

TECHNICAL FIELD The present invention relates to an imine compound or a salt thereof, a pest control agent containing the compound as an active ingredient, and a method for controlling pests.

Patent Document 1 describes that certain heteroarylazole compounds have ectoparasite-controlling activity on animals, but neither describes nor suggests the compound having an imine skeleton of the present invention. Nothing is known about the control activity of the compounds against pests such as agricultural pests and animal parasites.

International Publication No. 2017/192385 pamphlet

In the production of useful crops such as agriculture and horticulture, the damage caused by pests is enormous. However, the development of new agricultural and horticultural pest control agents is still important in the agricultural and horticultural field due to the emergence of pests resistant to existing drugs and the demand for drugs with physical properties suitable for various labor-saving application methods. is one of the important issues. In addition, the control of parasites is also an important issue in breeding animals such as livestock and pets. Infection with parasites is a novel animal parasite because both the parasite infection itself and the diseases caused by viruses, bacteria, etc., transmitted by the parasite cause significant suffering in animals and cause enormous economic losses in livestock. Development of an insect control agent is desired.

The present inventors have extensively studied to develop a novel agricultural and horticultural pest control agent or animal parasite control agent, and as a result, the imine compound represented by the general formula (I) or a salt thereof They found that it is useful as an agricultural and horticultural pest control agent and an animal parasite control agent, and completed the present invention.

{式中、Ｒ^１は、
（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル基；
（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
フェニル（Ｃ_１－Ｃ_６）アルキル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル（Ｃ_１－Ｃ_６）アルキル基；
ヘテロ環（Ｃ_１－Ｃ_６）アルキル基；
置換基群Ａから選択される１～４個の置換基を環上に有する置換ヘテロ環（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_２－Ｃ_６）アルケニル基；
ハロ（Ｃ_２－Ｃ_６）アルケニル基；
（Ｃ_２－Ｃ_６）アルキニル基；
ハロ（Ｃ_２－Ｃ_６）アルキニル基；
フェニル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル基；
ヘテロ環基；または置換基群Ａから選択される１～４個の置換基を環上に有する置換ヘテロ環基を示し、
Ｒ^２は、
フェニル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル基；
ピリジル基；
置換基群Ａから選択される１～４個の置換基を環上に有する置換ピリジル基；
ピリミジニル基；
置換基群Ａから選択される１～３個の置換基を環上に有する置換ピリミジニル基；
ピラジニル基；
置換基群Ａから選択される１～３個の置換基を環上に有する置換ピラジニル基；
ピリダジニル基；または置換基群Ａから選択される１～３個の置換基を環上に有する置換ピリダジニル基を示し、
Ｒ^３およびＲ^４はそれぞれ独立に、水素原子；（Ｃ_１－Ｃ_６）アルキル基またはハロ（Ｃ_１－Ｃ_６）アルキル基を示し、
Ｒ^５は、
ピリジル基；
置換基群Ａから選択される１～４個の置換基を環上に有する置換ピリジル基；
ピリミジニル基；
置換基群Ａから選択される１～３個の置換基を環上に有する置換ピリミジニル基；
ピラジニル基；
置換基群Ａから選択される１～３個の置換基を環上に有する置換ピラジニル基；
ピリダジニル基；または置換基群Ａから選択される１～３個の置換基を環上に有する置換ピリダジニル基を示し、
Ｘは、
酸素原子；硫黄原子；またはＮＲ^６（式中、Ｒ^６は（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基またはハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基を示す。）を示し、
Ｙは、単結合；またはＣＨ_２を示し、
Ｑ^１およびＱ^２はそれぞれ独立に、
ＣＲ^７（式中、Ｒ^７は水素原子、ハロゲン原子、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、ジ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、ハロ（Ｃ_３－Ｃ_６）シクロアルコキシ基または（Ｃ_１－Ｃ_６）アルコキシカルボニル基を示す）；または窒素原子を示し（ただし、Ｑ^１およびＱ^２のうち少なくとも１つは窒素原子である）、
置換基群Ａは、
ハロゲン原子、シアノ基、ニトロ基、ヒドロキシル基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_３－Ｃ_６）シクロアルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基、（Ｃ_３－Ｃ_６）シクロアルコキシカルボニル基、モノ（Ｃ_１－Ｃ_６）アルキルアミノカルボニル基およびジ（Ｃ_１－Ｃ_６）アルキルアミノカルボニル基からなる。}
で表される化合物またはその塩；
[２]Ｒ^１が、
（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル基；
（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
フェニル（Ｃ_１－Ｃ_６）アルキル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル（Ｃ_１－Ｃ_６）アルキル基；
ヘテロ環（Ｃ_１－Ｃ_６）アルキル基；
置換基群Ａから選択される１～４個の置換基を環上に有する置換ヘテロ環（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_２－Ｃ_６）アルケニル基；
ハロ（Ｃ_２－Ｃ_６）アルケニル基；
（Ｃ_２－Ｃ_６）アルキニル基；
ハロ（Ｃ_２－Ｃ_６）アルキニル基；
フェニル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル基；
ヘテロ環基；または置換基群Ａから選択される１～４個の置換基を環上に有する置換ヘテロ環基を示し、
Ｒ^２が、
フェニル基；
置換基群Ａから選択される１～５個の置換基を環上に有する置換フェニル基；
ピリジル基；または置換基群Ａから選択される１～４個の置換基を環上に有する置換ピリジル基を示し、
Ｒ^３およびＲ^４がそれぞれ独立に、水素原子；（Ｃ_１－Ｃ_６）アルキル基またはハロ（Ｃ_１－Ｃ_６）アルキル基を示し、
Ｒ^５が、
ピリジル基；
置換基群Ａから選択される１～４個の置換基を環上に有する置換ピリジル基；
ピリミジニル基；または置換基群Ａから選択される１～３個の置換基を環上に有する置換ピリミジニル基を示し、
Ｘが、
酸素原子；硫黄原子；またはＮＲ^６（式中、Ｒ^６は（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基またはハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基を示す。）を示し、
Ｙが単結合を示し、
Ｑ^１およびＱ^２がそれぞれ独立に、ＣＲ^７（式中、Ｒ^７は水素原子、ハロゲン原子、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、ジ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、ハロ（Ｃ_３－Ｃ_６）シクロアルコキシ基または（Ｃ_１－Ｃ_６）アルコキシカルボニル基を示す。）；または窒素原子を示し（ただし、Ｑ^１およびＱ^２のうち少なくとも１つは窒素原子である）、
置換基群Aが、
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基またはハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基を示す、前記［１］に記載の化合物またはその塩；
[３]Ｒ^１が、
（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル基；
（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルコキシ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキルチオ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ベンジル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～５個の置換基を環上に有する置換ベンジル基；
ピリジルメチル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～４個の置換基を環上に有する置換ピリジルメチル基；
（Ｃ_２－Ｃ_６）アルケニル基；
ハロ（Ｃ_２－Ｃ_６）アルケニル基；
（Ｃ_２－Ｃ_６）アルキニル基；またはハロ（Ｃ_２－Ｃ_６）アルキニル基を示し、
Ｒ^２が、
フェニル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～５個の置換基を環上に有する置換フェニル基；
ピリジル基；またはハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～４個の置換基を環上に有する置換ピリジル基を示し、
Ｒ^３が、（Ｃ_１－Ｃ_６）アルキル基；またはハロ（Ｃ_１－Ｃ_６）アルキル基を示し、
Ｒ^４が、水素原子を示し、
Ｒ^５が、
ピリジル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～４個の置換基を環上に有する置換ピリジル基；
ピリミジニル基；またはハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基、（Ｃ_３－Ｃ_６）シクロアルキル基、ハロ（Ｃ_３－Ｃ_６）シクロアルキル基、（Ｃ_１－Ｃ_６）アルコキシ基、ハロ（Ｃ_１－Ｃ_６）アルコキシ基、（Ｃ_３－Ｃ_６）シクロアルコキシ基、（Ｃ_１－Ｃ_６）アルキルチオ基、ハロ（Ｃ_１－Ｃ_６）アルキルチオ基、（Ｃ_１－Ｃ_６）アルキルスルフィニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルフィニル基、（Ｃ_３－Ｃ_６）シクロアルキルスルフィニル基、（Ｃ_１－Ｃ_６）アルキルスルホニル基、ハロ（Ｃ_１－Ｃ_６）アルキルスルホニル基、（Ｃ_１－Ｃ_６）アルキルカルボニル基、ハロ（Ｃ_１－Ｃ_６）アルキルカルボニル基、（Ｃ_３－Ｃ_６）シクロアルキルカルボニル基、（Ｃ_１－Ｃ_６）アルコキシカルボニル基およびハロ（Ｃ_１－Ｃ_６）アルコキシカルボニル基から選択される１～３個の置換基を環上に有する置換ピリミジニル基を示し、
Ｘが酸素原子；または硫黄原子を示し、
Ｙが単結合を示し、
Ｑ^１がＣＨ；または窒素原子を示し、
Ｑ^２が窒素原子を示す、前記［１］に記載の化合物またはその塩；
[４]Ｒ^１が、
（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_１－Ｃ_６）アルキル基；
（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ハロ（Ｃ_３－Ｃ_６）シクロアルキル（Ｃ_１－Ｃ_６）アルキル基；
ベンジル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～５個の置換基を環上に有する置換ベンジル基；
ピリジルメチル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～４個の置換基を環上に有する置換ピリジルメチル基；
（Ｃ_２－Ｃ_６）アルケニル基；
ハロ（Ｃ_２－Ｃ_６）アルケニル基；
（Ｃ_２－Ｃ_６）アルキニル基；またはハロ（Ｃ_２－Ｃ_６）アルキニル基を示し、
Ｒ^２が、
フェニル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～５個の置換基を環上に有する置換フェニル基；
ピリジル基；またはハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～４個の置換基を環上に有する置換ピリジル基を示し、
Ｒ^３が、（Ｃ_１－Ｃ_６）アルキル基を示し、
Ｒ^４が、水素原子を示し、
Ｒ^５が、
ピリジル基；
ハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～４個の置換基を環上に有する置換ピリジル基；
ピリミジニル基；またはハロゲン原子、シアノ基、（Ｃ_１－Ｃ_６）アルキル基、ハロ（Ｃ_１－Ｃ_６）アルキル基およびハロ（Ｃ_１－Ｃ_６）アルコキシ基から選択される１～３個の置換基を環上に有する置換ピリミジニル基を示し、
Ｘが、酸素原子；または硫黄原子を示し、
Ｙが、単結合を示し、
Ｑ^１が、ＣＨを示し、
Ｑ^２が、窒素原子を示す、前記［１］に記載の化合物またはその塩；
[５]前記[１]乃至[４]のいずれかに記載の化合物またはその塩を有効成分とする有害生物防除剤；
[６]前記[１]乃至[４]のいずれかに記載の化合物またはその塩を有効成分とする農園芸用害虫防除剤；
[７]前記[１]乃至[４]のいずれかに記載の化合物またはその塩を有効成分とする動物用寄生虫防除剤；
[８]前記[１]乃至[４]のいずれかに記載の化合物またはその塩を有効成分とする動物用外部寄生虫防除剤；
[９]前記[１]乃至[４]のいずれかに記載の化合物またはその塩を有効成分とする動物用内部寄生虫防除剤；
[１０]前記[６]に記載の農園芸用害虫防除剤の有効量を対象植物または土壌に処理することを特徴とする農園芸分野の害虫防除方法；
[１１] 前記[７]に記載の動物用寄生虫防除剤の有効量を対象動物に、経口または非経口投与することを特徴とする動物の寄生虫防除方法；
[１２] 前記[８]に記載の動物用外部寄生虫防除剤の有効量を対象動物に、経口または非経口投与することを特徴とする動物の外部寄生虫防除方法；ならびに
[１３]前記[９]に記載の動物用内部寄生虫防除剤の有効量を対象動物に、経口または非経口投与することを特徴とする動物の内部寄生虫防除方法。 Thus, the present invention relates to at least the following inventions:
[1] General formula (I):

{Wherein, R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
a phenyl (C ₁ -C ₆ ) alkyl group;
a substituted phenyl(C ₁ -C ₆ )alkyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic (C ₁ -C ₆ ) alkyl group;
a substituted heterocyclic (C ₁ -C ₆ )alkyl group having 1 to 4 substituents on the ring selected from Substituent Group A;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ ) alkynyl group;
halo(C ₂ -C ₆ )alkynyl groups;
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic group; or a substituted heterocyclic group having 1 to 4 substituents on the ring selected from Substituent Group A,
^R2 is
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group;
A substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from Substituent Group A;
pyrazinyl group;
A substituted pyrazinyl group having 1 to 3 substituents on the ring selected from substituent group A;
a pyridazinyl group; or a substituted pyridazinyl group having 1 to 3 substituents on the ring selected from the substituent group A,
R ³ and R ⁴ each independently represent a hydrogen atom; (C ₁ -C ₆ )alkyl group or halo(C ₁ -C ₆ )alkyl group;
^R5 is
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group;
A substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from Substituent Group A;
pyrazinyl group;
A substituted pyrazinyl group having 1 to 3 substituents on the ring selected from substituent group A;
a pyridazinyl group; or a substituted pyridazinyl group having 1 to 3 substituents on the ring selected from the substituent group A,
X is
oxygen atom; sulfur atom; or NR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo( C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ —C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ ) an alkyl group or a halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group),
Y represents a single bond; or _CH2 ;
Q ¹ and Q ² are each independently
CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C _{3 -} C6)cycloalkyl group, (C1 _- C6)alkoxy(C1 _- C6)alkyl group, di(C1 _{- C6} )alkoxy( _{C1 - C6} ) _alkyl group, ( _C1- C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, halo(C ₃ -C ₆ )cycloalkoxy group or (C ₁ -C ₆ )alkoxycarbonyl group or a nitrogen atom (provided that at least one of Q ¹ and Q ² is a nitrogen atom),
Substituent group A is
halogen atom, cyano group, nitro group, hydroxyl group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ ) alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group, halo (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group , (C ₁ -C ₆ )alkylthio group, halo(C ₁ -C ₆ )alkylthio group, (C ₃ -C ₆ )cycloalkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C3 _- C6) cycloalkylsulfinyl group, (C1 _- C6) alkylsulfonyl group, halo(C1 _{- C6} ) _{alkylsulfonyl} group _, (C3 _{- C6} ) cycloalkyl sulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ -C ₆ )alkoxycarbonyl group, halo (C ₁ -C ₆ )alkoxycarbonyl group, (C ₃ -C ₆ )cycloalkoxycarbonyl group, mono(C ₁ -C ₆ )alkylaminocarbonyl group and di(C ₁ -C ₆ )alkylaminocarbonyl group; . }
A compound or a salt thereof represented by;
[2] R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
a phenyl (C ₁ -C ₆ ) alkyl group;
a substituted phenyl(C ₁ -C ₆ )alkyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic (C ₁ -C ₆ ) alkyl group;
a substituted heterocyclic (C ₁ -C ₆ )alkyl group having 1 to 4 substituents on the ring selected from Substituent Group A;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ ) alkynyl group;
halo(C ₂ -C ₆ )alkynyl groups;
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic group; or a substituted heterocyclic group having 1 to 4 substituents on the ring selected from Substituent Group A,
^R2 is
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
pyridyl group; or a substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A,
R ³ and R ⁴ each independently represent a hydrogen atom; (C ₁ -C ₆ )alkyl group or halo(C ₁ -C ₆ )alkyl group;
^R5 is
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group; or a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from substituent group A,
X is
oxygen atom; sulfur atom; or NR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo( C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ —C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ ) an alkyl group or a halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group),
Y represents a single bond,
Q ¹ and Q ² are each independently CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ - C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, di(C ₁ -C ₆ )alkoxy(C ₁ - C ₆ )alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, halo(C ₃ -C ₆ )cycloalkoxy group or (C ₁ -C ₆ ) represents an alkoxycarbonyl group); or represents a nitrogen atom (with the proviso that at least one of Q ¹ and Q ² is a nitrogen atom),
Substituent group A is
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - C ₆ ) alkoxycarbonyl group or halo(C ₁ -C ₆ ) alkoxycarbonyl group, the compound or salt thereof according to [1] above;
[3] R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
benzyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted benzyl group having 1 to 5 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
pyridylmethyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted pyridylmethyl group having 1 to 4 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,
^R2 is
phenyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted phenyl group having 1 to 5 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
pyridyl group; or halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ —C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C ₃ -C ₆ ) cycloalkylsulfinyl group, (C ₁ -C ₆ ) alkyl sulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, a substituted pyridyl group having 1 to 4 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group,
R ³ represents a (C ₁ -C ₆ )alkyl group; or a halo(C ₁ -C ₆ )alkyl group;
R ⁴ represents a hydrogen atom,
^R5 is
pyridyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - C ₆ ) substituted pyridyl groups having 1 to 4 substituents on the ring selected from alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups;
pyrimidinyl group; or halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ —C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C ₃ -C ₆ ) cycloalkylsulfinyl group, (C ₁ -C ₆ ) alkyl sulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group,
X represents an oxygen atom; or a sulfur atom,
Y represents a single bond,
Q ¹ is CH; or represents a nitrogen atom,
The compound or salt thereof according to [1] above, wherein Q ² represents a nitrogen atom;
[4] R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
benzyl group;
1 to 5 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted benzyl group bearing thereon;
pyridylmethyl group;
1 to 4 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted pyridylmethyl group bearing thereon;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,
^R2 is
phenyl group;
1 to 5 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted phenyl group bearing thereon;
pyridyl group; or 1 to 4 selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups represents a substituted pyridyl group having a substituent on the ring,
R ³ represents a (C ₁ -C ₆ ) alkyl group,
R ⁴ represents a hydrogen atom,
^R5 is
pyridyl group;
1 to 4 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted pyridyl group bearing thereon;
pyrimidinyl group; or 1 to 3 groups selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups represents a substituted pyrimidinyl group having a substituent on the ring,
X represents an oxygen atom; or a sulfur atom,
Y represents a single bond,
Q ¹ represents CH,
The compound or salt thereof according to [1] above, wherein Q ² represents a nitrogen atom;
[5] A pesticide containing the compound or a salt thereof according to any one of [1] to [4] as an active ingredient;
[6] An agricultural and horticultural pest control agent containing the compound or a salt thereof according to any one of [1] to [4] as an active ingredient;
[7] An animal parasite control agent comprising the compound or a salt thereof according to any one of [1] to [4] as an active ingredient;
[8] An ectoparasite control agent for animals containing the compound or a salt thereof according to any one of [1] to [4] as an active ingredient;
[9] An endoparasite control agent for animals containing the compound or a salt thereof according to any one of [1] to [4] as an active ingredient;
[10] A method for controlling pests in the agricultural and horticultural field, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [6] above to a target plant or soil;
[11] A method for controlling animal parasites, which comprises orally or parenterally administering an effective amount of the animal parasite control agent according to [7] above to a subject animal;
[12] A method for controlling ectoparasites in animals, which comprises orally or parenterally administering an effective amount of the ectoparasite control agent for animals according to [8] above to a subject animal;
[13] A method for controlling endoparasites in animals, which comprises orally or parenterally administering an effective amount of the agent for controlling endoparasites for animals according to [9] above to a subject animal.

The present invention provides an imine compound represented by the general formula (I) or a salt thereof, which has excellent effects as an agricultural and horticultural pest control agent and an animal parasite control agent.

In the definition of the general formula (I) of the imine compound of the present invention, "halo" means "halogen atom" and indicates a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. "(C ₁ -C ₆ )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, A linear or branched C 1-6 alkyl group such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group and 3,3-dimethylbutyl group.

“(C ₂ -C ₆ )alkenyl group” includes, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- linear or branched alkenyl groups having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group and 3,3-dimethyl-1-butenyl group; show. “(C ₂ -C ₆ )alkynyl group” includes, for example, ethynyl group, 1-propynyl group, 2-propynyl group (propargyl group), 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl - Linear or branched chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group represents an alkynyl group having 2 to 6 carbon atoms.

“(C ₂ -C ₆ )alkoxy group” means a linear or branched carbon number such as methoxy group, ethoxy group, propoxy group, butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, etc. Represents 1-6 alkoxy groups. The “(C ₃ -C ₆ ) cycloalkyl group” refers to a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group, and “(C ₁ -C ₆ ) alkoxy group" includes, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normalhexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyloxy group represents a linear or branched alkoxy group having 1 to 6 carbon atoms, such as

"(C ₁ -C ₆ )alkylthio group" includes, for example, methylthio, ethylthio, normal-propylthio, isopropylthio, normal-butylthio, secondary-butylthio, tertiary-butylthio, normal-pentylthio group, isopentylthio 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 or a straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms. "(C ₁ -C ₆ )alkylsulfinyl group" includes, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso It represents a linear or branched C 1-6 alkylsulfinyl group such as a hexylsulfinyl group and a 1,1,2-trimethylpropylsulfinyl group.

"(C ₁ -C ₆ )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, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso It represents a linear or branched C 1-6 alkylsulfonyl group such as a hexylsulfonyl group and a 1,1,2-trimethylpropylsulfonyl group.

The above "(C ₁ -C ₆ ) alkyl group", "(C ₂ -C ₆ ) alkenyl group", "(C ₂ -C ₆ ) alkynyl group", "(C ₁ -C ₆ ) alkoxy group" and "(C ₁ - 1 or 2 or more halogen atoms may be substituted at substitutable positions of the C ₆ ) alkylthio group, '(C ₁ -C ₆ ) alkylsulfinyl group' and '(C ₁ -C ₆ ) alkylsulfonyl group'. , when two or more halogen atoms are substituted, the halogen atoms may be the same or different. These are respectively “(haloC ₁ -C ₆ )alkyl group”, “halo(C ₂ -C ₆ )alkenyl group”, “halo(C ₂ -C ₆ )alkynyl group” and “halo(C ₁ -C ₆ )alkoxy group”. group", "halo(C1 _- C6)alkylthio group", "halo(C1 _{- C6} )alkylsulfinyl group" and "halo(C1 _{- C6} ) _{alkylsulfonyl} group".

Expressions such as "(C ₁ -C ₆ )", "(C ₂ -C ₆ )", "(C ₃ -C ₆ )" indicate the range of carbon numbers of the various substituents. Furthermore, the above _definitions can also be shown for _groups to which the _above substituents are _linked . Indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms. A phenyl(C ₁ -C ₆ )alkyl group means a linear or branched C 1-6 phenylalkyl group such as a benzyl group, a phenethyl group and an α-methylbenzyl group.

The heterocyclic group means a 5- or 6-membered aromatic group containing an oxygen atom, a nitrogen atom, a sulfur atom such as a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a thienyl group, a furyl group, a thiazolyl group and an oxazolyl group. monocyclic non-aromatic heterocycles such as heterocyclic groups, pyrrolidinyl groups, piperidinyl groups, morpholinyl groups, thiomorpholinyl groups, piperazinyl groups, oxazolidinyl groups, thiazolidinyl groups, imidazolidinyl groups, oxazolinyl groups, thiazolinyl groups, isoxazolinyl groups and imidazolinyl groups; indicates a group.

Examples of the salt of the compound represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates, oxalates, Organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium can be exemplified.

The imine compound represented by the general formula (I) of the present invention and its salt may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. However, the present invention also includes all optical isomers and mixtures containing them in any proportion. In addition, the compound represented by the general formula (I) of the present invention and its salt have two or more geometric isomers derived from carbon-carbon double bonds or carbon-nitrogen double bonds in their structural formulas. However, the present invention also includes all geometric isomers and mixtures thereof in any proportion.

Preferred embodiments of the imine compound represented by formula (I) of the present invention are shown below. R ¹ is preferably (C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ )cycloalkyl group; halo(C ₃ -C ₆ )cycloalkyl group; (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group; (C ₁ -C ₆ )alkylthio(C ₁ -C ) ₆ ) alkyl group; halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; phenyl(C ₁ -C ₆ )alkyl group; substituted phenyl (C ₁ - C ₆ )alkyl group; heterocyclic (C ₁ -C ₆ )alkyl group; substituted heterocyclic (C ₁ -C ₆ )alkyl group having 1 to 4 substituents on the ring selected from Substituent Group A (C ₂ -C ₆ ) alkenyl group; halo (C ₂ -C ₆ ) alkenyl group; (C ₂ -C ₆ ) alkynyl group; halo (C ₂ -C ₆ ) alkynyl group; phenyl group; A substituted phenyl group having 1 to 5 substituents on the ring selected from; a heterocyclic group; or a substituted heterocyclic group having 1 to 4 substituents on the ring selected from Substituent Group A can be,

More preferably, (C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ )cycloalkyl group; halo(C ₃ -C ₆ )cycloalkyl group; ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group; (C ₁ -C ₆ )alkylthio(C ₁ -C ₆ ) Alkyl group; halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; halo(C ₃ -C ₆ )cyclo Alkyl(C ₁ -C ₆ )alkyl group; benzyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ - C ₆ )alkylthio group, halo(C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl (C ₁ -C ₆ )alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl, (C ₁ -C ₆ )alkoxycarbonyl and halo(C ₁ -C ₆ )substituted benzyl having 1 to 5 substituents on the ring selected from alkoxycarbonyl; group; pyridylmethyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo( C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkyl sulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo 1 selected from (C ₁ -C ₆ )alkylcarbonyl, (C ₃ -C ₆ )cycloalkylcarbonyl, (C ₁ -C ₆ )alkoxycarbonyl and halo(C ₁ -C ₆ )alkoxycarbonyl; (C ₂ -C ₆ )alkenyl groups; halo (C ₂ -C ₆ )alkenyl groups; (C ₂ -C ₆ )alkynyl groups; or halo( C ₂ -C ₆ ) alkynyl group,

(C ₁ -C ₆ )alkyl; halo(C ₁ -C ₆ )alkyl; (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl; halo(C ₃ -C ₆ ) ) cycloalkyl(C ₁ -C ₆ )alkyl groups; benzyl groups; halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ ) substituted benzyl group having 1 to 5 substituents on the ring selected from alkoxy group; pyridylmethyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ ) substituted pyridylmethyl groups having 1 to 4 substituents on the ring selected from alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; (C ₂ -C ₆ )alkenyl groups; halo(C ₂ - C ₆ )alkenyl group; (C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group.

R ² is preferably a phenyl group; a substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A; a pyridyl group; substituted pyridyl group having a group on the ring; pyrimidinyl group; substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from substituent group A; pyrazinyl group; A substituted pyrazinyl group having 3 substituents on the ring; a pyridazinyl group; or a substituted pyridazinyl group having 1 to 3 substituents on the ring selected from Substituent Group A,

Halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo( C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ ) ) alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl substituted phenyl groups having 1 to 5 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups; pyridyl groups; or halogen atoms , cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C _{1 -} C6)alkoxy group, halo(C1 _- C6)alkoxy group, (C3 _{- C6} )cycloalkoxy group, (C1 _{- C6} )alkylthio group, halo(C1 _{- C6} ) _alkylthio group , (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C _{1 -} C6) alkylsulfonyl group, (C1 _- C6) alkylcarbonyl group, halo(C1 _- C6) alkylcarbonyl group _, (C3 _{- C6} ) cycloalkylcarbonyl group, ( _{C1 - C6} ) ) a substituted pyridyl group having 1 to 4 substituents on the ring selected from an alkoxycarbonyl group and a halo(C ₁ -C ₆ )alkoxycarbonyl group,

1 to 5 selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups, particularly preferably phenyl groups; a substituted phenyl group having one substituent on the ring; a pyridyl group, a halogen atom, a cyano group, a (C ₁ -C ₆ )alkyl group, a halo(C ₁ -C ₆ )alkyl group; or a halo(C ₁ -C ₆ ) A substituted pyridyl group having 1 to 4 substituents on the ring selected from alkoxy groups.

R ³ is preferably a hydrogen atom; (C ₁ -C ₆ )alkyl group; or halo(C ₁ -C ₆ )alkyl group, particularly preferably (C ₁ -C ₆ )alkyl group. R ⁴ is preferably a hydrogen atom; (C ₁ -C ₆ )alkyl group or halo(C ₁ -C ₆ )alkyl group, particularly preferably a hydrogen atom.

R ⁵ is preferably a pyridyl group; a substituted pyridyl group having 1 to 4 substituents on the ring selected from Substituent Group A; a pyrimidinyl group; substituted pyrimidinyl group having a group on the ring; pyrazinyl group; substituted pyrazinyl group having 1 to 3 substituents on the ring selected from Substituent Group A; pyridazinyl group; or 1 selected from Substituent Group A A substituted pyridazinyl group having ~3 substituents on the ring,

more preferably pyridyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo( C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ ) ) alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl substituted pyridyl groups having 1 to 4 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups; pyrimidinyl groups; or halogen atoms , cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C _{1 -} C6)alkoxy group, halo(C1 _- C6)alkoxy group, (C3 _{- C6} )cycloalkoxy group, (C1 _{- C6} )alkylthio group, halo(C1 _{- C6} ) _alkylthio group , (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C _{1 -} C6) alkylsulfonyl group, (C1 _- C6) alkylcarbonyl group, halo(C1 _- C6) alkylcarbonyl group _, (C3 _{- C6} ) cycloalkylcarbonyl group, ( _{C1 - C6} ) ) a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from an alkoxycarbonyl group and a halo(C ₁ -C ₆ )alkoxycarbonyl group,

1 to 4 selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups, particularly preferably pyridyl groups; a substituted pyridyl group having one substituent on the ring; a pyrimidinyl group; or a halogen atom, a cyano group, a (C ₁ -C ₆ )alkyl group, a halo(C ₁ -C ₆ )alkyl group or a halo(C ₁ -C ₆ ) A substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from alkoxy groups.

X is _{preferably an oxygen} ^atom _{; sulfur} ^atom _; halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group , (C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl(C ₁ —C ₆ )alkyl group or halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group), particularly preferably an oxygen atom; or a sulfur atom.
Y is preferably a single bond; or _CH2 , particularly preferably a single bond.

Q ¹ is preferably CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, di(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group , (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, halo(C ₃ -C ₆ )cycloalkoxy or (C ₁ -C ₆ ) represents an alkoxycarbonyl group); or a nitrogen atom, particularly preferably a nitrogen atom.

Q ² is preferably CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, di(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group , (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, halo(C ₃ -C ₆ )cycloalkoxy or (C ₁ -C ₆ ) represents an alkoxycarbonyl group); or a nitrogen atom, particularly preferably CH (provided that at least one of Q ¹ and Q ² is a nitrogen atom).

Substituent group A is preferably halogen atom, cyano group, nitro group, hydroxyl group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group , halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups, (C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ - C ₆ )alkyl group, halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ —C ₆ ) cycloalkoxy group, (C ₁ -C ₆ ) alkylthio group, halo(C ₁ -C ₆ ) alkylthio group, (C ₃ -C ₆ ) cycloalkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group , halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C _{3 -} C6) cycloalkylsulfonyl group, (C1 _- C6) alkylcarbonyl group, halo(C1 _- C6) alkylcarbonyl group, (C3 _{- C6} ) cycloalkylcarbonyl group _, (C1 _{- C 6} ) alkoxycarbonyl group, halo(C ₁ -C ₆ )alkoxycarbonyl group, (C ₃ -C ₆ )cycloalkoxycarbonyl group, mono(C ₁ -C ₆ )alkylaminocarbonyl group or di(C ₁ -C ₆ ) ) is an alkylaminocarbonyl group,

More preferably, halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cyclo alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo(C ₁ - C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C ₃ -C ₆ ) cycloalkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, ( C ₁ -C ₆ )alkoxycarbonyl group or halo(C ₁ -C ₆ )alkoxycarbonyl group, particularly preferably halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ ) ) alkyl groups and halo(C ₁ -C ₆ )alkoxy groups.

Further, as specific combinations of R ¹ to R ⁵ , X, Y, Q ¹ and Q ² , R ¹ is preferably a (C ₁ -C ₆ )alkyl group; a halo(C ₁ -C ₆ )alkyl group; _{3 -} C6) cycloalkyl group; halo(C3 _- C6) cycloalkyl group; (C1 _- C6) alkoxy(C1 _{- C6} ) alkyl group; halo(C1 _{- C6} ) _alkoxy ( _C (C ₁ -C ₆ )alkyl group; (C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ ) cycloalkyl(C ₁ -C ₆ )alkyl group; halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; benzyl group; halogen atom, cyano group, (C ₁ -C ₆ ) alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C _{1 -} C6) alkoxy group, (C3 _- C6) cycloalkoxy group, (C1 _- C6) alkylthio group, halo(C1 _{- C6} ) _alkylthio group, (C1 _{- C6} ) _{alkylsulfinyl} group , halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl, halo(C ₁ -C ₆ )alkylcarbonyl, (C ₃ -C ₆ )cycloalkylcarbonyl, (C ₁ -C ₆ )alkoxycarbonyl and halo(C ₁ -C ₆ ) substituted benzyl group having 1 to 5 substituents on the ring selected from alkoxycarbonyl group; pyridylmethyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ - C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo(C ₁ -C ₆ )alkylthio group, ( C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C ₁ - C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo(C ₁ -C ₆ ) alkylcarbonyl group, (C ₃ -C ₆ ) cycloalkylcarbonyl group, (C ₁ -C ₆ ) alkoxy substituted pyridylmethyl groups having from 1 to 4 substituents on the ring selected from carbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups; (C ₂ -C ₆ )alkenyl groups; halo(C ₂ - C ₆ )alkenyl group; (C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,

R ² is a phenyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo( C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ ) ) alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl substituted phenyl groups having 1 to 5 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups; pyridyl groups; or halogen atoms , cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C _{1 -} C6)alkoxy group, halo(C1 _- C6)alkoxy group, (C3 _{- C6} )cycloalkoxy group, (C1 _{- C6} )alkylthio group, halo(C1 _{- C6} ) _alkylthio group , (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C _{1 -} C6) alkylsulfonyl group, (C1 _- C6) alkylcarbonyl group, halo(C1 _- C6) alkylcarbonyl group _, (C3 _{- C6} ) cycloalkylcarbonyl group, ( _{C1 - C6} ) ) a substituted pyridyl group having from 1 to 4 substituents on the ring selected from an alkoxycarbonyl group and a halo(C ₁ -C ₆ )alkoxycarbonyl group,
R ³ represents a (C ₁ -C ₆ )alkyl group; or a halo(C ₁ -C ₆ )alkyl group, R ⁴ represents a hydrogen atom,

R ⁵ is a pyridyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, (C ₁ -C ₆ )alkylthio group, halo( C ₁ -C ₆ )alkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ ) ) alkylsulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl substituted pyridyl groups having 1 to 4 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups; pyrimidinyl groups; or halogen atoms , cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C _{1 -} C6)alkoxy group, halo(C1 _- C6)alkoxy group, (C3 _{- C6} )cycloalkoxy group, (C1 _{- C6} )alkylthio group, halo(C1 _{- C6} ) _alkylthio group , (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ )alkylsulfinyl group, (C ₃ -C ₆ )cycloalkylsulfinyl group, (C ₁ -C ₆ )alkylsulfonyl group, halo(C _{1 -} C6) alkylsulfonyl group, (C1 _- C6) alkylcarbonyl group, halo(C1 _- C6) alkylcarbonyl group _, (C3 _{- C6} ) cycloalkylcarbonyl group, ( _{C1 - C6} ) ) represents a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from an alkoxycarbonyl group and a halo(C ₁ -C ₆ )alkoxycarbonyl group, X represents an oxygen atom; or a sulfur atom, Y represents a single bond, Q ¹ represents CH; or represents a nitrogen atom, and Q ² represents a nitrogen atom is the case and

Particularly preferably, R ¹ is (C ₁ -C ₆ )alkyl group; halo(C ₁ -C ₆ )alkyl group; (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; halo(C ₃ —C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group; benzyl group; halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group and halo(C ₁ ) —C ₆ ) substituted benzyl group having 1 to 5 substituents on the ring selected from alkoxy group; pyridylmethyl group; halogen atom, cyano group, (C ₁ -C ₆ ) alkyl group, halo(C ₁ ) ( _{C 2 -C 6 ) alkenyl} group; halo( C ₂ -C ₆ )alkenyl group; (C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,

R ² is a phenyl group; 1 to 5 selected from a halogen atom, a cyano group, a (C ₁ -C ₆ )alkyl group, a halo(C ₁ -C ₆ )alkyl group and a halo(C ₁ -C ₆ )alkoxy group a substituted phenyl group having five substituents on the ring; a pyridyl group; or a halogen atom, a cyano group, a (C ₁ -C ₆ )alkyl group, a halo(C ₁ -C ₆ )alkyl group and a halo(C ₁ -C ₆ ) a substituted pyridyl group having 1 to 4 substituents on the ring selected from alkoxy groups, R ³ represents a (C ₁ -C ₆ )alkyl group, R ⁴ represents a hydrogen atom, R ⁵ is a pyridyl group; 1 to 4 selected from a halogen atom, a cyano group, a (C ₁ -C ₆ )alkyl group, a halo(C ₁ -C ₆ )alkyl group and a halo(C ₁ -C ₆ )alkoxy group; pyrimidinyl group; or halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group and halo(C ₁ -C ₆ ) represents a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from an alkoxy group, X represents an oxygen atom; or represents a sulfur atom, Y represents a single bond, Q ¹ represents CH, When ^Q2 represents a nitrogen atom.

Various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited thereto.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｑ_１、Ｑ_２およびＹは前記に同じくし、Ｌはハロゲン原子などの脱離基を示す。） Manufacturing method 1

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Q ₁ , Q ₂ and Y are the same as above, and L represents a leaving group such as a halogen atom.)

The compound represented by the general formula (I-1) in which X is a sulfur atom is obtained by using a known compound represented by the general formula (II) disclosed in WO 2017/192385 as a starting material, a base and It can be produced by reacting it with a compound represented by general formula (III) in the presence of an inert solvent.

Bases that can be used in this reaction include, for example, triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, nitrogen-containing organic bases such as pyridine, sodium carbonate, potassium carbonate, and hydrogen carbonate. Inorganic bases such as sodium, sodium hydroxide, potassium hydroxide, sodium hydride and metallic sodium; organic bases such as sodium acetate and potassium acetate; alcoholates such as sodium ethoxide and potassium t-butoxide; can. The amount of the base to be used may be appropriately selected within the range of about 0.5 to 5 times the molar amount of the compound represented by the general formula (II).

The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly hinder the progress of this reaction. aromatic hydrocarbons such as benzene, toluene and xylene; amides such as dimethylformamide, N-methylacetamide, N-methylpyrrolidone and hexamethylphosphoroamide; halogenated compounds such as methylene chloride, chloroform and carbon tetrachloride. Inert solvents such as hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene can be mentioned, and these inert solvents can be used alone or in combination of two or more. . The amount of the inert solvent to be used is not particularly limited, and there is no problem as long as it is an amount capable of dissolving the compounds represented by general formulas (II) and (III). It may be appropriately selected within the range of 0.01 mol/L to 100 mol/L.

The reaction temperature may be selected from the range of about -20 to 150°C, and the reaction time may vary depending on the scale of reaction, reaction temperature, etc., but may be appropriately selected from the range of several minutes to about 48 hours. After completion of the reaction, the target product is isolated from the reaction system containing the compound represented by general formula (I-1) by a conventional method, and if necessary, is purified by recrystallization, distillation, column chromatography, or the like. can produce a compound represented by general formula (I-1). Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in excess.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｑ_１、Ｑ_２、ＬおよびＹは前記に同じくし、ＰＴＣは相間移動触媒を示す。） Manufacturing method 2

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Q ₁ , Q ₂ , L and Y are the same as above, and PTC indicates a phase transfer catalyst.)

The compound represented by the general formula (I-2) in which X is an oxygen atom is obtained by using a known compound represented by the general formula (IV) disclosed in WO 2017/192385 as a starting material, a base, It can be produced by reacting a compound represented by general formula (III) using a two-layer solvent system of water and an inert solvent in the presence of a phase transfer catalyst (PTC).

Phase transfer catalysts that can be used in this reaction include, for example, ammonium salts such as benzyldimethyltetradecylammonium chloride, benzyltributylammonium bromide, methyltrioctylammonium hydrogensulfate, tetrabutylammonium hydrogensulfate, tetrabutylammonium bromide, tributyl Phosphonium salts such as dodecylphosphonium bromide, tetrabutylphosphonium bromide, tetraethylphosphonium tetrafluoroborate, and crown ethers such as 15-crown 5-ether and 18-crown 6-ether can be mentioned, and these phase transfer catalysts can be used. can be used alone or in combination of two or more. The amount of the phase transfer catalyst to be used may be appropriately selected within the range of 0.01 to 2 moles per mole of the compound represented by general formula (IV).

Bases that can be used in this reaction include, for example, triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, nitrogen-containing organic bases such as pyridine, sodium carbonate, potassium carbonate, and hydrogen carbonate. Inorganic bases such as sodium, sodium hydroxide, potassium hydroxide, sodium hydride and metallic sodium; organic bases such as sodium acetate and potassium acetate; alcoholates such as sodium ethoxide and potassium t-butoxide; can. The amount of the base to be used may be appropriately selected within the range of about 0.5 to 5 times the molar amount of the compound represented by the general formula (II).

As the inert solvent that can be used in this reaction, any solvent can be used as long as it is sparingly soluble in water, forms a bilayer system, and does not significantly hinder the progress of this reaction. Ethers, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated compounds such as chlorobenzene and dichlorobenzene Inert solvents such as aromatic hydrocarbons can be mentioned, and these inert solvents can be used alone or in combination of two or more. The amount of the inert solvent to be used is not particularly limited, and may be appropriately selected within the range of 0.01 mol/L to 100 mol/L with respect to the compound represented by general formula (II). The mixing ratio (volume ratio) of water and the inert solvent may be appropriately selected from the range of 1:10 to 10:1.

The reaction temperature may be selected from the range of about 0 to 150° C., and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to about 48 hours. After completion of the reaction, the desired product is isolated from the reaction system containing the compound represented by general formula (I-2) by a conventional method, and, if necessary, is purified by recrystallization, distillation, column chromatography, or the like. can produce a compound represented by general formula (I-2). Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but either reactant may be used in excess.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｑ_１、Ｑ_２、ＸおよびＹは前記に同じくし、ｈａｌはハロゲン原子を示す。） Manufacturing method 3

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Q ₁ , Q ₂ , X and Y are the same as above, and hal represents a halogen atom.)

In addition to production methods 1 and 2, the compound represented by the general formula (I) is obtained by using a known compound represented by the general formula (IV) disclosed in WO 2017/192385 pamphlet as a starting material, reacting with a halogenating agent in the presence or absence of an active solvent to give a compound of the general formula (V), isolating the compound, or without isolation, in the presence of a base and an inert solvent; can be produced by reacting with a compound represented by the general formula (VI).

Method for producing general formula (IV) to general formula (V) Examples of halogenating agents that can be used in this reaction include halogenated carbonyl compounds such as oxalyl chloride, phosgene, diphosgene and triphosgene, and halogenated compounds such as thionyl chloride and thionyl bromide. sulfur compounds, phosphorous compounds such as phosphorous oxychloride, phosphorous oxybromide, phosphorous trichloride, phosphorous tribromide, phosphorous pentachloride, and the like, and these halogenating agents may be used alone or in combination of two A mixture of the above can be used. The amount of the halogenating agent to be used may be appropriately selected from the range of 0.5 to 10 times the molar amount of the compound represented by the general formula (IV). Moreover, the halogenating agent itself can also be used as a solvent. Furthermore, a catalyst such as DMF (dimethylformamide) generally known to accelerate the halogenation reaction can also be used.

As the inert solvent that can be used in this reaction, any solvent that does not significantly hinder the progress of this reaction can be used. Inactive solvents such as halogenated hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene can be mentioned, and these inert solvents can be used alone or in combination of two or more. can be done. The amount of the inert solvent used is not particularly limited, and there is no problem as long as it is an amount that can dissolve the compound represented by the general formula (IV). It may be appropriately selected in the range of L to 100 mol/L. Moreover, when using the halogenating agent itself as a solvent, an inert solvent is not used.

The reaction temperature may be selected from the range of about -20 to 150°C, and the reaction time may vary depending on the scale of reaction, reaction temperature, etc., but may be appropriately selected from the range of several minutes to about 48 hours. After completion of the reaction, the target product is isolated from the reaction system containing the compound represented by the general formula (V) by a conventional method, and if necessary, is purified by recrystallization, distillation, column chromatography or the like, A compound represented by general formula (V) can be produced. Moreover, when the compound represented by the general formula (V) is unstable, it can be used as it is for the next reaction without isolation. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in excess.

Method for producing general formula (I) from general formula (V) Examples of bases that can be used in this reaction include triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine and the like. Nitrogen-containing organic bases, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, inorganic bases such as sodium metal, organic bases such as sodium acetate, potassium acetate, sodium ethoxide , potassium t-butoxide and other alcoholates. The amount of the base to be used may be appropriately selected within the range of about 0.5 to 5 times the molar amount of the compound represented by formula (V).

The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly hinder the progress of this reaction. aromatic hydrocarbons such as benzene, toluene and xylene; amides such as dimethylformamide, N-methylacetamide, N-methylpyrrolidone and hexamethylphosphoroamide; halogenated compounds such as methylene chloride, chloroform and carbon tetrachloride. Inert solvents such as hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene can be mentioned, and these inert solvents can be used alone or in combination of two or more. . The amount of the inert solvent to be used is not particularly limited, and there is no problem as long as it is an amount capable of dissolving the compounds represented by general formulas (V) and (VI). It may be appropriately selected within the range of 0.01 mol/L to 100 mol/L.

The reaction temperature may be selected from the range of about -20 to 150°C, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected from the range of several minutes to about 48 hours. After completion of the reaction, the target product is isolated from the reaction system containing the compound represented by formula (I) by a conventional method, and if necessary, is purified by recrystallization, distillation, column chromatography, or the like. Compounds represented by general formula (I) can be produced. Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but either reactant may be used in excess.

Representative examples of the compounds represented by formula (I) of the present invention are shown in Tables 1 to 3 below, but the present invention is not limited to these.
In the table, "Me" is methyl, "Et" is ethyl, "Pr" is propyl, "Bu" is butyl, "Pen" is pentyl, "Hex" is hexyl, and "Oct" is octyl. , "Bn" for benzyl, "Ph" for phenyl, "Py" for pyridine, "Pym" for pyrimidine, "Pyr" for pyrazine, "Pyd" for pyridazine, "n-" for normal , “t-” indicates tertiary, and “c-” indicates cyclo. Physical properties are indicated by melting point (°C) or 1H-NMR data. A number in each substituent indicates a substitution position. In addition, the compounds of the present invention illustrated in Tables 1 to 3 are either geometric isomers (E form or Z form) based on carbon-nitrogen double bonds or mixtures thereof. Table 4 shows ¹ H-NMR data of the compounds described as "NMR" in the column of physical properties in Tables 1 to 3.

The pest control agent containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is suitable for controlling insect pests in agricultural and horticultural fields, animal ectoparasites and endoparasites. It can be used as a horticultural pest control agent and an animal parasite control agent.

Pests that can be controlled by the agricultural and horticultural pest control agent include various agricultural and forestry pests, horticultural pests, grain storage pests, sanitary pests, etc. that damage paddy rice, fruit trees, vegetables, other crops and flowers. In addition to insects, the pests include mites, nematodes, and the like, and the following pests are specifically exemplified.

Lepidoptera (Lepidoptera) pests include, for example, Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapularis, African armyworm (Spotox America)シロヒトリ（Ｈｙｐｈａｎｔｒｉａ ｃｕｎｅａ）、アワノメイガ（Ｏｓｔｒｉｎｉａ ｆｕｒｎａｃａｌｉｓ）、アワヨトウ（Ｐｓｅｕｄａｌｅｔｉａ ｓｅｐａｒａｔａ）、イガ（Ｔｉｎｅａ ｔｒａｎｓｌｕｃｅｎｓ）、イグサシンムシガ（Ｂａｃｔｒａ ｆｕｒｆｕｒａｎａ）、イチモンジセセリ（Ｐａｒｎａｒａ ｇｕｔｔａｔａ）、イネタテハマキ（Ｍａｒａｓｍｉａ ｅｘｉｇｕａ）、イネツトムシ（Ｐａｒｎａｒａ ｇｕｔｔａｔａ）、イネヨトウ（ Ｓｅｓａｍｉａ ｉｎｆｅｒｅｎｓ）、イモキバガ（Ｂｒａｃｈｍｉａ ｔｒｉａｎｎｕｌｅｌｌａ）、イラガ（Ｍｏｎｅｍａ ｆｌａｖｅｓｃｅｎｓ）、イラクサギンウワバ（Ｔｒｉｃｈｏｐｌｕｓｉａ ｎｉ）、ウコンノメイガ（Ｐｌｅｕｒｏｐｔｙａ ｒｕｒａｌｉｓ）、ウメエダシャク（Ｃｙｓｔｉｄｉａ ｃｏｕａｇｇａｒｉａ）、ウラナミシジミ（Ｌａｍｐｉｄｅｓ ｂｏｅｔｉｃｕｓ）、オオスカシバ（Ｃｅｐｈｏｎｏｄｅｓ ｈｙｌａｓ）、オオタバコガ（Ｈｅｌｉｃｏｖｅｒｐａ ａｒｍｉｇｅｒａ）、オオトビモンシャチホコ（Ｐｈａｌｅｒｏｄｏｎｔａ ｍａｎｌｅｙｉ）、オオミノガ（Ｅｕｍｅｔａ ｊａｐｏｎｉｃａ）、オオモンシロチョウ（Ｐｉｅｒｉｓ ｂｒａｓｓｉｃａｅ）、オビカレハ（Ｍａｌａｃｏｓｏｍａ ｎｅｕｓｔｒｉａ ｔｅｓｔａｃｅａ）、カキノヘタムシガ（Ｓｔａｔｈｍｏｐｏｄａ ｍａｓｉｎｉｓｓａ）、カキホソガ（Ｃｕｐｈｏｄｅｓ ｄｉｏｓｐｙｒｏｓｅｌｌａ）、カクモンハマキ（Ａｒｃｈｉｐｓ xylosteanus), Agrotis segetum, Tetramoera schistaceana, Papilio machaon hippocrates,

キマダラコウモリ（Ｅｎｄｏｃｌｙｔａ ｓｉｎｅｎｓｉｓ）、ギンモンハモグリガ（Ｌｙｏｎｅｔｉａ ｐｒｕｎｉｆｏｌｉｅｌｌａ）、キンモンホソガ（Ｐｈｙｌｌｏｎｏｒｙｃｔｅｒ ｒｉｎｇｏｎｅｅｌｌａ）、クリミガ（Ｃｙｄｉａ ｋｕｒｏｋｏｉ）、クリミドリシンクイガ（Ｅｕｃｏｅｎｏｇｅｎｅｓ ａｅｓｔｕｏｓａ）、グレープベリーモス（Ｌｏｂｅｓｉａ ｂｏｔｒａｎａ）、クロシタアオイラガ（Ｌａｔｏｉａ ｓｉｎｉｃａ） 、クロフタモンマダラメイガ（Ｅｕｚｏｐｈｅｒａ ｂａｔａｎｇｅｎｓｉｓ）、クワイホソハマキ（Ｐｈａｌｏｎｉｄｉａ ｍｅｓｏｔｙｐａ）、クワゴマダラヒトリ（Ｓｐｉｌｏｓｏｍａ ｉｍｐａｒｉｌｉｓ）、クワノメイガ（Ｇｌｙｐｈｏｄｅｓ ｐｙｌｏａｌｉｓ）、クワヒメハマキ（Ｏｌｅｔｈｒｅｕｔｅｓ ｍｏｒｉ）、コイガ（Ｔｉｎｅｏｌａ ｂｉｓｓｅｌｌｉｅｌｌａ）、コウモリガ（Ｅｎｄｏｃｌｙｔａ ｅｘｃｒｅｓｃｅｎｓ）、コクガ（ Ｎｅｍａｐｏｇｏｎ ｇｒａｎｅｌｌｕｓ）、コスカシバ（Ｓｙｎａｎｔｈｅｄｏｎ ｈｅｃｔｏｒ）、コドリンガ（Ｃｙｄｉａ ｐｏｍｏｎｅｌｌａ）、コナガ（Ｐｌｕｔｅｌｌａ ｘｙｌｏｓｔｅｌｌａ）、コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓ ｍｅｄｉｎａｌｉｓ）、サザンピンクボーラー（Ｓｅｓａｍｉａ ｃａｌａｍｉｓｔｉｓ）、サンカメイガ（Ｓｃｉｒｐｏｐｈａｇａ ｉｎｃｅｒｔｕｌａｓ）、シバツトガ（Ｐｅｄｉａｓｉａ ｔｅｔｅｒｒｅｌｌｕｓ）、ジャガイモガ（Ｐｈｔｈｏｒｉｍａｅａ ｏｐｅｒｃｕｌｅｌｌａ）、シャチホコガ（Ｓｔａｕｒｏｐｕｓ ｆａｇｉ ｐｅｒｓｉｍｉｌｉｓ）、シロイチモジマダラメイガ（Ｅｔｉｅｌｌａ ｚｉｎｃｋｅｎｅｌｌａ）、シロイチモジヨトウ（Ｓｐｏｄｏｐｔｅｒａ ｅｘｉｇｕａ）、シロテンコウモリ（Ｐａｌｐｉｆｅｒ ｓｅｘｎｏｔａｔａ）、シロナヨトウ（Ｓｐｏｄｏｐｔｅｒａ ｍａｕｒｉｔｉａ）、イネシロオオメイガ（Ｓｃｉｒｐｏｐｈａｇａ ｉｎｎｏｔａｔａ） , Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angelona prunaria, Seguro killer whale (Clostera anastomosis), soybean looper (Pseudoplusia includens), soybean moth (Matsumuraeses falcana), tobacco moth (Helicoverpa assulta), stag beetle (Autographa nigrisigna),

タマナヤガ（Ａｇｒｏｔｉｓ ｉｐｓｉｌｏｎ）、チャドクガ（Ｅｕｐｒｏｃｔｉｓ ｐｓｅｕｄｏｃｏｎｓｐｅｒｓａ）、チャノコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ ｏｒａｎａ）、チャノホソガ（Ｃａｌｏｐｔｉｌｉａ ｔｈｅｉｖｏｒａ）、チャハマキ（Ｈｏｍｏｎａ ｍａｇｎａｎｉｍａ）、チャマダラメイガ（Ｅｐｈｅｓｔｉａ ｅｌｕｔｅｌｌａ）、チャミノガ（Ｅｕｍｅｔａ ｍｉｎｕｓｃｕｌａ）、ツマアカシャチホコ(Clostera anachoreta), Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Tomato fruit Hibustois ｚｅａ）、ナカジロシタバ（Ａｅｄｉａ ｌｅｕｃｏｍｅｌａｓ）、ナシイラガ（Ｎａｒｏｓｏｉｄｅｕｓ ｆｌａｖｉｄｏｒｓａｌｉｓ）、ナシケンモン（Ｖｉｍｉｎｉａ ｒｕｍｉｃｉｓ）、ナシチビガ（Ｂｕｃｃｕｌａｔｒｉｘ ｐｙｒｉｖｏｒｅｌｌａ）、ナシヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ ｍｏｌｅｓｔａ）、ナシホソガ（Ｓｐｕｌｅｒｉｎａ ａｓｔａｕｒｏｔａ）、ナシマダラメイガ（Ｅｃｔｏｍｙｅｌｏｉｓ ｐｙｒｉｖｏｒｅｌｌａ）、ニカメイガ（Ｃｈｉｌｏ ｓｕｐｐｒｅｓｓａｌｉｓ）、ネギコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ ｓａｐｐｏｒｅｎｓｉｓ）、ノシメマダラメイガ（Ｐｌｏｄｉａ ｉｎｔｅｒｐｕｎｃｔｅｌｌａ）、ハイマダラノメイガ（Ｈｅｌｌｕｌａ ｕｎｄａｌｉｓ）、バクガ（Ｓｉｔｏｔｒｏｇａ ｃｅｒｅａｌｅｌｌａ）、ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ ｌｉｔｕｒａ）、ハマキガの一種（Ｅｕｃｏｓｍａ ａｐｏｒｅｍａ）、バラハマキ（Ａｃｌｅｒｉｓ ｃｏｍａｒｉａｎａ） , Scopelodes contractus, Orgyia thyellana, Fall army worm (Spodoptera frugiperda), Ostrinia zaguliaevi, Naran ｇａ ａｅｎｅｓｃｅｎｓ）、フタテンカギバモドキ（Ａｎｄｒａｃａ ｂｉｐｕｎｃｔａｔａ）、ブドウスカシバ（Ｐａｒａｎｔｈｒｅｎｅ ｒｅｇａｌｉｓ）、ブドウスズメ（Ａｃｏｓｍｅｒｙｘ ｃａｓｔａｎｅａ）、ブドウハモグリガ（Ｐｈｙｌｌｏｃｎｉｓｔｉｓ ｔｏｐａｒｃｈａ）、ブドウヒメハマキ（Ｅｎｄｏｐｉｚａ ｖｉｔｅａｎａ）、ブドウホソハマキ（Ｅｕｐｏｅｃｉｌｌｉａ ａｍｂｉｇｕｅｌｌａ）、ベルベットビーンキャタピラー（Ａｎｔｉｃａｒｓｉａ ｇｅｍｍａｔａｌｉｓ）、ホソバハイイロハマキ（Ｃｎｅｐｈａｓｉａ ｃｉｎｅｒｅｉｐａｌｐａｎａ）、マイマイガ（Ｌｙｍａｎｔｒｉａ ｄｉｓｐａｒ）、マツカレハ（Ｄｅｎｄｒｏｌｉｍｕｓ ｓｐｅｃｔａｂｉｌｉｓ）、マメシンクイガ（Ｌｅｇｕｍｉｎｉｖｏｒａ ｇｌｙｃｉｎｉｖｏｒｅｌｌａ）、マメノメイガ（Ｍａｒｕｃａ ｔｅｓｔｕｌａｌｉｓ）、マメヒメサヤムシガ（Ｍａｔｓｕｍｕｒａｅｓｅｓ ｐｈａｓｅｏｌｉ）、

マメホソガ（Ｃａｌｏｐｔｉｌｉａ ｓｏｙｅｌｌａ）、ミカンハモグリガ（Ｐｈｙｌｌｏｃｎｉｓｔｉｓ ｃｉｔｒｅｌｌａ）、マエウスキノメイガ（Ｏｍｉｏｄｅｓ ｉｎｄｉｃａｔｅ）、ミダレカクモンハマキ（Ａｒｃｈｉｐｓ ｆｕｓｃｏｃｕｐｒｅａｎｕｓ）、ミツモンキンウワバ（Ａｃａｎｔｈｏｐｌｕｓｉａ ａｇｎａｔａ）、ミノガ（Ｂａｍｂａｌｉｎａ ｓｐ．）、モモシンクイガ（Ｃａｒｐｏｓｉｎａ ｎｉｐｏｎｅｎｓｉｓ ）、モモノゴマダラノメイガ（Ｃｏｎｏｇｅｔｈｅｓ ｐｕｎｃｔｉｆｅｒａｌｉｓ）、モモスカシバ類（Ｓｙｎａｎｔｈｅｄｏｎ ｓｐ．）、モモハモグリガ（Ｌｙｏｎｅｔｉａ ｃｌｅｒｋｅｌｌａ）、モンキアゲハ（Ｐａｐｉｌｉｏ ｈｅｌｅｎｕｓ）、モンキチョウ（Ｃｏｌｉａｓ ｅｒａｔｅ ｐｏｌｉｏｇｒａｐｈｕｓ）、モンクロシャチホコ（Ｐｈａｌｅｒａ ｆｌａｖｅｓｃｅｎｓ）、モンシロチョウ（Ｐｉｅｒｉｓ ｒａｐａｅ ｃｒｕｃｉｖｏｒａ ), white butterflies such as Pieris rapae, Euproctis similis, Acrolepiopsis suzukiella, European corn borer (Ostrinia nubilalis), armyworm (Mamestra brassicae), Artemis officinalis, Asencotis （Ｐｈｔｈｅｏｃｈｒｏｉｄｅｓ ｃｌａｎｄｅｓｔｉｎａ）、リンゴオオハマキ（Ｈｏｓｈｉｎｏａ ａｄｕｍｂｒａｔａｎａ）、リンゴカレハ（Ｏｄｏｎｅｓｔｉｓ ｐｒｕｎｉ ｊａｐｏｎｅｎｓｉｓ）、リンゴケンモン（Ｔｒｉａｅｎａ ｉｎｔｅｒｍｅｄｉａ）、リンゴコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ ｏｒａｎａ ｆａｓｃｉａｔａ）、リンゴコシンクイ（Ｇｒａｐｈｏｌｉｔａ ｉｎｏｐｉｎａｔａ）、リンゴシロヒメハマキ（ Spilonota ocellana), Spilonota lechriaspis, Illiberis pruni, Argyrestia conjugella, Caloptilia zachrysa, Archip ｓ ｂｒｅｖｉｐｌｉｃａｎｕｓ）、ワタアカキリバ（Ａｎｏｍｉｓ ｆｌａｖａ）、ワタアカミムシ（Ｐｅｃｔｉｎｏｐｈｏｒａ ｇｏｓｓｙｐｉｅｌｌａ）、ワタノメイガ（Ｎｏｔａｒｃｈａ ｄｅｒｏｇａｔａ）、ワタヘリクロノメイガ（Ｄｉａｐｈａｎｉａ ｉｎｄｉｃａ）、ニセアメリカタバコガ（Ｈｅｌｉｏｔｈｉｓ ｖｉｒｅｓｃｅｎｓ）、およびワタリンガ（Ｅａｒｉａｓ ｃｕｐｒｅｏｖｉｒｉｄｉｓ）などが挙げられる。

Examples of Hemiptera pests (Nezara antennata), Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc. （Ａｅｓｃｈｙｎｔｅｌｅｓ ｍａｃｕｌａｔｕｓ）、アカホシカスミカメ（Ｃｒｅｏｎｔｉａｄｅｓ ｐａｌｌｉｄｉｆｅｒ）、アカホシカメムシ（Ｄｙｓｄｅｒｃｕｓ ｃｉｎｇｕｌａｔｕｓ）、アカホシマルカイアガラムシ（Ｃｈｒｙｓｏｍｐｈａｌｕｓ ｆｉｃｕｓ）、アカマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ ａｕｒａｎｔｉｉ）、アブラゼミ（Ｇｒａｐｔｏｐｓａｌｔｒｉａ ｎｉｇｒｏｆｕｓｃａｔａ）、アメリカコバネナガカメムシ（Ｂｌｉｓｓｕｓｌｅｕｃｏｐｔｅｒｕｓ）、イセリヤカイガラムシ（Ｉｃｅｒｙａ ｐｕｒｃｈａｓｉ）、イチモンジカメムシ（Ｐｉｅｚｏｄｏｒｕｓ ｈｙｂｎｅｒｉ）、イネカメムシ（Ｌａｇｙｎｏｔｏｍｕｓ ｅｌｏｎｇａｔｕｓ）、イネキイロヒメヨコバイ（Ｔｈａｉａ ｓｕｂｒｕｆａ）、イネクロカメムシ（Ｓｃｏｔｉｎｏｐｈａｒａ ｌｕｒｉｄａ）、イバラヒゲナガアブラムシ（Ｓｉｔｏｂｉｏｎ ｉｂａｒａｅ）、イワサキカメムシ（Ｓｔａｒｉｏｄｅｓ ｉｗａｓａｋｉｉ ）、ウスイロマルカイガラムシ（Ａｓｐｉｄｉｏｔｕｓ ｄｅｓｔｒｕｃｔｏｒ）、ウスモンミドリカスミカメ（Ｔａｙｌｏｒｉｌｙｇｕｓ ｐａｌｌｉｄｕｌｕｓ）、ウメコブアブラムシ（Ｍｙｚｕｓ ｍｕｍｅｃｏｌａ）、ウメシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ ｐｒｕｎｉｃｏｌａ）、エンドウヒゲナガアブラムシ（Ａｃｙｒｔｈｏｓｉｐｈｏｎ ｐｉｓｕｍ）、オオクモヘリカメムシ（Ａｎａｃａｎｔｈｏｃｏｒｉｓ striicornis), blue-spotted milk turtle (Ectometopterus micantulus), rhinoceros beetle (Eysarcoris lewisi), leafhopper (Molipteryx fuliginosa), leafhopper (Cicadella viridis), green aphid (Rhopalosophalosophyllum) Abdominalis), olive mealybug (Saissetia oleate),

オンシツコナジラミ（Ｔｒｉａｌｅｕｒｏｄｅｓ ｖａｐｏｒａｒｉｏｒｕｍ）、カシヒメヨコバイ（Ａｇｕｒｉａｈａｎａ ｑｕｅｒｃｕｓ）、カスミカメムシ類（Ｌｙｇｕｓ ｓｐｐ．）、カバワタフキマダラアブラムシ（Ｅｕｃｅｒａｐｈｉｓ ｐｕｎｃｔｉｐｅｎｎｉｓ）、カンキツカイガラムシ（Ａｎｄａｓｐｉｓ ｋａｓｈｉｃｏｌａ）、カンキツカタカイガラムシ（Ｃｏｃｃｕｓ ｐｓｅｕｄｏｍａｇｎｏｌｉａｒｕｍ）、カンシャコバネナガカメムシ（Ｃａｖｅｌｅｒｉｕｓ ｓａｃｃｈａｒｉｖｏｒｕｓ）、キクグンバイ（Ｇａｌｅａｔｕｓ ｓｐｉｎｉｆｒｏｎｓ）、キクヒメヒゲナガアブラムシ（Ｍａｃｒｏｓｉｐｈｏｎｉｅｌｌａ ｓａｎｂｏｒｎｉ）、キマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ ｃｉｔｒｉｎａ）、クサギカメムシ（Ｈａｌｙｏｍｏｒｐｈａ ｍｉｓｔａ）、クスグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ ｆａｓｃｉｉｃａｒｉｎａ）、クストガリキジラミ（Ｔｒｉｏｚａ ｃａｍｐｈｏｒａｅ）、クモLeptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Black-footed stink bug (Paromius exiguus),ツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ ｎｉｇｒｏｐｉｃｔｕｓ）、クロトビカスミカメ（Ｈａｌｔｉｃｉｅｌｌｕｓ ｉｎｓｕｌａｒｉｓ）、クロフツノウンカ（Ｐｅｒｋｉｎｓｉｅｌｌａ ｓａｃｃｈａｒｉｃｉｄａ）、クロリンゴキジラミ（Ｐｓｙｌｌａ ｍａｌｉｖｏｒｅｌｌａ）、クワキジラミ（Ａｎｏｍｏｍｅｕｒａ ｍｏｒｉ）、クワコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ ｌｏｎｇｉｓｐｉｎｉｓ）、クワシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ ｐｅｎｔａｇｏｎａ ), Pulvinaria kuwacola, Apolygus lucorum, Togo hemipterus, Toxoptera aurantii, Sugarcane mealybug (Saccharicoccus sacchari), sugarcane bollworm (Geoica lucifuga), sugar planthopper (Numata muiri), San Jose scale (Comstockaspis perniciosa), citrus snow scale (Unaspis citri),

ジャガイモヒゲナガアブラムシ（Ａｕｌａｃｏｒｔｈｕｍ ｓｏｌａｎｉ）、シラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ ｖｅｎｔｒａｌｉｓ）、シルバーリーフコナジラミ（Ｂｅｍｉｓｉａ ａｒｇｅｎｔｉｆｏｌｉｉ）、シロオオヨコバイ（Ｃｉｃａｄｅｌｌａ ｓｐｅｃｔｒａ）、シロマルカイガラムシ（Ａｓｐｉｄｉｏｔｕｓ ｈｅｄｅｒａｅ）、スカシヒメヘリカメムシ（Ｌｉｏｒｈｙｓｓｕｓ ｈｙａｌｉｎｕｓ）、セグロヒメキジラミ（Ｃａｌｏｐｈｙａ ｎｉｇｒｉｄｏｒｓａｌｉｓ）、セジロウンカ（Ｓｏｇａｔｅｌｌａ ｆｕｒｃｉｆｅｒａ）、ソラマメヒゲナガアブラムシ（Ｍｅｇｏｕｒａ ｃｒａｓｓｉｃａｕｄａ）、ダイコンアブラムシ（Ｂｒｅｖｉｃｏｒｙｎｅ ｂｒａｓｓｉｃａｅ）、ダイズアブラムシ（Ａｐｈｉｓ ｇｌｙｃｉｎｅｓ）、タイワンクモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ ｏｒａｔｏｒｉｕｓ）、タイワンツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ ｖｉｒｅｓｃｅｎｓ）、タイワンヒゲナガアブラムシ（Ｕｒｏｅｕｃｏｎ ｆｏｒｍｏｓａｎｕｍ）、タバコカスミカメ（Ｃｙｒｔｏｐｅｌｔｉｓ ｔｅｎｎｕｉｓ）、タバココナジラミ（Ｂｅｍｉｓｉａ ｔａｂａｃｉ）、チャノカタカイガラムシ（Ｌｅｃａｎｉｕｍ ｐｅｒｓｉｃａｅ）、チャノクロホシカイガラムシ（Ｐａｒｌａｔｏｒｉａ ｔｈｅａｅ）、チャノマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ ｐａｅｏｎｉａｅ）、チャノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ ｏｎｕｋｉｉ）、チャバネアオカメムシ（Ｐｌａｕｔｉａ ｓｔａｌｉ）、チューリップネアブラムシ（Ｄｙｓａｐｈｉｓ ｔｕｌｉｐａｅ）、チューリップヒゲナガアブラムシ（Ｍａｃｒｏｓｉｐｈｕｍ ｅｕｐｈｏｒｂｉａｅ）、ツツジグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ ｐｙｒｉｏｉｄｅｓ）、ツノロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ ｃｅｒｉｆｅｒｕｓ）、ツバキクロホシカイガラムシ（Ｐａｒｌａｔｏｒｉａ ｃａｍｅｌｌｉａｅ） , Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Orthotylus flavosparsus, cornブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ ｍａｉｄｉｓ）、トウモロコシウンカ（Ｐｅｒｅｇｒｉｎｕｓ ｍａｉｄｉｓ）、トゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ ｐａｒｖｕｓ）、トコジラミ（Ｃｉｍｅｘ ｌｅｃｔｕｌａｒｉｕｓ）、トドキジラミ（Ｐｓｙｌｌａ ａｂｉｅｔｉ）、トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ ｌｕｇｅｎｓ）、トベラキジラミ（Ｐｓｙｌｌａ ｔｏｂｉｒａｅ）、ナガメ（Ｅｕｒｙｄｅｍａ ｒｕｇｏｓｕｍ） 、ナシアブラムシ（Ｓｃｈｉｚａｐｈｉｓ ｐｉｒｉｃｏｌａ）、ナシキジラミ（Ｐｓｙｌｌａ ｐｙｒｉｃｏｌａ）、ナシクロホシカイガラムシ（Ｐａｒｌａｔｏｒｅｏｐｓｉｓ ｐｙｒｉ）、ナシグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ ｎａｓｈｉ）、ナシコナカイガラムシ（Ｄｙｓｍｉｃｏｃｃｕｓ ｗｉｓｔａｒｉａｅ）、ナシシロナガカイガラムシ（Ｌｅｐｈｏｌｅｕｃａｓｐｉｓ ｊａｐｏｎｉｃａ）、ナシマルアブラムシ（ Sappaphis piri), radish aphid (Lipaphis erysimi), onion aphid (Neotoxoptera formosana), husky aphid (Rhopalosophum nymphaeae),

バラヒメヨコバイ（Ｅｄｗａｒｄｓｉａｎａｒｏｓａｅ）、ハランナガカイガラムシ（Ｐｉｎｎａｓｐｉｓａｓｐｉｄｉｓｔｒａｅ）、ハンノキジラミ（Ｐｓｙｌｌａ ａｌｎｉ）、ハンノナガヨコバイ（Ｓｐｅｕｓｏｔｅｔｔｉｘ ｓｕｂｆｕｓｃｕｌｕｓ）、ハンノヒメヨコバイ（Ａｌｎｅｔｏｉｄｉａ ａｌｎｅｔｉ）、ヒエウンカ（Ｓｏｇａｔｅｌｌａ ｐａｎｉｃｉｃｏｌａ）、ヒゲナガカスミカメ（Ａｄｅｌｐｈｏｃｏｒｉｓ ｌｉｎｅｏｌａｔｕｓ）、ヒメアカホシカメムシ（Ｄｙｓｄｅｒｃｕｓ ｐｏｅｃｉｌｕｓ）、ヒメクロカイガラムシ（Ｐａｒｌａｔｏｒｉａ ｚｉｚｉｐｈｉ）、ヒメグンバイ（Ｕｈｌｅｒｉｔｅｓ ｄｅｂｉｌｅ）、ヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ ｓｔｒｉａｔｅｌｌｕｓ）、ヒメナガメ（Ｅｕｒｙｄｅｍａ ｐｕｌｃｈｒｕｍ）、ヒメハリカメムシ（Ｃｌｅｔｕｓ ｔｒｉｇｏｎｕｓ）、ヒメフタテンナガアワフキ（Ｃｌｏｖｉａ ｐｕｎｃｔａｔａ）、ヒメヨコバイ類（Ｅｍｐｏａｓｃａ ｓｐ．）、ヒラタカタカイガラムシ（Ｃｏｃｃｕｓ ｈｅｓｐｅｒｉｄｕｍ）、ヒラタヒョウタンナガカメムシ（Ｐａｃｈｙｂｒａｃｈｉｕｓ ｌｕｒｉｄｕｓ）、フジコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ ｋｒａｕｎｈｉａｅ）、フタスジカスミカメ（Ｓｔｅｎｏｔｕｓ ｂｉｎｏｔａｔｕｓ）、フタテンヒメヨコバイ（Ａｒｂｏｒｉｄｉａ ａｐｉｃａｌｉｓ ）、フタテンヨコバイ（Ｍａｃｒｏｓｔｅｌｅｓ ｆａｓｃｉｆｒｏｎｓ）、ブチヒゲカメムシ（Ｄｏｌｙｃｏｒｉｓ ｂａｃｃａｒｕｍ）、ブチヒゲクロカスミカメ（Ａｄｅｌｐｈｏｃｏｒｉｓ ｔｒｉａｎｎｕｌａｔｕｓ）、ブドウネアブラムシ（Ｖｉｔｅｕｓ ｖｉｔｉｆｏｌｉｉ）、 ホオズキカメムシ（Ａｃａｎｔｈｏｃｏｒｉｓ ｓｏｒｄｉｄｕｓ）、ホソクモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ ａｃｕｔａ） , Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli, Aphrophora costalis, Lygis disponsis （Ｌｙｇｕｓ ｓａｕｎｄｅｒｓｉ）、マツコナカイガラムシ（Ｃｒｉｓｉｃｏｃｃｕｓ ｐｉｎｉ）、マツヒメヨコバイ（Ｅｍｐｏａｓｃａ ａｂｉｅｔｉｓ）、マツモトコナカイガラムシ（Ｃｒｉｓｉｃｏｃｃｕｓ ｍａｔｓｕｍｏｔｏｉ）、マメアブラムシ（Ａｐｈｉｓ ｃｒａｃｃｉｖｏｒａ）、マルカメムシ（Ｍｅｇａｃｏｐｔａ ｐｕｎｃｔａｔｉｓｓｉｍｕｍ）、マルシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ ｇｕｔｔｉｇｅｒ） , Lepidosaphes beckii,

ミカンキジラミ（Ｄｉａｐｈｏｒｉｎａ ｃｉｔｒｉ）、ミカンクロアブラムシ（Ｔｏｘｏｐｔｅｒａ ｃｉｔｒｉｃｉｄｕｓ）、ミカンコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ ｃｉｔｒｉ）、ミカンコナジラミ（Ｄｉａｌｅｕｒｏｄｅｓ ｃｉｔｒｉ）、ミカントゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ ｓｐｉｎｉｆｅｒｕｓ）、ミカンヒメコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ ｃｉｔｒｉｃｕｌｕｓ）、ミカンヒメヨコバイ（ Ｚｙｇｉｎｅｌｌａ ｃｉｔｒｉ）、ミカンヒメワタカイガラムシ（Ｐｕｌｖｉｎａｒｉａ ｃｉｔｒｉｃｏｌａ）、ミカンヒラタカイガラムシ（Ｃｏｃｃｕｓ ｄｉｓｃｒｅｐａｎｓ）、ミカンマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ ｄｕｐｌｅｘ）、ミカンワタカイガラムシ（Ｐｕｌｖｉｎａｒｉａ ａｕｒａｎｔｉｉ）、ミズキカタカイガラムシ（Ｌｅｃａｎｉｕｍ ｃｏｒｎｉ）、ミナミアオカメムシ（Ｎｅｚａｒａ ｖｉｒｉｄｕｌａ）、ムギカスミカメ（Ｓｔｅｎｏｄｅｍａ ｃａｌｃａｒａｔｕｍ）、ムギクビレアブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ ｐａｄｉ）、ムギヒゲナガアブラムシ（Ｓｉｔｏｂｉｏｎ ａｋｅｂｉａｅ）、ムギミドリアブラムシ（Ｓｃｈｉｚａｐｈｉｓ ｇｒａｍｉｎｕｍ）、ムギヨコバイ（Ｓｏｒｈｏａｎｕｓ ｔｒｉｔｉｃｉ）、ムギワラギクオマルアブラムシ（Ｂｒａｃｈｙｃａｕｄｕｓ ｈｅｌｉｃｈｒｙｓｉ）、ムラサキカメムシ（Ｃａｒｐｏｃｏｒｉｓ ｐｕｒｐｕｒｅｉｐｅｎｎｉｓ）、モモアカアブラムシ（Ｍｙｚｕｓ ｐｅｒｓｉｃａｅ）、モモコフキアブラムシ（Ｈｙａｌｏｐｔｅｒｕｓ ｐｒｕｎｉ）、ヤナギアブラムシ（Ａｐｈｉｓ ｆａｒｉｎｏｓｅ ｙａｎａｇｉｃｏｌａ）、ヤナギグンバイ（Ｍｅｔａｓａｌｉｓ ｐｏｐｕｌｉ）、ヤノネカイガラムシ（Ｕｎａｓｐｉｓ ｙａｎｏｎｅｎｓｉｓ）、ヤマアサキジラミ（Ｍｅｓｏｈｏｍｏｔｏｍａ ｃａｍｐｈｏｒａｅ）、 Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes, Myz Aphidonuguis mali), Orientus ishidai, Ovatus malicolens, Eriosoma lanigerum, Ceroplastes rubens, and Aphispygo gossypii mentioned.

Coleoptera pests, for example, Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus uschinensis, Cylas formicゾウムシ（Ｈｙｐｅｒａ ｐｏｓｔｉｃａ）、イネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕｓ ｓｑｕａｍｅｕｓ）、イネドロオイムシ（Ｏｕｌｅｍａ ｏｒｙｚａｅ）、イネドロオイムシ（Ｏｕｌｅｍａ ｏｒｙｚａｅ）、イネネクイハムシ（Ｄｏｎａｃｉａ ｐｒｏｖｏｓｔｉ）、イネミズゾウムシ（Ｌｉｓｓｏｒｈｏｐｔｒｕｓ ｏｒｙｚｏｐｈｉｌｕｓ）、イモサルハムシ（Ｃｏｌａｓｐｏｓｏｍａ ｄａｕｒｉｃｕｍ）、イモゾウムシ（Ｅｕｓｃｅｐｅｓ ｐｏｓｔｆａｓｃｉａｔｕｓ）、インゲンテントウ（Ｅｐｉｌａｃｈｎａ ｖａｒｉｖｅｓｔｉｓ）、インゲンマメゾウムシ（Ａｃａｎｔｈｏｓｃｅｌｉｄｅｓ ｏｂｔｅｃｔｕｓ）、ウエスタンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ ｖｉｒｇｉｆｅｒａ ｖｉｒｇｉｆｅｒａ）、ウメチョッキリゾウムシ（Ｉｎｖｏｌｖｕｌｕｓ ｃｕｐｒｅｕｓ）、ウリハムシ（Ａｕｌａｃｏｐｈｏｒａ ｆｅｍｏｒａｌｉｓ）、エンドウゾウムシ（Ｂｒｕｃｈｕｓ ｐｉｓｏｒｕｍ）、オオニジュウヤホシテントウ（ Ｅｐｉｌａｃｈｎａ ｖｉｇｉｎｔｉｏｃｔｏｍａｃｕｌａｔａ）、ガイマイデオキスイ（Ｃａｒｐｏｐｈｉｌｕｓ ｄｉｍｉｄｉａｔｕｓ）、カメノコハムシ（Ｃａｓｓｉｄａ ｎｅｂｕｌｏｓａ）、キアシノミハムシ（Ｌｕｐｅｒｏｍｏｒｐｈａ ｔｕｎｅｂｒｏｓａ）、キスジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ ｓｔｒｉｏｌａｔａ）、キボシカミキリ（Ｐｓａｃｏｔｈｅａ ｈｉｌａｒｉｓ）、キマダラカミキリ（Ａｅｏｌｅｓｔｈｅｓ ｃｈｒｙｓｏｔｈｒｉｘ）、クリシギゾウムシ（Ｃｕｒｃｕｌｉｏ sikkimensis), Carpophilus hemipterus, Oxycetonia jucunda,

コーンルートワーム類（Ｄｉａｂｒｏｔｉｃａ ｓｐｐ．）、コガネムシ（Ｍｉｍｅｌａ ｓｐｌｅｎｄｅｎｓ）、コクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ ｚｅａｍａｉｓ）、コクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ ｃａｓｔａｎｅｕｍ）、ココクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ ｏｒｙｚａｅ）、コヒメコクヌストモドキ（Ｐａｌｏｒｕｓ ｓｕｂｄｅｐｒｅｓｓｕｓ）、コフキコガネ（Ｍｅｌｏｌｏｎｔｈａ ｊａｐｏｎｉｃａ）、ゴマダラカミキリ（Ａｎｏｐｌｏｐｈｏｒａ ｍａｌａｓｉａｃａ）、ゴミムシダマシ（Ｎｅａｔｕｓ ｐｉｃｉｐｅｓ）、コロラドハムシ（Ｌｅｐｔｉｎｏｔａｒｓａ ｄｅｃｅｍｌｉｎｅａｔａ）、サザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ ｕｎｄｅｃｉｍｐｕｎｃｔａｔａ ｈｏｗａｒｄｉ）、シバオサゾウムシ（Ｓｐｈｅｎｏｐｈｏｒｕｓ ｖｅｎａｔｕｓ）、ジュウシホシクビナガハムシ（Ｃｒｉｏｃｅｒｉｓ ｑｕａｔｕｏｒｄｅｃｉｍｐｕｎｃｔａｔａ）、スモモゾウムシ（ Ｃｏｎｏｔｒａｃｈｅｌｕｓ ｎｅｎｕｐｈａｒ）、ダイコンサルゾウムシ（Ｃｅｕｔｈｏｒｈｙｎｃｈｉｄｉｕｓ ａｌｂｏｓｕｔｕｒａｌｉｓ）、ダイコンハムシ（Ｐｈａｅｄｏｎ ｂｒａｓｓｉｃａｅ）、タバコシバンムシ（Ｌａｓｉｏｄｅｒｍａ ｓｅｒｒｉｃｏｒｎｅ）、チビコフキゾウムシ（Ｓｉｔｏｎａ ｊａｐｏｎｉｃｕｓ）、チャイロコガネ（Ａｄｏｒｅｔｕｓ ｔｅｎｕｉｍａｃｕｌａｔｕｓ）、チャイロコメノゴミムシダマシ（Ｔｅｎｅｂｒｉｏ ｍｏｌｉｔｏｒ）、チャイロサルハムシ（Ｂａｓｉｌｅｐｔａ ｂａｌｙｉ）、ツメクサタコゾウムシ（Ｈｙｐｅｒａ ｎｉｇｒｉｒｏｓｔｒｉｓ）、テンサイトビハムシ（Ｃｈａｅｔｏｃｎｅｍａ ｃｏｎｃｉｎｎａ）、ドウガネブイブイ（Ａｎｏｍａｌａ ｃｕｐｒｅａ）、ナガチャコガネ（Ｈｅｐｔｏｐｈｙｌｌａ ｐｉｃｅａ）、ニジュウヤホシテントウ（Ｅｐｉｌａｃｈｎａ ｖｉｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）、ノーザンコーンルートワーム（ Diabrotica longicornis), Eucetonia pilifera, Wireworms (Agriotes spp.), Attagenus unicolor japonicus, Lamb beetle ( Ｐａｇｒｉａ ｓｉｇｎａｔａ）、ヒメコガネ（Ａｎｏｍａｌａ ｒｕｆｏｃｕｐｒｅａ）、ヒメコクヌストモドキ（Ｐａｌｏｒｕｓ ｒａｔｚｅｂｕｒｇｉｉ）、ヒメゴミムシダマシ（Ａｌｐｈｉｔｏｂｉｕｓ ｌａｅｖｉｇａｔｕｓ）、ヒメマルカツオブシムシ（Ａｎｔｈｒｅｎｕｓ ｖｅｒｂａｓｃｉ）、ヒラタキクイムシ（Ｌｙｃｔｕｓ ｂｒｕｎｎｅｕｓ）、ヒラタコクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ ｃｏｎｆｕｓｕｍ）、フタスジヒメハムシ（Ｍｅｄｙｔｈｉａ ｎｉｇｒｏｂｉｌｉｎｅａｔａ）、ブドウトラカミキリ（Ｘｙｌｏｔｒｅｃｈｕｓ ｐｙｒｒｈｏｄｅｒｕｓ）、ポテトフリービートル（Ｅｐｉｔｒｉｘ ｃｕｃｕｍｅｒｉｓ）、マツノキクイムシ（Ｔｏｍｉｃｕｓ ｐｉｎｉｐｅｒｄａ）、マツノマダラカミキリ（Ｍｏｎｏｃｈａｍｕｓ ａｌｔｅｒｎａｔｕｓ）、マメコガネ（Ｐｏｐｉｌｌｉａ ｊａｐｏｎｉｃａ）、マメハンミョウ（Ｅｐｉｃａｕｔａ ｇｏｒｈａｍｉ）、メイズウィービル（Ｓｉｔｏｐｈｉｌｕｓ ｚｅａｍａｉｓ）、モモチョッキリゾウムシ（Ｒｈｙｎｃｈｉｔｅｓ ｈｅｒｏｓ）、ヤサイゾウムシ（Ｌｉｓｔｒｏｄｅｒｅｓ ｃｏｓｔｉｒｏｓｔｒｉｓ）、ヨツモンマメゾウムシ（Ｃａｌｌｏｓｏｂｒｕｃｈｕｓ ｍａｃｕｌａｔｕｓ）、リンゴコフキゾウムシ（Ｐｈｙｌｌｏｂｉｕｓ ａｒｍａｔｕｓ）、リンゴハナゾウムシ（Ａｎｔｈｏｎｏｍｕｓ ｐｏｍｏｒｕｍ）、ルリハムシ（Ｌｉｎａｅｉｄｅａ ａｅｎｅａ ), boll weevil (Anthonomus grandis), and the like.

Diptera (Diptera) pests include, for example, Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Oryhloropsミギワバエ（Ｈｙｄｒｅｌｌｉａ ｓａｓａｋｉｉ）、イネハモグリバエ（Ａｇｒｏｍｙｚａ ｏｒｙｚａｅ）、イネヒメハモグリバエ（Ｈｙｄｒｅｌｌｉａ ｇｒｉｓｅｏｌａ）、イネミギワバエ（Ｈｙｄｒｅｌｌｉａ ｇｒｉｓｅｏｌａ）、インゲンモグリバエ（Ｏｐｈｉｏｍｙｉａ ｐｈａｓｅｏｌｉ）、ウリミバエ（Ｄａｃｕｓ ｃｕｃｕｒｂｉｔａｅ）、オウトウショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ ｓｕｚｕｋｉｉ）、オウトウハマダラミバエ（Ｒｈａｃｏｃｈｌａｅｎａ ｊａｐｏｎｉｃａ）、オオイエバエ（Ｍｕｓｃｉｎａ ｓｔａｂｕｌａｎｓ）、オオキモンノミバエ（Ｍｅｇａｓｅｌｉａ ｓｐｉｒａｃｕｌａｒｉｓ）などのノミバエ類、オオチョウバエ（Ｃｌｏｇｍｉａ ａｌｂｉｐｕｎｃｔａｔａ）、キリウジガガンボ（Ｔｉｐｕｌａ ａｉｎｏ）、クロキンバエ（Ｐｈｏｒｍｉａ ｒｅｇｉｎａ）、コガタアカイエカ（Ｃｕｌｅｘ ｔｒｉｔａｅｎｉｏｒｈｙｎｃｈｕｓ ）、シナハマダラカ（Ａｎｏｐｈｅｌｅｓ ｓｉｎｅｎｓｉｓ）、ダイコンバエ（Ｈｙｌｅｍｙａ ｂｒａｓｓｉｃａｅ）、ダイズサヤタマバエ（Ａｓｐｈｏｎｄｙｌｉａ ｓｐ．）、タネバエ（Ｄｅｌｉａ ｐｌａｔｕｒａ）、タマネギバエ（Ｄｅｌｉａ ａｎｔｉｑｕａ）、ヨーロッパオウトウミバエ（Ｒｈａｇｏｌｅｔｉｓ ｃｅｒａｓｉ）、チカイエカ（Ｃｕｌｅｘ ｐｉｐｉｅｎｓ ｍｏｌｅｓｔｕｓ Ｆｏｒｓｋａｌ） 、チチュウカイミバエ（Ｃｅｒａｔｉｔｉｓ ｃａｐｉｔａｔａ）、チビクロバネキノコバエ（Ｂｒａｄｙｓｉａ ａｇｒｅｓｔｉｓ）、テンサイモグリハナバエ（Ｐｅｇｏｍｙａ ｃｕｎｉｃｕｌａｒｉａ）、トマトハモグリバエ（Ｌｉｒｉｏｍｙｚａ ｓａｔｉｖａｅ）、ナスハモグリバエ（Ｌｉｒｉｏｍｙｚａ ｂｒｙｏｎｉａｅ）、ナモグリバエ（Ｃｈｒｏｍａｔｏｍｙｉａ ｈｏｒｔｉｃｏｌａ）、ネギハモグリバエ（Ｌｉｒｉｏｍｙ ｚａ ｃｈｉｎｅｎｓｉｓ）、ネッタイイエカ（Ｃｕｌｅｘ ｑｕｉｎｑｕｅｆａｓｃｉａｔｕｓ）、ネッタイシマカ（Ａｅｄｅｓ ａｅｇｙｐｔｉ）、ヒトスジシマカ（Ａｅｄｅｓ ａｌｂｏｐｉｃｔｕｓ）、マメハモグリバエ（Ｌｉｒｉｏｍｙｚａ ｔｒｉｆｏｌｉｉ）、トマトハモグリバエ（Ｌｉｒｉｏｍｙｚａ ｓａｔｉｖａｅ）、ミカンコミバエ（Ｄａｃｕｓ ｄｏｒｓａｌｉｓ）、ミカンバエ（Ｄａｃｕｓ ｔｓｕｎｅｏｎｉｓ）、ムギアカThese include the ball fly (Sitodiplosis moselana), the wheat fly (Meromuza nigriventris), the Mexican fruit fly (Anastrepha ludens), and the apple fly (Rhagoletis pomonella).

膜翅目（ハチ目）害虫として、例えば、アミメアリ（Ｐｒｉｓｔｏｍｙｒｍｅｘ ｐｕｎｇｅｎｓ）、アリガタバチ類、イエヒメアリ（Ｍｏｎｏｍｏｒｉｕｍ ｐｈａｒａｏｈｎｉｓ）、オオズアリ（Ｐｈｅｉｄｏｌｅ ｎｏｄａ）、カブラハバチ（Ａｔｈａｌｉａ ｒｏｓａｅ）、クリタマバチ（Ｄｒｙｏｃｏｓｍｕｓ ｋｕｒｉｐｈｉｌｕｓ）、クロヤマアリ（Ｆｏｒｍｉｃａ ｆｕｓｃａ ｊａｐｏｎｉｃａ ), Wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Fire ant (Solenopsis spp.), Apple sawfly (Arge), and Luria (Ochetellus glaver) and the like.

Orthoptera (Grasshopper) pests include, for example, Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Opinyaponia Examples include Homorocoryphus jezoensis and Teleogryllus emma.

アザミウマ目害虫として、例えば、アカオビアザミウマ（Ｓｅｌｅｎｏｔｈｒｉｐｓ ｒｕｂｒｏｃｉｎｃｔｕｓ）、イネアザミウマ（Ｓｔｅｎｃｈａｅｔｏｔｈｒｉｐｓ ｂｉｆｏｒｍｉｓ）、イネクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ ａｃｕｌｅａｔｕｓ）、カキクダアザミウマ（Ｐｏｎｔｉｃｕｌｏｔｈｒｉｐｓ ｄｉｏｓｐｙｒｏｓｉ）、キイロハナアザミウマ（Ｔｈｒｉｐｓ ｆｌａｖｕｓ）、クサキイロアザミウマ（Ａｎａｐｈｏｔｈｒｉｐｓ ｏｂｓｃｕｒｕｓ ）、クスクダアザミウマ（Ｌｉｏｔｈｒｉｐｓ ｆｌｏｒｉｄｅｎｓｉｓ）、グラジオラスアザミウマ（Ｔｈｒｉｐｓ ｓｉｍｐｌｅｘ）、クロゲハナアザミウマ（Ｔｈｒｉｐｓ ｎｉｇｒｏｐｉｌｏｓｕｓ）、クロトンアザミウマ（Ｈｅｌｉｏｔｈｒｉｐｓ ｈａｅｍｏｒｒｈｏｉｄａｌｉｓ）、クワアザミウマ（Ｐｓｅｕｄｏｄｅｎｄｒｏｔｈｒｉｐｓ ｍｏｒｉ）、コスモスアザミウマ（Ｍｉｃｒｏｃｅｐｈａｌｏｔｈｒｉｐｓ ａｂｄｏｍｉｎａｌｉｓ）、シイオナガクダアザミウマ（Ｌｅｅｕｗｅｎｉａ ｐａｓａｎｉｉ）、シイマルクダアザミウマ（Ｌｉｔｏｔｅｔｏｔｈｒｉｐｓ ｐａｓａｎｉａｅ）、シトラススリップス（Ｓｃｉｒｔｏｔｈｒｉｐｓ ｃｉｔｒｉ）、シナクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ ｃｈｉｎｅｎｓｉｓ）、ダイズアザミウマ（Ｍｙｃｔｅｒｏｔｈｒｉｐｓ ｇｌｙｃｉｎｅｓ）、ダイズウスイロアザミウマ（Ｔｈｒｉｐｓ ｓｅｔｏｓｕｓ）、チャノキイロアザミウマ（Ｓｃｉｒｔｏｔｈｒｉｐｓ ｄｏｒｓａｌｉｓ）、チャノクロアザミウマ（Ｄｅｎｄｒｏｔｈｒｉｐｓ ｍｉｎｏｗａｉ）、ツメクサクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ ｎｉｇｅｒ）、ネギアザミウマ（Ｔｈｒｉｐｓ ｔａｂａｃｉ）、ネギクロアザミウマ（Ｔｈｒｉｐｓ ａｌｌｉｏｒｕｍ）、ハナアザミウマ（Ｔｈｒｉｐｓ ｈａｗａｉｉｅｎｓｉｓ）、ハナクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ ｋｕｒｄｊｕｍｏｖｉ）、ヒゲPig thrips (Chirothrips manicatus), Black thrips (Frankliniella intonsa), Loquat thrips (Thrips coloratus), Western flower thrips (Franklinella occidentalis), Southern yellow thrips thrips palmi, Frankliniella lilivora, Liothrips vaneeckei, and the like.

ダニ目害虫として、例えば、アオツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ ａｋａｍｕｓｈｉ）、アシノワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｌｕｄｅｎｉ）、アメリカンドックチック（Ｄｅｒｍａｃｅｎｔｏｒ ｖａｒｉａｂｉｌｉｓ）、イシイナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｔｒｕｎｃａｔｕｓ）、イエダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ ｂａｃｏｔｉ）、イヌニキビダニ（Ｄｅｍｏｄｅｘ ｃａｎｉｓ）、オウトウハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｖｉｅｎｎｅｎｓｉｓ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｋａｎｚａｗａｉ）、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ ｓａｎｇｕｉｎｅｕｓ）などのマダニ類、クワガタツメダニ（Ｃｈｅｙｌｅｔｕｓ ｍａｌａｃｃｅｎｓｉｓ）、ケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ ｐｕｔｒｅｓｃｅｎｔｉａｅ）、コナヒョウヒダニ（Ｄｅｒｍａｔｏｐｈａｇｏｉｄｅｓ ｆａｒｉｎａｅ）、セアカゴケグモ（Ｌａｔｒｏｄｅｃｔｕｓ ｈａｓｓｅｌｔｉｉ）、タイワンカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ ｔａｉｗａｎｉｃｕｓ）、チャノナガサビダニ（Ａｃａｐｈｙｌｌａ ｔｈｅａｖａｇｒａｎｓ）、チャノホコリダニ（Ｐｏｌｙｐｈａｇｏｔａｒｓｏｎｅｍｕｓ ｌａｔｕｓ）、トマトサビダニ（Ａｃｕｌｏｐｓ ｌｙｃｏｐｅｒｓｉｃｉ）、トリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ ｓｙｌｖａｉｒｕｍ）、ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｕｒｔｉｃａｅ）、ニセナシサビダニ（Ｅｒｉｏｐｈｙｅｓ ｃｈｉｂａｅｎｓｉｓ）、ヒゼンダニ（ Ｓａｒｃｏｐｔｅｓ ｓｃａｂｉｅｉ）、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｌｏｎｇｉｃｏｒｎｉｓ）、ブラックレッグドチック（Ｉｘｏｄｅｓ ｓｃａｐｕｌａｒｉｓ）、ホウレンソウケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ ｓｉｍｉｌｉｓ）、ホソツメダニ（Ｃｈｅｙｌｅｔｕｓ ｅｒｕｄｉｔｕｓ）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ ｃｉｔｒｉ）、ミナミツメダニ（Ｃｈｅｙｌｅｔｕｓ ｍｏｏｒｅｉ）、ミナミヒメハダニ（Ｂｒｅｖｉｐａｌｐｕｓ phoenicis), Octodectes cynotis, Dermatophagoides ptrenyssnus, Haemap ｈｙｓａｌｉｓ ｆｌａｖａ）、ヤマトマダニ（Ｉｘｏｄｅｓ ｏｖａｔｕｓ）、リュウキュウミカンサビダニ（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ ｃｉｔｒｉ）、リンゴサビダニ（Ａｃｕｌｕｓ ｓｃｈｌｅｃｈｔｅｎｄａｌｉ）、リンゴハダニ（Ｐａｎｏｎｙｃｈｕｓ ｕｌｍｉ）、ローンスターチック（Ａｍｂｌｙｏｍｍａ ａｍｅｒｉｃａｎｕｍ）、およびワクモ（Ｄｅｒｍａｎｙｓｓｕｓ ｇａｌｌｉｎａｅ）、ロビンネダニ（Ｒｈｙｚｏｇｌｙｐｈｕｓ robini), a kind of mite (Sancassonia sp. ) and the like.

Examples of termite pests include Reticulites miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticutermes sp. ）、クシモトシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ ｋｕｓｈｉｍｅｎｓｉｓ）、コウシュウイエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ ｇｕａｎｇｚｈｏｅｎｓｉｓ）、コウシュンシロアリ（Ｎｅｏｔｅｒｍｅｓ ｋｏｓｈｕｎｅｎｓｉｓ）、コダマシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ ｋｏｄａｍａｉ）、サツマシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ ｓａｔｓｕｍｅｎｓｉｓ）、ダイコクシロアリ（Ｃｒｙｐｔｏｔｅｒｍｅｓ ｄｏｍｅｓｔｉｃｕｓ）、タイワンシロアリ（Ｏｄｏｎｔｏｔｅｒｍｅｓ ｆｏｒｍｏｓａｎｕｓ ), Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.

ゴキブリ目害虫として、例えば、クロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ ｆｕｌｉｇｉｎｏｓａ）、チャバネゴキブリ（Ｂｌａｔｔｅｌｌａ ｇｅｒｍａｎｉｃａ）、トウヨウゴキブリ（Ｂｌａｔｔａ ｏｒｉｅｎｔａｌｉｓ）、トビイロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ ｂｒｕｎｎｅａ）、ヒメチャバネゴキブリ（Ｂｌａｔｔｅｌｌａ ｌｉｔｕｒｉｃｏｌｌｉｓ）、ヤマトゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ ｊａｐｏｎｉｃａ）、およびAmerican cockroach (Periplaneta americana) and the like.

As nematodes, for example, strawberry mesenchu (Nothotylenchus acris), rice shingare nematode (Aphelenchoides besseyi), rice shingare nematode (Pratylenchus penetrans), tubercle nematode (Meloidogyne hapla), sweet potato root nematode (Meloidogyne nematode) (Meloidogyne potato) Ｇｌｏｂｏｄｅｒａ ｒｏｓｔｏｃｈｉｅｎｓｉｓ）、ジャワネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ ｊａｖａｎｉｃａ）、ダイズシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ ｇｌｙｃｉｎｅｓ）、ミナミネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ ｃｏｆｆｅａｅ）、ムギネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ ｎｅｇｌｅｃｔｕｓ）、およびミカンネセンチュウ（Ｔｙｌｅｎｃｈｕｓ ｓｅｍｉｐｅｎｅｔｒａｎｓ）などが挙げられる。

Mollusks include, for example, Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus slugs, and Acacia snails. etc.

The agricultural and horticultural pest control agent containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient causes damage to paddy field crops, field crops, fruit trees, vegetables, other crops and flowers. Since it has a remarkable control effect against pests, it can be applied to nursery facilities, paddy fields, fields, fruit trees, vegetables, and other crops before the pests appear or when pests are confirmed to occur in accordance with the time when pests are expected to occur. The desired effect of the agricultural and horticultural pest control agent of the present invention can be obtained by treating seeds such as flowers, paddy water, foliage, soil and other cultivation carriers. In addition, the compounds of the present invention can be absorbed from the roots, with or without soil, by treating seedling soil for crops, flowers, etc., planting hole soil for transplanting, plant roots, irrigation water, cultivation water in hydroponics, etc. It is also possible to adopt a form of use that utilizes so-called penetrability, which is caused by

Useful plants for which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited. , red beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruit vegetables (cabbage) , tomato, spinach, broccoli, lettuce, onion, green onion, bell pepper, eggplant, strawberry, pepper, okra, chive, etc.), root vegetables (carrot, potato, sweet potato, taro, Japanese radish, turnip, lotus root, burdock, garlic, shallots, etc.), processed crops (cotton, hemp, beets, hops, sugarcane, sugar beet, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, makuwa melon, melon) etc.), pasture grasses (orchardgrass, sorghum, timothy, clover, alfalfa, etc.), grasses (Korai grass, bentgrass, etc.), ornamental crops such as fragrances (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), Flowers (chrysanthemums, roses, carnations, orchids, tulips, lilies, etc.), garden trees (ginkgo, cherry blossoms, aoki, etc.), forest trees (todomatsu, spruce, pines, cypress, cedar, cypress, eucalyptus, etc.) Plants may be mentioned.

The above useful plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl Also included are plants that have been given tolerance to herbicides such as CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.

Examples of useful plants that have been made tolerant by classical breeding methods include rapeseed, wheat, sunflower and rice that are tolerant to imidazolinone ALS-inhibiting herbicides such as imazethapyr under the trade name Clearfield (registered trademark). Already sold. Similarly, there are soybeans tolerant to sulfonylurea-based ALS-inhibiting herbicides, such as thifensulfuron-methyl, by classical breeding methods and are already marketed under the trade name STS soybeans. Similarly, SR corn and the like are examples of plants that have been given resistance to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides by classical breeding methods.

In addition, plants endowed with resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) vol.87, pp.7175-7179 (1990). Mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has also been reported in Weed Science, Vol. 53, pp. 728-746 (2005). A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a plant acetyl-CoA carboxylase-related mutation into a plant acetyl-CoA carboxylase. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318. By introducing substitution mutations, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can be produced, and the agricultural and horticultural pest control agent of the present invention can also be used for these plants. can.

Furthermore, toxins expressed in transgenic plants include insecticidal proteins derived from Bacillus cereus and Bacillus popiliae; insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; filamentous fungal toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, bryozin; Steroid metabolizing enzymes such as hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel, calcium channel inhibitors; juvenile hormone esterase; stilbene synthase; bibenzyl synthase; chitinase; glucanase;

Toxins expressed in such transgenic plants include δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, VIP1, VIP2, VIP3 or VIP3A. Also included are insecticidal protein hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are created using recombinant techniques by new combinations of different domains of these proteins. As a partially deleted toxin, Cry1Ab with partially deleted amino acid sequence is known. A modified toxin has one or more of the amino acids of the native toxin substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP0374753, WO93/07278, WO95/34656, EP0427529, EP0451878, WO03/052073 and others.

The toxins contained in these recombinant plants confer on the plants resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, Nematodes, among others. The agricultural and horticultural pest control agent of the present invention can be used in combination with those techniques or systematized.

To control various pests, the agricultural and horticultural pest control agent of the present invention is used as it is, or in the form of being diluted or suspended with water as appropriate, and added in an amount effective for pest control to plants where the pests are expected to occur. For example, for pests that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the foliage, seed treatments such as immersion in chemicals, seed dressing, and culper treatment, and all layers of the soil It can also be used by treating the soil and allowing it to be absorbed from the roots, such as mixing, row application, bed soil mixing, cell seedling treatment, planting hole treatment, stock base treatment, top dressing, rice box treatment, water surface application, etc. . In addition, it can also be applied to a nutrient solution in nutrient (hydroponic) cultivation, and used by smoking or trunk injection.

Furthermore, the agricultural and horticultural pest control agent of the present invention can be used as it is or in a form of being diluted or suspended with water in an effective amount for pest control at a place where the occurrence of the pest is expected. For example, in addition to spraying against grain pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on building materials, as smoke, as a bait, and the like.

Seed treatment methods include, for example, a method of immersing seeds in a liquid or undiluted liquid state with a liquid or solid preparation to penetrate the drug, a method of mixing a solid or liquid preparation with seeds, and a method of dressing. Examples include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as a resin or polymer, and a method of spraying near the seed at the same time as planting.
The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation. Mention may be made of plants for vegetative propagation.

The "soil" or "cultivation carrier" for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that allows plants to grow may be used, such as so-called soil, seedling mats, water, etc. Specific materials include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chips, bark, and the like.

For spraying on foliage of crops, grain pests, house pests, sanitary pests, forest pests, etc., liquid formulations such as emulsifiable concentrates and flowable formulations, or solid formulations such as wettable powders or wettable granules, should be diluted with water as appropriate. , dusting methods, dusting methods, or smoking.
As a method of applying to soil, for example, a method of applying a liquid formulation to the stock of a plant or a seedling nursery without diluting it with water, or a method of applying granules to the stock of a plant or a seedling A method of spraying on nurseries, a method of spraying powders, wettable powders, wettable granules, granules, etc. before sowing or transplanting and mixing them with the entire soil, a method of planting holes before sowing or planting plants, Examples include a method of spraying powders, wettable powders, wettable granules, granules, etc. on the lines.

As for the method of application to nursery boxes for paddy rice, the dosage form may vary depending on the application period, such as application at the time of sowing, application at the time of greening, and application at the time of transplanting. It should be applied in a mold. It can also be applied by mixing with potting soil, and mixing potting soil with powders, wettable granules or granules, for example, mixing with bed soil, mixing with covering soil, mixing with the whole potting soil, etc. Can be done. Simply alternating layers of potting soil and various formulations may be applied.
As a method of application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules and wettable granules, and liquid formulations such as flowables and emulsions are usually sprayed over flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed or injected into the soil as it is or mixed with fertilizer. In addition, by using chemical liquids such as emulsions and flowables at water inlets, irrigation systems, and other water inflow sources into paddy fields, it is possible to apply them with less labor as water is supplied.

In field crops, the treatment can be applied to the seeds or cultivation carriers close to the plant during the period from sowing to seedling raising. For plants that are directly sown in a field, it is preferable to apply the agent directly to the seeds as well as to the base of the plant under cultivation. It is possible to perform a spraying treatment using granules, or an irrigation treatment in the form of a liquid diluted or undiluted drug. It is also a preferred treatment to mix the granules with the cultivation carrier before sowing and then sowing.
As for the sowing of the cultivated plants to be transplanted and the treatment during the seedling-raising period, it is preferable to directly treat the seeds, or to irrigate the seedbeds for raising the seedlings with liquefied chemicals or to spray the granules. It is also preferable to apply granules to the planting holes at the time of planting or to mix them with cultivation carriers in the vicinity of the place of transplantation.

The agricultural and horticultural pest control agent of the present invention is generally used after being formulated into a form convenient for use according to a conventional method for agricultural chemical formulations. That is, the compound represented by the general formula (I) of the present invention or a salt thereof is mixed with a suitable inert carrier or, if necessary, together with an adjuvant in a suitable proportion, dissolved, separated, suspended. Turbidity, mixing, impregnation, adsorption or adhesion may be used by formulating into appropriate dosage forms such as suspensions, emulsions, liquids, wettable powders, wettable granules, granules, powders, tablets, packs, etc. Just do it.

The agricultural and horticultural pest control agent of the present invention can contain, if necessary, additive components that are commonly used in agricultural chemical formulations, in addition to the active ingredient. Examples of the additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreaders, spreading agents, and antifreeze agents. , anti-caking agents, disintegrants, anti-degradants and the like. In addition, preservatives, plant pieces, and the like may be used as additive components, if necessary. These additive components may be used alone or in combination of two or more.

Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as plant powders (e.g. sawdust, coconut shells, corn cobs, tobacco stalks, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), and the like. These may be used alone or in combination of two or more.

Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin. alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc. ethers, normal paraffin, naphthene, isoparaffin, kerosene, mineral oil and other aliphatic hydrocarbons, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene and other aromatic hydrocarbons, dichloromethane, chloroform, carbon tetrachloride, etc. Halogenated hydrocarbons, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.

Examples of surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Alkylene-added acetylene diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-based surfactants, nonionic surfactants such as polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil, alkyl sulfates, polyoxyethylene alkyl ethers Sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzenesulfonates, alkylarylsulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfones salt, formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, fatty acid salt, polycarboxylate, polyacrylate, N-methyl-fatty acid sarcosinate, resinate, polyoxy Anionic surfactants such as ethylene alkyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, Cationic surfactants such as alkyltrimethylammonium chloride, alkylamine salts such as alkyldimethylbenzalkonium chloride, amino acid type or betaine type and amphoteric surfactants such as These surfactants may be used alone or in combination of two or more.

Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weights of 6,000 to 20,000. polyethylene glycol with an average molecular weight of 100,000 to 5,000,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g. cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymerization of maleic acid and styrenes. coalescence, (meth)acrylic acid-based copolymer, half ester of polyhydric alcohol polymer and dicarboxylic acid anhydride, water-soluble salt of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylate, polyoxy Ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.

Examples of thickening agents include xanthan gum, guar gum, daiyutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, fumed silica ( Inorganic fine powder such as fumed silica, white carbon) and the like.

Examples of coloring agents include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

Antifreeze agents include, for example, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and glycerin.

Auxiliaries for preventing caking and promoting disintegration include, for example, starch, polysaccharides such as alginic acid, mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate. , sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft A copolymer etc. are mentioned.

Examples of antidegradants include drying agents such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. be done.

Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Furthermore, if necessary, other aids such as functional spreading agents, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers. agents can also be used.

The blending ratio of the active ingredient compound can be adjusted as necessary, and it may be appropriately selected from the range of 0.01 to 90 parts by mass in 100 parts by mass of the agricultural and horticultural pest control agent of the present invention. For example, 0.01 to 50 parts by mass (0.01 to 50% by mass based on the total mass of the agricultural and horticultural pest control agent) is suitable for powders, granules, emulsions or wettable powders.

The use amount of the agricultural and horticultural pest control agent of the present invention is determined by various factors such as purpose, target pests, crop growth conditions, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, and the like. Depending on the purpose, the amount of the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares.

The agricultural and horticultural pest control agent of the present invention can be used with other agricultural and horticultural insecticides, acaricides, nematicides, and fungicides for the purpose of expanding the pests to be controlled, the appropriate period for control, or reducing the amount of the drug. , biopesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.

Other agricultural and horticultural insecticides, acaricides and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC) ), Bt toxin insecticidal compound, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), Ｏ－ｅｔｈｙｌ Ｏ－４－ｎｉｔｒｏｐｈｅｎｙｌ ｐｈｅｎｙｌｐｈｏｓｐｈｏｎｏｔｈｉｏａｔｅ（ＥＰＮ）、ｔｒｉｐｒｏｐｙｌｉｓｏｃｙａｎｕｒａｔｅ（ＴＰＩＣ）、アクリナトリン（ａｃｒｉｎａｔｈｒｉｎ）、アザディラクチン（ａｚａｄｉｒａｃｈｔｉｎ）、アシノナピル（ａｃｙｎｏｎａｐｙｒ）、アジンホス・メチル（ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、アセキノシル（ａｃｅｑｕｉｎｏｃｙｌ）、アセタミプリド(acetamiprid), acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanicarb, alanycarb aldicarb), aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidophos ( isamidofos), isoamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-monfluthrin ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb,

ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydimeton-methyl, oxydeprofos (ESP), oxybendazole, oxfendazole , Potassium oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuran ( carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezin,クロマフェノジド（ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、クロラントラニリプロール（ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、クロルエトキシホス（ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、クロルジメホルム（ｃｈｌｏｒｄｉｍｅｆｏｒｍ）、クロルデン（ｃｈｌｏｒｄａｎｅ）、クロルピリホス（ｃｈｌｏｒｐｙｒｉｆｏｓ）、クロルピリホス－メチル（ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、クロルフェナピル（ｃｈｌｏｒｐｈｅｎａｐｙｒ）、 chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilat e), chlorobenzoate, chloroprallethrin, kersene (dicofol),

salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienol dienochlor), cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (ECP) ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、ジクロルボス（ｄｉｃｈｌｏｒｖｏｓ： ＤＤＶＰ）、ジクロロメゾティアズ（ｄｉｃｌｏｒｏｍｅｚｏｔｉａｚ）、ジスルホトン（ｄｉｓｕｌｆｏｔｏｎ）、ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、シハロジアミド（ｃｙｈａｌｏｄｉａｍｉｄｅ）、シハロトリン（ｃｙｈａｌｏｔｈｒｉｎ）、シフェノトリン（ｃｙｐｈｅｎｏｔｈｒｉｎ）、シフルトリン（ｃｙｆｌｕｔｈｒｉｎ）、ジフルベンズロン（ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、シフルメトフェン（ｃｙｆｌｕｍｅｔｏｆｅｎ）、ジフロビダジン（ｄｉｆｌｏｖｉｄａｚｉｎ）、シヘキサチン（ｃｙｈｅｘａｔｉｎ）、シペルメトリン（ｃｙｐｅｒｍｅｔｈｒｉｎ）、ジメチルビンホス（ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、ジメトエート（ｄｉｍｅｔｈｏａｔｅ）、ジムプロピリダヅ（ｄｉｍｐｒｏｐｙｒｉｄａｚ）、ジメフルスリン（ｄｉｍｅｆｌｕｔｈｒｉｎ）、シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ ), cyromazine, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spiromesifen, sulfluramide, sulflurami (d) sulprofos), sulfoxaflor, zeta-cypermethrin (zeta-cype rmethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiocyclam ), thiosultap-sodium, thionazin, thiometon, deet, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, Tetrachlorbinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenozide,

tefluthrin, teflubenzuron, demeton-S-methyl, temefos, deltamethrin, terbufos, doramectin, tralopyril, tralopyril tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumezopyrium, triflumuron, tolflumuron (red) (naled: BRP), nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion-methyl, parathion (parathion-methyl), halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch, binapacryl 、ピフルブミド（ｐｙｆｌｕｂｕｍｉｄｅ）、ビフェナゼート（ｂｉｆｅｎａｚａｔｅ）、ビフェントリン（ｂｉｆｅｎｔｈｒｉｎ）、ピメトロジン（ｐｙｍｅｔｒｏｚｉｎｅ）、ピラクロホス（ｐｙｒａｃｌｏｒｆｏｓ）、ピラフルプロール（ｐｙｒａｆｌｕｐｒｏｌｅ）、ピリダフェンチオン（ｐｙｒｉｄａｆｅｎｔｈｉｏｎ）、ピリダベン（ｐｙｒｉｄａｂｅｎ）、ピリダリル（ｐｙｒｉｄａｌｙｌ）、ピリフルキナゾン（ pyrifluquinazon, pyriprole, pyriproxyfen, pirimicab arb), pyrimidifen, pyriminostrobin, pirimiphos-methy1, pyrethrins, fiproni1, fenazaquin, fenamiphos (bromopro), phenisobromo , fenitrothion (MEP), fenoxycarb, phenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate, fenvalerate, fenpyroximate, fenpropathrin, fenbendazole,

fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizin, fluazaindolizin, fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole (flupyradifurone), flupyrazofos, flupyrimin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, fenprox (flu) fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiofos, protrifenbute, flonidlamide ), propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, α-bromahdiol-bromodiolone ( ), bromopropylate, beta-cyfluthrin, hexafluムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、ヘキシチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、ヘプタフルトリン（ｈｅｐｔａｆｌｕｔｈｒｉｎ）、ヘプテノホス（ｈｅｐｔｅｎｏｐｈｏｓ）、ペルメトリン（ｐｅｒｍｅｔｈｒｉｎ）、ベンクロチアズ（ｂｅｎｃｌｏｔｈｉａｚ）、ベンジオカルブ（ｂｅｎｄｉｏｃａｒｂ）、ベンズピリモキサン（ｂｅｎｚｐｙｒｉｍｏｘａｎ）、ベンスルタップ（ｂｅｎｓｕ１ｔａｐ）、 benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (MP),

Polynactin complexes, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin ), mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium 、メチオカルブ（ｍｅｔｈｉｏｃａｒｂ）、メチダチオン（ｍｅｔｈｉｄａｔｈｉｏｎ： ＤＭＴＰ）、メチルイソチオシアネート（ｍｅｔｈｙｌｉｓｏｔｈｉｏｃｙａｎａｔｅ）、メチルネオデカナミド（ｍｅｔｈｙｌｎｅｏｄｅｃａｎａｍｉｄｅ）、メチルパラチオン（ｍｅｔｈｙｌｐａｒａｔｈｉｏｎ）、メトキサジアゾン（ｍｅｔｏｘａｄｉａｚｏｎｅ）、メトキシクロル（ｍｅｔｈｏｘｙｃｈｌｏｒ）、メトキシフェノジド（ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、メトフルトリン(metofluthrin), methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyclothrin , ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide (morantate tartrate), ), methyl bromide, tricyclohexyltin hydroxide (cyh exatin, calcium cyanamide, calcium polysulfide, sulfur, and nicotine-sulfate, and salts thereof.

Agricultural and horticultural fungicides used for the same purpose include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S- methyl, azoxystrobin, anilazine, amisulbrom, aminopyrifen, ampropylfos, ametoctradin, allyl alcohol, aldimorph ), amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole ), ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-al , iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, eclomezole, edifenphos etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestrobur in), enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline (oxytetracycline), copper-oxinate,

oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamide, quinacetol, quinoxyphene, quinoxyfen ), chinomethionat, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufuraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, clozolinate, clotrimazole , clobenthiazone, chloraniformethane, chloranil, chlorquinox, chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil ), chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyropacarbonate, diethofencarb, cyclafuramid, dicclocymet, diclozoline, diclobutrazol, dichloxfluanid, dichloxfluanid dihlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, Minoconazole (diniconazole-M), zineb,

ジノカップ（ｄｉｎｏｃａｐ）、ジノクトン（ｄｉｎｏｃｔｏｎ）、ジノスルホン（ｄｉｎｏｓｕｌｆｏｎ）、ジノテルボン（ｄｉｎｏｔｅｒｂｏｎ）、ジノブトン（ｄｉｎｏｂｕｔｏｎ）、ジノペントン（ｄｉｎｏｐｅｎｔｏｎ）、ジピメチトロン（ｄｉｐｙｍｅｔｉｔｒｏｎｅ）、ジピリチオン（ｄｉｐｙｒｉｔｈｉｏｎｅ）、ジフェニルアミン（ｄｉｐｈｅｎｙｌａｍｉｎｅ）、ジフェノコナゾール（ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、ジフルメトリム（ｄｉｆｌｕｍｅｔｏｒｉｍ）、シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、シプロフラム（ｃｙｐｒｏｆｕｒａｍ）、シペンダゾール（ｃｙｐｅｎｄａｚｏｌｅ）、シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）、ジメチリモール（ｄｉｍｅｔｈｉｒｉｍｏｌ）、ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）、シモキサニル（ｃｙｍｏｘａｎｉｌ ), dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet (thiadiazin), tiadinil, thiadifluor, thiabendazole, tioxymid, thioquinox, thiochlorfenphim, thiophanate, thiophanate-thiophanate-methyl, thifluzamide, thikyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb ), dehydroacetic acid, tebuconazole (tebuco nazole), tebufloquin, dodicin, dodine, bisethylenediamine copper complex (II) dodecylbenzenesulfonate (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole,

triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofosmethyl ( tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate , halacrinate, validamycin, valifenalate, harpin protein, picarbutrazox, bixafen, picoxystrobin, picobenzamide , pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl, ｐｉｐｅｒａｌｉｎ）、ヒメキサゾール（ｈｙｍｅｘａｚｏｌ）、ピラオキシストロビン（ｐｙｒａｏｘｙｓｔｒｏｂｉｎ）、ピラカルボリド（ｐｙｒａｃａｒｂｏｌｉｄ）、ピラクロストロビン（ｐｙｒａｃｌｏｓｔｒｏｂｉｎ）、ピラジフルミド（ｐｙｒａｚｉｆｌｕｍｉｄ）、ピラゾホス（ｐｙｒａｚｏｐｈｏｓ）、ピラプロポイン（ｐｙｒａｐｒｏｐｏｙｎｅ）、ピラメトストロビン（ｐｙｒａｍｅｔｏｓｔｒｏｂｉｎ）、 pyriofenone, pyridinitril, pyrifenox, pyridiflumetofen etofen, pyrisoxazole, pyridachlormethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor,

pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminosulfin, ), fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamide, fenpyrazamine, fenbuconazole ( fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberimazole fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapistrobin Fluoxapiprolin, fluotrimazole, fluopicolide, fluopimimide, fluopyram, fluoroimide, furcarbanil, fluxapyroxax, fluquinconazole, fluconazole, fluconazole-cis, fludioxonil, flusilaz ole), flusulfamide, flutianil, flutolanil, flutriafol, flufenoxystrobin, furfural, furmecyclox, flumetover , flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole,

pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamide, florylpicoxadiene (hexachlorobutadiene), hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benopefurate, benomymyl benquinox, penconazole, benzamorph, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazol, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl aluminum-fosetyl, Polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamide, mandipropamide destrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl,

metalaxyl-M, metiram, methyl isothiocyanate, meptyldinocap, methyltetraprole, metconazole, metsulfovax, metofloxam methfuroxam), metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil (mebronil) ( , iodomethane, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, Inorganic fungicides such as metallic silver, sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, carbonate Potassium Hydrogen Carbonate, Sodium Hydrogen Carbonate, Inorganic Sulfur, Copper Sulfate Anhydride, Nickel Dimethyldithiocarbamate, 8 ), zinc sulfate, and copper sulfate pentahydrate, and salts thereof.

Similarly herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, oracetoch ), atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole , aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametrin, alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole ), isoxaben, isocil, isonoruron, isoproturon, isopropalin, isoporinate, isomethiozin, inabenfide,

イパジン（ｉｐａｚｉｎｅ）、イプフェンカルバゾン（ｉｐｆｅｎｃａｒｂａｚｏｎｅ）、イプリミダム（ｉｐｒｙｍｉｄａｍ）、イマザキン（ｉｍａｚａｑｕｉｎ）、イマザピック（ｉｍａｚａｐｉｃ）、イマザピル（ｉｍａｚａｐｙｒ）、イマザメタピル（ｉｍａｚａｍｅｔｈａｐｙｒ）、イマザメタベンズ（ｉｍａｚａｍｅｔｈａｂｅｎｚ）、イマザメタベンズメチル（ｉｍａｚａｍｅｔｈａｂｅｎｚ －ｍｅｔｈｙｌ）、イマザモックス（ｉｍａｚａｍｏｘ）、イマゼタピル（ｉｍａｚｅｔｈａｐｙｒ）、イマゾスルフロン（ｉｍａｚｏｓｕｌｆｕｒｏｎ）、インダジフラム（ｉｎｄａｚｉｆｌａｍ）、インダノファン（ｉｎｄａｎｏｆａｎ）、インドール酪酸（ｉｎｄｏｌｅｂｕｔｙｒｉｃ ａｃｉｄ）、ウニコナゾール－Ｐ（ｕｎｉｃｏｎａｚｏｌｅ－Ｐ）、エグリナジン（ｅｇｌｉｎａｚｉｎｅ）、 esprocarb, ethamesulfuron, ethamesulfuron-methyl, ethalfluralin, ethiolate, ethichlozate ethyl, ethidimurone, ethinofen(et) ), ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon, endothal , oxadiazon, oxadiargyl, oxadiclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb ( ), cafenstrole, cambendichlor, carbasulam, carfentrazone (c arfentrazone), carfentrazone-ethyl, karbutilate, carbetaamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl ( quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, cliodinate () glyphosate),

glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, rotoluron, clopyralid, cloproxydim, cloprop, chlorobromuron, clofop, clomazone, clomethoxyni1, chloromethoxyfen, clomeprop, chlorazifop, chlorazine, chloransulam, chloranocryl, chloramben, chloransulam, chloransulam-methyl, chloridazon, chlorimuron - chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamide, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam (chlorbufam), chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chlorreturon, chloroxynil ), chloroxuron, chlorotoluron, chloropone on), saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dicamba, cycloron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop,

dicloprop-P, dichlobenil, diclofop, diclofop-methyl, dichromate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate ), dinoprop, cyhalofop-butyl, diphenamide, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazine (cyprazole), diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexanodimethyl ）、ジメダゾン（ｄｉｍｉｄａｚｏｎ）、ジメタメトリン（ｄｉｍｅｔｈａｍｅｔｒｙｎ）、ジメテナミド（ｄｉｍｅｔｈｅｎａｍｉｄ）、シメトリン（ｓｉｍｅｔｒｙｎ）、シメトン（ｓｉｍｅｔｏｎ）、ジメピペレート（ｄｉｍｅｐｉｐｅｒａｔｅ）、ジメフロン（ｄｉｍｅｆｕｒｏｎ）、シンメチリン（ｃｉｎｍｅｔｈｙｌｉｎ）、スエップ（ｓｗｅｐ）、スルグリカピン（ｓｕｌｇｌｙｃａｐｉｎ ), sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron methyl (su lfometuron-methyl, secbumeton, sethoxydim, sebutylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr,チアフェナシル（ｔｉａｆｅｎａｃｉｌ）、チエンカルバゾン（ｔｈｉｅｎｃａｒｂａｚｏｎｅ）、チエンカルバゾンメチル（ｔｈｉｅｎｃａｒｂａｚｏｎｅ－ｍｅｔｈｙｌ）、チオカルバジル（ｔｉｏｃａｒｂａｚｉｌ）、チオクロリム（ｔｉｏｃｌｏｒｉｍ）、チオベンカルブ（ｔｈｉｏｂｅｎｃａｒｂ）、チジアジミン（ｔｈｉｄｉａｚｉｍｉｎ）、チジアズロン（ｔｈｉｄｉａｚｕｒｏｎ）、チフェンスルフロン（ｔｈｉｆｅｎｓｕｌｆｕｒｏｎ ), thifensulfuron-methyl, desmedipham,

desmethrin, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione ), tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbutylazine, terbutryn, topramezone, tralcoxydim ( triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron (tritosulfuron), trifludimoxazine, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, triprin tribenuron, tribenuron-methyl, trifop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide , nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipiraclofen fen), neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, haluxifen , haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bifenox , piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron,

pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac sodium ( pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyribenzoxim, pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisoham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P , fenoxaprop-ethyl, phenothio1, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthibutybutylate, buthidazole ), buturon, butenachlor, butoxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate ), fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidin, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, phenacet, flufenican,

flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropin, flumipropan flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinadine, proglinazin, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide (propyzamide), propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione calcium ), propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometrin, promethrin, bromoxynil phenoxim, bromobutide, bromobonil, florasulam, florpyrauxifene (flo rpyrauxifen, hexachloroacetone, hexazinone, pethoxamide, benazolin, penoxsulam, pebulate, beflubutamide, beflubutamide, beflubutamide (Mbutamide) (vernolate), perfluidone, bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulfuron-methyl, benzoylprop, benzobicyclone, benzofenap, benzofluor,

bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, fomesafen ramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb, mesosulfuron methyl, mesosulfuron methyl (mesosulfuron-methyl), mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazurone (methabenzrone), , metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metsulam, metsulfuron, metsulfuron-methy1, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzine (methribuzin) mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monisouron monuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil (iodobonil), iodomethane, lactofen, lancotrione, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and Methyl bromide as well as salts thereof.

In addition, as biological pesticides, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopox virus (Entomopoxi virus, EPV ), Nematocide or Penetranria penetricide such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans Microbial pesticides used as agents, as fungicides such as Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis A similar effect can be expected by mixing with a microbial pesticide used, a biopesticide used as a herbicide such as Xanthomonas campestris, and the like.

Furthermore, as biological pesticides, for example, Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibiricus, persimilis), Amblyseius cucumeris, natural enemy organisms such as Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E, Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, 14-methyl-1 - Can be used in combination with pheromones such as octadecene.

In addition, the compounds represented by the general formula (I) of the present invention or salts thereof are also suitable for controlling parasites in animals. Animal parasites live inside or on the body of the host animal and bring disadvantages to the host animal. Apart from that, the compound represented by the general formula (I) of the present invention or a salt thereof can also be applied as an agent for controlling ectoparasites for animals or an agent for controlling endoparasites for animals.

When the compound represented by the general formula (I) of the present invention or a salt thereof is applied as an animal parasite control agent, applicable animals include, for example, pigs, horses, cattle, sheep, goats, rabbits, camels, Domestic animals such as buffaloes, deer, minks, and chinchillas Pet animals such as dogs, cats, small birds and monkeys Laboratory animals such as rats, mice, golden hamsters and guinea pigs Chickens, ducks, ducks, quails, ducks, geese, turkeys Examples include, but are not limited to, domestic poultry, humans, and the like. It can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, and crustaceans and shellfish such as shrimp, crab, scallops, oysters, short-necked clams, and clams.

When the veterinary parasite control agent of the present invention is used to control ectoparasites, the controllable ectoparasites include, for example, Rhipicephalus (Rhipicaphalus (Boophilus) microplus, Rhipicephalus sanguineus, etc.), Amblyomma, Dermacentor, Haemaphysalis.属、Ｈｙａｌｏｍｍａ属、Ｉｘｏｄｅｓ属、Ｒｈｉｐｉｃｅｎｔｏｒ属、Ｍａｒｇａｒｏｐｕｓ属、Ａｒｇａｓ属、Ｏｔｏｂｉｕｓ属、Ｏｒｎｉｔｈｏｄｏｒｏｓ属、Ｃｈｏｒｉｏｐｔｅｓ属（Ｃｈｏｒｉｏｐｔｅｓ ｂｏｖｉｓなど）、Ｐｓｏｒｏｐｔｅｓ属（Ｐｓｏｒｏｐｔｅｓ ｏｖｉｓなど）、Ｃｈｅｙｌｅｔｉｅｌｌａ属、Ｄｅｒｍａｎｙｓｓｕｓ属（Ｄｅｒｍａｎｙｓｓｕｓ ｇａｌｌｉｎａｅなど）、 Ｏｒｔｎｉｔｈｏｎｙｓｓｕｓ属、Ｄｅｍｏｄｅｘ属（Ｄｅｍｏｄｅｘ ｃａｎｉｓなど）、Ｓａｒｃｏｐｔｅｓ属（Ｓａｒｃｏｐｔｅｓ ｓｃａｂｉｅｉなど）、Ｐｓｏｒｅｒｇａｔｅｓ属、Ｓｉｐｈｏｎａｐｔｅｒａ目（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ ｆｅｌｉｓ、Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ ｃａｎｉｓなど）、Ｄｉｐｔｅｒａ目（Ｍｕｓｃａ ｓｐｐ、Ｇａｓｔｅｒｏｐｈｉｌｕｓ ｉｎｔｅｓｔｉｎａｌｉｓ、Ｏｅｓｔｒｕｓ ｏｖｉｓなど）、Ｐｈｔｈｉｒａｐｔｅｒａ目（ Bovicola Ovis, Bovicola Bovis, etc.), the order Lepidoptera, the order Coleoptera, the order Homoptera, the genera Haematopota, the genera Tabunus, the genera Haematobia (such as Haematobia irritans), the genera Stomoxys, the genera Lucilia, and the like.

さらに具体的には、ダニ類として例えば、オウシマダニ（Ｂｏｏｐｈｉｌｕｓ ｍｉｃｒｏｐｌｕｓ）、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ ｓａｎｇｕｉｎｅｕｓ）、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｌｏｎｇｉｃｏｒｎｉｓ）、キチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｆｌａｖａ）、ツリガネチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｃａｍｐａｎｕｌａｔａ）、イスカチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｃｏｎｃｉｎｎａ ）、ヤマトチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｊａｐｏｎｉｃａ）、ヒゲナガチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｋｉｔａｏｋａｉ）、イヤスチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｉａｓ）、ヤマトマダニ（Ｉｘｏｄｅｓ ｏｖａｔｕｓ）、タネガタマダニ（Ｉｘｏｄｅｓ ｎｉｐｐｏｎｅｎｓｉｓ）、シュルツェマダニ（Ｉｘｏｄｅｓ ｐｅｒｓｕｌｃａｔｕｓ）、タカサゴキララマダニ（Ａｍｂｌｙｏｍｍａ ｔｅｓｔｕｄｉｎａｒｉｕｍ）、オオトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ ｍｅｇａｓｐｉｎｏｓａ）、アミノカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ ｒｅｔｉｃｕｌａｔｕｓ）、およびタイワンカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ ｔａｉｗａｎｅｓｉｓ）のようなマダニ類、ワクモ（Ｄｅｒｍａｎｙｓｓｕｓ ｇａｌｌｉｎａｅ）、トリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ ｓｙｌｖｉａｒｕｍ）、およびミナミトリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ ｂｕｒｓａ）のようなトリサシダニ類、ナンヨウツツガムシ（Ｅｕｔｒｏｍｂｉｃｕｌａ ｗｉｃｈｍａｎｎｉ）、アカツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ ａｋａｍｕｓｈｉ）、フトゲツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ ｐａｌｌｉｄｕｍ）、フジツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ ｆｕｊｉ）、トサツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ ｔｏｓａ）、ヨーロッパアキダニ（Ｎｅｏｔｒｏｍｂｉｃｕｌａ ａｕｔｕｍｎａｌｉｓ）、アメリカツツガムシ（Ｅｕｔｒｏｍｂｉｃｕｌａ alfreddugesi), and chiggers such as Helenicula miyagawai, Cheyletiella yasguri, Cheyletiella ｐａｒａｓｉｔｉｖｏｒａｘ）、およびネコツメダニ（Ｃｈｅｙｌｅｔｉｅｌｌａ ｂｌａｋｅｉ）のようなツメダニ類、ウサギキュウセンダニ（Ｐｓｏｒｏｐｔｅｓ ｃｕｎｉｃｕｌｉ）、ウシショクヒダニ（Ｃｈｏｒｉｏｐｔｅｓ ｂｏｖｉｓ）、イヌミミヒゼンダニ（Ｏｔｏｄｅｃｔｅｓ ｃｙｎｏｔｉｓ）、ヒゼンダニ（Ｓａｒｃｏｐｔｅｓ ｓｃａｂｉｅｉ）、およびネコショウセンコウヒゼンダニ（Ｎｏｔｏｅｄｒｅｓ ｃａｔｉ ), and demodex mites such as Demodex canis.

Fleas include, for example, Pulicidae and Ceratephyllus. Examples of fleas belonging to the family Human Flea include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, and Xenopsylla cheopis. Leptopsylla segnis), European rat flea (Nosopsyllus fasciatus), and black rat flea (Monopsyllus anisus).

また、ウシジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ ｅｕｒｙｓｔｅｒｎｕｓ）、ウマジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ ａｓｉｎｉ）、ヒツジジラミ（Ｄａｌｍａｌｉｎｉａ ｏｖｉｓ）、ウシホソジラミ（Ｌｉｎｏｇｎａｔｈｕｓ ｖｉｔｕｌｉ）、ブタジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ ｓｕｉｓ）、ケジラミ （Ｐｈｔｈｉｒｕｓ ｐｕｂｉｓ）、およびアタマジラミ（Ｐｅｄｉｃｕｌｕｓ ｃａｐｉｔｉｓ）のようなシラミ類、 and lice such as dog lice (Trichodectes canis), cow flies (Tabanus trigonus), Culicoides schultzei, and blood-sucking Diptera pests such as Simulium ornatum, and the like, as well as the animal parasiticides of the present invention. Therefore, it is included as an ectoparasite that can be controlled.

In order to use the veterinary parasite control agent of the present invention for control of ectoparasites, a suitable solid carrier or liquid carrier is used according to the generally used pharmaceutical formulation, and if necessary, an appropriate adjuvant is used. It is used by dissolving, suspending, mixing, impregnating, adsorbing or adhering by blending in appropriate proportions, and preparing appropriate dosage forms such as liquids, emulsifiers, creams, ointments, suspensions, and aerosols according to the purpose of use. do it. The amount of the active ingredient in these formulations can range from 0.01 to 80.0 parts by mass as the active ingredient per 100 parts by mass of the formulation.
As the solid carrier or liquid carrier to be used, a carrier generally used for veterinary drugs may be used, and a liquid carrier is preferably used because it is easy to treat the target animal. Examples of liquid carriers include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, water and the like. Auxiliaries can be used as necessary, and surfactants, antioxidants, emulsifiers, etc. can be used as auxiliary agents, for example, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, Surfactants such as alkylarylsorbitan monolaurate, alkylbenzenesulfonate, alkylnaphthalenesulfonate, ligninsulfonate, higher alcohol sulfate, glycol monoalkyl ether, glycols, sorbitan monooleate, sorbitan monolaurate, caprylic acid Emulsifiers such as monoglyceride, capric monoglyceride, isostearic monoglyceride, and propylene glycol monocaprylate, and antioxidants such as BHA and BHT.

When the veterinary parasite control agent of the present invention is applied to control ectoparasites, it may be administered to animals by a route having a desired effect, such as topically, orally, parenterally, and subcutaneously. Although not recommended, topical administration is preferred. For topical administration, spot-on treatment in which a liquid drug is dropped onto the skin of the dorsum of the target animal, pour-on treatment in which a liquid drug is applied along the back line of the target animal, and liquid aerosol drug by spraying. It can be administered by a treatment method using spray-on treatment, spray race treatment, chemical bath (dip), drug-loaded ear tag or collar (collar), and the like. The amount to be applied may be appropriately selected from the range of usually about 0.1 to 500 mg as the active ingredient compound and about 0.01 to 20 ml as the control agent of the present invention per 1 kg body weight of the subject animal.

In addition, if necessary, other active ingredients can be used in combination, for example, afoxolaner, fluralaner, lotilaner, surolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxyfendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, rafoxanide, cyphenothrin, flumethrin, permethrin, cyromazine （ｃｙｒｏｍａｚｉｎｅ）、デルクアンテル（ｄｅｒｑｕａｎｔｅｌ）、ジアンフェネチド（ｄｉａｍｐｈｅｎｅｔｉｄｅ）、ジシクラニル（ｄｉｃｙｃｌａｎｉｌ）、ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、イミダクロプリド（ｉｍｉｄａｃｌｏｐｒｉｄ）、ニテンピラム（ｎｉｔｅｎｐｙｒａｍ）、チアメトキサム（ｔｈｉａｍｅｔｈｏｘａｍ）、アバメクチン（ａｂａｍｅｃｔｉｎ）、ドラメクチン（ｄｏｒａｍｅｃｔｉｎ）、エマメクチン(emamectin), eprinomectin, ivermectin, moxidectin, selamectin, milbemycin oxime, emmodepside, epsiprantel, fipronil, fluazuron, fluhexafon, indoxacarb, levamisole, lufenuron, metaflumonemolemone, methaflumizone, , niclosamide, nitroscanate, nitroxynil, novaluron, oxantel, praziquantel, pyrantel, pyriprol, pyriproxyfen, cisapronil, spinosad, spinetoram, triflumezopyrim, and the like.

When the animal parasite control agent of the present invention is used to control internal parasites, the internal parasites that can be controlled are roughly classified into protozoa and helminths. Examples of protozoa that parasitize humans include amoebas such as Entamoeba histolytica (Rhizopoda), flagellates such as Leishmania, Trypanosoma, and Trichomonas (Mastigophora), malaria parasites, sporozoa such as Toxoplasma (Sporozoea), colon Ciliophora such as Balantidium, and helminths that parasitize humans include, for example, Ascaris, Anisakis, Ascaris canis, Hairy nematodes, Pinworms, and hookworms (such as Zubini hookworm, American hookworm, and Brazilian hookworm). , blood nematodes, jaw stoma, heartworms (filariae, Bancroft's heartworm, Malayan heartworm, etc.), roundworms (onchocerca), guinea worms, caterpillars, strongyloides and other nematodes (Nematoda ), Acanthocephala such as acanthocephala, Iron nematodes such as wireworms (Gordiacea), Leeches such as thysuivir (Hirudinea), Schistosoma japonicum, Schistosoma mansoni, Schistosoma mansoni, Schistosoma billharz, Liver fluke, Trematoda such as heteromorphic fluke, fluke fluke, lung fluke (Trematoda), tapeworm broadly segmented, tapeworm mansoni, budding tapeworm, tapeworm Taenia large, Taenia genus, (Taenia unagi, Taenia solium, hydatid (Echinococcus, etc.), tapeworm tapeworm, tapeworm tapeworm, tapeworm tapeworm, monkey barehead tapeworm, tapeworm tapeworm (Cestoda), etc., but these include It is not limited.

Examples of protozoa parasitic on mammals other than humans or animals belonging to birds include Apicomplexes, Eimeria, Isospora, Toxoplasma, Neospora, Sarcocystis, Cocidia such as Besnoitia, Hammondia, Cryptosporidium, Caryospora, etc.; ), Theileria, Anaplasma, Eperythrozoon, Heamobartonella, Rhrlichia and other Piroplasma, as other apicomplexes, Hepatozoon , Haemogregarina, etc., as Microspora, Encephalitozoon, Nosema, etc., as Mastigophora, Trypanosoma, Leishmania, etc. Trichomonadida such as Trypanosomatid, Chilomastix, Trichomonas, Monocercomonas, Histomonas, Diplomonas such as Hexamita, Giardia, etc. Diplomonadida, Sarcodina, Amoebas such as Entamoeba, Ciliophora, Balantidium, Buxtonella, Entodinium Such,

Examples of helminths that parasitize mammals other than humans or animals belonging to birds include nematodes such as Ascaris, Ascaris, Toxocara, Toxascaris, and Parascaris. ), Ascarida such as chicken Ascaridia, Heterakis, and Anisakis, Oxyurida such as Oxyuris, Passalurus, etc. Strongylus, Haemonchus, Ostertagia, Trichostrongylus, Cooperia, Nematodirus, Ruby Hystrongylus, Oesophagostomum, Chabertia, Ancylostoma, Uncinaria, Necator, Bunostomum, Bovine lungworm (Dictyocaulus), pig lungworm (Metastrongylus), dog lungworm (Filaroides), cat lungworm (Aelurostrongulus), Guangdong Angiostrongylus (Angiostrongylus), tracheostomy beetle (Syngamus), pig kidneyworm (Stephanurus), etc. Strongylida, Strongyloides, Rhabditida such as Micronema, Thelazia, Oxyspirura, Spirocerca, Beautiful Tails of Gongylonema, Drascia, Habronema, Ascarops, Physaloptera, Gnathostoma, etc. Filariida such as Spirurida, Dirofilaria, Setaria, Dipetalonema, Parafilaria, Onchocerca ), Parafilaria, Okinawa heartworm (Stephanofilari a), Enoplida such as Trichuris, Capillaria, Trichosomoides, Trichinella, Dioctophyma, etc.

As flukes, Fasciolata such as Fasciola and Fasciolopsis, Paramphistomatidae such as Homalogaster, Eurytrema, Spear-shaped Dicrocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma Asada, Echinochasmus, etc. Troglotrematoidea such as Echinostomata, Paragonimus, Nanophyetus, Opisthorchiida such as Clonorchis, Heterophyes , Heterophyida such as Metagonimus, Plagiorchiida such as Prosthogonimus, and Schistosoma such as Schistoma As, Pseudophylidea such as Japan Sea (Diphyllobothrium), mansoni (Spirometra) and other pseudophyllides (Pseudophylidea), foliate tapeworm (Anoplocephara), papillary tapeworm (Paranoplocephala), Beneden tapeworm (Moniezia), Dipylidium, Mesocestoides, Beans, Tenia, Hydatigera, Multiceps, Echinococcus, Multicysts Echinococcus, Taenia, Taeniarhynchus, Hymenolepis, Vampirolepis, Railietina, Amoebotaenia, etc. Cyclophyllidea, etc., such as Macracanthorhynchus, Moniliformis, etc., Linguatula and other various parasites, but are not limited to these.

Furthermore, another name for helminths, for example, nematode genus Enoplida (Trichuris spp.), Capillaria spp., Trichomosoides spp., Trichomosoides spp., Trichinella spp.), and the genus Rhabditia includes, for example, Micronema spp. and Strongyloides spp., and the genus Strongylida includes, for example, Stronylus Stronylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp. Cylindropharynx spp.), Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Cabertia spp. Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus, Syngamus spp. Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp. ), Cystocaulus spp., Pneumostrongillus spp. strongylus spp. ), Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp. Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp. (Haemonchus spp.), Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides Obeliscoides spp., Amidostomum spp. and Ollulanus spp.

As the genus Oxyurida, for example, Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculus spp. and Heterakis spp., etc. Ascaridia include, for example, Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp.), Anisakis spp., and Ascaridia spp., and the genus Spirurida includes, for example, Gnathosma spp., Physaloptera spp. ), Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp. and Dracunculus spp. The genus Filariida includes, for example, Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Deirofilaria Species (Dirofilaria spp.), Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp.

Acanthocephala includes, for example, Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., Prostenorchis spp. Examples of the monogenea subclass of flukes (Monogenea) include, for example, Gyrodactylus spp., Dactylogyrus spp. and Polystoma spp. For example, Diplostomum spp., Postdiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilhardzia spp. Ornithbilharzia spp.), Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., spinous fluke Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp. Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp. , Gigantcotyle spp., Fischoederius spp., Gastroti Lacus sp. (Gastrothylacus spp. ), Notocotylus spp., Catatropis spp., Plagiorchis spp., Prostogonymus spp., Dicrocoelium spp., Eurytrema spp. Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. , Metorchis spp., Heterophyes spp. and Metagonimus spp.

Pseudophyllidea of tapeworms, for example, Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp. spp.), Bothridium spp., and Diplogonoporus spp., and as Cyclophyllidea, for example, Mesocestoides spp. Anoplocephala spp., Paranoplocehala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., Avitelina spp. Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., taenia spp., Echinococcus spp. (Hydatigera spp.), Davainea spp., Railietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Parasites belonging to species such as Diorchis spp., Dipylidium spp., Joyeuxiella spp. Examples include, but are not limited to, various parasites belonging to Reptiles.

The veterinary parasite control agent of the present invention is effective not only in controlling parasites living in intermediate and final hosts, but also in controlling parasites in reservoir hosts. In addition, the compound represented by the general formula (I) of the present invention exerts a controlling effect on all developmental stages of parasites. For example, in protozoa, there are cysts, pre-cysts, vegetative or asexual mitotic bodies, amoeba bodies, sexual gametocytes, gametes, fusion bodies, sporophytes and the like. In nematodes, they are eggs, larvae and adults. Furthermore, the compound according to the present invention not only exterminates parasites in vivo, but can prevent parasite infection prophylactically by applying it to an environment that is an infection route. For example, soil-borne infection from the soil of fields and parks, percutaneous infection from water systems such as rivers, lakes, wetlands, and paddy fields, oral infection from feces of animals such as dogs and cats, saltwater fish, freshwater fish, and crustaceans. , shellfish, raw meat of domestic animals, etc., and infections from mosquitoes, horseflies, flies, cockroaches, mites, fleas, lice, kissing bugs, tsutsugamushi, etc. can be prevented.

The veterinary parasite control agent of the present invention can be administered as a pharmaceutical to humans, mammals other than humans, or animals belonging to birds for the purpose of treating or preventing parasitic diseases. Either oral administration or parenteral administration is possible for the administration method. In the case of oral administration, capsules, tablets, pills, powders, granules, fine granules, powders, syrups, enteric agents, suspensions, pastes, or by blending in liquid beverages or feeds for animals, can be administered. For parenteral administration, injections, drops, suppositories, emulsions, suspensions, drops, ointments, creams, liquids, lotions, sprays, aerosols, poultices, and tapes can be applied to mucous membranes or It is administered in a dosage form that can maintain percutaneous absorption.

When the veterinary parasite control agent of the present invention is used as a pharmaceutical for humans, mammals other than humans, or animals belonging to birds, the optimum amount (effective amount) of the active ingredient is different from treatment or prevention, the type of infected parasite, Although it varies depending on the type and degree of infection, dosage form, etc., it is generally in the range of about 0.0001 to 10,000 mg/kg body weight per day for oral administration. Parenteral administration ranges from about 0.0001 to 10,000 mg/kg body weight per day, administered in single or divided doses.

The concentration of the active ingredient in the internal parasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably 0.001 to 99%, more preferably about 0.005 to 20% by mass. The endoparasite control agent of the present invention may be a composition to be administered as it is, or a high-concentration composition diluted to an appropriate concentration at the time of use.

Moreover, an existing internal parasite control agent can be used together for the purpose of reinforcing or complementing the effect of the internal parasite control agent of the present invention. For combined use, a formulation in which two or more active ingredients are mixed before administration may be used, or two or more different formulations may be administered separately.

Production examples, formulation examples and test examples are shown below as representative examples of the present invention, but the present invention is not limited to these. Production examples are shown below.

Ｎ－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚａｍｉｄｅ（６３ｍｇ，０．１４６ｍｍｏｌ）のトルエン（３ｍＬ）溶液に臭化ベンジル（３５μＬ，０．２９２ｍｍｏｌ）、テトラブチルアンモニウム硫酸水素塩（５．０ｍｇ，０．１４６ｍｍｏｌ）および水酸化ナトリウム水溶液（２５重量％，０．２ｍＬ）を加え、室温下２時間撹拌した。反応混合物に水を加え、酢酸エチルで２回抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下留去した。得られた残渣をシリカゲルクロマトグラフィーにて精製し、２９ｍｇのＢｅｎｚｙｌ Ｎ－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚｉｍｉｄａｔｅをＥ／Ｚ混合物として得た。
収率：３８％
^１ＨＮＭＲ（４００ＭＨＺ、ＣＤＣｌ_３）δ値（ｐｐｍ）
２．００（３Ｈ，ｄ，Ｊ＝７．２Ｈｚ），５．２８（２Ｈ，ｓ），６．２９（１Ｈ，ｑ，Ｊ＝６．８Ｈｚ），６．９１（１Ｈ，ｔ，Ｊ＝５．２Ｈｚ），７．１７－７．１９（２Ｈ，ｍ），７．３１－７．３５（３Ｈ，ｍ），７．７９（１Ｈ，ｓ），７．８８（２Ｈ，ｓ），７．９１（１Ｈ，ｓ），８．３７（２Ｈ，ｄ，Ｊ＝４．８Ｈｚ）． Production example 1.
Benzyl N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzimidate (Compound No. 1-2 )Manufacturing of

of N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (63 mg, 0.146 mmol) Benzyl bromide (35 μL, 0.292 mmol), tetrabutylammonium hydrogensulfate (5.0 mg, 0.146 mmol) and aqueous sodium hydroxide solution (25% by weight, 0.2 mL) were added to a toluene (3 mL) solution, and the mixture was stirred at room temperature. Stirred for 2 hours. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography to give 29 mg of Benzyl N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3 , 5-bis(trifluoromethyl)benzimidate was obtained as an E/Z mixture.
Yield: 38%
¹ H NMR (400 MHZ, CDCl ₃ ) δ value (ppm)
2.00 (3H, d, J = 7.2Hz), 5.28 (2H, s), 6.29 (1H, q, J = 6.8Hz), 6.91 (1H, t, J = 5 .2 Hz), 7.17-7.19 (2 H, m), 7.31-7.35 (3 H, m), 7.79 (1 H, s), 7.88 (2 H, s), 7. 91 (1 H, s), 8.37 (2 H, d, J=4.8 Hz).

水素化ナトリウム（２０ ｍｇ，０．４９３ｍｍｏｌ）のＴＨＦ（３ｍＬ）溶液を氷浴で冷却し、Ｎ－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚｏｔｈｉｏａｍｉｄｅ（２００ｍｇ，０．４４８ｍｍｏｌ）を、ゆっくりと加えて１０分間撹拌した。反応混合物にヨウ化エチル（５４μＬ，０．６７３ｍｍｏｌ）を加え、室温に昇温しながら５時間撹拌した。反応混合物に水を加え、酢酸エチルで２回抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下留去した。得られた残渣をシリカゲルクロマトグラフィーにて精製し、９５ｍｇのＥｔｈｙｌ Ｎ－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚｉｍｉｄｏｔｈｉｏａｔｅをＥ／Ｚ混合物として得た。^１ＨＮＭＲから炭素－窒素二重結合に由来するＥ／Ｚ比率は８２：１８であった。
収率：４５％
融点：１４１－１４９℃ Production example 2.
Ethyl N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzimidothioate (Compound No. 2-4 )Manufacturing of

A solution of sodium hydride (20 mg, 0.493 mmol) in THF (3 mL) was cooled in an ice bath and N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol- 5-yl)ethyl)-3,5-bis(trifluoromethyl)benzothioamide (200mg, 0.448mmol) was slowly added and stirred for 10 minutes. Ethyl iodide (54 μL, 0.673 mmol) was added to the reaction mixture, and the mixture was stirred for 5 hours while warming to room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography to give 95 mg of Ethyl N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3 , 5-bis(trifluoromethyl)benzimidothioate was obtained as an E/Z mixture. The E/Z ratio derived from the carbon-nitrogen double bond from ¹ H NMR was 82:18.
Yield: 45%
Melting point: 141-149°C

Ｎ－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚａｍｉｄｅ（５０ｍｇ，０．１１６ｍｍｏｌ）のクロロホルム（３ｍＬ）溶液にＤＭＦ（３滴）及び塩化チオニル（０．５ｍＬ）を加え、７０℃で２時間撹拌した。反応混合物を減圧下留去し、得られた残渣にクロロホルム（３ｍＬ）及びジメチルアミンメタノール溶液（２Ｍ，０．５８ｍＬ，１．１６ ｍｍｏｌ）を加えて室温で３時間撹拌した。反応混合物に水を加え、クロロホルムで２回抽出した。得られた有機層を無水硫酸ナトリウムで乾燥後、減圧下留去した。得られた残渣をシリカゲルクロマトグラフィーにて精製し、１６ｍｇのＮ，Ｎ－ｄｉｍｅｔｈｙｌ－Ｎ’－（１－（１－（ｐｙｒｉｍｉｄｉｎ－２－ｙｌ）－１Ｈ－１，２，４－ｔｒｉａｚｏｌ－５－ｙｌ）ｅｔｈｙｌ）－３，５－ｂｉｓ（ｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌ）ｂｅｎｚｉｍｉｄａｍｉｄｅを得た。
収率：３０％
融点：１７６－１７８℃ Production example 3.
N,N-dimethyl-N'-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzimidamide ( Production of compound No. 3-3)

N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (50mg, 0.116mmol) DMF (3 drops) and thionyl chloride (0.5 mL) were added to a chloroform (3 mL) solution, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was evaporated under reduced pressure, chloroform (3 mL) and dimethylaminemethanol solution (2M, 0.58 mL, 1.16 mmol) were added to the resulting residue, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was extracted twice with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography to give 16 mg of N,N-dimethyl-N'-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl)ethyl)-3,5-bis(trifluoromethyl)benzimidamide was obtained.
Yield: 30%
Melting point: 176-178°C

Formulation examples of agricultural and horticultural pest control agents are shown below. In the formulation examples, parts indicate parts by mass.
Formulation example 1.
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above ingredients are uniformly mixed and dissolved to form an emulsion.

Formulation example 2.
The compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain powders.

Formulation example 3.
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.

Formulation example 4.
Compound of the present invention 20 parts kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.

Formulation examples of animal parasite control agents are shown below. Parts in the formulation examples indicate parts by mass.
Formulation example 5
Compound of the present invention 10 parts Solpol 355S (manufactured by Toho Kagaku, surfactant) 6 parts Solvesso 150 (manufactured by Exxon) 84 parts The above are uniformly stirred and mixed to form an emulsion.

Formulation example 6
Compound of the present invention 1 part Bleached beeswax 50 parts White petrolatum 49 parts The above are uniformly stirred and mixed to prepare an ointment.

Formulation example 7
Compound of the present invention 2 parts Vegetable oil (olive oil) 10 parts Crystalline cellulose 3 parts White carbon 20 parts Kaolin 65 parts The above are uniformly mixed and compressed into tablets.

Formulation example 8
10 parts of the compound of the present invention, 10 parts of propylene glycol for food additives, and 80 parts of vegetable oil (corn oil) are mixed to prepare an injection.

Formulation example 9
Compound of the present invention 5 parts Surfactant commonly used for the purpose of dissolution or suspension 20 parts Ion-exchanged water 75 parts The above are uniformly mixed to prepare a liquid preparation.

A test example is shown below.
Test example 1.
Control value test against green peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot of 8 cm in diameter and 8 cm in height to propagate green peach aphid, and the number of parasites in each pot was investigated. The compound of the present invention is dispersed in water and diluted to a chemical solution of 500 ppm, and the chemical solution is sprayed on the stems and leaves of Chinese cabbage planted in pots, air-dried, and the pots are stored in a greenhouse. The number of parasites of the green peach aphid that has been treated was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria. As a result of this test, compounds Nos. 1-2, 2-1 to 2-11, 2-13, 2-16 and 3-3 of the present invention showed activity equal to or higher than C.

Ta: Number of parasites before spraying in treated area T: Number of parasites after spraying in treated area Ca: Number of parasites before spraying in untreated area C: Number of parasites after spraying in untreated area

Judgment criteria A: control value 100%
B: control value 99% to 90%
C... control value 89% to 80%
D... control value 79% to 50%

判定基準
Ａ・・・補正死虫率１００％
Ｂ・・・補正死虫率９９％～９０％
Ｃ・・・補正死虫率８９％～８０％
Ｄ・・・補正死虫率７９％～５０％
Test example 2. Insecticidal test against Laodelphax striatellus The compound of the present invention is dispersed in water and diluted with a chemical solution of 500 ppm, rice seedlings (variety: Nipponbare) are immersed in the chemical solution for 30 seconds, air-dried, placed in a glass test tube, and placed in a glass test tube. After inoculation of 10 each of the 3rd instars, cotton plugging was carried out, and the number of living and dead insects was investigated 8 days after inoculation.
As a result of this test, compounds Nos. 1-2, 2-1 to 2-11, 2-13, 2-16, 2-17 and 3-3 of the present invention showed activity equal to or higher than C.

Judgment Criteria A: Corrected mortality rate of 100%
B: Corrected mortality rate of 99% to 90%
C: Corrected mortality rate of 89% to 80%
D: Corrected mortality rate 79% to 50%

Test example 3. Insecticidal test against diamondback moth (Plutella xylostella) Adults of diamondback moth were released to Chinese cabbage seedlings to lay eggs. It was immersed in the chemical solution for about 30 seconds, air-dried, and left in a constant temperature room at 25°C. Six days after immersion in the chemical solution, the number of hatched insects was investigated, the mortality rate was calculated according to the following formula, and the determination was made according to the following criteria. 1 ward 10 horses 3 consecutive system. As a result of this test, compounds Nos. 1-2, 1-4, 2-1 to 2-11, 2-13, 2-14, 2-16 and 3-3 of the present invention showed activity of C or higher.

判定基準
Ａ・・・死虫率１００％
Ｂ・・・死虫率９９％～９０％
Ｃ・・・死虫率８９％～８０％
Ｄ・・・死虫率７９％～５０％

Judgment criteria A: 100% dead insect rate
B: Mortality rate of 99% to 90%
C: 89% to 80% dead insect rate
D: 79% to 50% dead insect rate

判定基準
Ａ・・・死虫率１００％
Ｂ・・・死虫率９９％～９０％
Ｃ・・・死虫率８９％～８０％
Ｄ・・・死虫率７９％～５０％
Test example 4. Insecticidal test against Spodoptera litura Cabbage leaf pieces (cultivar: Shiki) are immersed in a chemical solution diluted to 500 ppm with the compound of the present invention as an active ingredient for about 30 seconds, air-dried, placed in a plastic petri dish with a diameter of 9 cm, and Spodoptera litura. After inoculation with second instar larvae, the container was covered and allowed to stand in a constant temperature room at 25°C. Eight days after the inoculation, the number of live and dead insects was investigated, the mortality rate was calculated by the following formula, and the determination was made according to the following criteria. 1 ward 10 horses 3 consecutive system. As a result of this test, compounds Nos. 1-2, 2-1 to 2-11, 2-13, 2-16 and 3-3 of the present invention showed activity equal to or higher than C.

Judgment criteria A: 100% dead insect rate
B: Mortality rate of 99% to 90%
C: 89% to 80% dead insect rate
D: 79% to 50% dead insect rate

The imine compound or its salt of the present invention can be applied as an agricultural and horticultural pest control agent and an animal parasite control agent.

Claims (13)

general formula (I)

{Wherein, R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
a phenyl (C ₁ -C ₆ ) alkyl group;
a substituted phenyl(C ₁ -C ₆ )alkyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic (C ₁ -C ₆ ) alkyl group;
a substituted heterocyclic (C ₁ -C ₆ )alkyl group having 1 to 4 substituents on the ring selected from Substituent Group A;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ ) alkynyl group;
halo(C ₂ -C ₆ )alkynyl groups;
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic group; or a substituted heterocyclic group having 1 to 4 substituents on the ring selected from Substituent Group A,
^R2 is
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group;
A substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from Substituent Group A;
pyrazinyl group;
A substituted pyrazinyl group having 1 to 3 substituents on the ring selected from substituent group A;
a pyridazinyl group; or a substituted pyridazinyl group having 1 to 3 substituents on the ring selected from the substituent group A,
R ³ and R ⁴ each independently represent a hydrogen atom; (C ₁ -C ₆ )alkyl group or halo(C ₁ -C ₆ )alkyl group;
^R5 is
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group;
A substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from Substituent Group A;
pyrazinyl group;
A substituted pyrazinyl group having 1 to 3 substituents on the ring selected from substituent group A;
a pyridazinyl group; or a substituted pyridazinyl group having 1 to 3 substituents on the ring selected from the substituent group A,
X is
oxygen atom; sulfur atom; or NR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo( C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ —C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ ) an alkyl group or a halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group),
Y represents a single bond; or _CH2 ;
Q ¹ and Q ² are each independently
CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C _{3 -} C6)cycloalkyl group, (C1 _- C6)alkoxy(C1 _- C6)alkyl group, di(C1 _{- C6} )alkoxy( _{C1 - C6} ) _alkyl group, ( _C1- C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, halo(C ₃ -C ₆ )cycloalkoxy group or (C ₁ -C ₆ )alkoxycarbonyl group or a nitrogen atom (provided that at least one of Q ¹ and Q ² is a nitrogen atom),
Substituent group A is
halogen atom, cyano group, nitro group, hydroxyl group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ ) alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group, halo (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group , (C ₁ -C ₆ )alkylthio group, halo(C ₁ -C ₆ )alkylthio group, (C ₃ -C ₆ )cycloalkylthio group, (C ₁ -C ₆ )alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C3 _- C6) cycloalkylsulfinyl group, (C1 _- C6) alkylsulfonyl group, halo(C1 _{- C6} ) _{alkylsulfonyl} group _, (C3 _{- C6} ) cycloalkyl sulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ -C ₆ )alkoxycarbonyl group, halo (C ₁ -C ₆ )alkoxycarbonyl group, (C ₃ -C ₆ )cycloalkoxycarbonyl group, mono(C ₁ -C ₆ )alkylaminocarbonyl group and di(C ₁ -C ₆ )alkylaminocarbonyl group; . }
A compound represented by or a salt thereof. R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
a phenyl (C ₁ -C ₆ ) alkyl group;
a substituted phenyl(C ₁ -C ₆ )alkyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic (C ₁ -C ₆ ) alkyl group;
a substituted heterocyclic (C ₁ -C ₆ )alkyl group having 1 to 4 substituents on the ring selected from Substituent Group A;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ ) alkynyl group;
halo(C ₂ -C ₆ )alkynyl groups;
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
heterocyclic group; or a substituted heterocyclic group having 1 to 4 substituents on the ring selected from Substituent Group A,
^R2 is
phenyl group;
A substituted phenyl group having 1 to 5 substituents on the ring selected from Substituent Group A;
pyridyl group; or a substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A,
R ³ and R ⁴ each independently represent a hydrogen atom; (C ₁ -C ₆ )alkyl group or halo(C ₁ -C ₆ )alkyl group;
^R5 is
pyridyl group;
A substituted pyridyl group having 1 to 4 substituents on the ring selected from substituent group A;
a pyrimidinyl group; or a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from substituent group A,
X is
oxygen atom; sulfur atom; or NR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo( C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, (C ₁ —C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ ) an alkyl group or a halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group),
Y represents a single bond,
Q ¹ and Q ² are each independently CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ - C ₆ )cycloalkyl group, halo(C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group, di(C ₁ -C ₆ )alkoxy(C ₁ - C ₆ )alkyl group, (C ₁ -C ₆ )alkoxy group, halo(C ₁ -C ₆ )alkoxy group, (C ₃ -C ₆ )cycloalkoxy group, halo(C ₃ -C ₆ )cycloalkoxy group or (C ₁ -C ₆ ) represents an alkoxycarbonyl group); or represents a nitrogen atom (with the proviso that at least one of Q ¹ and Q ² is a nitrogen atom),
Substituent group A is
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - 2. The compound or salt thereof according to claim 1, which represents a C ₆ )alkoxycarbonyl group or a halo(C ₁ -C ₆ )alkoxycarbonyl group. R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ ) cycloalkyl group;
halo(C ₃ -C ₆ )cycloalkyl group;
(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkoxy(C ₁ -C ₆ )alkyl groups;
(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl group;
halo(C ₁ -C ₆ )alkylthio(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
benzyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted benzyl group having 1 to 5 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
pyridylmethyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted pyridylmethyl group having 1 to 4 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,
^R2 is
phenyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - a substituted phenyl group having 1 to 5 substituents on the ring selected from C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group;
pyridyl group; or halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ —C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C ₃ -C ₆ ) cycloalkylsulfinyl group, (C ₁ -C ₆ ) alkyl sulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, a substituted pyridyl group having 1 to 4 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group,
R ³ represents a (C ₁ -C ₆ )alkyl group; or a halo(C ₁ -C ₆ )alkyl group;
R ⁴ represents a hydrogen atom,
^R5 is
pyridyl group;
halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups, (C ₃ -C ₆ )cycloalkyl groups, halo(C ₃ -C ₆ )cycloalkyl groups, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ -C ₆ ) Alkylthio, (C ₁ -C ₆ )alkylsulfinyl, halo(C ₁ -C ₆ )alkylsulfinyl, (C ₃ -C ₆ )cycloalkylsulfinyl, (C ₁ -C ₆ )alkylsulfonyl, halo (C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, (C ₁ - C ₆ ) substituted pyridyl groups having 1 to 4 substituents on the ring selected from alkoxycarbonyl groups and halo(C ₁ -C ₆ )alkoxycarbonyl groups;
pyrimidinyl group; or halogen atom, cyano group, (C ₁ -C ₆ )alkyl group, halo(C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, halo(C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₆ )alkoxy, halo(C ₁ -C ₆ )alkoxy, (C ₃ -C ₆ )cycloalkoxy, (C ₁ -C ₆ )alkylthio, halo(C ₁ —C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo(C ₁ -C ₆ ) alkylsulfinyl group, (C ₃ -C ₆ ) cycloalkylsulfinyl group, (C ₁ -C ₆ ) alkyl sulfonyl group, halo(C ₁ -C ₆ )alkylsulfonyl group, (C ₁ -C ₆ )alkylcarbonyl group, halo(C ₁ -C ₆ )alkylcarbonyl group, (C ₃ -C ₆ )cycloalkylcarbonyl group, a substituted pyrimidinyl group having 1 to 3 substituents on the ring selected from (C ₁ -C ₆ )alkoxycarbonyl group and halo(C ₁ -C ₆ )alkoxycarbonyl group,
X represents an oxygen atom; or a sulfur atom,
Y represents a single bond,
Q ¹ is CH; or represents a nitrogen atom,
The compound or its salt according to claim 1, wherein ^Q2 represents a nitrogen atom. R ¹ is
(C ₁ -C ₆ ) alkyl group;
halo(C ₁ -C ₆ )alkyl groups;
(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl group;
halo(C ₃ -C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl groups;
benzyl group;
1 to 5 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted benzyl group bearing thereon;
pyridylmethyl group;
1 to 4 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted pyridylmethyl group bearing thereon;
(C ₂ -C ₆ ) alkenyl group;
halo(C ₂ -C ₆ )alkenyl groups;
(C ₂ -C ₆ )alkynyl group; or halo(C ₂ -C ₆ )alkynyl group,
^R2 is
phenyl group;
1 to 5 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted phenyl group bearing thereon;
pyridyl group; or 1 to 4 selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups represents a substituted pyridyl group having a substituent on the ring,
R ³ represents a (C ₁ -C ₆ ) alkyl group,
R ⁴ represents a hydrogen atom,
^R5 is
pyridyl group;
1 to 4 substituents selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups; a substituted pyridyl group bearing thereon;
pyrimidinyl group; or 1 to 3 groups selected from halogen atoms, cyano groups, (C ₁ -C ₆ )alkyl groups, halo(C ₁ -C ₆ )alkyl groups and halo(C ₁ -C ₆ )alkoxy groups represents a substituted pyrimidinyl group having a substituent on the ring,
X represents an oxygen atom; or a sulfur atom,
Y represents a single bond,
Q ¹ represents CH,
The compound and its salt according to claim 1, wherein ^Q2 represents a nitrogen atom. A pest control agent comprising the compound according to any one of claims 1 to 4 or a salt thereof as an active ingredient. An agricultural and horticultural pest control agent comprising the compound according to any one of claims 1 to 4 or a salt thereof as an active ingredient. An animal parasite control agent comprising the compound or a salt thereof according to any one of claims 1 to 4 as an active ingredient. An ectoparasite control agent for animals comprising the compound or a salt thereof according to any one of claims 1 to 4 as an active ingredient. An internal parasite control agent for animals comprising the compound or a salt thereof according to any one of claims 1 to 4 as an active ingredient. A method for controlling pests in the agricultural and horticultural field, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to claim 6 to a target plant or soil. A method for controlling parasites in animals, which comprises orally or parenterally administering an effective amount of the parasite control agent for animals according to claim 7 to a subject animal. A method for controlling ectoparasites in animals, which comprises orally or parenterally administering an effective amount of the ectoparasite control agent for animals according to claim 8 to a subject animal. A method for controlling endoparasites in animals, which comprises orally or parenterally administering an effective amount of the veterinary endoparasite control agent according to claim 9 to a subject animal.