JP2023175057A - Fused heterocycle derivative and herbicide containing the same as active ingredient - Google Patents

Abstract

To provide a novel fused heterocycle derivative or an agriculturally acceptable salt thereof and a herbicide containing the derivative as an active ingredient.SOLUTION: Provided are a fused heterocycle derivative represented by general formula [I] (Q: substituted indolyl or the like. R7: halogen, C1-C6 haloalkyl, cyano or the like. Z: O, S. A: N, C-R13. R13: H, halogen, cyano) or a salt thereof and a herbicide containing the same as an active ingredient.SELECTED DRAWING: None

Description

The present invention relates to a novel fused heterocyclic derivative or an agriculturally acceptable salt thereof, and a herbicide containing the derivative as an active ingredient.

Conventionally, the following are known as fused heterocyclic derivatives (see, for example, Patent Documents 1 to 7).

Patent Document 1 describes a pyrimidinyloxy fused heterocyclic derivative having a herbicidal effect.

Patent Document 2 describes pyrimidinyloxy or pyridinyloxy fused heterocyclic derivatives having Kv3 channel inhibitory activity.

Patent Document 3 describes a 7-(pyridin-2-yloxy)-1H-benzimidazole derivative having an antifungal effect.

Patent Document 4 describes 7-(pyridin-2-yloxy)-1H-indazole derivatives having tyrosine kinase inhibitory activity.

Patent Document 5 describes a 7-(pyridin-2-yloxy)-1H-indole derivative that has collagen synthesis inhibitory activity.

Patent Documents 6 and 7 describe 7-(pyridin-2-yloxy)indolin-2-one derivatives having bromodomain inhibitory activity.

International Publication No. 2018/204164 International Publication No. 2012/076877 International Publication No. 2008/101682 US Publication No. 20060079564 International Publication No. 2009/057811 International Publication No. 2018/109271 International Publication No. 2016/203112

However, the compound described in Patent Document 1 does not have sufficient herbicidal effects.

In the compound described in Patent Document 2, the 5-position of the pyrimidine ring or pyridine ring is limited to a 2,5-dioxoimidazolidin-1-yl group, and Patent Document 2 does not focus on herbicidal effects. .

In the compound described in Patent Document 3, the 5-position of the pyridine ring is limited to a formimidamide group, and Patent Document 3 does not focus on herbicidal effects.

In the compound described in Patent Document 4, the 3-position of the indazole ring is limited to a 1H-benzimidazol-2-yl group, and Patent Document 4 does not focus on herbicidal effects.

In the compound described in Patent Document 5, the 5-position of the pyridine ring is limited to a benzamide group, etc., and Patent Document 5 does not focus on herbicidal effects.

The compounds described in Patent Documents 6 and 7 are limited to derivatives in which the 5-position of the indolin-2-one ring is substituted with a 1-phenyl-1H-pyrazol-5-yl group or a phenylsulfonamide group. , Patent Documents 6 and 7 do not pay attention to the herbicidal effect.

In the cultivation of useful plants, the occurrence of various weeds has a significant impact on the production efficiency of plants, crops, and products. Therefore, in order to control these weeds, weed killers with superior properties at lower doses are needed. There is a need for the creation of new agents. In addition, there are increasing demands for the safety of chemical substances and their impact on the environment, and the development of safer herbicides is desired.

The present invention has been made in view of the above circumstances, and its purpose is to eliminate various weeds that occur in fields, orchards, paddy fields, non-agricultural lands, etc. without causing phytotoxicity to useful plants. It is an object of the present invention to provide a compound having a herbicidal activity that can be controlled at a low dose, and a herbicide containing the same.

In order to achieve the above object, the present inventors synthesized a large number of fused heterocyclic derivatives and conducted extensive studies on their herbicidal activity and usefulness. As a result, by applying the fused heterocyclic derivative represented by the following general formula [I] (hereinafter referred to as "the compound of the present invention") to plants, various weeds can be controlled over a long period of time, They discovered that it exhibits a remarkable herbicidal effect without causing any phytotoxicity to plants, and after further research, they completed the present invention.

That is, the present invention has the following features.
(1) General formula [I]

[In general formula [I],
Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8,

Ｒ^１は、水素原子、Ｃ_１～Ｃ_６アルキル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、Ｃ_２～Ｃ_６アルケニル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、Ｃ_２～Ｃ_６アルキニル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）又はヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）を示し、
Ｒ^８は、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ホルミル基、Ｃ_１～Ｃ_６アルキルカルボニル基、Ｃ_１～Ｃ_６ハロ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、ベンゾイル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、－Ｃ（Ｒ^１０）＝ＮＯＲ^１１、カルボキシ基、Ｃ_１～Ｃ_６アルコキシカルボニル基、Ｃ_１～Ｃ_６ハロアルコキシカルボニル基、アミノカルボニル基、Ｃ_１～Ｃ_６アルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、ピロリジン－１－イルカルボニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ピペリジン－１－イルカルボニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６アルケニルオキシ基、Ｃ_３～Ｃ_６アルキニルオキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、Ｃ_３～Ｃ_６シクロアルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルコキシ基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルコキシ基、フェノキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニルＣ_１～Ｃ_６アルコキシ基（該フェニル基はＲ^９によりモノ置換又はポリ置換されてもよい）、チオール基、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、Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、Ｃ_３～Ｃ_６シクロアルキルチオ基、Ｃ_３～Ｃ_６シクロアルキルスルフィニル基、Ｃ_３～Ｃ_６シクロアルキルスルホニル基、Ｃ_３～Ｃ_６ハロシクロアルキルチオ基、Ｃ_３～Ｃ_６ハロシクロアルキルスルフィニル基、Ｃ_３～Ｃ_６ハロシクロアルキルスルホニル基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルキルチオ基、Ｃ_３～Ｃ_６シクロアルキル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Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルキルチオ基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルキルスルフィニル基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルキルスルホニル基、フェニルチオ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニルスルフィニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニルスルホニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、アミノ基、Ｃ_１～Ｃ_６アルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、フェニルカルボニルアミノ基（該フェニル基はＲ^９によりモノ置換又はポリ置換されてもよく、該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルコキシカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルコキシカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルアミノカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、フェニルスルホニルアミノ基（該フェニル基はＲ^９によりモノ置換又はポリ置換されてもよく、該アミノ基はＲ^１２により置換されてもよい）、トリ（Ｃ_１～Ｃ_６アルキル）シリル基、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、１，３－ベンゾジオキソリル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロシクロアルキル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、シアノ基、ニトロ基又はチオシアナト基を示し、
Ｒ^９は、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ホルミル基、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、チオール基、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、Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、シアノ基又はニトロ基を示し、
Ｒ^１０は、水素原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）又はヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）を示し、
Ｒ^１１は、水素原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基又はＣ_３～Ｃ_６ハロシクロアルキル基を示し、
Ｒ^１２は、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６アルコキシＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルコキシＣ_１～Ｃ_６アルキル基、シアノＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６アルキルカルボニル基、Ｃ_１～Ｃ_６ハ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、Ｃ_１～Ｃ_６ハロアルコキシカルボニル基、Ｃ_１～Ｃ_６アルキルアミノカルボニル基、Ｃ_１～Ｃ_６ハロアルキルアミノカルボニル基又はベンゾイル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）を示し、
Ｒ^２は、水素原子、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ホルミル基、Ｃ_１～Ｃ_６アルキルカルボニル基、Ｃ_１～Ｃ_６ハロ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（Ｒ^１０）＝ＮＯＲ^１１、カルボキシ基、Ｃ_１～Ｃ_６アルコキシカルボニル基、Ｃ_１～Ｃ_６ハロアルコキシカルボニル基、アミノカルボニル基、アミノチオカルボニル基、Ｃ_１～Ｃ_６アルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６アルケニルオキシ基、Ｃ_３～Ｃ_６アルキニルオキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、Ｃ_３～Ｃ_６シクロアルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルコキシ基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルコキシ基、フェニルＣ_１～Ｃ_６アルコキシ基（該フェニル基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、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、Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、アミノ基、Ｃ_１～Ｃ_６アルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルコキシカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、シアノ基又はニトロ基を示し、
Ｒ^３は、水素原子、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、Ｃ_１～Ｃ_６アルコキシＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルコキシ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、Ｃ_１～Ｃ_６アルキルスルフィニルＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６アルキルスルホニルＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキルチオＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキルスルフィニルＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキルスルホニルＣ_１～Ｃ_６アルキル基、シアノＣ_１～Ｃ_６アルキル基、ホルミル基、Ｃ_１～Ｃ_６アルキルカルボニル基、Ｃ_１～Ｃ_６ハロ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（Ｒ^１０）＝ＮＯＲ^１１、カルボキシ基、Ｃ_１～Ｃ_６アルコキシカルボニル基、Ｃ_１～Ｃ_６ハロアルコキシカルボニル基、アミノカルボニル基、アミノチオカルボニル基、Ｃ_１～Ｃ_６アルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノカルボニル基（該アミノ基はＲ^１２により置換されてもよい）、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６アルケニルオキシ基、Ｃ_３～Ｃ_６アルキニルオキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、Ｃ_３～Ｃ_６シクロアルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルコキシ基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルコキシ基、Ｃ_３～Ｃ_６ハロシクロアルキルＣ_１～Ｃ_６アルコキシ基、フェニルＣ_１～Ｃ_６アルコキシ基（該フェニル基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、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、Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、アミノ基、Ｃ_１～Ｃ_６アルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルコキシカルボニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６アルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、Ｃ_３～Ｃ_６シクロアルキルスルホニルアミノ基（該アミノ基はＲ^１２により置換されてもよい）、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、シアノ基又はニトロ基を示し、
Ｒ^４は、独立してハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキル基、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、シアノ基又はニトロ基を示し、
ｍは、０、１、２又は３の整数を示し、
Ｙは、酸素原子又は硫黄原子を示し、
Ｒ^５は、独立して水素原子、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、トリ（Ｃ_１～Ｃ_６アルキル）シリルオキシ基又はシアノ基を示し、また２つのＲ^５は一緒になってオキソ基（＝Ｏ）、又はＣ_１～Ｃ_６アルコキシイミノ基を形成してもよく、さらに２つのＲ^５は相互に結合してこれらの結合する炭素原子とともに３～６員の炭素環、又は窒素原子、酸素原子及び硫黄原子（該硫黄原子は１又は２個のオキソ基（＝Ｏ）により置換されてもよい）より選択される１～４個のヘテロ原子を有する３～６員の複素環を形成してもよく、
Ｒ^６は、水素原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６アルコキシＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルコキシＣ_１～Ｃ_６アルキル基、シアノＣ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６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又はＣ_１～Ｃ_６アルキルスルホニル基を示し、
Ｒ^７は、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_２～Ｃ_６アルキニル基、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ヒドロキシ基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、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、Ｃ_１～Ｃ_６アルキルスルホニル基、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、シアノ基又はニトロ基を示し、
Ｚは、酸素原子又は硫黄原子を示し、
Ａは、Ｎ又はＣ－Ｒ^１３を示し、
Ｒ^１３は、水素原子、ハロゲン原子又はシアノ基を示す］
で表される縮合ヘテロ環誘導体、又はその農業上許容される塩。

R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group (the group may be mono- or polysubstituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono- or polysubstituted by R ⁸ ); C ₂ -C ₆ alkynyl groups (which groups may be mono- or polysubstituted by R ⁸ ), C ₃ -C ₆ cycloalkyl groups (which groups may be mono- or polysubstituted by R 8 ), C 2 -C 6 alkynyl groups (which groups may be mono- or polysubstituted by R ⁸ a phenyl group (which may be mono- or polysubstituted by R ⁹ ) or a heteroaryl group (which may be mono- or polysubstituted by R ⁹ ); ,
R ⁸ is a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, a formyl group, a C ₁ to C ₆ Alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₃ -C ₆ cycloalkylcarbonyl group, benzoyl group (the group may be mono- or polysubstituted with R ⁹ ), -C(R ¹⁰ )= NOR ¹¹ , carboxy group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, aminocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (even if the amino group is substituted by R ¹² C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted by R ¹² ), pyrrolidin-1-ylcarbonyl group (the group may be mono- or polysubstituted by R ⁹ ) ), piperidin-1-ylcarbonyl group (which group may be mono- or polysubstituted by R ⁹ ), hydroxy group, C ₁ -C ₆ alkoxy group, C _{3 -C 6} alkenyloxy group, C ₃ - C ₆ alkynyloxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C ₃ -C ₆ halocycloalkoxy group, C ₃ -C ₆ cycloalkylC ₁ -C ₆ alkoxy group, C ₃ - _C6 halocycloalkylC1 _{- C6} alkoxy group, phenoxy group (which group may be mono- or polysubstituted with ^R9 ), _phenylC1 - _C6 alkoxy group (the phenyl group is R9 ⁾ ), thiol group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylthio group, C ₁ - C ₆ haloalkylsulfinyl group, C ₁ - C ₆ haloalkylsulfonyl group, C ₃ - C ₆ cycloalkylthio group, C ₃ - C ₆ cycloalkylsulfinyl group, C ₃ - C ₆ cycloalkylsulfonyl group, C ₃ - C ₆ halocycloalkylthio group, C ₃ to C ₆ halocycloalkylsulfinyl group, C ₃ to C ₆ halocycloalkylsulfonyl group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylthio group, C ₃ to C ₆ cyclo Alkyl C ₁ - C ₆ alkylsulfinyl group, C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkylsulfonyl group, C ₃ - C ₆ halocycloalkyl C ₁ - C ₆ alkylthio group, C ₃ - C ₆ halocycloalkyl C ₁ -C ₆ alkylsulfinyl group, C ₃ -C ₆ halocycloalkylC ₁ -C ₆ alkylsulfonyl group, phenylthio group (the group may be mono- or polysubstituted by R ⁹ ), phenylsulfinyl group ( The group may be mono- or polysubstituted by R ⁹ ), phenylsulfonyl group (the group may be mono- or polysubstituted by R ⁹ ), amino group, C ₁ -C ₆ alkylamino group ( The amino group may be substituted by R ¹² ), the C ₁ -C ₆ haloalkylamino group (the amino group may be substituted by R ¹² ), the C ₁ -C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ cycloalkylcarbonylamino group (the amino group may be substituted by R 12), ), phenylcarbonylamino group (the phenyl group may be mono- or polysubstituted with R ⁹ and the amino group may be substituted with R ¹² ), C ¹ _{-C 6} alkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ Alkylaminocarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylaminocarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ Alkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ cycloalkyl a sulfonylamino group (the amino group may be substituted by R ¹² ), a phenylsulfonylamino group (the phenyl group may be mono- or polysubstituted by R ⁹ , and the amino group may be substituted by R ¹² ); ), tri(C ₁ -C ₆ alkyl)silyl group, phenyl group (said group may be mono- or polysubstituted with R ⁹ ), 1,3-benzodioxolyl group (said group may be mono- or polysubstituted with R Heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryloxy groups (which groups may be mono- or polysubstituted by R ⁹ ), a heterocycloalkyl group (which group may be mono- or polysubstituted by R ⁹ ), a cyano group, a nitro group or a thiocyanato group;
R ⁹ is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group, formyl group, hydroxy group, C _{1 -C 6} alkoxy group, C _{1 -C 6} haloalkoxy group, thiol group, C ₁ -C ₆ alkylthio group, C 1 -C ₆ alkylsulfinyl group , C ₁ to C ₆ alkylsulfonyl group, C ₁ to C ₆ haloalkylthio group, C ₁ to C ₆ haloalkylsulfinyl group, C ₁ to C ₆ haloalkylsulfonyl group, cyano group or nitro group,
R ¹⁰ is a hydrogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a phenyl group (the group may be mono- or polysubstituted by R ⁹ ) or a heteroaryl group (the group may be mono- or polysubstituted by R ⁹ );
R ¹¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, or a C ₃ ~C ₆ halocycloalkyl group,
R ¹² is a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ Halocycloalkyl group, _C3 - _{C6cycloalkylC1} -C6alkyl group, C1 _{- C6alkoxyC1} - _{C6alkyl group , C1-C6haloalkoxyC1 - C6alkyl group , cyano} C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ haloalkoxycarbonyl group, C ₁ to C ₆ represents an alkylaminocarbonyl group, a C ₁ -C ₆ haloalkylaminocarbonyl group or a benzoyl group (which group may be mono- or polysubstituted by R ⁹ );
R ² is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group , C ₃ to C ₆ halocycloalkyl group, formyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₃ to C ₆ cycloalkylcarbonyl group, -C(R ¹⁰ )=NOR ¹¹ , carboxy group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, aminocarbonyl group, aminothiocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (the amino group is defined by R ¹² ), C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted by R ¹² ), hydroxy group, C ₁ -C ₆ alkoxy group, C ₃ -C ₆ alkenyloxy group , C ₃ -C ₆ alkynyloxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C ₃ -C ₆ halocycloalkoxy group, C ₃ -C ₆ cycloalkylC ₁ -C ₆ Alkoxy group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group, phenyl C ₁ to C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted with R ⁹ ), heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ halo Alkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ haloalkylsulfonyl group, amino group, C ₁ -C ₆ alkylamino group (the amino group may be substituted by R ¹² ), C ₁ - C ₆ haloalkylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkyl carbonylamino group (the amino group may be substituted with R ¹² ), C ₃ -C ₆ cycloalkylcarbonylamino group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ alkoxycarbonyl Amino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), a C ₃ -C ₆ cycloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), a phenyl group (the group may be monosubstituted by R ⁹ ), (which may be substituted or polysubstituted), a heteroaryl group (which group may be mono- or polysubstituted by R ⁹ ), a cyano group or a nitro group;
R ³ is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group , C ₃ -C ₆ halocycloalkyl group, C ₁ -C ₆ alkoxyC 1 _{-C 6} alkyl group, C _{1 -C 6} haloalkoxyC ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthioC ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkylthioC ₁ -C ₆ alkyl group, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl group, cyano C ₁ to C ₆ alkyl group, formyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₃ to C ₆ cycloalkylcarbonyl group, -C(R ¹⁰ )=NOR ¹¹ , carboxy group, C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ haloalkoxycarbonyl group , aminocarbonyl group, aminothiocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted with R ¹² ) ), hydroxy group, C ₁ -C ₆ alkoxy group, C ₃ -C 6 alkenyloxy group, C ₃ -C ₆ alkynyloxy group, C _{1 -C 6 haloalkoxy} group, C ₃ -C ₆ cycloalkoxy group, C ₃ - C ₆ halocycloalkoxy group, C ₃ - C ₆ cycloalkyl C ₁ - C 6 alkoxy group, C _{3 - C 6 halocycloalkyl} C ₁ - C ₆ alkoxy group, phenyl C ₁ - C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted with R ⁹ ), heteroaryloxy group (the group may be mono- or polysubstituted with R ⁹ ), C ₁ -C ₆ Alkylthio group, C ₁ - C ₆ alkylsulfinyl group, C ₁ - C 6 alkylsulfonyl group, C ₁ - C ₆ haloalkylthio group, C ₁ - _{C 6 haloalkylsulfinyl} group, C ₁ - C ₆ haloalkylsulfonyl group, amino group , C ₁ -C ₆ alkylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylamino group (the amino group may be substituted by R 12), C 1 -C 6 alkylamino group (the amino group may be substituted by R ¹² ₎ C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ Cycloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkyl Sulfonylamino group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted with R ¹² ), C ₃ -C ₆ cycloalkylsulfonyl an amino group (the amino group may be substituted with R ¹² ), a phenyl group (the group may be mono- or polysubstituted with R ⁹ ), a heteroaryl group (the group may be mono-substituted or polysubstituted with R ⁹ ); (which may be polysubstituted), represents a cyano group or a nitro group,
R ⁴ is independently a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a hydroxy group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, a cyano group, or a nitro group. Indicates the group,
m represents an integer of 0, 1, 2 or 3,
Y represents an oxygen atom or a sulfur atom,
R ⁵ is independently a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C _{3 -C 6} halocycloalkyl group, a hydroxy group , C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, heteroaryloxy group (which group may be mono- or polysubstituted by R ⁹ ), tri(C ₁ -C ₆ alkyl)silyloxy or a cyano group, and two R ^5s may be combined to form an oxo group (=O) or a C ₁ -C ₆ alkoxyimino group, and two R ^5s are bonded to each other. selected from a 3- to 6-membered carbon ring together with the carbon atoms to which they are bonded, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom may be substituted with one or two oxo groups (=O)) may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms,
R ⁶ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group, C ₃ - C ₆ cycloalkylC 1 -C ₆ alkyl group, C ₁ -C 6 alkoxyC _{1 -C 6} alkyl group, C _{1 -C 6 haloalkoxyC 1} -C ₆ alkyl group, a cyano C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a C ₁ -C ₆ alkylsulfonyl group,
R ⁷ is a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ ~C ₆ halocycloalkyl group, hydroxy group, C ₁ ~ C ₆ alkoxy group, C ₁ ~ C 6 haloalkoxy group, C ₁ ~ C ₆ alkylthio group, C _{1 ~ C 6 alkylsulfinyl} group, C ₁ ~ C ₆ It represents an alkylsulfonyl group, a C ₁ -C ₆ haloalkylthio group, a C ₁ -C ₆ haloalkylsulfinyl group, a C ₁ -C ₆ haloalkylsulfonyl group, a cyano group or a nitro group,
Z represents an oxygen atom or a sulfur atom,
A represents N or CR ¹³ ,
R ¹³ represents a hydrogen atom, a halogen atom, or a cyano group]
A fused heterocyclic derivative represented by or an agriculturally acceptable salt thereof.

(2) In the general formula [I], Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8,

Ｒ^１は、水素原子、Ｃ_１～Ｃ_６アルキル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、Ｃ_２～Ｃ_６アルケニル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、Ｃ_２～Ｃ_６アルキニル基（該基はＲ^８によりモノ置換又はポリ置換されてもよい）、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）又はヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）を示し、
Ｒ^８は、ハロゲン原子、Ｃ_１～Ｃ_６ハロアルキル基、Ｃ_３～Ｃ_６シクロアルキル基、Ｃ_３～Ｃ_６ハロシクロアルキル基、ベンゾイル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、Ｃ_１～Ｃ_６アルコキシカルボニル基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、Ｃ_３～Ｃ_６シクロアルコキシ基、Ｃ_３～Ｃ_６シクロアルキルＣ_１～Ｃ_６アルコキシ基、フェノキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、Ｃ_１～Ｃ_６ハロアルキルチオ基、Ｃ_１～Ｃ_６ハロアルキルスルフィニル基、Ｃ_１～Ｃ_６ハロアルキルスルホニル基、フェニルチオ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニルスルフィニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニルスルホニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリール基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、ヘテロシクロアルキル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、シアノ基又はチオシアナト基を示し、
Ｒ^９は、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキル基、ホルミル基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基又はシアノ基を示し、
Ｒ^１０は、水素原子、を示し、
Ｒ^１１は、Ｃ_１～Ｃ_６アルキル基を示し、
Ｒ^２は、水素原子、Ｃ_１～Ｃ_６アルキル基又はＣ_１～Ｃ_６ハロアルキル基を示し、
Ｒ^３は、水素原子、ハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_２～Ｃ_６アルケニル基、Ｃ_１～Ｃ_６ハロアルキル基、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、ホルミル基、－Ｃ（Ｒ^１０）＝ＮＯＲ^１１、アミノカルボニル基、Ｃ_１～Ｃ_６アルコキシ基、Ｃ_１～Ｃ_６ハロアルコキシ基、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）、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、Ｃ_１～Ｃ_６アルキルスルホニル基、フェニル基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）又はシアノ基を示し、
Ｒ^４は、ハロゲン原子を示し、
ｍは、０又は１の整数を示し、
Ｙは、酸素原子又は硫黄原子を示し、
Ｒ^５は、独立してハロゲン原子、Ｃ_１～Ｃ_６アルキル基、Ｃ_１～Ｃ_６ハロアルキル基、ヘテロアリールオキシ基（該基はＲ^９によりモノ置換又はポリ置換されてもよい）又はトリ（Ｃ_１～Ｃ_６アルキル）シリルオキシ基を示し、また２つのＲ^５は一緒になってオキソ基（＝Ｏ）、又はＣ_１～Ｃ_６アルコキシイミノ基を形成してもよく、さらに２つのＲ^５は相互に結合してこれらの結合する炭素原子とともに３～６員の炭素環、又は窒素原子、酸素原子及び硫黄原子（該硫黄原子は１又は２個のオキソ基（＝Ｏ）により置換されてもよい）より選択される１～４個のヘテロ原子を有する３～６員の複素環を形成してもよく、
Ｒ^６は、Ｃ_１～Ｃ_６アルキル基又はＣ_１～Ｃ_６ハロアルキル基を示し、
Ｒ^７は、ハロゲン原子、Ｃ_１～Ｃ_６ハロアルキル基又はシアノ基を示し、
Ｚは、酸素原子を示し、
Ａは、Ｎ又はＣ－Ｒ^１３を示し、
Ｒ^１３は、水素原子、ハロゲン原子又はシアノ基を示す、前記（１）に記載の縮合ヘテロ環誘導体、又はその農業上許容される塩。

R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group (the group may be mono- or polysubstituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono- or polysubstituted by R ⁸ ); C ₂ -C ₆ alkynyl groups (which may be mono- or polysubstituted by R ⁸ ), phenyl groups (which may be mono- or polysubstituted by R ⁹ ) ) or a heteroaryl group (which group may be mono- or polysubstituted by R ⁹ ),
R ⁸ is a halogen atom, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, a benzoyl group (the group is mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C _{3 -C 6} cycloalkylC _{1 -C 6} alkoxy group, phenoxy group (which group may be mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ haloalkylsulfonyl group , a phenylthio group (the group may be mono- or polysubstituted by R ⁹ ), a phenylsulfinyl group (the group may be mono- or polysubstituted by R ⁹ ), a phenylsulfonyl group (the group may be mono- or polysubstituted by R 9 ), phenyl groups (which groups may be mono- or polysubstituted by ^{R 9} ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), ), a heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), a heterocycloalkyl group (the group may be mono- or polysubstituted by R ⁹ ), a cyano group or represents a thiocyanato group,
R ⁹ represents a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a formyl group, a C ₁ to C ₆ alkoxy group, a C ₁ to C ₆ haloalkoxy group, or a cyano group,
R ¹⁰ represents a hydrogen atom,
R ¹¹ represents a C ₁ to C ₆ alkyl group,
R ² represents a hydrogen atom, a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group,
R ³ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxyC ₁ to C ₆ alkyl group, formyl group, -C(R ¹⁰ )=NOR ¹¹ , aminocarbonyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, heteroaryloxy group (the group is R ⁹ ), C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, phenyl group (the group may be mono-substituted or polysubstituted by R ⁹ or may be polysubstituted) or a cyano group,
R ⁴ represents a halogen atom,
m represents an integer of 0 or 1,
Y represents an oxygen atom or a sulfur atom,
R ⁵ is independently a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), or a tri( C ₁ -C ₆ alkyl)silyloxy group, and two R ⁵ may be taken together to form an oxo group (=O) or a C ₁ -C ₆ alkoxyimino group, and two R ⁵ are mutually bonded together with these bonding carbon atoms to form a 3- to 6-membered carbon ring, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom is substituted with one or two oxo groups (=O)). may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms selected from
R ⁶ represents a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group,
R ⁷ represents a halogen atom, a C ₁ to C ₆ haloalkyl group, or a cyano group,
Z represents an oxygen atom,
A represents N or CR ¹³ ,
The fused heterocyclic derivative according to (1) above, or an agriculturally acceptable salt thereof, wherein R ¹³ represents a hydrogen atom, a halogen atom, or a cyano group.

(3) An agrochemical composition containing the fused heterocyclic derivative according to any one of (1) to (2) above, or an agriculturally acceptable salt thereof as an active ingredient.

(4) The agrochemical composition according to (3) above, further containing a surfactant.

(5) A herbicide containing the fused heterocyclic derivative according to any one of (1) to (2) above, or an agriculturally acceptable salt thereof as an active ingredient.

(6) Against weeds that occur in fields, paddy fields, orchards, lawns, non-agricultural lands, greenhouses, seedling facilities, or plant factories where useful plants for agricultural, horticultural, and industrial purposes are cultivated. , the herbicide according to (5) above, which has a herbicidal effect.

(7) The herbicide according to (6) above, wherein the useful plant having agricultural, horticultural, and industrial uses is a trait plant when cultivated by a breeding method or genetic recombination technology.

The fused heterocyclic derivative represented by the general formula [I] of the present invention or its agriculturally acceptable salt can control various weeds occurring in fields, paddy fields, orchards, and non-agricultural lands, and is further useful. It has excellent effects as a pesticide, such as being highly safe for plants.

The symbols and terms described in this specification will be explained.

In the present invention, "halogen atom" refers to fluorine atom, chlorine atom, bromine atom, and iodine atom.

In the present invention, a notation such as "C ₁ to C ₆ " indicates that the number of carbon atoms in the substituent that follows is 1 to 6 in this case.

In the present invention, the term "C ₁ to C ₆ alkyl group" refers to a straight or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, unless otherwise specified. Isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl , neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl- Mention may be made of groups such as 1-methylpropyl or 1-ethyl-2-methylpropyl.

In the present invention, the term "C ₂ to C ₆ alkenyl group" refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, 1-propenyl, isopropenyl, unless otherwise specified. , 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1 , 3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3 -butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2 -dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2 -hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1- (isobutyl)vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-(isopropyl)-2-propenyl, 2-methyl-2-pentenyl, 3-methyl -3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 , 2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl or 2,4-hexadienyl The following groups can be mentioned.

In the present invention, the term "C ₂ -C ₆ alkynyl group" refers to a straight or branched alkynyl group having 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2- Propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3- Hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl- Mention may be made of groups such as 1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl or 2,2-dimethyl-3-butynyl.

In the present invention, the term "C ₃ to C ₆ cycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms, and includes, for example, groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, unless otherwise specified. be able to.

In the present invention, a "heteroaryl group" means a 5- or 6-membered monomer having, in addition to carbon atoms, 1 to 6 heteroatoms selected from nitrogen atoms, oxygen atoms, and sulfur atoms, unless otherwise specified. The ring represents a heterocyclic ring, such as thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, Oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl , thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, pyrazol-1-yl yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1, 2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,5-oxadiazol- 3-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,3,4-triazol-1-yl, tetrazol-1-yl, tetrazol-2-yl, tetrazol- 5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl Examples include groups such as yl, pyrazin-2-yl, 1,3,5-triazinin-2-yl, and the like.

In the present invention, the term "C ₁ to C ₆ haloalkyl group" refers to a straight or branched alkyl group having 1 to 6 carbon atoms and substituted with 1 to 13 of the same or different halogen atoms, unless otherwise specified. represents a haloalkyl group, such as fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1 -Fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1 -Chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2 -bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-fluoropropyl, 2- Fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-penta Fluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 1-fluoropropan-2-yl, 2-fluoropropan-2-yl, 1,1-difluoropropan-2- yl, 1,2-difluoropropan-2-yl, 1,3-difluoropropan-2-yl, 1,2,3-trifluoropropan-2-yl, 1,1,3,3-tetrafluoropropan-yl 2-yl, 1,1,1,3,3,3-hexafluoropropan-2-yl, heptafluoropropan-2-yl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1 -dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropane-2 -yl, 2-chloropropan-2-yl, 1,1-dichloropropan-2-yl, 1,2-dichloropropan-2-yl, 1,3-dichloropropan-2-yl, 1,2,3-yl Trichloropropan-2-yl, 1,1,3,3-tetrachloropropan-2-yl, 1,1,1,3,3,3-hexachloropropan-2-yl, heptachloropropan-2-yl, 1- Bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropan-2-yl, 2-bromopropan-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropane -2-yl, 2-iodopropan-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl , 4,4,4-trifluoro-3-methylbutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3, 3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluorobutan-2-yl, 4,4,4-trifluorobutan-2-yl, 3,3,4, 4,4-pentafluorobutan-2-yl, nonafluorobutan-2-yl, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl, 3, 4,4,4-tetrafluoro-3-(trifluoromethyl)butyl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4,4-trichlorobutyl, Nonachlorobutyl, 1,1,1-trichlorobutan-2-yl, 4,4,4-trichlorobutan-2-yl, nonachlorobutan-2-yl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4- Bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 4-bromo-1,1, 2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 5,5-difluoropentyl, 5, 5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4, 4,5,5-octafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloro Pentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-hepta Chloropentyl, 2,2,3,3,4,4,5,5,5-nonachloropentyl, undecachloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6- Nonafluorohexyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl, 2,2,3,3,4,4,5,5,6,6 -decafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, Mention may be made of groups such as 5-iodohexyl or 6-iodohexyl.

In the present invention, the term "C ₃ - C ₆ halocycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 11 halogen atoms, which may be the same or different, unless otherwise specified. , for example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2, 2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3- Fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-dichlorobutyl Iodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl , 2,2-dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl , 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3 , 3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl or 4,4-diiodocyclohexyl. .

In the present invention, the term "C ₁ -C ₆ alkylcarbonyl group" refers to a (C ₁ -C ₆ alkyl)-C(=O)- group in which the alkyl portion has the above meaning, unless otherwise specified, such as , acetyl, propionyl, 2-methylpropionyl, 2,2-dimethylpropionyl, butanoyl, 2-methylbutanoyl, 3-methylbutanoyl, 2-ethylbutanoyl, 2,2-dimethylbutanoyl, 2,3-dimethyl Mention may be made of groups such as butanoyl, 3,3-dimethylbutanoyl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl or hexanoyl.

In the present invention, the term "C ₁ -C ₆ haloalkylcarbonyl group" refers to a (C ₁ -C ₆ haloalkyl)-C(=O)- group in which the haloalkyl moiety has the above meaning, unless otherwise specified, such as , fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, trichloroacetyl, tribromoacetyl, 3,3,3-trifluoropropionyl, 3,3-difluoropropionyl or 4,4,4-trifluorobutyryl, etc. The following groups can be mentioned.

In the present invention, the term "C ₃ to C ₆ cycloalkylcarbonyl group" refers to a (C ₃ to C ₆ cycloalkyl)-C(=O)- group in which the cycloalkyl moiety has the above meaning, unless otherwise specified. Examples include groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl or cyclohexanecarbonyl.

In the present invention, the term "C ₁ -C ₆ alkoxycarbonyl group" refers to a (C ₁ -C ₆ alkoxy)-C(=O)- group in which the alkoxy moiety has the above meaning, unless otherwise specified, such as , methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methyl Mention may be made of groups such as butoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl or 2,2-dimethylpropoxycarbonyl.

In the present invention, a "C ₁ -C ₆ haloalkoxycarbonyl group" refers to a (C ₁ -C ₆ haloalkyl)-O-C(=O)- group in which the haloalkyl moiety has the above meaning, unless otherwise specified. 2-fluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl or heptafluoro-2- Groups such as propoxycarbonyl can be mentioned.

In the present invention, the term "C ₁ to C ₆ alkylaminocarbonyl group" refers to a (C ₁ to C ₆ alkyl)-NH-C(=O)- group in which the alkyl moiety has the above meaning, unless otherwise specified. For example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, n-pentylaminocarbonyl, 1-Methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1-ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2- Mention may be made of groups such as dimethylpropylaminocarbonyl or n-hexylaminocarbonyl.

In the present invention, a "C ₁ -C ₆ haloalkylaminocarbonyl group" refers to a (C ₁ -C ₆ haloalkyl)-NH-C(=O)- group in which the haloalkyl moiety has the above meaning, unless otherwise specified. for example, 2-fluoroethylaminocarbonyl, 2,2-difluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl, pentafluoroethylaminocarbonyl or 1 , 1,1,3,3,3-hexafluoro-2-propylaminocarbonyl.

In the present invention, the term "C ₁ -C ₆ alkoxy group" refers to a (C ₁ -C ₆ alkyl)-O- group in which the alkyl moiety has the above meaning, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethyl Mention may be made of groups such as propoxy, 1,2-dimethylpropoxy or n-hexyloxy.

In the present invention, the term "C ₃ to C ₆ alkenyloxy group" refers to a (C ₃ to C ₆ alkenyl)-O- group in which the alkenyl moiety has the above meaning, unless otherwise specified, such as 2-propenyl oxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5 -Hexenyloxy and other groups can be mentioned.

In the present invention, the term "C ₃ -C ₆ alkynyloxy group" refers to a (C ₃ -C ₆ alkynyl)-O- group in which the alkynyl moiety has the above meaning, for example, 2-propynyl, unless otherwise specified. oxy, 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 2-pentynyloxy, 4-pentynyloxy or 4, Groups such as 4-dimethyl-2-pentynyloxy can be mentioned.

In the present invention, the term "C ₁ -C ₆ haloalkoxy group" refers to a (C ₁ -C ₆ haloalkyl)-O- group in which the haloalkyl moiety has the above meaning, unless otherwise specified, such as difluoromethoxy, Dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2 -difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, penta Fluoroethoxy, 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1-chloropropoxy, 2 -Chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3 ,3-trifluoropropoxy, 3,3,3-trifluoro-2-propoxy, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy, 2,2-difluoropropoxy, 3,3 -dichloro-3-fluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2, 2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1,2,3 , 3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1,1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2 -Bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3 , 3-trifluoro-1-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-trichlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy, 4 -Chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy, 2,4-dibromo-4,4-difluorobutoxy, 3,4-dichloro -3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4-bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro -3,4,4-trifluorobutoxy, 2,2,3,3,4,4-hexafluorobutoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2,2,2-tri Fluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3 , 4,4,4-pentafluoro-2-butoxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropoxy, 1,1,2,2,3,3,4,4-octafluoro Butoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutoxy, 5,5,5-trifluoropentoxy, 4, 4,5,5,5-pentafluoropentoxy, 3,3,4,4,5,5,5-heptafluoropentoxy, 3,3,4,4,5,5,5-heptafluoro-2 -Pentoxy, 2,2,3,3,4,4,5,5,5-nonafluoropentoxy, 2,2,3,3,4,4,5,5-octafluoropentoxy, perfluoropene Toxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2-bis(trifluoromethyl)propoxy, 2,2,3,3,4,4,5,5,6,6 , 6-undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy , 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butyloxy or perfluorohexyl Groups such as oxy can be mentioned.

In the present invention, the term "C ₃ to C ₆ cycloalkoxy group" refers to a (C ₃ to C ₆ cycloalkyl)-O- group in which the cycloalkyl moiety has the above meaning, for example, cycloalkyl group, unless otherwise specified. Mention may be made of groups such as propoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy.

In the present invention, the term "C ₃ to C ₆ halocycloalkoxy group" refers to a (C ₃ to C ₆ halocycloalkyl)-O- group in which the halocycloalkyl moiety has the above meaning, unless otherwise specified. For example, 2,2-difluorocyclopropoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3-fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluoro Mention may be made of groups such as cyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy or 4,4-dichlorocyclohexyloxy.

In the present invention, the term "C ₃ -C ₆ cycloalkylC ₁ -C ₆ alkoxy group" means that the cycloalkyl moiety has the above meaning (C ₃ -C ₆ cycloalkyl)-(C ₁ -C 6 cycloalkyl) unless otherwise specified. -C ₆ alkyl)-O-, and can include, for example, groups such as cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 2-cyclopropylethoxy, 2-cyclobutylethoxy or 2-cyclopentylethoxy.

In the present invention, the term "C ₃ - C ₆ halocycloalkyl C ₁ - C ₆ alkoxy group" means that unless otherwise specified, the halocycloalkyl moiety has the above meaning (C ₃ -C ₆ halocycloalkyl) - (C ₁ -C ₆ alkyl)-O-, such as (1-fluorocyclopropyl)methoxy, (2-fluorocyclopropyl)methoxy, (2,2-difluorocyclopropyl)methoxy, (2-chloro Mention may be made of groups such as cyclopropyl)methoxy or (2,2-dichlorocyclopropyl)methoxy.

In the present invention, the term "phenyl C ₁ -C ₆ alkoxy group" refers to a phenyl-(C ₁ -C ₆ alkyl)-O- group in which the alkyl moiety has the above meaning, unless otherwise specified. For example, phenyl Mention may be made of groups such as methoxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylpropoxy, 2-phenylbutoxy or 1-phenylpentoxy.

In the present invention, the term "C ₁ -C ₆ alkylthio group" refers to a (C ₁ -C ₆ alkyl)-S- group in which the alkyl moiety has the above meaning, for example, methylthio, ethylthio, Mention may be made of groups such as n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio.

In the present invention, the term "C ₁ -C ₆ alkylsulfinyl group" refers to a (C ₁ -C ₆ alkyl)-S(=O)- group in which the alkyl moiety has the above meaning, unless otherwise specified, such as , methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl.

In the present invention, the term "C ₁ -C ₆ alkylsulfonyl group" refers to a (C ₁ -C ₆ alkyl)-S(=O) ₂ - group in which the alkyl portion has the above meaning, unless otherwise specified; Examples include groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl.

In the present invention, the term "C ₁ -C ₆ haloalkylthio group" refers to a (C ₁ -C ₆ haloalkyl)-S- group in which the haloalkyl moiety has the above meaning, for example, fluoromethylthio, unless otherwise specified. Difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1 , 2,3,3,3-hexafluoropropyl, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio or 4,4, Examples include groups such as 4-trifluorobutylthio.

In the present invention, the term "C ₁ -C ₆ haloalkylsulfinyl group" refers to a (C ₁ -C ₆ haloalkyl)-S(=O)- group in which the haloalkyl moiety has the above meaning, unless otherwise specified, such as , difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl , heptafluoropropylsulfinyl or heptafluoro-2-propylsulfinyl.

In the present invention, the term "C ₁ to C ₆ haloalkylsulfonyl group" refers to a (C ₁ to C ₆ haloalkyl)-S(=O) ₂ - group in which the haloalkyl moiety has the above meaning, unless otherwise specified. For example, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl or heptafluoro- Groups such as 2-propylsulfonyl can be mentioned.

In the present invention, the term "C ₃ to C ₆ cycloalkylthio group" refers to a (C ₃ to C ₆ cycloalkyl)-S- group in which the cycloalkyl moiety has the above meaning, for example, cycloalkylthio group, unless otherwise specified. Mention may be made of groups such as propylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio.

In the present invention, the term "C ₃ -C ₆ cycloalkylsulfinyl group" refers to a (C ₃ -C ₆ cycloalkyl)-S(=O)- group in which the cycloalkyl moiety has the above meaning, unless otherwise specified. Examples include groups such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl or cyclohexylsulfinyl.

In the present invention, the term "C ₃ -C ₆ cycloalkylsulfonyl group" means a (C ₃ -C ₆ cycloalkyl)-S(=O) ₂ - group in which the cycloalkyl moiety has the above meaning unless otherwise specified. Examples include groups such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, and cyclohexylsulfonyl.

In the present invention, the term "C ₃ to C ₆ halocycloalkylthio group" refers to a (C ₃ to C ₆ halocycloalkyl) -S- group in which the halocycloalkyl moiety has the above meaning, unless otherwise specified. Examples include groups such as 2,2-difluorocyclopropylthio, 2,2-dichlorocyclopropylthio, 3,3-difluorocyclobutylthio, 3,3-difluorocyclopentylthio, or 4,4-difluorocyclohexylthio. be able to.

In the present invention, the term "C ₃ to C ₆ halocycloalkylsulfinyl group" means that the halocycloalkyl moiety has the above meaning (C ₃ to C ₆ halocycloalkyl)-S(=O) unless otherwise specified. - group, such as 2,2-difluorocyclopropylsulfinyl, 2,2-dichlorocyclopropylsulfinyl, 3,3-difluorocyclobutylsulfinyl, 3,3-difluorocyclopentylsulfinyl or 4,4-difluorocyclohexyl Mention may be made of groups such as sulfinyl.

In the present invention, the term "C ₃ to C ₆ halocycloalkylsulfonyl group" means that unless otherwise specified, the halocycloalkyl moiety has the above meaning (C ₃ to C ₆ halocycloalkyl)-S(=O) ₂ - represents a group such as 2,2-difluorocyclopropylsulfonyl, 2,2-dichlorocyclopropylsulfonyl, 3,3-difluorocyclobutylsulfonyl, 3,3-difluorocyclopentylsulfonyl or 4,4-difluorocyclo Groups such as xylsulfonyl can be mentioned.

In the present invention, the term "C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkylthio group" means that the cycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ cycloalkyl)- unless otherwise specified. (C ₁ -C ₆ alkyl)-S- group, such as cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, 4-cyclopropylbutylthio, 5-cyclopropylpentylthio, cyclo Mention may be made of groups such as butylmethylthio, cyclopentylmethylthio or cyclohexylmethylthio.

In the present invention, the term "C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkylsulfinyl group" means that the cycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ cycloalkyl) unless otherwise specified. -(C ₁ -C ₆ alkyl) -S(=O)- group, such as (cyclopropylmethyl)sulfinyl, (cyclobutylmethyl)sulfinyl, (cyclopentylmethyl)sulfinyl, (2-cyclopropylethyl)sulfinyl , (2-cyclobutylethyl)sulfinyl or (2-cyclopentylethyl)sulfinyl.

In the present invention, the term "C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkylsulfonyl group" means that the cycloalkyl moiety and the alkyl moiety have the above meaning unless otherwise specified (C ₃ -C ₆ cycloalkyl) -(C ₁ -C ₆ alkyl) -S(=O) ₂ - group, such as (cyclopropylmethyl)sulfonyl, (cyclobutylmethyl)sulfonyl, (cyclopentylmethyl)sulfonyl, (2-cyclopropylethyl) Mention may be made of groups such as sulfonyl, (2-cyclobutylethyl)sulfonyl or (2-cyclopentylethyl)sulfonyl.

In the present invention, the term "C ₃ - C ₆ halocycloalkylC ₁ -C ₆ alkylthio group" means that the halocycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ halocycloalkyl alkyl)-(C ₁ -C ₆ alkyl)-S-, such as 2,2-difluorocyclopropylmethylthio, 2,2-dichlorocyclopropylmethylthio, 2-(2,2-difluorocyclopropyl)ethylthio , 2-(2,2-dichlorocyclopropyl)ethylthio, 2,2-difluorocyclobutylmethylthio or 4,4-difluorocyclohexylmethylthio.

In the present invention, the term "C ₃ - C ₆ halocycloalkylC ₁ -C ₆ alkylsulfinyl group" means that the halocycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ halocycloalkyl group), unless otherwise specified. cycloalkyl)-(C ₁ -C ₆ alkyl)-S(=O)-, such as (1-fluorocyclopropyl)methylsulfinyl, (2-fluorocyclopropyl)methylsulfinyl, (2,2- Mention may be made of groups such as difluorocyclopropyl)methylsulfinyl, (2-chlorocyclopropyl)methylsulfinyl or (2,2-dichlorocyclopropyl)methylsulfinyl.

In the present invention, the term "C ₃ - C ₆ halocycloalkylC ₁ -C ₆ alkylsulfonyl group" means that the halocycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ halocycloalkyl group), unless otherwise specified. cycloalkyl)-(C ₁ -C ₆ alkyl)-S(=O) ₂ - group, such as (1-fluorocyclopropyl)methylsulfonyl, (2-fluorocyclopropyl)methylsulfonyl, (2,2 Mention may be made of groups such as -difluorocyclopropyl)methylsulfonyl, (2-chlorocyclopropyl)methylsulfonyl or (2,2-dichlorocyclopropyl)methylsulfonyl.

In the present invention, the term "C ₁ -C ₆ alkylamino group" refers to a (C ₁ -C ₆ alkyl)-NH- group in which the alkyl moiety has the above meaning, for example, methylamino, Mention may be made of groups such as ethylamino, n-propylamino or isopropylamino.

In the present invention, the term "C ₁ -C ₆ haloalkylamino group" refers to a (C ₁ -C ₆ haloalkyl) -NH- group in which the haloalkyl moiety has the above meaning, for example, 2-fluoro ethylamino, 2,2-difluoroethylamino, 2,2,2-trifluoroethylamino, 2,2,2-trichloroethylamino, pentafluoroethylamino, 3,3,3-trifluoropropylamino or 1, Examples include groups such as 1,1,3,3,3-hexafluoro-2-propylamino.

In the present invention, the term "C ₁ to C ₆ alkylcarbonylamino group" refers to a (C ₁ to C ₆ alkyl)-C(=O)-NH- group in which the alkyl moiety has the above meaning, unless otherwise specified. Examples include groups such as acetylamino, propionylamino, butyrylamino or isobutyrylamino.

In the present invention, a "C ₁ -C ₆ haloalkylcarbonylamino group" refers to a (C ₁ -C ₆ haloalkyl)-C(=O)-NH- group in which the haloalkyl moiety has the above meaning, unless otherwise specified. for example, fluoroacetylamino, difluoroacetylamino, trifluoroacetylamino, chloroacetylamino, trichloroacetylamino, tribromoacetylamino, 3,3,3-trifluoropropionylamino, pentafluoropropionylamino or 3,3- Groups such as difluoropropionylamino can be mentioned.

In the present invention, the term "C ₃ to C ₆ cycloalkylcarbonylamino group" means that the cycloalkyl moiety has the above meaning (C ₃ to C ₆ cycloalkyl)-C(=O)-NH, unless otherwise specified. - represents a group such as cyclopropylcarbonylamino, cyclobutylcarbonylamino, cyclopentylcarbonylamino or cyclohexylcarbonylamino.

In the present invention, the term "C ₁ -C ₆ alkoxycarbonylamino group" refers to a (C ₁ -C ₆ alkoxy)-C(=O)-NH- group in which the alkoxy moiety has the above meaning, unless otherwise specified. Examples include groups such as methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino or isobutoxycarbonylamino.

In the present invention, the term "C ₁ to C ₆ haloalkoxycarbonylamino group" means that unless otherwise specified, the haloalkoxy moiety has the above meaning (C ₁ to C ₆ haloalkoxy)-C(=O)-NH- For example, 2-fluoroethoxycarbonylamino, 2,2,2-trifluoroethoxycarbonylamino, 2,2,2-trichloroethoxycarbonylamino, pentafluoroethoxycarbonylamino, 3,3,3-trifluoro Mention may be made of groups such as propoxycarbonylamino or heptafluoro-2-propoxycarbonylamino.

In the present invention, a "C ₁ -C ₆ alkylaminocarbonylamino group" means, unless otherwise specified, that the alkyl moiety has the above meaning (C ₁ -C ₆ alkyl)-NH-C(=O)-NH - group, such as methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino or tert-butylaminocarbonylamino.

In the present invention, "C ₁ -C ₆ haloalkylaminocarbonylamino group" means that unless otherwise specified, the haloalkyl moiety has the above meaning (C ₁ -C ₆ haloalkyl)-NH-C(=O)-NH - group, such as 2-fluoroethylaminocarbonylamino, 2,2,2-trifluoroethylaminocarbonylamino, 2,2,2-trichloroethylaminocarbonylamino, pentafluoroethylaminocarbonylamino or 1,1 , 1,3,3,3-hexafluoro-2-propylaminocarbonylamino.

In the present invention, the term "C ₁ -C ₆ alkylsulfonylamino group" refers to a (C ₁ -C ₆ alkyl)-S(=O) ₂ -NH- group in which the alkyl portion has the above meaning, unless otherwise specified. Examples thereof include groups such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino, and tert-butylsulfonylamino.

In the present invention, the term "C ₁ -C ₆ haloalkylsulfonylamino group" means a (C ₁ -C ₆ haloalkyl)-S(=O) ₂ -NH- group in which the haloalkyl moiety has the above meaning, unless otherwise specified. For example, fluoromethylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, chloromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 2,2-difluoroethylsulfonylamino Mention may be made of groups such as amino or 3,3,3-trifluoropropylsulfonylamino.

In the present invention, the term "C ₃ to C ₆ cycloalkylsulfonylamino group" means that the cycloalkyl moiety has the above meaning unless otherwise specified (C ₃ to C ₆ cycloalkyl) -S(=O) ₂ - It represents an NH- group and includes, for example, groups such as cyclopropylsulfonylamino, cyclobutylsulfonylamino, cyclopentylsulfonylamino or cyclohexylsulfonylamino.

In the present invention, the term "tri(C ₁ -C ₆ alkyl)silyl group" refers to a (C ₁ -C ₆ alkyl) ₃ -Si- group in which the alkyl moiety has the above meaning, unless otherwise specified. The alkyl groups may be the same or different from each other, and include, for example, groups such as trimethylsilyl, triethylsilyl, triisopropylsilyl, dimethylisopropylsilyl or tert-butyldimethylsilyl.

In the present invention, "1,3-benzodioxolyl group" means, for example, 1,3-benzodioxol-4-yl or 1,3-benzodioxol-5-yl, unless otherwise specified. The following groups can be mentioned.

In the present invention, the term "heteroaryloxy group" refers to a (heteroaryl)-O- group in which the heteroaryl moiety has the above meaning, for example, (pyridin-2-yl)oxy, ( pyridin-3-yl)oxy, (pyridin-4-yl)oxy, (pyrimidin-2-yl)oxy, (pyrimidin-4-yl)oxy, (pyrimidin-5-yl)oxy, (pyridazin-3-yl) )oxy, (pyridazin-4-yl)oxy, (pyrazin-2-yl)oxy, (1,3,5-triazinin-2-yl)oxy, (thiazol-2-yl)oxy, (thiazol-4- yl)oxy, (thiazol-5-yl)oxy, (pyrazol-1-yl)oxy, (pyrazol-3-yl)oxy, (pyrazol-4-yl)oxy or (pyrazol-5-yl)oxy, etc. The following groups can be mentioned.

In the present invention, the term "heterocycloalkyl group" refers to a 3- to 6-membered saturated heterocycle containing one or more atoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms, unless otherwise specified. , for example, pyrrolidin-1-yl, piperidin-1-yl, oxetan-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3 Mention may be made of groups such as -yl or tetrahydropyran-4-yl.

In the present invention, the term "C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkyl group" means that the cycloalkyl moiety and the alkyl moiety have the above meanings (C ₃ -C ₆ cycloalkyl)- unless otherwise specified. (C ₁ -C ₆ alkyl)- group, for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-(cyclopropyl)ethyl, 2-(cyclopropyl)ethyl or 1-(cyclopropyl) ) Propyl and other groups can be mentioned.

In the present invention, the term "C ₁ -C ₆ alkoxyC ₁ -C ₆ alkyl group" means that the alkoxy and alkyl parts have the above-mentioned meanings (C ₁ -C 6 alkoxy)-(C 1 -C ₆ alkyl group) unless otherwise _specified . ~C ₆ alkyl)- group, such as methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, Mention may be made of groups such as 1-methyl-3-methoxybutyl or 3-butoxybutyl.

In the present invention, the term "C ₁ -C ₆ haloalkoxyC ₁ -C ₆ alkyl group" means that unless otherwise specified, the haloalkoxy moiety and the alkyl moiety have the above meaning (C ₁ -C ₆ haloalkoxy)- (C ₁ -C ₆ alkyl)- group, such as 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy)ethyl, 2-(2,2 ,2-trifluoroethoxy)ethyl, 2-(3,3-difluoropropioxy)ethyl, 2-(3,3,3-trifluoropropioxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoropropoxy)ethyl fluoromethoxy)propyl, 3-(2,2-difluoroethoxy)propyl, 3-(2,2,2-trifluoroethoxy)propyl, 3-(3,3-difluoropropioxy)propyl, 3-(3, Mention may be made of groups such as 3,3-trifluoropropioxy)propyl, 4-(trifluoromethoxy)butyl or 5-(trifluoromethoxy)pentyl.

In the present invention, the term "C ₁ -C ₆ alkylthioC ₁ -C ₆ alkyl group" means that the alkylthio moiety and the alkyl moiety have the above meanings (C ₁ -C 6 alkylthio)-(C 1 -C ₆ alkylthio) unless otherwise specified _. ~C ₆ alkyl)- group, such as methylthiomethyl, ethylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-methylthiopropyl, 3-methylthiopropyl, 2 Mention may be made of groups such as -ethylthiopropyl or 3-ethylthiopropyl.

In the present invention, the term "C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group" means that the alkylsulfinyl moiety and the alkyl moiety have the above meanings (C ₁ -C ₆ alkylsulfinyl)- unless otherwise specified. (C ₁ -C ₆ alkyl)- group, such as methylsulfinylmethyl, ethylsulfinylmethyl, isopropylsulfinylmethyl, 1-methylsulfinylethyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2-methylsulfinylpropyl , 3-methylsulfinylpropyl, 2-ethylsulfinylpropyl or 3-ethylsulfinylpropyl.

In the present invention, the term "C ₁ -C ₆ alkylsulfonylC ₁ -C ₆ alkyl group" means that the alkylsulfonyl moiety and the alkyl moiety have the above meanings (C ₁ -C ₆ alkylsulfonyl)- unless otherwise specified. (C ₁ -C ₆ alkyl)- group, such as methylsulfonylmethyl, ethylsulfonylmethyl, isopropylsulfonylmethyl, 1-methylsulfonylethyl, 2-methylsulfonylethyl, 2-ethylsulfonylethyl, 2-methylsulfonylpropyl , 3-methylsulfonylpropyl, 2-ethylsulfonylpropyl or 3-ethylsulfonylpropyl.

In the present invention, "C ₁ - C ₆ haloalkylthio C ₁ - C ₆ alkyl group" means that unless otherwise specified, the haloalkylthio moiety and the alkyl moiety have the above meaning (C ₁ -C ₆ haloalkylthio) - (C ₁ -C ₆ alkyl)- group, such as (difluoromethylthio)methyl, (trifluoromethylthio)methyl, (2,2-difluoroethylthio)methyl, (2,2,2-trifluoroethylthio) ) Methyl, 2-(difluoromethylthio)ethyl, 2-(trifluoromethylthio)ethyl, 2-(2,2-difluoroethylthio)ethyl, 2-(2,2,2-trifluoroethylthio)ethyl, 3 Mention groups such as -(difluoromethylthio)propyl, 3-(trifluoromethylthio)propyl, 3-(2,2-difluoroethylthio)propyl or 3-(2,2,2-trifluoroethylthio)propyl I can do it.

In the present invention, the term "C ₁ -C ₆ haloalkylsulfinyl C ₁ -C ₆ alkyl group" means that unless otherwise specified, the haloalkylsulfinyl moiety and the alkyl moiety have the above meaning (C ₁ -C ₆ haloalkylsulfinyl) - (C ₁ -C ₆ alkyl)- group, such as (difluoromethylsulfinyl)methyl, (trifluoromethylsulfinyl)methyl, (2,2-difluoroethylsulfinyl)methyl, (2,2,2-trifluoro ethylsulfinyl)methyl, 2-(difluoromethylsulfinyl)ethyl, 2-(trifluoromethylsulfinyl)ethyl, 2-(2,2-difluoroethylsulfinyl)ethyl, 2-(2,2,2-trifluoroethylsulfinyl) ) ethyl, 3-(difluoromethylsulfinyl)propyl, 3-(trifluoromethylsulfinyl)propyl, 3-(2,2-difluoroethylsulfinyl)propyl or 3-(2,2,2-trifluoroethylsulfinyl)propyl The following groups can be mentioned.

In the present invention, the term "C ₁ - C ₆ haloalkylsulfonyl C ₁ - C ₆ alkyl group" means that unless otherwise specified, the haloalkylsulfonyl moiety and the alkyl moiety have the above meaning (C ₁ -C ₆ haloalkylsulfonyl) - (C ₁ -C ₆ alkyl)- group, such as (difluoromethylsulfonyl)methyl, (trifluoromethylsulfonyl)methyl, (2,2-difluoroethylsulfonyl)methyl, (2,2,2-trifluoro ethylsulfonyl)methyl, 2-(difluoromethylsulfonyl)ethyl, 2-(trifluoromethylsulfonyl)ethyl, 2-(2,2-difluoroethylsulfonyl)ethyl, 2-(2,2,2-trifluoroethylsulfonyl) ) ethyl, 3-(difluoromethylsulfonyl)propyl, 3-(trifluoromethylsulfonyl)propyl, 3-(2,2-difluoroethylsulfonyl)propyl or 3-(2,2,2-trifluoroethylsulfonyl)propyl The following groups can be mentioned.

In the present invention, the term "cyano C ₁ -C ₆ alkyl group" refers to a (cyano)-(C ₁ -C ₆ alkyl) group in which the alkyl moiety has the above meaning, for example, cyanomethyl, Mention may be made of groups such as 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl. I can do it.

In the present invention, the term "tri(C ₁ -C ₆ alkyl)silyloxy group" refers to a (C ₁ -C ₆ alkyl) ₃ -Si-O- group in which the alkyl portion has the above meaning, unless otherwise specified. , the three alkyl groups may be the same or different from each other, and include, for example, groups such as trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy or tert-butyldimethylsilyloxy.

In the present invention, the term "C ₁ -C ₆ alkoxyimino group" refers to a (C ₁ -C ₆ alkyl)-O-N=C- group in which the alkyl moiety has the above meaning, unless otherwise specified, such as , methoxyimino, ethoxyimino or isopropoxyimino.

In the present invention, the term "C ₃ - C ₆ halocycloalkyl C ₁ - C ₆ alkyl group" means that unless otherwise specified, the halocycloalkyl moiety and the alkyl moiety have the above meaning (C ₃ -C ₆ halocycloalkyl group). alkyl)-(C ₁ -C ₆ alkyl)- group, such as 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, 2-(2,2-difluorocyclopropyl)ethyl, 2 Mention may be made of groups such as -(2,2-dichlorocyclopropyl)ethyl, 2,2-difluorocyclobutylmethyl or 4,4-difluorocyclohexylmethyl.

In the present invention, the term "phenyl C ₁ -C ₆ alkyl group" refers to a phenyl-(C ₁ -C ₆ alkyl) group in which the alkyl moiety has the above meaning, unless otherwise specified, such as benzyl, 2 Mention may be made of groups such as -methylbenzyl, 2,3-dimethylbenzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl or 6-phenylhexyl.

In the present invention, "carbocycle" means a non-aromatic, 3- to 6-membered monocyclic ring in which all the atoms constituting the ring are 1 to 6 carbon atoms. Specific examples of carbocycles include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, and the like.

In the present invention, a "heterocycle" refers to a ring having 1 to 5 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms (the sulfur atom has one or two oxo groups (=O)). means a non-aromatic, monocyclic 3- to 6-membered heterocycle of 1 to 4 heteroatoms independently selected from Specific examples of the heterocycle include pyrrolidine, tetrahydrofuran, piperidine, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran 1-oxide, tetrahydrothiopyran 1,1-dioxide, thiane, piperazine, morpholine, thiomorpholine, dioxane, dioxolane, These include, but are not limited to, dithiane and the like.

In the present invention, "may be mono- or polysubstituted by R ⁸ " means "may be substituted by one or more R ⁸ ". When substituted with two or more R ^{8 s} , each of the two or more R ^8s may be the same or different, and may be a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, formyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₃ to C ₆ cycloalkylcarbonyl group, benzoyl group ( (the group may be mono- or polysubstituted by R ⁹ ), -C(R ¹⁰ )=NOR ¹¹ , carboxy group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, aminocarbonyl a C ₁ -C ₆ alkylaminocarbonyl group (the amino group may be substituted by R ¹² ), a C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted by R ¹² ), a pyrrolidin-1-ylcarbonyl group (the group may be mono- or polysubstituted by R ⁹ ), a piperidin-1-ylcarbonyl group (the group may be mono- or polysubstituted by R ⁹ ), Hydroxy group, C ₁ - C ₆ alkoxy group, C ₃ - C ₆ alkenyloxy group, C ₃ - C 6 alkynyloxy group, C ₁ - C ₆ haloalkoxy group, C ₃ - _{C 6 cycloalkoxy} group, C ₃ - C ₆ halocycloalkoxy group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group, phenoxy group (the group is ^{monosubstituted} or ), phenyl C ₁ -C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted with R ⁹ ), thiol group, C ₁ -C ₆ alkylthio group, C ₁ -C 6 alkylthio group ₆ -alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C 6 haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C _{1 -C 6 haloalkylsulfonyl} group, C ₃ -C ₆ cycloalkylthio group, C ₃ - C ₆ cycloalkylsulfinyl group, C ₃ - C ₆ cycloalkylsulfonyl group, C ₃ - C ₆ halocycloalkylthio group, C ₃ - C ₆ halocycloalkylsulfinyl group, C ₃ - C ₆ halocycloalkylsulfonyl group, _C3 - _{C6cycloalkylC1} - _C6alkylthio group, _{C3 - C6cycloalkylC1 -} C6alkylsulfinyl group, _{C3 - C6cycloalkylC1} - _{C6alkylsulfonyl} group, _{C 3} to C ₆ halocycloalkyl C ₁ to C ₆ alkylthio group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkylsulfinyl group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkylsulfonyl group, phenylthio (the group may be mono- or polysubstituted by R ⁹ ), phenylsulfinyl (the group may be mono- or polysubstituted by R ⁹ ), phenylsulfonyl (the group may be mono- or polysubstituted by R 9 ), phenylsulfinyl (the group may be mono- or polysubstituted by R ⁹ ), (which may be mono- or polysubstituted), an amino group, a C ₁ -C ₆ alkylamino group (the amino group may be substituted by R ¹² ), a C ₁ -C ₆ haloalkylamino group (the amino group may be substituted with C 1 -C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C 6 haloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylcarbonylamino group (the amino group may be substituted by R ^{12 )} ), a C ₃ -C ₆ cycloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), a phenylcarbonylamino group (the phenyl group may be mono- or polysubstituted by R ⁹ (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkoxy carbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkylaminocarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylamino carbonylamino group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ alkylsulfonylamino group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino a C ₃ -C ₆ cycloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), a phenylsulfonylamino group (the phenyl group may be substituted by R 12 ), a C 3 -C 6 cycloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), may be mono- or polysubstituted by R ⁹ , and the amino group may be substituted by R ¹² ), tri(C ₁ -C ₆ alkyl)silyl group, phenyl group (the group may be mono-substituted by R ⁹ 1,3-benzodioxolyl group (which group may be mono- or polysubstituted by R ⁹ ), heteroaryl group (which group may be mono- or polysubstituted by R 9 ), 1,3-benzodioxolyl group (which group may be mono- or polysubstituted by R ⁹ ), heteroaryloxy groups (which may be mono- or polysubstituted by R ⁹ ), heterocycloalkyl groups (which may be mono- or polysubstituted by R ⁹ ) , represents a cyano group, a nitro group or a thiocyanato group.

In the present invention, "which may be mono- or polysubstituted by R ⁹ " means "which may be substituted by one or more R ^9. " When substituted with two or more ^R9s , the two or more ^R9s may be the same or different, and may be a halogen atom, a _C1 -C6 alkyl group, a _C1 - _C6 haloalkyl group, a _C3 - _C6 haloalkyl group, or a C1-C6 haloalkyl group. ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, hydroxy group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, thiol group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ haloalkylsulfonyl group, cyano group or nitro group.

In the present invention, an agriculturally acceptable salt refers to a compound of the present invention represented by the general formula [I] in which a hydroxyl group, a carboxyl group, an amino group, etc. are present in the structure, or when a nitrogen atom of a pyridine ring is present. , salts of these with metals or organic bases, or salts with mineral acids or organic acids; metals include alkali metals such as sodium or potassium; alkaline earth metals such as magnesium or calcium; Examples of mineral acids include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, and sulfuric acid. Examples of organic acids include triethylamine and diisopropylamine. , formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid or trifluoromethanesulfonic acid, etc. I can do it.

Next, representative examples of compounds included in the fused heterocyclic derivative of the present invention represented by general formula [I] are shown in Tables 1 to 36. However, the compounds included in the derivatives of the present invention are not limited to these. In addition, the compound numbers in the table are referred to in the subsequent description.

Note that the compounds included in the fused heterocyclic derivatives of the present invention may have geometric isomers such as E-form and Z-form depending on the type of substituent, but the present invention covers these E-form, It includes the Z-form or a mixture containing the E-form and the Z-form in arbitrary proportions. Further, the compounds included in the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention covers all optically active compounds. including the stereoisomer, racemate, or diastereomer.

The following notations in the tables in this specification each represent the corresponding group, for example, as shown below.
Me: methyl;
Et: ethyl;
n-Pr: n-propyl;
i-Pr: isopropyl;
n-Bu: n-butyl;
i-Bu: isobutyl;
t-Bu: tert-butyl;
n-Pen: n-pentyl;
t-Pen: tert-pentyl;
n-Hex: n-hexyl;
c-Pr: cyclopropyl;
c-Pen: cyclopentyl;
c-Hex: cyclohexyl;
_CHF2 : difluoromethyl;
_CF3 : trifluoromethyl;
Ph(4-CF ₃ ): 4-trifluoromethylphenyl;
Ph(2-F-4-CF ₃ ): 2-fluoro-4-trifluoromethylphenyl;
Ph(3,4,5-Cl ₃ ): 3,4,5-trichlorophenyl;
c-Pr(2,2-F ₂ ): 2,2-difluorocyclopropyl;

The compound of the present invention represented by general formula [I] can be produced according to the production method shown below, but is not limited to these methods. In addition, hereinafter, for example, "a compound represented by general formula [I]", "a compound represented by formula [I]", and "compound [I]" have the same meaning.

<Manufacturing method 1>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced using the compound represented by the general formula [II-1] according to the method consisting of the reaction formula illustrated below. .

(In the formula, K represents K-1, K-2, K-3, K-4, K-5, K-6, K-7 or K-8,

Ｌ^１はハロゲン原子又はメタンスルホニルオキシ基を示し、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、ｍ、Ｙ、Ｚ及びＡは前記と同じ意味を示す。）

L ¹ represents a halogen atom or a methanesulfonyloxy group, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , m, Y, Z and A have the same meanings as above. )

That is, the compound represented by the general formula [I-1] is prepared by combining the compound represented by the general formula [II-1] and the compound [IV-1] in the presence of an appropriate base and an appropriate catalyst. It can be produced by reacting in a suitable solvent in the presence or absence of a compound.

The amount of compound [IV-1] used in this reaction may be appropriately selected from the range of 1 to 100 mol, preferably 1.0 to 3.3 mol, per 1 mol of compound [II-1]. It is.

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 2.0 mol, per 1 mol of compound [II-1].

Examples of catalysts that can be used in this reaction include copper (I) chloride, copper (I) bromide, copper (I) iodide, and copper. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 5 mol, preferably 0.01 to 1.2 mol, per 1 mol of compound [II-1].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; grade amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 100 liters, preferably 0.3 to 25 liters, per 1 mole of compound [II-1].

The reaction temperature of this reaction may be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is complete, compound [I-1] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. be able to. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 2>
The compound represented by the general formula [II-3] can be produced using the compound represented by the general formula [II-2] according to the method consisting of the reaction formula illustrated below.

(In the formula, R ¹⁴ represents a methyl group, ethanoyl group, methoxymethyl group, benzyl group or 4-methoxybenzyl group, and R ¹ , R ⁴ , m and K have the same meanings as above.)

That is, the compound represented by general formula [II-3] can be obtained from compound [II-2] by GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G.M. .Wuts) It can be manufactured according to the method described in .

Compound [II-3] can also be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 3>
Among the compounds of the present invention, the compound represented by the general formula [I-3] can be produced using the compound represented by the general formula [I-2] according to the method consisting of the reaction formula illustrated below. .

(wherein R ^1a is a C ₁ -C ₆ alkyl group (the group may be mono- or polysubstituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group is mono- or polysubstituted by R ⁸ ), C ₂ -C ₆ alkynyl groups (which groups may be mono- or polysubstituted by R ⁸ ), C ₃ -C ₆ cycloalkyl groups (which groups may be mono- or polysubstituted by R 8 ), C 2 -C 6 alkynyl groups (which groups may be mono- or polysubstituted by R ^{8 )} , a phenyl group (which may be mono- or polysubstituted by R ⁹ ) or a heteroaryl group (which may be mono- or polysubstituted by R ⁹ ); , R ¹⁵ is a methyl group, ethanoyl group, methoxymethyl group, benzyl group, 4-methoxybenzyl group, or

を示し、Ｌ^２はハロゲン原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、ノナフルオロブタンスルホニルオキシ基、ベンゼンスルホニルオキシ基又はｐ－トルエンスルホニルオキシ基を示し、Ｒ^４、Ｒ^７、Ｒ^８、Ｒ^１４、ｍ、Ｚ、Ａ及びＫは前記と同じ意味を示す。）

, L ² represents a halogen atom, methanesulfonyloxy group, trifluoromethanesulfonyloxy group, nonafluorobutanesulfonyloxy group, benzenesulfonyloxy group or p-toluenesulfonyloxy group, R ⁴ , R ⁷ , R ⁸ , R ¹⁴ , m, Z, A and K have the same meanings as above. )

That is, the compound represented by the general formula [I-3] can be obtained by combining compound [I-2] and compound [IV-2] in an appropriate solvent, in the presence of an appropriate base, and in the presence of an appropriate catalyst. Alternatively, it can be produced by reacting in the absence of the compound.

The amount of compound [IV-2] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol, preferably 1.0 to 15.0 mol, per 1 mol of compound [I-2]. It is 6.0 mol.

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [I-2].

Examples of catalysts that can be used in this reaction include tetra-n-butylammonium bromide and tetra-n-butylammonium iodide. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1.0 mol, preferably 0.05 to 0.5 mol, per 1 mol of compound [I-2].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 50 liters, per 1 mole of compound [I-2].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 30 hours.

After the reaction is completed, compound [I-3] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [I-3] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 4>
Among the compounds of the present invention, the compounds represented by general formulas [I-5] and [I-6] can be prepared by a method consisting of the reaction formula illustrated below using a compound represented by general formula [I-4]. It can be manufactured according to the following.

^{( wherein ,} _{_ _ _ _ _ _} C ₁ - C ₆ haloalkoxy group, C ₃ - C ₆ cycloalkoxy group, C ₃ - C ₆ halocycloalkoxy group, C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkoxy group, C ₃ - C ₆ halocyclo Alkyl C ₁ -C ₆ alkoxy group, phenyl C ₁ -C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted by R ⁹ ), heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), R 3b represents a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfonyl group, a C ₁ -C ₆ haloalkylthio group, or a C ₁ -C 6 haloalkylsulfonyl group (which may be polysubstituted), and R ^3b is a C ₁ -C ₆ haloalkylthio group ~C ₆ alkyl group, C ₂ ~ C ₆ alkenyl group, C ₂ ~ C ₆ alkynyl group, C ₁ ~ C ₆ haloalkyl group, C ₃ ~ C ₆ cycloalkyl group, C ₃ ~ C ₆ halocycloalkyl group, C ₃ - _C6 cycloalkylC1- _C6 alkyl group, _C3 - _C6 halocycloalkylC1 _{- C6} alkyl group, _{phenylC1 - C6} alkyl group (the group is mono- or polysubstituted by ^R9) R ¹ , R ² , R ⁴ , R ⁷ , ^{R 9 ,} R ¹⁵ , m and Z has the same meaning as above.)

(Step 4-1)
That is, the compound represented by general formula [I-5] is produced by reacting compound [I-4] and a cyanide compound in an appropriate solvent in the presence or absence of an appropriate catalyst. be able to.

Examples of the cyanide compound used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, or mixtures thereof. Incidentally, the amount of the cyanide compound to be used may be appropriately selected from the range of 1 to 100 mol, preferably 1.0 to 5.0 mol, per 1 mol of compound [I-4].

Examples of the catalyst used in this reaction include tetrakis(triphenylphosphine)palladium, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and the like. The amount of the catalyst to be used may be selected as appropriate from the range of 0.001 to 0.5 mol, preferably 0.01 to 0.2 mol, per 1 mol of compound [I-4]. be.

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 500 liters, preferably 0.3 to 50 liters, per 1 mole of compound [I-4].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

After the reaction is complete, the compound can be removed by filtering off unnecessary substances from the reaction mixture and concentrating it directly, or by pouring it into water and collecting the precipitated solid by filtration, or by extracting it with an organic solvent and then concentrating it. [I-5] can be isolated. The isolated compound [I-5] can be further purified by column chromatography, recrystallization, etc., if necessary.

(Step 4-2)
That is, the compound represented by general formula [I-6] can be prepared by combining compound [I-4] and compound [IV-3] in a suitable solvent in the presence or absence of a suitable base. It can be produced by reacting in the presence of a catalyst.

The amount of compound [IV-3] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol, preferably 1.0 to 15.0 mol, per 1 mol of compound [I-4]. It is 6.0 mol.

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [I-2].

As a catalyst that can be used in this reaction, a transition metal complex or a combination of a transition metal and a ligand may be used. For example, examples of the transition metal complex include tetrakis(triphenylphosphine)palladium(0), [1,1 -Bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, bis(triphenylphosphine)palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium( Palladium catalysts such as 0), copper salts such as copper(I) iodide, and ligands such as trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2- Bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1,10-phenanthroline, 3,4,7,8-tetramethyl -1,10-phenanthroline and the like can be mentioned. The amount of the catalyst used is 0.001 to 0.1 mol, preferably 0.01 to 0.05 mol, per 1 mol of compound [I-4].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 500 liters, preferably 0.3 to 50 liters, per 1 mole of compound [I-4].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

After the reaction is complete, remove unnecessary substances from the reaction mixture and concentrate, or add the reaction mixture to water and collect the precipitated solid by filtration, or extract with an organic solvent and then concentrate. , compound [I-6] can be isolated. The isolated compound [I-6] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 5>
Among the compounds of the present invention, the compound represented by the general formula [I-4] can be produced using the compound represented by the general formula [I-7] according to the method consisting of the reaction formula illustrated below. .

In the formula, R ¹ , R ⁴ , R ¹⁵ , m, A ² , X and Z have the same meanings as above.

That is, the compound represented by the general formula [I-4] can be produced by reacting the compound [I-7] with a halogenating agent in an appropriate solvent in the presence or absence of an appropriate base. can do.

Halogenating agents that can be used in this reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, sodium hypochlorite, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and iodine. , N-iodosuccinimide, 1,3-diiodo-5,5-dimethylhydantoin, potassium iodate, or a mixture thereof. The amount of the halogenating agent to be used may be appropriately selected from the range of 0.01 to 10 mol, preferably 0.02 to 2.0 mol, per 1 mol of compound [I-7].

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound [I-7].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; dichloromethane, chloroform, and 1,2- Halogenated hydrocarbons such as dichloroethane; Protic polar solvents; Nitriles such as acetonitrile and propionitrile; Aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; Carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; Hydrochloric acid and hydrobromic acid , inorganic acids such as sulfuric acid, nitric acid, and phosphoric acid; water or a mixed solvent thereof; and the like. The amount of solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mole of compound [I-7].

The reaction temperature for this reaction may generally be selected from any temperature range from -70°C to the reflux temperature of the reaction system, preferably in the range of -20°C to 100°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, the compound [I -4] can be isolated. The isolated compound [I-4] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 6>
The compound represented by the general formula [II-4] can be produced using the compound represented by the general formula [III-1] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^3c is a hydrogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group) , C ₃ -C ₆ halocycloalkyl group, C ₁ -C ₆ alkoxyC 1 _{-C 6} alkyl group, C _{1 -C 6} haloalkoxyC ₁ -C ₆ alkyl group, R ⁴ , R ¹⁴ , m, (X and Z have the same meanings as above.)

That is, the compound represented by general formula [II-2] can be produced by reacting compound [III-1] and hydrazine in an appropriate solvent in the presence or absence of an appropriate base. I can do it.

Hydrazine that can be used in this reaction includes anhydrous hydrazine, hydrazine hydrate, hydrazine hydrochloride, and the like. The amount of hydrazine to be used may be appropriately selected from the range of 1 to 30 mol, preferably 1 to 20 mol, per 1 mol of compound [III-1].

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-1].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; N,N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol, tert-butyl Alcohols such as alcohol and methyl cellosolve; Nitriles such as acetonitrile and propionitrile; Pyridines such as pyridine, picoline and lutidine; Tertiary amines such as triethylamine and tributylamine; Water or mixed solvents thereof, etc. be able to. The amount of solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mole of compound [III-1].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is complete, compound [II-4] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. be able to. The isolated compound [II-4] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 7>
The compound represented by the general formula [III-1] can be produced using the compound represented by the general formula [III-2] according to a method consisting of the reaction formula illustrated below.

(In the formula, L ³ represents a halogen atom, a C ₁ to C ₆ alkoxy group, -OC(=O)R ^3c , -N(Me)OMe, R ^3c , R ⁴ , R ¹⁴ , m, X and Z has the same meaning as above.)

That is, the compound represented by general formula [III-1] is produced by reacting compound [III-2] and compound [IV-4] in an appropriate solvent in the presence of an appropriate base. be able to.

The amount of compound [IV-4] used in this reaction may be appropriately selected from the range of 1 to 15 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound [III-2]. It is.

Examples of the base that can be used in this reaction include lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, and the like. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-2].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Examples include aromatic hydrocarbons such as chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or mixed solvents thereof. The amount of solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mole of compound [III-2].

The reaction temperature for this reaction may generally be selected from any temperature range from -100°C to the reflux temperature of the reaction system, preferably in the range of -100°C to 40°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is complete, compound [III-1] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. be able to. The isolated compound [III-1] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 8>
The compound represented by the general formula [II-5] can be produced using the compound represented by the general formula [III-3] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^1a , R ⁴ , R ¹⁴ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [II-5] can be produced by reacting the compound [III-3] with a nitrite or a nitrite in an appropriate solvent.

Examples of the nitrite or nitrite ester that can be used in this reaction include sodium nitrite, t-butyl nitrite, and isoamyl nitrite. The amount of nitrite or nitrite ester to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 2.5 mol, per 1 mol of compound [III-3].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; dichloromethane, chloroform, and 1,2- Halogenated hydrocarbons such as dichloroethane; Nitriles such as acetonitrile and propionitrile; Carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; Inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; Examples include water and a mixed solvent thereof. The amount of solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mole of compound [III-3].

The reaction temperature for this reaction may generally be selected from any temperature range from -20°C to the reflux temperature of the reaction system, preferably in the range of -10°C to 40°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is complete, compound [II-5] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. be able to. The isolated compound [II-5] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 9>
The compound represented by the general formula [III-3] can be produced, for example, using the compound represented by the general formula [III-4] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^1a , R ⁴ , R ¹⁴ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [III-3] is represented by the general formula [III-4] according to the "General Reduction Section" of Experimental Chemistry Course, 4th Edition (Maruzen), Volume 26. It can be produced by reducing a nitro compound.

Compound [III-3] can also be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 10>
The compound represented by the general formula [III-4] can be produced, for example, using the compound represented by the general formula [III-5] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^1a , R ⁴ , R ¹⁴ , m, L ² and Z have the same meanings as above.)

That is, the compound represented by the general formula [III-4] can be obtained by combining compound [III-5] and compound [IV-2] in an appropriate solvent, in the presence of an appropriate base, and in the presence of an appropriate catalyst. Alternatively, it can be produced by reacting in the absence of the compound.

Compound [IV-2], base, catalyst, solvent, reaction temperature, and reaction time that can be used in this reaction are the same as in Production Method 3.

After the reaction is complete, compound [III-4] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. can do. The isolated compound [III-4] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 11>
The compound represented by the general formula [II-6] can be produced, for example, using the compound represented by the general formula [III-3] according to a method consisting of the reaction formula illustrated below.

(In the formula, L ⁴ represents a halogen atom, -OC(=O)R ² , R ¹⁶ represents a C ₁ to C ₆ alkyl group, and R ^1a , R ² , R ⁴ , R ¹⁴ , m and Z are (Same meaning as above)

That is, the compound represented by the general formula [II-6] can be prepared by combining compound [III-3] and compound [IV-5] or compound [IV-6] in an appropriate solvent in the presence of an appropriate acid. Alternatively, it can be produced by reacting in the presence or absence of an appropriate base.

The amount of compound [IV-5] or compound [IV-6] used in this reaction may be appropriately selected from the range of 1 mol to mol equivalent to the amount of solvent per 1 mol of compound [III-3]. Preferably it is 1.0 to 10.0 mol. However, compound [IV-6] can also be used as the above solvent.

Acids that can be used in this reaction include, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid, and trifluoromethanesulfonic acid. Examples include sulfonic acids such as. The amount of acid to be used may be appropriately selected from the range of 0.1 to mol equivalent to the amount of solvent per 1 mol of compound [III-3], preferably 0.1 to 100.0 mol.

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-3].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; Examples include orthoesters such as trimethyl orthoformate, triethyl orthoformate, trimethyl orthoacetate, and triethyl orthoacetate, and mixed solvents thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mole of compound [III-3].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of -10°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, compound [II-6] can be isolated by concentrating the reaction mixture as it is, or by pouring the reaction mixture into water, etc., extracting with an organic solvent, and then concentrating. can do. The isolated compound [II-6] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 12>
The compound represented by the general formula [II-7] can be produced, for example, using the compound represented by the general formula [III-6] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^1a , R ⁴ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [II-7] can be produced by reacting the compound [III-6] with carbon disulfide in an appropriate solvent in the presence of an appropriate base. .

The amount of carbon disulfide used in this reaction may be appropriately selected from the range of 1 to 35 mol, preferably 1 to 25 mol, per 1 mol of compound [III-6].

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 2.0 mol, per 1 mol of compound [III-6].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mole of compound [III-6].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, compound [II-7] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [II-7] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 13>
The compound represented by the general formula [III-6] can be produced, for example, using the compound represented by the general formula [III-7] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ¹⁷ represents -C(=O)Me, -C(=O)Ph, -CH ₂ OMe, -CH ₂ SMe, tri(C ₁ -C ₆ alkyl)silyl group, and R ¹⁸ represents H, Me, O (t-Bu), and R ^1a , R ⁴ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [III-6] can be produced by reacting the compound [III-7] in a suitable solvent in the presence of a suitable acid.

Acids that can be used in this reaction include, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid, and trifluoromethanesulfonic acid. Examples include sulfonic acids such as. The amount of acid to be used may be appropriately selected from the range of 0.1 to mol equivalent to the amount of solvent per 1 mol of compound [III-7], preferably 0.1 to 100 mol.

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Examples include aromatic hydrocarbons such as chlorobenzene; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; water or a mixed solvent thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 25 liters, per 1 mole of compound [III-6].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, compound [III-6] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [III-6] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 14>
The compound represented by the general formula [III-7] can be produced, for example, using the compound represented by the general formula [III-8] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ^1a , R ⁴ , R ¹⁷ , R ¹⁸ , m, L ² and Z have the same meanings as above.)

That is, the compound represented by the general formula [III-7] can be obtained by combining compound [III-8] and compound [IV-2] in an appropriate solvent, in the presence of an appropriate base, and in the presence of an appropriate catalyst. Alternatively, it can be produced by reacting in the absence of the compound.

Compound [IV-2], base, catalyst, solvent, reaction temperature, and reaction time that can be used in this reaction are the same as in Production Method 3.

After the reaction is complete, compound [III-7] is isolated by pouring the reaction mixture into water, filtering the precipitated solid, or extracting with an organic solvent and then concentrating. can do. The isolated compound [III-7] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 15>
The compound represented by the general formula [III-8] can be produced, for example, using the compound represented by the general formula [III-9] according to a method consisting of the reaction formula illustrated below.

(In the formula, L ⁵ represents a halogen atom, -OC(=O)R ¹⁸ , a C ₁ -C ₆ alkyl group, 1,1-dioxide-3-oxobenziisothiazol-2-yl, R ⁴ , R ¹⁷ , R ¹⁸ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [III-8] is obtained from the compound [III-9] in GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. .M.Wuts) It can be manufactured according to the method described in .

Compound [III-8] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 16>
Among the compounds of the present invention, the compound represented by the general formula [I-8] is produced, for example, using the compound represented by the general formula [III-10] according to the method consisting of the reaction formula illustrated below. be able to.

(In the formula, L ⁶ represents a leaving group such as 1H-imidazol-1-yl, -OCCl ₃ , -NH ₂ , -O(N-succinimidyl), and R ⁴ , R ⁷ , m, Z and A are (Same meaning as above)

That is, the compound represented by general formula [I-8] is produced by reacting compound [III-10] and compound [IV-8] in an appropriate solvent in the presence of an appropriate base. be able to.

The amount of compound [IV-8] used in this reaction may be appropriately selected from the range of 1 to 15 mol, preferably 1.0 to 5.0 mol, per 1 mol of compound [III-10]. It is.

Bases that can be used in this reaction include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; lithium hydride, sodium hydride, and hydrogenation. Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine , 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-10].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile, etc. Nitriles; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; amines; water or a mixed solvent thereof, and the like. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 80 liters, per 1 mole of compound [III-10].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 150°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, compound [I-8] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [I-8] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 17>
The compound represented by the general formula [III-11] can be produced, for example, using the compound represented by the general formula [III-12] according to the method consisting of the reaction formula illustrated below.

(In the formula, R ⁴ , R ⁷ , R ¹⁴ , m and A have the same meanings as above.)

That is, the compound represented by general formula [III-11] can be obtained from compound [III-12] by GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G.M.Wuts) It can be manufactured according to the method described in .

Compound [III-11] can also be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 18>
The compound represented by the general formula [III-12] can be produced, for example, using the compound represented by the general formula [III-13] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ⁴ , R ⁷ , R ¹⁴ , m and A have the same meanings as above.)

That is, the compound represented by the general formula [III-12] is represented by the general formula [III-13] according to the "General Reduction Section" of Experimental Chemistry Course, 4th Edition (Maruzen), Volume 26. It can be produced by reducing a nitro compound.

Compound [III-12] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 19>
The compound represented by the general formula [III-13] can be produced, for example, using the compound represented by the general formula [III-14] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ⁴ , R ⁷ , R ¹⁴ , m, L ¹ and A have the same meanings as above.)

That is, the compound represented by the general formula [III-13] can be prepared by combining the compound represented by the general formula [III-14] and the compound [IV-1] in the presence of an appropriate base and an appropriate catalyst. It can be produced by reacting in a suitable solvent in the presence or absence of a compound.

Compound [IV-1], base, catalyst, solvent, reaction temperature, and reaction time that can be used in this reaction are the same as in Production Method 1.

After the reaction is completed, the compound [III-13] is isolated by pouring the reaction mixture into water, collecting the precipitated solid by filtration, or extracting it with an organic solvent and then concentrating it. can do. The isolated compound [III-13] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 20>
The compound represented by the general formula [III-14] can be produced, for example, using the compound represented by the general formula [III-15] according to a method consisting of the reaction formula illustrated below.

(In the formula, R ⁴ , R ¹⁴ , m and X have the same meanings as above.)

That is, the compound represented by the general formula [III-14] can be produced by reacting the compound [III-15] with sodium sulfide or sodium hydrogen sulfide in an appropriate solvent.

The amount of sodium sulfide or sodium hydrogen sulfide used in this reaction may be appropriately selected from the range of 1 to 15 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound [III-15]. It is.

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; N,N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol, tert-butyl Examples include alcohols, alcohols such as methyl cellosolve; water, and mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mole of compound [III-15].

The reaction temperature for this reaction may be normally selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of 0°C to 100°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After the reaction is completed, compound [III-14] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [III-14] can be further purified by column chromatography, recrystallization, etc., if necessary.

<Manufacturing method 21>
Among the compounds of the present invention, the compound represented by the general formula [I-10] is produced, for example, using the compound represented by the general formula [I-9] according to the method consisting of the reaction formula illustrated below. be able to.

(In the formula, R ¹ , R ⁴ , R ¹⁵ , m and Z have the same meanings as above.)

That is, the compound represented by the general formula [I-10] can be produced by reacting the compound [I-9] with a nucleophilic fluorinating agent in a suitable solvent.

Examples of the nucleophilic fluorinating agent that can be used in this reaction include (diethylamino)sulfur trifluoride and bis(2-methoxyethyl)aminosulfur trifluoride. The amount of the nucleophilic fluorinating agent to be used may be appropriately selected from the range of 2 to 10 mol, preferably 2.0 to 5.0 mol, per 1 mol of compound [I-9].

Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, mesitylene, Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; acetonitrile, propiocarbons, etc. Examples include nitriles such as nitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mole of compound [I-9].

The reaction temperature for this reaction may generally be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably in the range of -10°C to 60°C.

The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

After the reaction is completed, compound [I-10] can be isolated by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating. The isolated compound [I-10] can be further purified by column chromatography, recrystallization, etc., if necessary.

The herbicide of the present invention contains the fused heterocyclic derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof as an active ingredient. The herbicides of the present invention have excellent herbicidal efficacy, and some exhibit excellent selectivity between useful plants and weeds, and are useful as agrochemical compositions, particularly herbicides, in farmland. That is, the compound of the present invention can be used for foliage treatment, soil treatment, seed dressing treatment, soil mixing treatment, pre-sowing soil treatment, simultaneous sowing treatment, post-sowing soil treatment, and sowing in fields where useful plants are cultivated or non-agricultural land. It has a herbicidal effect on various weeds when mixed with soil at the same time.

The herbicide of the present invention can contain additive components (carriers) that are normally used in agricultural chemical formulations, if necessary.

These additive components include carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, thickeners, colorants, extenders, spreading agents, antifreeze agents, anticaking agents, Disintegrants, decomposition inhibitors, etc. may be mentioned, and if necessary, preservatives, plant pieces, etc. may be used as additional components. Further, these additive components may be used alone or in combination of two or more.

The above-mentioned additional components will be explained below.

Examples of solid carriers include pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgus clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, synthetic silicates, etc.), mineral carriers such as titanium dioxide; vegetable carriers such as wood flour, corn stalks, walnut shells, fruit kernels, rice husks, sawdust, bran, soy flour, powdered cellulose, starch, dextrin, sugars; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc.; polymeric carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, urea-aldehyde resin, etc. can.

Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; Hydrolic alcohols; polyhydric alcohol derivatives such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone; ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether, Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, and mineral oil; aromatics such as toluene, _C9 - _C10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, and high-boiling aromatic hydrocarbons Group hydrocarbons; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone Amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone; Nitriles such as acetonitrile; Sulfur compounds such as dimethylsulfoxide; Examples include vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, and castor oil; lower alkyl esters of fatty acids derived from the vegetable oils; and water.

Examples of surfactants include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, and polyoxyethylene fatty acid ester. Oxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene Fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine surfactant , polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, and other nonionic surfactants; alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, Alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acids, salts of formalin condensates of alkylnaphthalenesulfonic acids, fatty acid salts, Anionic surfactants such as polycarboxylate, N-methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate; laurylamine hydrochloride, stearylamine hydrochloride Cationic surfactants such as alkylamine salts such as oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride; dialkyldiaminoethylbetaine, alkyldimethylbenzylbetaine Amphoteric surfactants include betaine type surfactants such as , and amino acid type surfactants such as dialkylaminoethylglycine and alkyldimethylbenzylglycine.

Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol, and polyethylene. Examples include oxides, natural phospholipids (eg, cephalic acid, lecithin, etc.).

Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, and polysaccharides; inorganic fine powders such as high-purity bentonite and white carbon. , organic fine powder such as organic bentonite, and the like.

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

Extending agents include, for example, silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, maleic acid/styrene copolymers, methacrylic acid copolymers, and polyhydric alcohols. and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, polyoxyethylene alkanediols, polyoxyethylene alkyne diols, alkyne diols, and the like.

Examples of spreading agents include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, and polyacrylate. , polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, and the like.

Examples of antifreeze agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

Examples of anticaking agents include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resins.

Examples of disintegrants include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride. Examples include acid copolymers and starch/polyacrylonitrile graft copolymers.

Examples of decomposition inhibitors include drying agents such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol, amine, sulfur, and phosphoric acid; and ultraviolet absorbers such as salicylic acid and benzophenone. can be mentioned.

Examples of preservatives include potassium sorbate and 1,2-benzthiazol-3-one.

Examples of plant pieces include sawdust, coconut shells, corncobs, tobacco stalks, and the like.

On the other hand, when the above-mentioned additive components are contained in the herbicide of the present invention, the content thereof is usually 5 to 95%, preferably 20 to 90% in a carrier such as a solid carrier or a liquid carrier, on a mass basis. The amount of surfactants is usually selected in the range of 0.1 to 30%, preferably 0.5 to 10%, and the amount of other additives is selected in the range of 0.1 to 30%, preferably 0.5 to 10%.

The herbicide of the present invention can be applied to powders, powders, granules, granules, wettable powders, aqueous solutions, wettable powders, tablets, jumbo tablets, emulsions, oils, liquids, flowables, emulsions, microemulsions, sachets, etc. Spray emulsion, micro-spraying agent, microcapsule, jumbo agent, soybean powder (registered trademark) agent, smoke agent, aerosol agent, bait agent, paste agent, foaming agent, carbon dioxide gas preparation, paint, wood protection paint, sealing agent It is used by formulating it into any dosage form such as a drug.

When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. Application of the various formulations or dilutions thereof containing the compounds of the present invention is usually carried out by conventional application methods, i.e., spraying (e.g., spraying, misting, atomizing, dusting, granulating, surface application, box application, etc.), soil application (e.g., mixing, irrigation, etc.), surface application (e.g., coating, dusting, covering, etc.), seed treatment (e.g., smearing, dusting, etc.), dipping, poison bait, fumes. This can be done by application etc.

The agrochemical composition of the present invention can be used by foliar spraying, soil application, water surface application, etc. The agrochemical composition, particularly the herbicide, of the present invention is used in soil, particularly in farmland or paddy fields where useful plants are cultivated.

The blending ratio of the active ingredients in the agrochemical composition of the present invention is appropriately selected as necessary, but when used as a powder or granule, it is 0.01 to 10% (by weight), preferably 0.05 to 5%. It is preferable to select it appropriately from the range of % (weight). In the case of emulsions, wettable powders, etc., the amount should be appropriately selected from the range of 1 to 50% (by weight), preferably 5 to 30% (by weight). Further, when used as a flowable agent, the amount should be appropriately selected from the range of 1 to 40% (by weight), preferably 5 to 30% (by weight).

The application amount of the agrochemical composition of the present invention varies depending on the type of compound used, the target weed, the tendency of occurrence, environmental conditions, the dosage form used, etc. For example, when the agrochemical composition of the present invention is used as a herbicide in the form of powder, granules, etc., the amount of active ingredient per hectare is preferably selected from the range of 1 g to 50 kg, preferably 10 g to 10 kg. . When used in liquid form, such as in emulsions, wettable powders, flowable preparations, etc., the amount should be appropriately selected from the range of 0.1 to 50,000 ppm, preferably 10 to 10,000 ppm.

In addition to the compound of the present invention, the agrochemical composition of the present invention may also include at least one other agrochemical active ingredient, such as another disease control agent component, insecticide component, acaricide component, depending on the purpose of use. Formulated with, mixed with, or mixed with nematicide ingredients, synergist ingredients, attractant ingredients, repellent ingredients, herbicide ingredients, phytotoxicity reducer ingredients, microbial pesticide ingredients, plant growth regulator ingredients, fertilizers, soil conditioners, etc. May be used together.

When mixed or used in combination with other agrochemical active ingredients or fertilizers, preparations of each individual ingredient can also be used in combination at the time of application. Furthermore, each single component formulation may be used sequentially or may be applied several days apart. When the treatment is applied at intervals of several days, the treatment may be performed at intervals of, for example, 1 to 40 days, depending on the other components used.

The agricultural chemical composition of the present invention comprises at least one compound selected from a fused heterocyclic derivative represented by the general formula [I] and an agriculturally acceptable salt, and at least one compound selected from other agricultural chemical active ingredients. When a mixture of the above is applied, it is usually applied at a mass ratio of 100:1 to 1:100, preferably 20:1 to 1:20, particularly 10:1 to 1:10.

The blending ratio (% by mass) of the active ingredients in the agrochemical composition of the present invention is appropriately selected as necessary. For example, when making powders, powders, granules, fine granules, etc., it is best to select the appropriate amount from the range of 0.01 to 20%, preferably from 0.05 to 10%, and when making granules, etc., it is preferably from 0.1 to 20%. 30%, preferably from the range of 0.5 to 20%, and in the case of wettable powders, hydrated granules, etc., it is suitably selected from the range of 1 to 70%, preferably 5 to 50%. When used as an aqueous solvent or liquid, it is preferably selected from a range of 1 to 95%, preferably 10 to 80%, and when used as an emulsion, it is preferably selected from a range of 5 to 90%, preferably 10 to 80%. It is best to select an appropriate amount from a range of 1 to 50%, preferably 5 to 30% when used as an oil agent, etc., and 5 to 60%, preferably 10 to 10% when used as a flowable agent. It is recommended to select the appropriate amount from the range of 50%, and for emulsions, microemulsions, suspoemulsions, etc., it is appropriate to select from the range of 5 to 70%, preferably 10 to 60%. When used as an agent, paste, etc., it is best to select the appropriate amount from the range of 1 to 80%, preferably 5 to 50%. When used as a smoke agent, etc., it is preferably 0.1 to 50%, preferably 1 to 50%. It is preferable to select the appropriate amount from the range of 30%, and when preparing an aerosol agent, it is preferably selected from the range of 0.05 to 20%, preferably 0.1 to 10%.

These preparations can be diluted to an appropriate concentration and sprayed, or applied directly.

When the agrochemical composition of the present invention is diluted with a diluent, it is generally applied at an active ingredient concentration of 0.1 to 5000 ppm. When the preparation is used as it is, the application amount per unit area of the active ingredient compound is 0.1 to 5000 g per ha, but is not limited thereto.

It goes without saying that the agrochemical composition of the present invention is sufficiently effective using the compound of the present invention alone as an active ingredient, but if necessary, other agrochemicals such as insecticides, acaricides, Can be mixed or used in combination with nematicides, synergists, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, spreaders, other agricultural materials, fertilizers, etc. In this case, even better effects may be obtained.

Next, examples of known herbicide compounds, herbicidal active ingredients, or plant growth regulator compounds that may be used in combination or in combination are illustrated below, but the invention is not limited to these examples.

Herbicide compound or herbicidal active ingredient:
ioxynil (including salts with lithium salt, sodium salt, octanoic acid, etc.), aclonifen, acrolein, azafenidine, acifluorfen (including salts with sodium, etc.) ), azimsulfuron, asulam, acetochlor, atrazine, anilofos, amicarbazone, amidosulfur on), amitrole, aminocyclopyra aminocyclopyrachlor, aminopyralid, amiprofos-methyl, ametryn, Araujia Mosaic Virus, ala chlor), Alternaria destruens, alloxydim (including salts with sodium etc.), ancymidol, isouron, isoxachlortole, isoxaflutole, isoxaben, isodecyl alcohol ethoxylate thoxylate ), isoproturon, ipfencarbazone, imazaquin, imazapic (contains salts with amines, etc.), imazapyr (contains salts such as isopropylamine), imazapyr (contains salts with isopropylamine, etc.), Zamethabenz ( imazamethabenz), imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, inda indaziflam, indanofan, eglinazine-ethyl, esprocarb , ethametsulfuron-methyl, ethalfluralin, ethidimuron, ethoxysulfuron, ethoxyfen, ethoxyfen ethyl ( ethoxyfen-ethyl), ethofumesate ), etobenzanid, epirifenacil, endothal-disodium, oxadiazon, oxadiargyl, oxadiclomefon (oxaz) iclomefone), oxasulfuron (oxasulfuron), oxyfluorfen (oxyfluorfen) , oryzalin, Obuda Pepper Virus, orthosulfamuron, orbencarb, oleic acid, cafenstrole, capryl caprylic acid, caprylic acid ( capric acid), carfentrazone-ethyl, carbutilate, carbetamide, Quizalofop, Quizalofop fop-ethyl), Quizalofop-P-ethyl (quizalofop-P- ethyl), Quizalofop-P-tefuryl, Xanthomonas campestris, Quinoclamine, Quinclorac, Quinclorac ( quinmerac), citric acid, cumyluron ( cumyluron), clacyfos, glyphosate (sodium, potassium, amine, propylamine, isopropylamine, ammonium, isopropylammonium, guanidine, monoethanolamine, choline, BAPMA (N,N-bis-(aminopropyl) glufosinate (including salts such as amine or sodium), glufosinate-P, glufosinate-P sodium salt (glufosinate-P-) sodium), clethodim, clodinafop, clodinafop-propargyl, clopyralid (including monoethanolamine salt), clomazone, clomethoxifene (ch lomethoxyfen), clomeprop ), chloransulam-methyl, chloramben, chloridazon, chlorrimuron, chlorimuron-ethyl, chlorsulfuron furon), chlorthal-dimethyl , chlorthiamide, chlorphthalim, chlorflurenol-methyl, chlorpropham, chlorbromuron, chloro roxuron), chlorotoluron, ketospiradox ( Colletotrichum orbiculare, Colletotrichum gloeosporioides, Colletotrichum truncatum (Colletotrichum truncatum), Chondrostercum purpureum, saflufenacil ( saflufenacil), sarmentine, cyanazine, cyanamide, diuron, diethatyl-ethyl, dicamba (amine, diethylamine, Propylamine, diglycolamine, dimethylammonium , diolamine, isopropylammonium, auramine, potassium, trollamine, BAPMA (N,N-bis-(aminopropyl)methylamine), choline, salts such as sodium or lithium, or esters such as methyl ester), cycloates (cycloate), cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlobenil benil), diclofop, diclofop-P-methyl (diclofop-P-methyl), diclofop-methyl, dichlorprop, dichlorprop-P (salts of dimethylammonium, potassium, sodium, choline, etc., or butotyl) ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), diquat, diquat dibromide, dithiopyr, siduron, dinitramine, sinidone - Ethyl (cinidon-ethyl), cinosulfuron (cinosulfuron), dinoseb (contains acetate), dinoterb (dinoterb), cyhalofop (cyhalofop), cyhalofop-butyl (cyhalofop-butyl), cipirafluon (c ypyrafluorone), diphenamide ( diphenomid), difenzoquat, diflufenican, diflufenzopyr, simazine, dimesulfazet, dimethachlor ( dimethachlor), dimethametryn, dimethenamid, dimethenamide・P (dimethenamid-P), simetryn, dimepiperate, dimefuron, Pseudomonas fluorescens, cinmethylin , swep, sulcotrione, sulfene Sulfentrazone, sulfosate, sulfosulfuron, sulfometuron-methyl, sethoxydim, Scelerothini minor a minor), terbacil, daimuron, thaxtomin A, Tobacco Mild Green Mosaic Tobamovirus, Tobacco Rattle Virus, dalapon, thia zopyr), thiafenacil, thiencarbazone ( (including sodium salt, methyl ester, etc.), tiocarbazil, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron methyl fensulfuron-methyl), Desmedi desmedipham, desmetryne, tetflupyrolimet, thenylchlor, tebutam, tebuthiuron, tepralox ydim), tefuryltrione, terbuthylazine ), terbutryn, terbumeton, tembotrione, topramezone, tralkoxydim, triaziflam, triasulfuron (trias) ulfuron), triafamone, tri-allate , trietazine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tritosulfuron , tripyrasulfone, trifludimoxazine ), triflusulfuron-methyl, trifluralin, trifloxysulfuron (including salts such as sodium), tribenuron-methyl, tolpyra late), Naputalum (naptalam) (including salts with sodium etc.), naproanilide, napropamide, napropamide-M, nicosulfuron, lactic acid, nebulon buron), norflurazone (norflurazon), Burkholderia rhinojensis, vernolate, paraquat, paraquat dichloride, halux ifen), haluxifen-benzyl, haluxifen-methyl ( haloxifen-methyl), Burkholderia rhinojensis, haloxyfop, haloxyfop-P, haloxyfop-etotyl, haloxyfop Hop-P-methyl (haloxyfop-P-methyl), halosafen (halosafen), halosulfuron-methyl, bixlozone, picloram (including salts with dichloroammonium, torollamine, etc.), picolinafen, bicyclopyrone yrone), Bispilibac・Sodium salt (bispiribac-sodium), pinoxaden (pinoxaden), bipyrazone (bipyrazone), bifenox, piperophos, pyraclonil, pyrasulfotole ), pyrazoxyfen, pyrazosulfuron ethyl -ethyl), pyrazolinate, bilanafos, pyraflufen, pyraflufen-ethyl, pyridafol, pyrithiobac sodium salt (pyrithiobac) c-sodium), pyridate, pyrifthalide ( pyriftalid), pyributicarb, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, pyroxasulfone e), pyroxsulam, Phytophthora palmivora, phenisophham ( phenisopham), fenuron, fenoxasulfone, fenoxaprop (contains methyl, ethyl, isopropyl esters), fenoxaprop-P (contains methyl, ethyl, isopropyl esters) ), fenquinotrone, fenthiaprop-ethyl, fentrazamide, fenpyrazone, phenmedipham, forma chenopodi Phoma chenopodicola, Phoma herbarum ), Phoma macrostoma, butachlor, butafenacil, butamifos, butylate, Puccinia canalicula ta), Puccinia thlaspeos, butenachlor , butralin, butroxydim, flazasulfuron, flamprop (including methyl, ethyl, isopropyl ester), flanprop-M (methyl, ethyl, isopropyl ester) ), primisulfuron, primisulfuron-methyl, fluazifop-butyl, fluazifop-P, fluazifop-P, fluaz ifop-P- butyl), fluazolate, fluometuron, fluoroglycofen-ethyl, flucarbazone-sodium, fluchlora lin), flucetosulfuron, flucetosulfuron, fluthiacet methyl (fluthiacet-methyl), flupyrsulfuron-methyl (including salts such as sodium, calcium or ammonia), flufenacet, flufenpyr-ethyl, flupropanate te ) (including sodium salt), flupoxame, flumioxazin, flumiclorac-pentyl, flumetsulam, fluridone, flurtamone ), fluroxypyr ( esters such as butomethyl, meptyl, or salts such as sodium, calcium, ammonia, etc.), flurochloridone, pretilachlor, procarbazone (including salts with sodium, etc.), prodiamine ( Prodiamine, Prosulfuron, Prosulfocarb, Propaquizafop, Propachlor, Propazine, Propanil ), propyzamide, propisochlor , propyrisulfuron, propham, profluazol, prohexadione-calcium, propoxycarbazone, propoxycarba propoxycarbazone-sodium , profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil (including esters such as butyric acid, octanoic acid or heptanoic acid), bromo Phenoxime ( bromofenoxim, bromobutide, florasulam, florpyrauxifen, florpyrauxifen-benzyl, hexazin one), petoxamide, benazolin, benazoline Benazolin-ethyl, penoxsulam, Pepino Mosaic Virus, heptamaloxyloglucan, beflubutamide, beflu beflubutamide-M, pebulate, pelargonic acid (pelargonic acid), bencarbazone (bencarbazone), benquitrione (benquitrione), benzfendizone (benzfendizone), bensulide (bensulide), bensulfuron (bensulfuron), bensulfuron Methyl (bensulfuron-methyl), benzobiciclon (benzobicyclone) , benzofenap, bentazone, pentanochlor, pendimethalin, pentoxazone, benfluralin, benfuresate (benfuresate), fosamine, fomesafen ), foramsulfuron, forchlorfenuron, mecoprop (salts of sodium, potassium, isopropylamine, triethanolamine, dimethylamine, diolamine, trollamine, choline, etc.), or ethylamine (including esters such as dielester, 2-ethylhexyl ester, isoctyl ester, methyl ester), mecoprop-P potassium salt (mecoprop-P-potassium), mesosulfuron (including esters such as methyl), mesotrione ( mesotrione), metazachlor, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam( metam) (including salts such as sodium), methane arsonic acid di Sodium (DSMA), methiozolin, methyldymuron, metoxuron, metosulam, metsulfuron-methyl, metobrom uron), metobenzuron, metolachlor , metribuzin, mepiquat chloride, mefenacet, monosulfuron (including methyl, ethyl, and isopropyl esters), monolinuron, molinate inate), iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, lactofen,
lancotrione, linuron, rimsulfuron, lenacil, 2,2,2-trichloroacetic acid (TCA) (including salts such as sodium, calcium or ammonia), 2,3, 6-Trichlorobenzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D) (amine , diethylamine, triethanolamine, isopropylamine, dimethylammonium, diolamine, dodecylammonium, heptylammonium, tetradecylammonium, triethylammonium, tris(2-hydroxypropyl)ammonium, trollamine, choline, salts such as sodium or lithium, or buttyl ester, 2-butoxypropyl ester, 2-ethylhexyl ester, methyl ester, ethyl ester, butyl ester, isobutyl ester, octyl ester, pentyl ester, propyl ester, isoctyl ester, isopropyl ester, meptyl ester, tefuryl esters), 2,4-dichlorophenoxybutyric acid (2,4-DB) (amines, salts such as diethylamine, triethanolamine, isopropylamine, dimethylammonium, choline, sodium or lithium, or isoctyl) (including esters such as esters), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (salts such as sodium, dimethylammonium, choline, etc.), 2-ethylhexyl ester, isoctyl ester, ethyl ester, etc.), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium salt, ethyl ester, etc.), 4-(2,4-dichloro) (5S)-3-(3,5-difluorophenyl)-N -[rel-(3R,5R)-5-(trifluoromethylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide ((5S)-3-(3, 5-difluorophenyl)-N-[rel-(3R,5R)-5-(trifluoromethylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carbo xamid) (chemical name, CAS registration number: 2266183- 40-6) (International Publication No. 2018/228986, International Publication No. 2020/114934), N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methyl-ethyl)-1 ,3,5-triazine-2,4-diamine (N4-(2,6-difluorophenyl)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine ) (Chemical name, CAS registration number: 1606999-43-2) (International Publication No. 2014/064094, International Publication No. 2015/162164), (5S)-3-(3,5-difluorophenyl)- N-[(3R)-5-(methylsulfonylcarbamoyl)-2,3-dihydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide ((5S)-3-(3,5 -difluorophenyl)-N-[(3R)-5-(methylsulfonylcarbamoyl)-2,3-dihydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide) (chemical name, CAS registration number :2266190- 06-9) (International Publication No. 2018/228986, International Publication No. 2020/114934), (5R)-3-(3,5-difluorophenyl)-5-methyl-N-[rel-(3R ,5R)-5-(methylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-4H-isoxazole-5-carboxamide((5R)-3-(3,5-difluorophenyl)-5-methyl-N-[ rel-(3R,5R)-5-(methylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-4H-isoxazole-5-carboxamide) (chemical name, CAS registration number: 2266164-36-5) (International Publication No. 2018/ No. 228986 Publication, International Publication No. 2020/114934), (5R)-3-(3,5-difluorophenyl)-N-[(3R)-5-(methoxycarbamoyl)-2,3-dihydrofuran-3- yl]-5-methyl-4H-isoxazole-5-carboxamide ((5R)-3-(3,5-difluorophenyl)-N-[(3R)-5-(methoxycarbamoyl)-2,3-dihydrofuran-3 -yl]-5-methyl-4H-isoxazole-5-carboxamide) (chemical name, CAS registration number: 2266170-31-2) (International Publication No. 2018/228986, International Publication No. 2020/114934), 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione (2-[2-(3,4-dimethoxyphenyl)-6 -methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione) (chemical name, CAS registration number: 2138855-12-4) (International Publication No. 2017/178582, International Publication No. 2018/ 015476), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (4-hydroxy-1-methyl-3-[4-(trifluoromethyl) )-2-pyridyl]imidazolidin-2-one) (chemical name, CAS registration number: 1708087-22-2) (International Publication No. 2015/059262, International Publication No. 2018/015476), 6-(1 -fluorocyclopentyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine(6-(1-fluorocyclopentyl)-N4-(2,3, 5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine) (chemical name, CAS registration number: 1820807-75-7) (International Publication No. 2015/162164), 6-(1 -Fluoro-1-methyl-ethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine(6-(1-fluoro-1-methyl -ethyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine) (chemical name, CAS registration number: 1606999-21-6) (International Publication No. (5S)-3-(3-fluoro-5-methyl-phenyl)-N-[rel-(3R,5R)-5-(methoxycarbamoyl) ) terorahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide ((5S)-3-(3-fluoro-5-methyl-phenyl)-N-[rel-(3R,5R )-5-(methoxycarbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamide) (chemical name, CAS registration number: 2266292-43-5) (International Publication No. 2018/228986) , International Publication No. 2020/114934), 6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-2,4-diamine ( 6-(1-methylcyclobutyl)-N4-(2,3,5,6-tetrafluorophenyl)-1,3,5-triazine-4,4-diamine) (chemical name, CAS registration number: 1607001-97-7) (International Publication No. 2014/064094, International Publication No. 2015/162164), AE-F-150944 (Code Number), F9960 (Code Number), IR-6396 (Code Number), MCPA/Thioethyl (MCPA- thioethyl), SYP-298 (code number), SYP-300 (code number), S-ethyldipropylthiocarbamate (EPTC), S-metolachlor, S-9750 (code number), MSMA ( MSMA), HW-02 (code number).

Plant growth regulator:
1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic acid -triiodobenzoic acid), 2-methyl-4-chlorophenoxybutyric acid (MCPB) [including sodium salt, ethyl ester, etc.], 2-(naphthalene-1-yl)acetamide , 2,6-diisopropylnaphthalene, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol (3-[(6-chloro-4- phenylquinazoline-2-yl)amino]propane-1-ol), 4-oxo-4-(2-phenylethyl)aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic acid ( 4-CPA), 5-aminolevulinic acid hydrochloride, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate 2-carboxylate), AVG (aminoethoxyvinylglycine), n-decyl alcohol (n-decanol), aviglycine, ancymidol, abscisic acid, isoprothiolane (iso) prothiolane), inabenfide, indole Indole acetic acid, indole butyric acid, uniconazole, uniconazole-P, Ecolyst, ethychloz ate), ethephon, epocholeone, Calcium chloride, choline chloride, oxine-sulfate, kinetin, calcium peroxide, carbone, calcium formate um format), cloxyfonac, cloxyfonac-potassium, cloprop, chlormequat, chlormequat-chloride, chlorpropham propham), choline, cytokinin (cytokinins), oxidized glutathione, cyanamide, sodium cyanate, cyclanilide, dichlorprop (dimethylammo) Salts of sodium, potassium, sodium, choline, etc., or (contains esters such as butotyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester, etc.), dichlorprop-P (contains salts of sodium, potassium, dimethylammonium, etc., or 2-ethylhexyl ester) ), diquat, diquat dibromide, dikegulac, gibberellinic acid, gibberellin A4, gibberellin A7 (gibb erellin A7), dimethipin, sintofen ), jasmone, cis-jasmone, jasmonic acid, methyl jasmonate, streptomycin, calcium polys ulfide), daminozide, calcium carbonate (calcium carbonate), thidiazuron, decan-1-ol, triacontanol, triapenthenol, trinexapac-ethy l), tribufos ( tribufos), paclobutrazol, paraffin, bispyribac-sodium, hymexazol, butralin, fluthiacetyl et-methyl), pyraflufen ethyl ( pyraflufen-ethyl), flumetralin, flurprimidol, flurenol, pronitridine, prohydrojasmon, prohexadione calcium Salt (prohexadione-calcium), heptamaloxyloglucan (heptamaloxyloglucan), 6-benzylaminopurine, pendimethalin, forchlorfenuron, formononetin, maleic hydrazide (maleic hydrazide), mepiquat chloride ), mefluidide, lipochitooligosaccharides (eg lipochitooligosaccharides SP104), calcium sulfate.

Next, the following are examples of known phytotoxicity-reducing compounds that may be used in combination or in combination.

Isoxadifen, isoxadifen-ethyl, oxabetrinil, octane-1,8-diamine, cloquintocet, cloquintocet -Mexyl (cloquintcet) -mexyl), dietholate, cyometrinil, dichlormid, dicyclonone, cyprosulfamide, daimuron, naphthalic acid Water (1,8-Naphthalic Anhydride), fenchlorazole, fenchlorazole-O-ethyl, fenclorim, furilazole, fluxofenim, flurazol e), benoxacor, metcamifen, Mephenoate, mefenpyr, mefenpyr-ethyl, mefenpyr-diethyl, lower alkyl-substituted benzoic acid, 2,2-dichloro-N-(1,3-dioxolane- 2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxane (MG-191), 3-dichloroacetyl-2,2,5- Trimethyl-1,3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), 4-carboxy-3,4-dihydro-2H-1 -Benzopyran-4-acetic acid (CL-304415, code number), MON4660 (code number), metcamifen (metcamifen), N1,N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, code number), 1-bromo -4-[(chloromethyl)sulfonyl]benzene (CSB), 2-propenyl 1-oxa-4-azaspiro[4,5]decane-4-carbodithioate (MG-838, code number), 3-(dichloro acetyl)-2,2-dimethyl-1,3-oxazolidine (R-28725, code number), R-29148 (code number), 1-(dichloroacetyl)azepane (TI-35, code number).

Next, we introduce known insecticides (insecticidal active ingredients), acaricides (acaricidal active ingredients), nematicides (nematicidal active ingredients), and synergist compounds (synergic active ingredients) that may be mixed or used in combination. Components) are illustrated below.

Insecticidal active ingredient, acaricidal active ingredient, nematicidal active ingredient, synergistic active ingredient:
Acrinathrin, azadirachtin, azamethiphos, acynonapyr, azinphos-ethyl, azinphos -methyl), acequinocyl, acetamiprid, acetoprole (acetoprole), acephate, azocyclotin, abamectin, afidopyropen, afoxolaner, amidoflumet, amino amitraz, alanycarb, aldicarb ), aldoxycarb, allethrin [including d-cis-trans-form and d-trans-form], isazophos, isamidofos, isocarbophos, isoxathion (isoxation) , isocycloseram, isofenphos-methyl, isoprocarb, epsilon-metofluthrin, epsilon-momf luorothrin), ivermectin, imicyafos ), imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole prole), ethylene dibromide, etoxazole (etoxazole), etofenprox, ethoprophos, etrimfos, emamectin, emamectin benzoate, endosulfan n), empenthrin, oxazosulfyl , oxamyl, oxydemeton-methyl, oxydeprofos, omethoate, nuclear polyhedrosis virus, cadusafos fos), kappa-tefluthrin (kappa- tefluthrin, kappa-bifenthrin, karanjin, cartap, granulosis virus, carbaryl, carbosulfan, carbaryl Carbofuran, Gamma-BHC (gamma-BHC), xylylcarb, quinalphos, kinoprene, chinomethionat, acute paralysis virus (Entero virus), coumaphos, cryolite ( cryolite), clothianidin , clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordane, chlorpicrin loropicrin), chlorpyrifos, chlorpyrifos methyl (chlorpyrifos- methyl), chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloropralethrin, insect pox Entomopoxi virus, Irido virus ), cyazypyr, cyanophos, diafenthiuron, diamidafos, cyantraniliprole, cyetpyrafen, dienochlor (d ienochlor), cyenopyrafen, dioxa Dioxabenzofos, diophenolan, Sigma virus, cyclaniliprole, cycloxaprid, dicrotophos, diclofenthion (dichlofenthion), cyclobutrifluram (cyclobutrifluram), cyclobutrifluram cycloprothrin, dichlorvos, dichloromezotiaz, dicofol, dicyclanil, disulfoton, dinotefuran furan), dinobuton, cyhalodiamide, cyhalothrin (cyhalothrin) [including gamma-form and lambda-form], cyphenothrin [including (1R)-trans-form], cyfluthrin [including beta-form], diflubenzuron, cyflu metophen (cyflumetofen), diflobidazin, cyproflanilide, cyhexatin, cypermethrin [alpha-form, beta-form, theta-form, zeta-body], dimpropyridaz ), dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate (DEP), dimethylvinphos, dimethoate, dimefluthrin, jasmone, cis-jasmo ne ), jasmonic acid, methyl jasmonate, silafluofen, cyromazine, Steinernema carpocapsae , Steinernema kushidai, Steinernema glaseri, spinetorum ( spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spiromesifen, sulcofuron sodium salt furon-sodium), sulfuramide, sulfoxaflor (sulfoxaflor), sulfotep, diazinon, thiacloprid, thiamethoxam, thioxazafen, thiodicarb, thio thiocyclam, thiosultap, thionazin, thio Thiofanox, thiometon, tyclopyrazoflor, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon ( tetradifon), tetraniliprole, tetra Tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin rin), teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralomethrin, transfluthrin, triazamate, triazophos ), trichlorfon, Trichoderma asperellum, Trichoderma Trichoderma paecilomyces, Trichoderma harzianum, triflumuron, triflumezopyrim, trimethacarb acarb), tolfenpyrad, naled, nicotine, nicofluprole ), nitenpyram, nemadectin, Denso virus, novaluron, noviflumuron, paecilomyces lilacinus , Burkholderia cepacia, Burkholderia cepacia Barkholderia rinojensis, Verticillium lecanii, hydroprene, Pasteuria nishizawae, Pasteuria penetrans euria penetrans), Bacillus amyloliquefaciens, Bacillus firmus firmus), Bacillus sphaericus, Bacillus subtillis, Bacillus thuringiensis, Bacillus thuringiensis Insect toxin produced by Bacillus thuringiensis subsp. Aizawai), Bacillus thuringiensis subsp. Israelensis, Bacillus thuringiensis subsp. Kurs taki), Bacillus thuringiensis subsp.
Bacillus popilliae, Bacillus licheniformis, vamidothion, parathion, parathion methyl n-methyl), halfenprox, halofenozide, bioallethrin (bioallethrin), bioallethrin S-cyclopentenyl, bioresmethrin, bis-(2-chloro-1-methylethyl)ether (DCIP), bistrifluron, hydramethyl Non ( hydramethylnon), bifenazate, bifenthrin, pyflubumide, piperonyl butoxide, pymetrozine, pyrazine pyraclofos, pyrafluprole, pyridaphenthion, pyridaben , pyridalyl, pyrifluquinazone, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pirimi nostrobin, pirimiphos-methyl, pyrethrine, famphur, fipronil, fenazaquin, fenamiphos, fenitrothion, fenoxycarb, pheno thiocarb, phenothrin [(1R)- trans-], fenobucarb, fenthion, phenthoate, fenvalerate, fenpyroximate, fenbutatin oxide ), fenpropathrin, fonofos, sulfuryl fluoride, butocarboxim, butoxycarboxim, buprofezin, furathiocarb , prallethrin, fluacrypyrim, fluazaindo lysine, fluazuron, fluensulfone, fluopyram, sodium fluoroacetate, fluxameta mide), flucycloxuron, flucythrinate, flusulfamide, fluthrin, fluvalinate [including tau-form], flupyradifurone, flupyrazofos, flupyrimin ), flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flupentiofenox, flumethrin ), fluralaner, flurimfen ), prothiofos, protrifenbute, flonicamid, propaphos, propargite, prohydrojasmon, profenofos enofos), broflanilide, profluthrin ), propetampphos, propoxur, flometoquin, bromopropylate, hexythiazox, hexaflumuron, Paecilomyces tenuipes, Paecilomyces fumosoroseus, Paecilomyces lilacinus, heptafluthrin, heptenophos, permethrin, benclothiaz, benzpyrimoxan zpyrimoxan), bensultap, benzoximate, vendor bendiocarb, benfuracarb, Pochonia chlamydosporia, Beauveria tenella, Beauveria bassian a), Beauveria brongniartii, phoxim, phosalone, hostiazate (fosthiazate), fosthietan, phosphamidon, phosmet, polynactins, formtanate, phorate, machine oil e oil), malathion, milbemectin ( milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metham, methiocarb, methidathion, methyl Methyl isothiocyanate, methyl bromide, methoxychlor, methoxyfenozide, meththrin, methofluthrin etofluthrin, methoprene, metolcarb, mevinphos, mepelfluthrin (meperfluthrin), Monacrosporium phymatophagum, Monacrosporium phymatophagum, Monocrotophos, Momfluorothrin (momfluorothrin), Trichoderma harzianum, litlure-A, litlure-B, aluminum phosphide, zinc phosphide, phosphine, lufenuron, rescalure, resme thrin), lepimectin , rotenone, cytoplasmic polyhedrosis virus, fenbutatin oxide, calcium cyanide, organotins, nicotine-sulfate, (Z)-11-tetradecenyl acetate, (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, (Z)-9,12-tetradecadienyl acetate, (Z)-9-tetradecene -1-ol, (Z,E)-9,11-tetradecadienyl acetate, (Z,E)-9,12-tetradecadienyl acetate, 1,1,1-trichloro-2,2 -bis(4-chlorophenyl)ethane (DDT), 1,3-dichloropropene, 2,4-dichloro-5-{2-[4-(trifluoromethyl)phenyl]ethoxy}phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472052-11-1), 2,4-dimethyl-5-[6-(trifluoromethylthio)hexyloxy]phenyl-2,2, 2-Trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-34-2), 2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenoxy} -5-(trifluoromethyl)pyridine (chemical name, CAS registration number: 1448758-62-0), 3-chloro-2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoromethyl)pyridine fluoroethyl)sulfinyl]phenoxy}-5-(trifluoromethyl)pyridine (chemical name, CAS registration number: 1448761-28-1), 4,6-dinitro-o-cresol (DNOC), 4-fluoro-2- Methyl-5-(5,5-dimethylhexyloxy]phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472047-71-4), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1), methyleugenol, 4-(p-acetoxyphenyl)-2-butanone, (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradeca Geniel acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, 14-methyl-1-octadecene, AKD-1193 (code number), BCS-AA10147 (code number), CL900167 (code number), NA-85 (code number), NI-30 (code number), O,O-diethyl-O-[4-(dimethylsulfamoyl) Phenyl]-phosphorothioate (DSP), O-ethyl-O-4-(nitrophenyl)phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosene-10- On, ZXI8901 (code number), F4260 (code number).

Next, examples of known fungicides (fungicidal active ingredients) or disease control compounds that may be used in combination or in combination are illustrated below.

Fungicidal active ingredient or disease control compound:
Agrobacterium radiobacter, azaconazole, acibenzolar-S-methyl, azoxystrobin, ani lazine), amisulbrom, aminopyrifene ( aminopyrifen), ametoctradin, aldimorph, isotianil, isopyrazam, isofetamide, isoflucypram ), isoprothiolane, ipconazole, ipflufenoquine ( ipflufenoquin), ipfentrifluconazole, iprodione, iprovalicarb, iprobenfos, imazalil, imi iminoctadine-albesilate, iminoctadine-triacetate , imibenconazole, impyrfluxam, imprimatin A, imprimatin B, edifenphos, etaconazol e), ethaboxam, ethyrimol (ethirimol), ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, organic oil (orga nic oils), oxadixyl, oxadinilla oxazinylazole, oxathiapiprolin, oxycarboxin, oxine-copper, oxytetracycline, oxpoconazole fumarate (oxp) oconazole-fumarate), oxolinic acid (oxolinic acid), copper dioctanoate, octilinone, ofurace, orysastrobin, orthophenylphenol, kasugamycin gamycin), captafol, carpropamide ), carbendazim, carboxin, carbone, Candida oleophila, Candida saitoana, quinoxyfen, quinoxyfen quinofumelin, chinomethionat, captan captan, quinconazole, quintozene, guazatine, cufraneb, coumethoxystrobin, coumo xystrobin), Gliocladium catenulatum , Cryptococcus albidus, kresoxim-methyl, clozylacon, Clonostachys rosea, chlozolina te), chloroinconazide, chlorothalonil, chloroneb ), Chaetomium cupreum, Coniothyrium minitans, cyazofamid, diethofencarb, diclocymet , dichlofluanid, dichlobentiazox, diclomezine , dichloran, dichlorophen, dithianon, diniconazole, diniconazole-M, zineb, dinocap, Dipymetitrone, diphenylamine , difenoconazole, cyflufenamide, diflumetrim, cyproconazole, cyprodinil, simecona zole), dimethirimol, dimethyl disulfide, dimethomorph, cymoxanil, dimoxystrobin, Pseudozyma flocculosa, Pseudomonas aureofaciens, Pseudomonas chlororaphis domonas chlororaphis), Pseudomonas syringae, Pseudomonas fluorescens ( Pseudomonas fluorescens), Pseudomonas rhodesiae, ziram, silthiofam, Zucchini yellow mos aic virus), streptomycin, Streptomyces griseoviridis, streptomyces Streptomyces lygicus, spiroxamine, sedaxane, zoxamide, solatenol, dazomet, Tala romyces flavus), thiadinil, thiabendazole, thiram, thiophanate, thiophanate-methyl, thifluzamide, thiram, tecnazene, tecloftal am), tetraconazole, debacarb , tebuconazole, tebufloquin, terbinafine, dodine, dodemorph, triadimenol, triadimefo n), triazoxide, trichlamide, triclopyri triclopyricarb, Trichoderma asperellum, Trichoderma atroviride, Trichoderma gamsii, Trichoderma gamsii Trichoderma stromaticum, Trichoderma paecilomyces, Trichoderma harzianum, Trichoderma Trichoderma viride, Trichoderma virens, Trichoderma polysporum, Trichoderma harzianum ri fai), Trichoderma lignorum, tricyclazole, triticonazole, tridemorph ( tridemorph), triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide ( tolnifanide), tolprocarb, nabam (nabam), natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, copper nonyl ph enol sulfonate), Paenibacillus polymyxa ), Burkholderia cepacia, Bacillus amyloliquefaciens, Bacillus simplex, Bacillus subtilis tilis), Bacillus pumilus, Bacillus mycoides, Bacillus Bacillus licheniformis, harpin protein, Variovorax paradoxus, validamycin, valifenalate, Pantoea a Pantoea agglomerans, picarbutrazox, Bixafen, picoxystrobin, Pythium oligandrum, pydiflumetofen, bitertanol, binapacryl, Hino hinokitiol, non-pathogenic Erwinia carotovora ( Erwinia carotovora), non-pathogenic Rhizobium vitis, biphenyl, piperalin, hymexazol, pyroxystrobin, pyracross pyraclostrobin, pyraziflumid, Pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone, pyrisoxazole, pyridachlomety l), pyrifenox, pyributicarb, pyribencarb , pyrimethanil, pyroquilon, vinclozolin, ferbam, famoxadone, phenazine oxide, fenamidone amidone), phenaminestrobin, fenarimol, fenoxanil, ferimzone, fenpiclonil, fenpicoxamide, fenpyrazamine, fenbuconazole, fenflam (fenfuram), fenpropidin, fenpropimorph (fenpropimorph), fenhexamide, folpet, phthalide, Fusarium oxysporum, bupirimate, fuberidazo le), blasticidin-S, furametpyr, furaxyl, furancarboxylic acid, fluazinam, fluindapyr, fluoxastrobin, fluoxa Piproline (fluoxapiprolin), fluopicolide (fluopicolide), fluopimomide (fluopimomide), fluopyram, fluoroimide, fluxapyroxad, fluquinconazole, fluconazole, flucona furconazole-cis, fludioxonil, flusilazole ( flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxystrobin, flubenete ram), flumetover, flumorph, Phlebiopsis gigantea (Phlebiopsis gigantea), proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole le), bronopol, propamocarb-hydrochloride, propiconazole ( propiconazole), propineb, probenazole, bromuconazole, flometoquin, florylpicoxamide, hexaconazole, benalaxyl, benalaxyl M ( benalaxyl-M), benodanil, benomyl, pefurazoate, penconazole, pencycuron, benzobindiflu pyr), benthiazole, bentiavaricarb isopropyl (benthiavalicarb-isopropyl), penthiopyrad, penflufen, boscalid, fosetyl (contains salts such as aluminum, calcium, sodium, etc.), polyoxin, polycarbamate (pol) ycarbamate), Bordeaux liquid (Bordeaux mixture), mancopper, mancozeb, mandipropamide, mandestrobin, maneb, myclobutanil, mineral oils, mildiomycin ), methasulfocarb, metam, metalaxyl, metalaxyl-M, metiram, methyltetraprole, metconazole zole), metominostrobin ), metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocap, mepronil, iodocarb, Laminarin, phosphorous acid and salts acid and salts), basic copper oxychloride, silver, copper (II) sulfate, cuprous oxide, copper hydroxide, hydrogen carbonate Potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate, (3,4-dichloroisothiazole-5-) yl) methyl 4- (tert-butyl)benzoic acid ester (chemical name, CAS registration number: 1231214-23-5), BAF-045 (code number), BAG-010 (code number), UK-2A (code number), dodecylbenzenesulfone Acid bisethylenediamine copper complex [II] (DBEDC), MIF-1002 (code number), NF-180 (code number), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide ( TPTH), F9650 (code number).

Next, known biological pesticides that may be used in combination or in combination are illustrated below.

Biological pesticides:
Haplothrips brevitubus, Franklinothrips vespiformis, Diglyphus isaea, Encarsia Amblyseius cucumeris, Pseudaphycus malinus, Pseudaphycus malinus (Amblyseius womersleyi), Aphidius colemani, Eretmocerus eremicus, Aphidoletes aphidimyza Amblyseius swirskii), Orius strigicollis, Phytoseius persimilis , Amblyseius degenerans, Phytoseius persimilis, Orius sauteri, Dacnusa sibirica, Dacnusa sibirica, Amblyseius californicus), Chrysoperla nipponensis, ruby red mistletoe Anicetus beneficus.

Next, known agricultural materials that may be used in combination or in combination are illustrated below.

Agricultural materials:
Ethylene, hypochlorous acid water (limited to that obtained by electrolyzing hydrochloric acid or potassium chloride aqueous solution), baking soda, vinegar, humus, humic acid, fulvic acid, seaweed extract, polysaccharides, amino acids, microorganisms Materials, functional ingredients derived from animals and plants, microbial metabolites, microbial activation materials, soil spreading agents, soil permeability regulating materials, soil water retention materials, etc., and biostimulants.

Next, known agricultural fertilizer components that may be mixed or used in combination are illustrated below. Fertilizers include inorganic fertilizers and organic fertilizers.

Agricultural fertilizer ingredients:
Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, ammonium urea nitrate, urea, lime nitrogen, potassium nitrate, lime superphosphate, lime heavy superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, Potassium silicate, oil cake, fish meal, rice bran, bat guano, fermented chicken manure.

The herbicide of the present invention can be applied simultaneously or separately to useful plants, to places where useful plants are to be grown or are growing, or to non-agricultural land. The growth of undesirable plants or plants that are undesirable in terms of land management can be controlled.

In addition, useful plants in the present invention include field crops or paddy crops, horticultural crops (vegetables, fruit trees), ornamental woody plants (flowering trees, roadside trees), grasses, flowers, ornamental plants, It includes medicinal plants and lumber, and examples include, but are not limited to, the following.

Field or paddy crops:
Corn, rice, wheat, durum wheat, barley, rye, triticale, spelt, club wheat, oats, sorghum, cotton, soybeans, alfalfa, peanuts, kidney beans, lima beans, adzuki beans, cowpeas, mung beans, black beans , red beans, bamboo shoots, moss beans, tepary beans, fava beans, peas, chickpeas, lentils, lupine, pigeon peas, buckwheat, sugar beets, rapeseed, canola, sunflowers, sugarcane, cassava, Chinese yam, oil palm, oil palm, hemp, flax, quinoa, Safflower, tea tree, mulberry, tobacco, etc.

Horticultural crops (vegetables):
Solanaceous vegetables (eggplants, tomatoes, green peppers, chili peppers, potatoes, etc.), Cucurbitaceous vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, squash, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock root, Chinese chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (green onions, onions, garlic, asparagus, etc.), Umbelliferous vegetables (carrots, parsley, celery, American cabbage, etc.) ), Chenopodiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (perilla, mint, basil, lavender, etc.), strawberries, sweet potatoes, yam, taro, sesame, etc.

Horticultural crops (fruit trees):
Pome fruits (apples, pears, Japanese pears, Chinese pears, quinces, quinces, etc.), stone fruits (peaches, plums, nectarines, plums, cherry blossoms, apricots, prunes, etc.), citrus fruits (unshu mandarin oranges, oranges, lemons, limes, etc.) Grapefruit, etc.), Nuts (chestnuts, walnuts, hazel, almonds, hazelnuts, pistachios, cashews, macadamia nuts, pecans, etc.), Berries (blueberries, cranberries, blackberries, raspberries, etc.), Grapes, Persimmons, Olives, Loquats , banana, coffee, date palm, coconut palm, oil palm etc.

Ornamental wood (flowering trees, street trees):
Ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redbud, sycamore, sycamore, zelkova, arborvitae, fir tree, hemlock, juniper, pine, spruce, yew, elm, horse chestnut, coralline, dogwood, cedar, Hinoki, croton, masaki, kanamemochi, etc.

Shiba species:
Grass (Japanese grass, Orioles, etc.), Bermudagrass (Japanese grass, etc.), Bentgrass (Japanese grass, Japanese grass, Japanese grass, etc.), Bluegrass (Japanese grass, Japanese grass, etc.), Fescue (Japanese grass, Japanese grass, Japanese grass, etc.) rye grasses (e.g., rat wheat, barley, etc.), staghorn grass, orientalis, etc.

Flowers and ornamental plants:
Roses, carnations, chrysanthemums, lisianthus, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, jabotan, primula, poinsettia, gladiolus, cattleya , daisy, verbena, cymbidium, begonia etc.

Medicinal plants:
Chamomiles, licorice, turmeric, ginseng, orchid, peonies, poppies, etc.

Timber:
Sakhalin spruce, Scots spruce, Pinus, Hiba, Japanese cedar, Cypress, Eucalyptus, etc.

In addition, the useful plants referred to in the present invention include 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors such as isoxaflutole, acetolactate synthase (ALS) inhibitors such as imazethapyr, thifensulfuron-methyl, etc. agents, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl-CoA carboxylase (ACCace) inhibitors such as settoxydim, flumioxazin, epirifenacyl Tolerance to protoporphyrinogen oxidase (PPO) inhibitors such as PPO, photosystem II inhibitors such as bromoxynil, and herbicides such as dicamba and 2,4-D is imparted by classical breeding methods and genetic recombination technology. This also includes plants that have been cultivated.

Examples of "useful plants" that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr. Already sold under the trade name.

Similarly, there is a soybean resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl through classical breeding methods, and it is already sold under the trade name STS soybean. Similarly, sorghum resistant to sulfonylurea-based acetolactate synthase (ALS)-inhibiting herbicides by classical breeding methods is already on the market. Similarly, sugar beets resistant to acetolactate synthase (ALS) inhibiting herbicides that are resistant to thiencarbazones by classical breeding methods are already on the market. Similarly, examples of useful plants that have been made resistant to acetyl-CoA carboxylase (ACCace) inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods include SR corn and quizalofop-resistant wheat. . Useful plants that have been conferred resistance to acetyl-CoA carboxylase (ACCace) 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). In addition, mutant acetyl-CoA carboxylase (ACCace) that is resistant to acetyl-CoA carboxylase (ACCace) inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005). Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing genes into plants using genetic recombination techniques or by introducing mutations that confer resistance into crop acetyl-CoA carboxylase (ACCace). Furthermore, base substitution mutagenic nucleic acids represented by chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) are introduced into plant cells to produce crops (acetyl-CoA carboxylase). Plants resistant to acetyl-CoA carboxylase (ACCace) inhibitors/herbicides can be created by causing site-specific amino acid substitution mutations in the (ACCace)/herbicide target) gene.

Examples of useful plants that have been made resistant by genetic engineering technology include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet, and alfalfa varieties, such as Roundup Ready (registered trademark) and Roundup Ready 2. (Roundup Ready 2) <registered trademark>, Agrisure GT (registered trademark), etc. are already on sale. Similarly, there are varieties of corn, soybean, cotton, and rapeseed that are resistant to glufosinate using genetic recombination technology, and are already being sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynil-resistant cotton produced using genetic recombination technology is already on sale under the trade name BXN. Similarly, soybeans resistant to HPPD inhibitors produced using genetic engineering technology are available under the trade name Herbicide-tolerant Soybean line, which is resistant to mesotrione and glufosinate, and Credenz, which is a variety resistant to HPPD inhibitors, glyphosate, and glufosinate. ) <Registered Trademark> and other product names. Similarly, corn, soybean, and cotton that are resistant to 2,4-D or ACCase inhibitors by genetic recombination technology are already on sale under trade names such as Enlist (registered trademark). Similarly, dicamba-resistant soybeans produced by genetic recombination technology are already on sale as varieties resistant to dicamba and glyphosate under trade names such as Roundup Ready 2 Xtend <registered trademark>. Similarly, a soybean variety that is resistant to HPPD inhibitors such as isoxaflutole and nematode due to HPPD inhibitor resistance through genetic recombination technology has been registered in the United States as GMB151.

Additional plants with engineered resistance to herbicides are widely known, such as alfalfa, apple, barley, eucalyptus, flax, grape, lentil, rapeseed, pea, potato, rice, sugar beet, which are tolerant to glyphosate. , sunflowers, tobacco, tomato beetles and wheat (see e.g. Maize, sorghum and sugarcane (see e.g. WO2008/051633, US7105724 and US5670454), soybean, sugar beet, potato, tomato and tobacco resistant to glufosinate (see e.g. US6376754, US5646024, US5561236), 2,4 - Cotton, peppers, apples, tomatoes, sunflowers, tobacco, potatoes, maize, cucumbers, wheat, soybeans, sorghum and cereals resistant to D ), canola, corn, millet, barley, cotton, mustard, lettuce, lentil, melon, millet, oats, which are resistant to ALS-inhibiting herbicides (e.g., sulfonylurea herbicides or imidazolinone herbicides) machete, potato, rice, rye, sorghum, soybean, sugar beet, sunflower, tobacco, tomato and wheat (see e.g. US5013659, WO2006/060634, US4761373, US5304732, US6211438, US6211439 and US6222100), especially imidazolinone herbicides to Rice plants with resistance are known, including rice plants with specific mutations (e.g., S653N, S654K, A122T, S653(At)N, S654(At)K, A122(At)T) in the acetolactate synthase gene (e.g. , US2003/0217381, WO2005/020673), HPPD-inhibiting herbicides (e.g., isoxazole herbicides such as isoxaflutole, triketone herbicides such as sulcotrione, mesotrione, and pyrazole herbicides such as pyrazolinate), or Barley, sugarcane, rice, corn, tobacco, soybean, cotton, rapeseed, sugar beet, wheat, and potato (e.g., WO2004/055191, WO1996/38567, WO1997/049816) are resistant to diketonitrile, a degradation product of isoxaflutole. and US6791014), and wheat, soybean, cotton, sugar beet, rapeseed, rice, corn, sorghum, sugarcane and sugar beet resistant to PPO-inhibiting herbicides (e.g. US2002/0073443, US2008/0052798, Pest Management Science , 61, 2005, 277-285).

Examples of plants that have been given herbicide resistance using conventional breeding techniques or genome breeding techniques include the rice "Clearfield (registered trademark) Rice" that is resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr and imazamox. ”, wheat “Clearfield <registered trademark> Wheat”, sunflower “Clearfield <registered trademark> Sunflower”, lentil “Clearfield <registered trademark> lentils” and canola “Clearfield <registered trademark> canola”, sulfonyluates such as thifensulfuron-methyl Rare series Soybean ``STS soybean'' is resistant to ALS-inhibiting herbicides, and corn ``SR corn'' is resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides (PoastProtected corn), sunflower ``ExpressSun reg.'', which is resistant to sulfonylurea herbicides such as tribenuron, and rice ``Provisia reg. trademark'', which is resistant to acetyl-CoA carboxylase inhibitors such as quizalofop. ``Rice'', canola ``Triazine Tolerant Canola'' that is resistant to photosystem II inhibitors, and sorghum ``Igrowth <registered trademark>'' that is resistant to imidazolinone herbicides.

SU Canola (<registered trademark>), a plant that is resistant to sulfonylurea herbicides, is a plant that has been given herbicide resistance by genome editing technology. RTDS (registered trademark) is a genome editing technology that refers to oligonucleotide-directed mutagenesis, and refers to Gene Repair Oligonucleotide (GRON), which is a chimeric oligonucleotide of DNA and RNA. This is a technology that allows mutations to be introduced without cutting DNA. Another example is that herbicide resistance and phytic acid content were reduced by deleting the endogenous gene IPK1 using zinc finger nuclease. Examples include corn (see, for example, Nature 459, 437-441, 2009), and rice that has been rendered herbicide tolerant using Crisper casnine (see, for example, Rice, 7, 5, 2014).

An example of a plant that has been given herbicide tolerance through a new breeding technique is soybean, whose scion has been given the properties of a GM rootstock using a breeding technique that utilizes grafting. Specifically, examples include soybean in which glyphosate resistance has been imparted to non-transgenic soybean scions using Roundup Ready (registered trademark) soybean, which has glyphosate resistance, as a rootstock (see Weed Technology 2013, 27, 412). .

The above-mentioned "useful plants" also include plants that have become capable of synthesizing selective toxins, such as those of the genus Bacillus, using genetic recombination technology.

Examples of insecticidal toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab and Cry1 derived from Bacillus thuringiensis. Ac , δ-endotoxin such as Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; scorpion toxin, spider toxin, bee toxins or toxins produced by animals such as insect-specific neurotoxins; filamentous toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Corn-ribosome inactivating proteins (RIPs) such as RIP, abrin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA Examples include reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase.

In addition, toxins expressed in such genetically modified plants include δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34A, Cry34Ab, or Cry35Ab, VIP1, etc. Also included are hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins such as , VIP2, VIP3, or VIP3A. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology. Cry1Ab, which has a partially deleted amino acid sequence, is known as a partially deleted toxin. A modified toxin has one or more amino acids substituted for the naturally occurring toxin.

Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878, WO03/052073, etc. It is described in the patent document of. The toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera, and Lepidoptera pests.

Furthermore, genetically modified plants containing one or more insecticidal insect resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include YieldGard® (a corn variety that expresses the Cry1Ab toxin), YieldGard Rootworm® (a corn variety that expresses the Cry3Bb1 toxin), YieldGard Plus® (a corn variety that expresses Cry1Ab and Cry3Bb1 toxins), Herculex I® (a phosphinophilic variety to confer resistance to Cry1Fa2 toxin and glufosinate) (corn variety expressing tricin N-acetyltransferase (PAT)), NuCOTN33B (registered trademark) (cotton variety expressing Cry1Ac toxin), Bollgard I (registered trademark) (cotton variety expressing Cry1Ac toxin), Bollgard II (registered trademark) (a cotton variety that expresses Cry1Ac and Cry2Ab toxins), VIPCOT (a cotton variety that expresses VIP toxins), NewLeaf (registered trademark) (a cotton variety that expresses Cry3A toxins) NatureGard Agrisure GT Advantage (GA21 glyphosate tolerance trait), Agrisure CB Advantage (Bt11 corn borer) (CB) trait), Protecta (registered trademark), and the like.

The above-mentioned useful plants also include those endowed with the ability to produce antipathogenic substances with selective action using genetic recombination technology.

Examples of antipathogenic substances include PR proteins (PRPs, described in EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (known toxins such as KP1, KP4, and KP6 produced by viruses); ion channel inhibitors such as stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics with heterocycles; protein factors involved in plant disease resistance (called plant disease resistance genes); Examples include substances produced by microorganisms, such as those described in WO03/000906. Such antipathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95/33818, EP-A-0353191, and the like.

The above-mentioned useful plants also include crops that have been endowed with useful traits such as improved oil components and enhanced amino acid content using genetic recombination technology. Examples include VISTIVE (registered trademark) (low linolenic soybean with reduced linolenic content) and high-lysine (high hoil) corn (corn with increased lysine or oil content).

The above-mentioned useful plants also include crops that have been endowed with useful traits such as drought tolerance using genetic modification techniques to maintain or increase yield. Examples include DroughtGard (registered trademark) (drought resistant corn) and the like.

The herbicide of the present invention exhibits a control effect against the above-mentioned pests that have acquired resistance to existing herbicides. Furthermore, the herbicide of the present invention can also be used for plants that have acquired properties such as pest resistance, disease resistance, herbicide resistance, etc. through genetic modification, artificial breeding, etc.

In the present invention, "plants that have been given resistance by breeding methods or genetic recombination technology" include not only plants that have been given resistance by classical breeding or genetic recombination technology, but also plants that have been given resistance by conventional hybridization techniques and molecular biology. This also includes plants that have been given resistance through new plant breeding techniques (NBTs) that combine traditional methods. New breeding techniques (NBTs) are described in the book ``Let's understand new plant breeding techniques'' (Kokusai Bibunsha, written by Ryo Osawa and Hiroshi Emen), and the review article ``Genome Editing Tools in Plants'' (Genes 2017, 8, 399, Tapan Kumar Mohanta). , Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd_Allah and Hanhong Bae), etc. Examples of the above-mentioned new breeding techniques include genome breeding techniques and genome editing techniques. Genomic breeding technology is a technology for increasing the efficiency of breeding using genomic information, and includes DNA marker (also referred to as genomic marker or genetic marker) breeding technology and genomic selection. For example, DNA marker breeding is a method of selecting progeny with a desired useful trait gene from a large number of crossed progeny using a DNA marker, which is a DNA sequence that marks the location of a specific useful trait gene in the genome. be. It has the characteristic that the time required for breeding can be effectively shortened by analyzing the hybrid progeny using DNA markers when they are young plants.

In addition, genomic selection is a method that creates a predictive formula from previously obtained phenotypes and genomic information, and predicts characteristics from the predictive formula and genomic information without evaluating the phenotype, contributing to more efficient breeding. This is a possible technology. New breeding techniques are a general term for breed improvement (breeding) techniques that combine molecular biological techniques. For example, cisgenesis/intragenesis, oligonucleotide-directed mutagenesis, RNA-dependent DNA methylation, genome editing, grafting onto GM rootstocks or scions, reverse breeding, agroinfiltration, and seed production techniques. Technology, SPT). Genome editing technology is a technology that converts genetic information in a sequence-specific manner, and allows deletion of base sequences, substitution of amino acid sequences, introduction of foreign genes, etc. Such tools include, for example, zinc-finger nucleases (ZFNs) capable of sequence-specific cleavage, TALEN, CRISPR/Cas9, and CRISPER/CFP1. Cpf1) and meganuclease. There are also sequence-specific genome modification techniques such as CAS9 nickase and Target-AID created by modifying the aforementioned tools.

Furthermore, regarding the above-mentioned classical herbicide traits or useful traits such as herbicide tolerance genes, insecticidal pest resistance genes, antipathogenic substance producing genes, oil component modification, amino acid content enhancement traits, and drought tolerance traits. , stack types that combine multiple of these are also included.

The non-agricultural land where the herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention are used include, for example, embankment slopes, riverbeds, road shoulders and slopes, railway beds, park green areas, and grounds. , non-agricultural land where it is necessary to control the growth of weeds, such as parking lots, airports, industrial facility sites such as factories and storage facilities, fallow land, or vacant land in urban areas, or orchards, meadows, and lawns. , forestry land, rivers, waterways, canals, reservoirs, etc.

As described above, the herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention have herbicidal efficacy against various weeds. Examples of such weeds are shown below, but the invention is not limited to these examples.

Urticaceae:
Urtica urens.

Polygonaceae:
Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum persicaria (Polygonum longisetum), Polygonum aviculare, Polygonum arenastrum, Japanese knotweed (Polygonum cuspidatum), Rumex japonicus, Rumex crispus, Rumex obtusifolius, Rumex acetosa, Rumex acetosella, Japanese sorrel (Persicaria nepalensis).

Portulacaceae:
Portulaca oleracea.

Caryophyllaceae:
Chickweed (Stellaria media), Stellaria aquatica, Cerastium holosteoides, Cerastium glomeratum, Spergula arvensis), Silene gallica, Stellaria alsine.

Molluginaceae:
Mollugo verticillata.

Amaranthaceae:
Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, Amaranthus spinosus thus hybridus), Amaranthus palmeri, Amaranthus patulus, Water Hemp (Amaranthus tuberculatus = Amaranthus rudis = Amaranthus tamariscinus), American beetle (Amaranthus blitoides), black beetle (Amaranthus deflexus), Amaranthus quitensis, Amaranthus spinosus, Alternanthera phyloxeroides, Alternanthera philoxeroides sessilis), Sanguinaria (Alternanthera tenella), Amaranthus powelii, Amaranthus rudis, Amaranthus albus, Am aranthus viridis), goldenrod (Amaranthus lividus), white-breasted beetle (Amaranthus patulus), and white-spotted plant (Chenopodium album) , Chenopodium ambrosioides, Kochia scoparia, Salsola kali, Atriplex spp.

Papaveraceae:
Papaver rhoeas, Papaver dubium, Argemone mexicana.

Brassicaceae:
Raphanus raphanistrum, Radish (Raphanus sativus), Sinapis arvensis, Capsella bursa-pastoris, Brassica j uncea), Brassica napus, Brassica rapa, and Brassica rapa (Brassica napus). Descurainia pinnata), Rorippa islandica, Rorippa sylvestris, Thlaspi arvense, Myagrum rugosum, Bean Lepidium virginicum, Coronapus didymus, Descurarinia sophia , Rorippa indica, Sisymnrium officinale, Cardamine flexuosa, Nasturtium officinale, Draba nemor osa).

Capparaceae:
Cleome affinis.

Fabaceae:
Aeschynomene indica, zigzag jointed vetch (Aeschynom enerudis), Aeschynomene denticulata, Aeschynomene rudis, American hornwort Sesbania exaltata, Cassia obtusifolia, Cassia occidentalis ), Desmodium tortuosum, Desmodium advances, Desmodium illinoense, Trifolium repens, Pueraria l obata), Vicia angustifolia, Indigofera hirsuta, Indigofera hirsuta Indigofera truxillensis, Vigna sinensis, Crotalaria incana, Vicia sativa, Medicago lupul ina), Vicia hirsuta; Kummerowia striata , Medicago polymorpha.

Oxalidaceae:
Oxalis corniculata, Oxalis strica, Oxalis oxyptera, Oxalis debilis.

Geraniaceae:
Geranium carolinense, Erodium cicutarium, Dove's Foot Crane's-bill (Geranium molle), Hedgerow Crabe's-bill (Geraniu) m pyrenaicum).

Euphorbiaceae (Euphorbiaceae):
Euphorbia helioscopia, Euphorbia maculata, Euphorbia hum istrata, Euphorbia esula, Euphorbia maculata Bia heterophylla), hyssop leaf sand mat (Euphorbia brasiliensis), hackberry (Acalypha australis), tropic Croton glandulosus, Croton lobatus, Phyllanthus corcovadensis, Ricinus com munis, Astraea lobat a), Chamaesyce hirta, Chamaesyce hyssopifolia .

Malvaceae:
Abutilon theophrasti, Sida rhombiforia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santalemnensis (Sida santaremnensis), Sida urens, Hibiscus trionum, Anoda cristata, Malvastrum corom andelianum, and Triumfetta rhomboidea.

Onagraceae:
Ludwigia epilobioides, Ludwigia octovalvis, Ludwigia decurre, Ludwigia leptocarpa, Oeno thera biennis), Oenothera laciniata.

Sterculiaceae (Sterculiaceae):
Walteria indica

Viola family weeds (Violaceae): Viola arvensis, wild pansy (Viola tricolor).

Cucurbitaceae:
Sicyos angulatus, wild cucumber (Echinocystis lobata), bitter melon (Momordica charantia).

Lythraceae:
Ammannia multiflora, Ammannia auriculata, Ammannia coccinea, Lythrum salicaria, Ro tala indica).

Elatinaceae:
Chickweed (Elatine triandra), California waterwort (Elatine californica).

Umbelliferous weeds (Apiaceae):
Japanese parsley (Oenanthe javanica), wild ginseng (Daucus carota), hemlock ginseng (Conium aculatum), and cyclospermum leptophyllum.

Araliaceae weeds (Araliaceae):
Hydrocotyle sibthorpioides, Brazilian Hydrocotyle ranunculoides.

Ceratophyllaceae:
Ceratophyllum demersum.

Cabom baceae:
Cabomba caroliniana.

Haloragaceae:
Myriophyllum aquaticum, Myriophyllum verticillatum, Myriophyllum matogrossense, Myriophyllum sp. icatum, Myriophyllum heterophyllum, etc.).

Sapindaceae:
Cardiospermum halicacabum.

Primulaceae (Prim ulaceae):
Blue chickweed (Anagallis arvensis).

Asclepiadaceae (Asclepiadaceae):
Milkweed (Asclepias syriaca), honeyvine milkweed (Ampelamus albidus).

Rubiaceae (Rubiaceae):
Gallium aparine, Gallium spurium var. echinospermon, Spermacoce latifolia, Diodella teres, Brazillian aparine Richardia brasiliensis, winged phallus buttonweed (Borreria alata).

Convolvulaceae:
Ipomoea nil, Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacea var. integriuscula, Ipomoea hederacea ea lacunosa), Ipomoea triloba, Ipooea acuminata, Ipomoea hederifolia, Ipomoea coccinea, Ipomoea quamoclit, Ipomoea grandifolia, Ipomoea aristolochiafolia oea aristolochiafolia), Ipomoea cairica, Convolvulus arvensis , Calystegia hederacea, Convolvulus (Calystegia japonica), Merremia hedeacea, Hairy woodrose (Merremia aegyptia), Roadside woodrose (Merremia cissoides), Jacquemontia tamnifolia.

Boraginaceae:
Forget-me-not (Myosotis arvensis), Myosotis arvensis, Lithospermum officinale, Echium plantagineum, Hel iotropium indicum).

Lamiaceae:
Lamium purpureum, Lamium amplexicaule, Leonotis nepetaefolia, Hyptis suaveolens, Hyptis suaveolens is lophanta), swordfish (Leonurus sibiricus), stagfish (Stachys arvensis), yakumosou (Leonurus sibiricus) , Marsypianthes chamaedrys.

Solanaceae weeds (Solanaceae):
Datura stramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum ptycanthum m sarrachoides), tomato solanum (Solanum rostratum), golden eggplant (Solanum aculeatissimum), Wild tomato (Solanum sisym briifolium), Solanum carolinense, Physalis angulata, Smooth ground cherry (Physalis subglabrata), Nicandra physaloids).

Linderniaceae:
Azena (Lindernia procumbens), American Zena (Lindernia dubia), Red pepper (Lindernia angustifolia).

Plantaginaceae:
Plantago asiatica, Plantago lanceolata, Plantago major, Callitriche palustris, Limnophila sessiliflora), Dopatrium junceum, Gratiola japonica, Bacopa rotundifolia, Bacopa rotundifolia (Veronica hederaefolia), Veronica persica, Veronica arvensis, Veronica anagallis-aquatica, Plantago mentosa (Plantago tomentosa).

Asteraceae weeds (Asteraceae):
Xantium pensylvanicum, Xantium occidentale, Xantium italicum, Sunflower (Helianthus annuus), Matricaria chamomilla), dog honey (Matricaria perforata), corn marigold (Chrysanthemum segetum), oroshagi (Matricaria matricarioides), Artemisia princeps, Artemisia vulgaris, Chinese mugwort (Artemisia verlotorum), Solidago altissima, Tara xacum officinale), Galinsoga ciliata, Galinsoga parviflora, Senecio Senecio brasiliensis, Senecio grisebachii, Conyza bonariensis, Conyza sumatrium Conyza canadensis), Conyza canadensis, Ambrosia artemisiifolia, Ambrosia trifida, Bidens tripartita, Bidens pilosa, Bidens frondosa, Bidens subalternans, Cirsium arvense ), Cirsium vulgare, Silybum marianum, Mask chistle (Carduus nutans), spiny teal (Lactuca serriola), Japanese poppy (Sonchus oleraceus), Japanese poppy (Sonchus asper), beach creeping oxeye (Wedelia glauca), perforated blackfoot (Mela) mpodium perfoliatum), Emilia sonchifolia, Nancaius Emilia fosbergii, Tagetes minuta, Blainvillea latifolia, Blainvillea dichotoma, Tridax pro cumbens), Yerba porosa (Porophyllum ruderale), Paraguayan starbur (Acanthospermum australe), Bristle tree Starbar (Acanthospermum hispidum), Cardiosperm um halicacabum, Cuckoo thistle (Ageratum conyzoides), Common bone set (Eupatorium perfoliatum), Americana Eclipta alba, Erechtites hieracifolia, American Everlasting (Gamochaeta spicata) , Gnaphalium spicatum, Jaegeria hirta, Parthenium hysterophorus, Siegesbeckia orientalis, S. oliva sessilis), Eclipta prostrata, Centipeda minima, Anthemis cotula), Cirsium setosum, Centurea cyanus, Coreopsis lanceolata, Rudbeckia hirta, Rudbe Rudbeckia laciniata), Rudbeckia laciniata var. hortensis Bailey), Bidens subaltemans, water sunflower (Gymnocoronis spilanthoides), Hypochaeris chillensis, Pulkea sagitalis (Pluchea sagittalis).

Alism ataceae:
Sagittaria pygmaea, Sagittaria trifolia, Sagittaria sagittifolia, Sagittaria montevidensis, Aginashi (Sagittaria aginashi), Alisma canaliculatum, and Alisma plantago-aquatica.

Limnocharitaceae:
Limnocharis flava.

Hydrocharitaceae:
Frogbit (Limnobium spongia), Black moth (Hydrilla verticillata), Common water nymph (Najas guadalupensis), Giant canada moth (Egeria densa).

Araceae (Araceae):
Pistia stratiotes.

Lemnaceae:
Lemna aoukikusa, Spirodela polyrhiza, Wolffia globosa.

Potamogetonaceae:
Potamogeton distinctus, pondweeds (Potamogeton crispus, Potamogeton illinoensis, Stuckenia pectinata, etc.).

Liliaceae (Liliaceae):
Wild onion (Allium canadense), wild garlic (Allium vineale), Nobile (Allium macrostemon).

Water mallow family weeds:
Eichhornia crassipes, Heteranthera limosa, Monochoria korsakowii, Monochoria vaginalis, Heteranthera reniformis ndera reniformis).

Commelinaceae:
Commelina communis, Commelina bengharensis, elect dayflower (Commelina erecta), Murdannia keisak, Doveweed (Murdannia nudiflora).

Poaceae:
Golden millet (Echinochloa crus-galli), Golden millet (Echinochloa oryzicola), Golden millet (Echinochloa crus-galli var formosensis), Late watergrass (Echinochloa oryzoides), Echinochloa corona, Gulf cockspur (Echinochloa crus-pavonis), Green foxtail grass (Setaria viridis), Setaria faberi, Setaria glauca, Setaria geniculata, Digitaria ciliaris, large crabgrass (D igitaria sanguinalis), Jamaican crabgrass (Digitaria horizontalis), silver grass ( Digitaria insularis), Eleusine indica, Poa annua, Poa trivialis, Poa pratensis, Alosp ecurus aequalis), blackgrass (Alopecurus myosuroides), oat (Avena fatua), Saban sorghum (Sorghum halepense), Sorghum vulgare, Sorghum arundinaceum, Agropyron repens, Lolium multiflorum, Hoso Wheat (Lolium perenne), barley (Lolium rigidum), barley (Bromus catharticus) ), Bromus sterilis, Bromus japonicus, Bromus secalinus, Bromus tectorum, Hordeum j ubatum), Goat wheat (Aegilops cylindrica), Phalaris arundinacea, Phalaris arundinacea Phalaris minor), Silky bentgrass (Apera spica-venti), Panicum dichotomiflorum, Texas Panicum (Panicum texanum), Guinea millet (Panicum maximum), Melicium Millet (Brachiaria platyphylla), Ruzi grass (Brachiaria ruziziensis), Alexander grass ( Brachiaria plantaginea), Surinam grass (Brachiaria decumbens), palisades grass (Brachiaria brizantha), Columbia grass (Brachiaria humidicola), paragrass (Urochloa muti) ca), Cenchrus echinatus, Cenchrus pauciflorus, Eriochloa villosa, Africa Chloris gayana, Chloris virgata, Eragrostis pilosa, Eragrostis plana, Rhynchelitrum repens, Tatsuno Dactyloctenium aegyptium, Ischaem um rugosum, Isachne globosa), rice (Oryza sativa), Paspalum notatum, Coastal sand Paspalum (Paspalum maritimum), Paspalum distichum, Kikuyu grass (Pennis) etum clandestinum), Pennisetum setosum, Horned snail (Rottboellia cochinchinensis) , Leptochloa chinensis, Leptochloa fascicularis, Leptochloa panicea, Leptochloa filiformis, Amazon sprangle top (Leptochloa filiformis) Leptochloroa panicoides), Leersia japonica, Formosan sea lion (Leersia hexandra), Leersia sayanuka), Leersia oryzoides, Glyceria leptorrhiza, Glyceria acutiflora, Glyceria acutiflora Maxima), Agrostis gigantea, Agrostis stolonifera, Cynodon dactylon, Cynodon dactylon ( Dactylis glomerata), Centipede (Eremochloroa ophiuroides), Festucaarun dinacea, Festuca rubra, Imperata cyli ndrica), Miscanthus sinensis, Switchgrass (Panicum virgatum), Zoysia japonica, Rudiolapel Viana (Luziola peruviana), ruby grass (Melinis repens), Spartina anglica (Spartina anglica).

Cyperaceae (Cyperaceae):
Cyperus microiria, Cyperus iria, Cyperus compressus, Cyperus difformis, Cyperus flaccidu s), Cyperus globosus, Cyperus nipponics, Cyperus odoratus, Cyperus odoratus ( Cyperus serotinus), Cyperus rotundus, Cyperus esculentus, Kyllinga gracilima, Kyllinga brevifolia, Hyderico (Fimbristylis miliacea), Japanese woodpecker (Fimbristylis dichotoma), Pine fly (Eleocharis acicularis), Black grub (Eleocharis kuroguwai) ), Schoenoplectiella hotarui, Schoenoplectiella juncoides, Schoenoplectiella wallichii, Schoenoplec Schoenoplectiella triangulatus), Schoenoplectiella triangulatus, Schoenoplectiella nipponicus, Schoenoplectiella triqueter ), Bolboschoenus koshevnikovii ), Bolboschoenus fluviatilis, Scirpus tabernaemontani.

Equisetaceae:
Equisetum arvense, Equiset umpalustre.

Salvinaceae:
Salvinia natans.

Azollaceae:
Azolla japonica, Azollaim bricata, Salvinia natanas, Azolla cristata.

Marsileaceae:
Marsilea quadrifolia.

Ricciaceae:
Ginkgo moss (Ricciocarpus natans).

Rosaceae weeds:
Alchemilla monticola.

Ranunculaceae:
Ranunculus muricatus, Ranunculus sardous.

Fumarioideae:
Fumaria officialis.

Characeae:
Chara braunii.

Eriocaulaceae:
Eriocaulon cinereum.

Zygnemataceae:
Spirogyra arcla.

others:
Filamentous algae (Pithophora, Cladophora), mosses, liverworts, hornworts, cyanobacteria, ferns, suckers of perennial crops (pome fruits, stone fruits, berry fruits, nuts, citrus fruits, hops, grapes, etc.) (sucker).

Regarding the above-mentioned weeds, intraspecific variation is not particularly limited. That is, it includes herbicides with reduced sensitivity (also referred to as resistance) to specific herbicides. The decrease in sensitivity may be due to a mutation in the target site (effecting point mutation) or may be due to a factor other than an effecting point mutation (non-effecting point mutation). Effect point mutations include amino acid substitutions in the protein target site due to mutations in the nucleic acid sequence portion (open reading frame) corresponding to the amino acid sequence of the protein, deletion of suppressor sequences in the promoter region, and enhancer sequences. This includes those in which the protein at the target site is expressed in excess or in a reduced amount due to amplification of the gene, or mutation such as increase or decrease in the copy number of the gene. Non-effect point mutations include increased metabolism, malabsorption, malabsorption, and excretion from the system. Factors for increased metabolism include increased activity of metabolic enzymes such as cytochrome P450 monooxygenase, arylacyl amidase, esterase, and glutathione S-transferase. Excretion from the system includes transport to the vacuole by ABC transporters.

Examples of herbicide-resistant weeds include resistance to 5-enolpyruvylshikimic acid-3-phosphate (EPSP) synthase inhibitors such as glyphosate, and hormone-disrupting herbicides such as 2,4-D and dicamba. resistance, acetolactate synthase (ALS) inhibitor resistance, acetyl-CoA carboxylase (ACCace) inhibitor resistance, protoporphyrinogen oxidase (PPO) inhibitor resistance, auxin herbicide resistance, 4-hydroxy Phenylpyruvate dioxygenase (4-HPPD) inhibitor resistance, photosystem II inhibitor resistance, photosystem I electron converter resistance, carotenoid biosynthesis inhibitor resistance, glutamine synthetase inhibitor resistance, phytoene depletion Saturation enzyme system (PDS) inhibitor resistance, fatty acid biosynthesis inhibitor resistance, very long chain fatty acid elongation enzyme (VLCFAE) inhibitor resistance, auxin transport inhibitor resistance, dihydropteroic acid (DHP) synthase Examples include resistance to inhibitors, resistance to cellulose synthase inhibitors, resistance to microtubule polymerase inhibitors, resistance to mitosis/microtubule formation inhibitors, and the like.

The resistant weeds belong to two or more of the above groups (2 groups arbitrarily selected, 3 groups arbitrarily selected, 4 groups arbitrarily selected, 5 groups arbitrarily selected, 6 groups, 7 groups, Even stacked resistant weeds that have resistance to (Group 8) can be effectively controlled. Examples of stacked resistant weeds include acetolactate synthase (ALS) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, photosystem II Waterhemp, which is known to be resistant to all inhibitors and 2,4-D, can also be effectively controlled. The above stack may be a combination of working point mutations, a combination of non-working point mutations, or a combination of working mutations and non-working point mutations.

The herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention are applied simultaneously or separately to useful plants, to areas where useful plants are to be grown or are being grown, or to non-agricultural land. If applied multiple times, apply once or multiple times. Weeds may already be present in the plant or the area where the plant is cultivated, or may even be present before the weeds emerge.

The herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention are applied simultaneously or separately to useful plants, to areas where useful plants are to be grown or are being grown, or to non-agricultural land. Examples of the application methods include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment, seed treatment, and hydroponic solution treatment.

As for foliage treatment, for example, the herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention are applied to foliage, tree trunks, fruits, flowers (including before, during, and after flowering), panicles, or whole plants. An example of this method is to treat the surface of

Examples of soil treatments include soil spraying, soil mixing, and irrigation of soil with chemical solutions. Places for soil treatment include, for example, the planting hole, the planting row, the vicinity of the planting hole, the vicinity of the planting row, the entire surface of the cultivation area, the edge of the plant, between plants, under the tree trunk, in the main stem ridge, in soil, in seedling boxes, and in the seedling nursery. Examples include trays, seedbeds, etc. Examples of the treatment time include before sowing, at the time of sowing, after sowing, during the seedling-raising period, before planting, at the time of planting, and during the growth period after planting. In addition, in the above soil treatment, the herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention may be mixed with irrigation solution, for example, by adding the herbicide of the present invention to irrigation equipment (irrigation tubes, irrigation pipes, sprinklers, etc.). Examples include injection, contamination with inter-row flooding solution, and contamination with hydroponic solution. Alternatively, the irrigation solution and the active ingredient may be mixed in advance and treated using, for example, the above-mentioned irrigation method or other appropriate irrigation methods such as sprinkling or flooding.

Root treatments include, for example, a method of immersing the roots in a chemical solution containing the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention; Examples include a method in which a solid preparation containing a substance is attached to the roots of a plant.

Examples of the shower treatment include a method of showering a diluted solution of the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention onto the stems and leaves of plants.

Examples of the fuming treatment include a method in which a diluted solution of the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention is made into a mist, dispersed in the air, and adhered to the foliage, etc. of plants. .

Water surface treatment includes, for example, a method of spraying a chemical solution or solid preparation containing the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention onto a flooded paddy field.

Seed treatments include, for example, treating seeds or vegetative reproductive organs with the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention. The above-mentioned vegetative reproductive organs include in particular seed potatoes.

As the hydroponic solution treatment, for example, a method of mixing or mixing into the hydroponic solution a chemical solution or solid preparation containing the herbicide of the present invention and an agricultural chemical composition containing the herbicide of the present invention (hydroponic solution mixing treatment, (cultivation liquid mixing treatment, etc.).

The herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention can also be applied by spot treatment. Spot treatment is a concept that is opposed to uniformly treating the herbicide of the present invention and the agrochemical composition containing the herbicide of the present invention. It means a treatment in which the herbicide of the present invention and an agrochemical composition containing the herbicide of the present invention are selectively sprayed on possible locations. "Treatment in place" means treating plants or soil where weeds are or are likely to be infested. In addition, spot treatment does not mean only when all areas where weeds are growing or where weeds are likely to grow in a continuous cultivation area are selectively treated. That is, if a part of the cultivated land is subjected to surface treatment, or if a part of the area where weeds are growing or where weeds are likely to grow is treated with the herbicide of the present invention or the herbicide of the present invention. Even if the crop is not treated with the agrochemical composition containing the crop, if there is a spot-treated area in a continuous cultivation area, it is included in the spot treatment.

Next, the manufacturing method, formulation method, and use of the compound of the present invention will be explained in detail in the following examples, but the present invention is not limited to these examples in any way.

The melting point, which is a physical property value, of the compound of the present invention was measured using a micro melting point measuring device manufactured by Yanaco MP-500V. The refractive index was measured using an Abbe refractometer manufactured by Atago. ^{The 1} H NMR spectrum was measured using JNM-LA400 (400 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL, with tetramethylsilane (TMS) as an internal standard. High-resolution mass spectrometry spectra (HRMS) were measured using Q Exactive Focus Hybrid Quadrupole-Orbitrap LC-MS/MS System (ESI, positive mode) manufactured by Thermo Fisher Scientific.

Further, production examples of production intermediates of the compounds of the present invention are also described.
[Example 1]
Production of 3-chloro-7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-indole (compound number of the present invention: A-0032) :
(1) Production of 7-[(5-chloropyrimidin-2-yl)oxy]-1H-indole (compound number of the present invention: A-0001):
To a mixture of 0.75 g (5.63 mmol) of 1H-indol-7-ol and 10 mL of N,N-dimethylformamide, 0.27 g (6.19 mmol, calculated as purity 55%) of sodium hydride was added under ice cooling. The mixture was stirred for 5 minutes while maintaining the same temperature. Thereafter, 1.01 g (6.78 mmol) of 2,5-dichloropyrimidine was added under ice cooling, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the mixture was made acidic by adding 1N hydrochloric acid, and then extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 20:1 to 3:1) to obtain 0.87 g (yield: 63%) of the target product. Ta.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.50 (2H, s), 8.24 (1H, brs), 7.56 (1H, d), 7.20 (1H, t), 7.14 (1H, t), 7.05 (1H, d), 6.62 (1H, dd)

(2) Production of 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-indole (compound number of the present invention: A-0004):
1 to a mixture of 0.33 g (1.34 mmol) of 7-[(5-chloropyrimidin-2-yl)oxy]-1H-indole, 0.37 g (2.68 mmol) of potassium carbonate, and 5 mL of N,N-dimethylformamide. , 0.38 g (1.60 mmol) of 1,1-trifluoro-4-iodobutane was added, and the mixture was stirred at 80°C for 11 hours. ), 0.87 g (2.67 mmol) of cesium carbonate was further added, and the mixture was stirred at 80° C. for 10.5 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 100:1 to 4:1) to obtain 0.28 g (yield: 59%) of the target product. Ta.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.51 (2H, s), 7.53 (1H, d), 7.11 (1H, t), 7.02 (1H, d), 6.96 (1H, d), 6.55 (1H, d), 4.21 (2H, t), 2.03-1.96 (4H, m)

(3) 3-chloro-7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-indole (compound number of the present invention: A-0032 )Manufacturing of:
A mixture of 0.20 g (0.56 mmol) of 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-indole and 8 mL of acetonitrile was cooled with ice. Next, 0.08 g (0.60 mmol) of N-chlorosuccinimide was added, and the mixture was stirred for 3 hours while maintaining the same temperature, and then stirred at room temperature for 18 hours. After the reaction was completed, an aqueous sodium thiosulfate solution was added, followed by extraction with dichloromethane and drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 20:1 to 6:1) to obtain 0.18 g (yield: 82%) of the target product. Ta.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.51 (2H, s), 7.54 (1H, d), 7.19 (1H, t), 7.04-7. 01 (2H, m), 4.18 (2H, t), 2.02-1.96 (4H, m)

[Example 2]
7-[(5-chloropyrimidin-2-yl)oxy]-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole-3-carbonitrile ( Production of compound number: B-0376) of the present invention:
(1) Production of 3-iodo-7-methoxy-1H-indazole:
A mixture of 7.51 g (51.1 mmol) of 7-methoxy-1H-indazole, 16.1 g (71.6 mmol) of N-iodosuccinimide, and 100 mL of isopropyl alcohol was stirred at 45° C. for 7 hours. After cooling at room temperature, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5:1) to obtain 8.75 g of the target product (yield: 63 %)Obtained.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.13 (1H, t), 7.08 (1H, d), 6.80 (1H, d), 3.98 (3H, s)

(2) Production of 3-iodo-7-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole:
2.39 g (8.72 mmol) of 3-iodo-7-methoxy-1H-indazole, 2.53 g (9.46 mmol) of 1-(2-bromoethyl)-3-(trifluoromethyl)-1H-pyrazole, potassium carbonate A mixture of 1.45 g (10.5 mmol) and 20 mL of N,N-dimethylformamide was stirred at 100° C. for 6 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 2.56 g (yield: 67%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.06 (1H, t), 7.00 (1H, d), 6.73 (1H, d), 6.66 (1H, d), 6.22 (1H, d), 5.08 (2H, t), 4.67 (2H, t)

(3) Production of 3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazol-7-ol:
In a mixture of 1.00 g (2.29 mmol) of 3-iodo-7-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole and 20 mL of dichloromethane. , 6.90 mL of boron tribromide (1 mol/L dichloromethane solution) was added under ice cooling, and the mixture was stirred at room temperature for 13 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was used as it was in the next step without purification.

(4) 7-[(5-chloropyrimidin-2-yl)oxy]-3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H- Production of indazole (compound number of the present invention: B-0304):
Crude 3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazol-7-ol, 0.44 g (2 A mixture of 0.41 g (2.97 mmol) of potassium carbonate, and 20 mL of N,N-dimethylformamide was stirred at 100° C. for 7 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 10:1) to obtain 1.26 g of the target product (yield quantitative, 2 steps). .

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.50 (2H, s), 7.41 (1H, d), 7.39 (1H, d), 7.25 (1H, t), 7.16 (1H, d), 6.33 (1H, d), 4.85 (2H, t), 4.62 (2H, t)

(5) 7-[(5-chloropyrimidin-2-yl)oxy]-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole-3- Production of carbonitrile (compound number of the present invention: B-0376):
7-[(5-chloropyrimidin-2-yl)oxy]-3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole0. A mixture of 70 g (1.31 mmol), 0.36 g (4.02 mmol) of copper(I) cyanide, and 5 mL of N,N-dimethylacetamide was stirred at 140° C. for 16 hours. After cooling at room temperature, insoluble matter was filtered through Celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4:1) to obtain the desired product. 0.35 g (yield 62%) of the product was obtained.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.52 (2H, s), 7.73 (1H, d), 7.38 (1H, t), 7.33 (1H, d), 7.23 (1H, d), 6.36 (1H, d), 4.96 (2H, t), 4.70 (2H, t)

[Example 3]
7-[(5-chloropyrimidin-2-yl)oxy]-3-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole Production of compound number of the invention: B-0384):
(1) Production of 7-(benzyloxy)-3-iodo-1H-indazole:
7-methoxy-1H-indazole 10.14g (45.2mmol), iodine 17.21g (67.8mmol), potassium hydroxide 8.41g (127.0mmol, converted as purity 85%), N,N-dimethylformamide The 200 mL mixture was stirred at room temperature for 4 hours. After the reaction was completed, an aqueous sodium thiosulfate solution was added, and the mixture was further stirred at room temperature for 1 hour. Ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 15.85 g of the crude target product (yield quantitative).

(2) Production of 7-(benzyloxy)-3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole:
7-(benzyloxy)-3-iodo-1H-indazole 7.86 g (22.4 mmol), 1-(2-bromoethyl)-3-(trifluoromethyl)-1H-pyrazole 5.99 g (24.6 mmol) , 3.40 g (24.6 mmol) of potassium carbonate, and 100 mL of N,N-dimethylformamide was stirred at 80° C. for 6 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 8.56 g (yield: 74%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.45-7.39 (5H, m), 7.08-7.04 (2H, m), 6.81 (1H, d ), 6.70 (1H, d), 6.25 (1H, d), 5.11 (2H, s), 5.05 (2H, t), 4.61 (2H, t)

(3) Production of 7-(benzyloxy)-3-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole:
7-(benzyloxy)-3-iodo-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole 1.00 g (1.95 mmol), cesium carbonate 1.27 g (3.90 mmol), copper(I) iodide 0.08 g (0.42 mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline 0.18 (0.76 mmol), methanol 30 mL of the mixture was stirred at 120° C. for 6 hours under nitrogen atmosphere. After cooling at room temperature, insoluble matter was filtered through Celite, the solvent was distilled off under reduced pressure, and the target product was purified by silica gel column chromatography (developing solvent: n-hexane: ethyl acetate = 10:1). 0.78 g (yield 96%) was obtained.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.19 (1H, t), 7.13-6.93 (9H, m), 5.22 (2H, s), 4. 17 (2H, t), 3.53 (2H, t), 3.53 (3H, s)

(4) Production of 3-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazol-7-ol:
7-(benzyloxy)-3-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazole 0.78 g (1.87 mmol), 10% A mixture of 0.16 g of Pd/C and 50 mL of tetrahydrofuran was stirred at room temperature under a hydrogen atmosphere (normal pressure) for 5 hours. After the reaction was completed, the mixture was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain 0.60 g (yield: 98%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.15 (1H, d), 7.02 (1H, d), 6.83 (1H, t), 6.68 (1H, d), 6.31 (1H, d), 4.94 (2H, t), 4.62 (2H, t), 4.04 (3H, s)

(5) 7-[(5-chloropyrimidin-2-yl)oxy]-3-methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H- Production of indazole (compound number of the present invention: B-0384):
3-Methoxy-1-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}-1H-indazol-7-ol 0.18 g (0.55 mmol), 2,5-dichloro A mixture of 0.11 g (0.74 mmol) of pyrimidine, 0.10 g (0.72 mmol) of potassium carbonate, and 5 mL of N,N-dimethylformamide was stirred at 80° C. for 4 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 8:1) to obtain 0.15 g (yield: 62%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.49 (2H, s), 7.54 (1H, d), 7.15 (1H, d), 7.11 (1H, d), 7.06 (1H, t), 6.32 (1H, d), 4.60 (2H, t), 4.53 (2H, t), 4.04 (3H, s)

[Example 4]
7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-3-(trifluoromethyl)-1H-indazole (compound number of the present invention: B- Production of 0328):
(1) Production of 2,2,2-trifluoro-1-[2-fluoro-3-(methoxymethoxy)phenyl]ethan-1-one:
To a mixture of 2.39 g (23.6 mmol) of diisopropylamine and 20 mL of tetrahydrofuran, 14.8 mL of n-butyllithium (1.6 mol/L hexane solution) was added dropwise at −78° C. under a nitrogen atmosphere. After the dropwise addition was completed, the mixture was stirred at 0°C for 30 minutes, and then 3.12 g (20.0 mmol) of 1-fluoro-2-(methoxymethoxy)benzene was added dropwise at -78°C. After the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining the same temperature. 3.50 g (24.6 mmol) of ethyl trifluoroacetate was added dropwise to the above reaction mixture while maintaining the same temperature, and the mixture was further stirred at 0° C. for 2 hours. After the reaction was completed, 2N hydrochloric acid was added and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 4:1) to obtain 1.82 g (yield: 36%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.57-7.47 (2H, m), 7.22 (1H, t), 5.26 (2H, s), 3. 54 (3H, s)

(2) Production of 7-(methoxymethoxy)-3-(trifluoromethyl)-1H-indazole:
2,2,2-trifluoro-1-[2-fluoro-3-(methoxymethoxy)phenyl]ethan-1-one 1.00 g (3.97 mmol), anhydrous hydrazine 2.53 g (79.3 mmol), 1 A mixture of 20 mL of ,4-dioxane was stirred at 100°C for 5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 3N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 2:1) to obtain 0.68 g (yield: 70%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.50 (1H, d), 7.20 (1H, t), 7.10 (1H, d), 5.34 (2H, s), 3.61 (3H, s)

(3) Production of 7-(methoxymethoxy)-1-(4,4,4-trifluorobutyl)3-(trifluoromethyl)-1H-indazole:
7-(methoxymethoxy)-3-(trifluoromethyl)-1H-indazole 0.30 g (1.22 mmol), 1,1,1-trifluoro-4-iodobutane 0.35 g (1.47 mmol), potassium carbonate A mixture of 0.20 g (1.45 mmol) and 10 mL of N,N-dimethylformamide was stirred at 100° C. for 5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.38 g (yield: 88%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.43 (1H, d), 7.17 (1H, t), 7.08 (1H, d), 5.38 (2H, s), 4.78 (2H, t), 3.55 (3H, s), 2.26-2.15 (4H, m)

(4) Production of 1-(4,4,4-trifluorobutyl)3-(trifluoromethyl)-1H-indazol-7-ol:
7-(methoxymethoxy)-1-(4,4,4-trifluorobutyl)3-(trifluoromethyl)-1H-indazole 0.38 g (1.07 mmol), 3N hydrochloric acid 1.78 mL (5.34 mmol) , tetrahydrofuran (5 mL) was stirred at 50° C. for 8 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 1:1) to obtain 0.19 g (yield: 57%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.39 (1H, d), 7.09 (1H, t), 6.74 (1H, d), 4.78 (2H, t), 2.27-2.11 (4H, m)

(5) 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-3-(trifluoromethyl)-1H-indazole (compound number of the present invention :B-0328) Production:
1-(4,4,4-trifluorobutyl)3-(trifluoromethyl)-1H-indazol-7-ol 0.18 g (0.58 mmol), 2,5-dichloropyrimidine 0.11 g (0.74 mmol) ), 0.11 g (0.80 mmol) of potassium carbonate, and 10 mL of N,N-dimethylformamide was stirred at 80° C. for 3 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.22 g (yield: 90%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.54 (2H, s), 7.76 (1H, d), 7.32 (1H, t), 7.27 (1H, d), 4.55 (2H, t), 2.10-2.05 (4H, m)

[Example 5]
7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole (compound number of the present invention :C-0002) Production:
(1) Production of 2-methoxy-6-nitro-N-(4,4,4-trifluorobutyl)aniline:
2-methoxy-6-nitroaniline 3.37g (20.0mmol), 1,1,1-trifluoro-4-iodobutane 5.71g (24.0mmol), sodium hydride 1.12g (28.0mmol, purity A mixture of 100 mL of N,N-dimethylformamide (calculated as 60%) was stirred at 100° C. for 7 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 10:1) to obtain 3.78 g (yield: 68%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.74 (1H, d), 6.94 (1H, d), 6.68 (1H, t), 3.86 (3H, s), 3.62 (2H, t), 2.23-2.14 (2H, m), 1.93-1.85 (2H, m)

(2) Production of 6-methoxy-N ¹ -(4,4,4-trifluorobutyl)benzene-1,2-dianiline:
A mixture of 2.45 g (8.81 mmol) of 2-methoxy-6-nitro-N-(4,4,4-trifluorobutyl)aniline, 0.25 g of 10% Pd/C, and 100 mL of methanol was heated under a hydrogen atmosphere (normal pressure). ) and stirred at room temperature for 16 hours. After the reaction was completed, the mixture was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain 2.17 (yield: 99%) of the crude target product.

^1H -NMR data (300MHz, DMSO/TMSδ (ppm)): 6.66 (1H, t), 6.29 (1H, d), 6.22 (1H, d), 4.63 (2H, brs ), 3.71 (3H, s), 2.94-2.86 (2H, m), 2.41-2.26 (2H, m), 1.66-1.56 (2H, m)

(3) Production of 7-methoxy-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole:
In a mixture of 0.97 g (3.91 mmol) of 6-methoxy-N ¹ -(4,4,4-trifluorobutyl)benzene-1,2-dianiline, 1.34 g (13.7 mmol) of sulfuric acid, and 50 mL of water, Under ice cooling, 0.54 g (7.83 mmol) of sodium nitrite was added, and the mixture was stirred at room temperature for 23 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 1:1) to obtain 0.70 g (yield: 69%) of the desired product.

^1H -NMR data (300MHz, DMSO/TMSδ (ppm)): 7.37 (1H, d), 7.33 (1H, t), 7.05 (1H, d), 4.51 (2H, t) ), 3.98 (3H, s), 3.02-2.93 (2H, m), 2.03-1.96 (2H, m)

(4) Production of 7-methoxy-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole:
To a mixture of 0.70 g (2.70 mmol) of 7-methoxy-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole and 20 mL of dichloromethane was added under ice cooling. , 13.5 mL of boron tribromide (1 mol/L dichloromethane solution) was added, and the mixture was stirred at room temperature for 15 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.56 g (yield: 85%) of the crude target product.

^1H -NMR data (300MHz, DMSO/TMSδ (ppm)): 10.77 (1H, brs), 7.42 (1H, d), 7.17 (1H, t), 6.82 (1H, d ), 4.87 (2H, t), 2.35-2.27 (2H, m), 2.22-2.13 (2H, m)

(5) 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole (the present invention Production of compound number: C-0002):
7-methoxy-1-(4,4,4-trifluorobutyl)-1H-benzo[d][1,2,3]triazole 0.35 g (1.43 mmol), 2,5-dichloropyrimidine 0.30 g (2.01 mmol), potassium carbonate 0.28 g (2.03 mmol), and N,N-dimethylformamide 10 mL was stirred at 80° C. for 3 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.38 g (yield: 74%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.54 (2H, s), 7.99 (1H, d), 7.41 (1H, t), 7.32 (1H, d), 4.71 (2H, t), 2.19-2.11 (4H, m)

[Example 6]
7-[(5-chloropyrimidin-2-yl)oxy]-2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazole (compound number of the present invention: D- Production of 0010):
(1) Production of 7-methoxy-2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazole:
A mixture of 0.88 g (3.54 mmol) of 6-methoxy-N ¹ -(4,4,4-trifluorobutyl)benzene-1,2-diamine, 5 mL of acetic acid, and 10 mL of triethyl orthoacetate was heated under reflux for 15 hours. After cooling at room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 4:1 to 1:20) to obtain the desired product. 46 g (yield 48%) was obtained.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.30 (1H, d), 7.13 (1H, t), 6.68 (1H, d), 4.40 (2H, t), 3.95 (3H, s), 2.57 (3H, s), 2.25-2.02 (4H, m)

(2) Production of 2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazol-7-ol:
To a mixture of 0.46 g (1.69 mmol) of 7-methoxy-2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazole and 5 mL of dichloromethane was added three odor under ice cooling. 10.10 mL (10.10 mmol) of boron oxide (approximately 1 mol/L dichloromethane solution) was added, and the mixture was stirred at room temperature for 3 days. After the reaction was completed, a saturated aqueous sodium bicarbonate solution was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.44 g of the crude target product (yield quantitative).

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.25 (1H, d), 7.02 (1H, t), 6.66 (1H, d), 4.49 (2H, t), 2.61 (3H, s), 2.28-2.13 (4H, m)

(3) 7-[(5-chloropyrimidin-2-yl)oxy]-2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazole (compound number of the present invention :D-0010) Production:
0.20 g (0.77 mmol) of 2-methyl-1-(4,4,4-trifluorobutyl)-1H-benzo[d]imidazol-7-ol, 0.14 g (0.77 mmol) of 2,5-dichloropyrimidine. A mixture of 94 mmol), 0.14 g (1.01 mmol) of potassium carbonate, and 5 mL of N,N-dimethylformamide was stirred at 80° C. for 4.5 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 3:2 to 1:4) to obtain 0.18 g (yield: 63%) of the target product. Ta.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.53 (2H, s), 7.60 (1H, d), 7.24 (1H, t), 7.02 (1H, d), 4.19 (2H, t), 2.59 (3H, s), 2.19-1.91 (4H, m)

[Example 7]
4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 (3H) Production of -one (compound number of the present invention: E-0211):
(1) Production of 4-[(5-chloropyrimidin-2-yl)oxy]benzo[d]oxazol-2(3H)-one (compound number of the present invention: E-0001):
4-hydroxybenzo[d]oxazol-2(3H)-one 23.60g (0.156mol), 2,5-dichloropyrimidine 34.68g (0.233mol), potassium carbonate 22.64g (0.164mol), A mixture of 320 mL of N,N-dimethylformamide was stirred at 50° C. for 8 hours. After the reaction was completed, ethyl acetate, hexane and water were added, the aqueous layer was extracted, 3N hydrochloric acid was added to the obtained aqueous layer, extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. , dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 20.20 g (yield: 49%) of the crude target product.

(2) 4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 Production of (3H)-one (compound number of the present invention: E-0211):
4-[(5-chloropyrimidin-2-yl)oxy]benzo[d]oxazol-2(3H)-one 11.20 g (42.5 mmol), 1-(2-bromoethyl)-3-(trifluoromethyl A mixture of 12.36 g (50.9 mmol) of )-1H-pyrazole, 7.06 g (51.1 mmol) of potassium carbonate, and 150 mL of N,N-dimethylformamide was stirred at 100° C. for 8 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 4:1) to obtain 11.25 g (yield: 62%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.53 (2H, s), 7.44 (1H, d), 7.16 (1H, t), 7.04 (1H, d), 7.02 (1H, d), 6.85 (1H, d), 6.44 (1H, d) 4.50 (2H, t), 4.26 (2H, t)

[Example 8]
4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 (3H) -Production of thione (compound number of the present invention: E-0280):
(1) Production of N-[2,6-bis(methoxymethoxy)phenyl]formamide:
A mixture of 0.66 g (3.10 mmol) of 2,6-bis(methoxymethoxy)aniline, 0.83 g (3.93 mmol) of N-formylsaccharin, and 20 mL of tetrahydrofuran was stirred at room temperature for 5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 2:1) to obtain 0.66 g (yield: 88%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.54 (1H, s), 7.23 (1H, t), 6.76 (2H, d), 6.02 (4H, s), 3.30 (6H, s)

(2) Production of N-[2,6-bis(methoxymethoxy)phenyl]-N-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}formamide:
N-[2,6-bis(methoxymethoxy)phenyl]formamide 0.60 g (2.49 mmol), 1-(2-bromoethyl)-3-(trifluoromethyl)-1H-pyrazole 0.85 g (3.50 mmol) ), N,N-dimethylformamide (10 mL) at room temperature, 0.30 g (7.50 mmol, calculated as purity 60%) of sodium hydride was added, and the mixture was stirred at 40° C. for 6 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 2:1) to obtain 0.39 g (yield: 39%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.02 (1H, s), 7.52 (1H, d), 7.22 (1H, t), 6.84 (2H, d), 6.44 (1H, d), 5.21 (4H, s), 4.40 (2H, t), 4.13 (2H, t), 3.44 (6H, s)

(3) Production of 2-({2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}amino)benzene-1,3-diol:
N-[2,6-bis(methoxymethoxy)phenyl]-N-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}formamide 0.35 g (0.87 mmol), 3N A mixture of 2.90 mL (8.70 mmol) of hydrochloric acid and 20 mL of methanol was heated under reflux for 3 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the crude target product. It was used as it was in the next step without purification.

(4) Production of 4-hydroxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2(3H)-thione:
Crude 2-({2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}amino)benzene-1,3-diol, 1.64 g (21.5 mmol) of carbon disulfide, water A mixture of 0.06 g (1.07 mmol) of potassium oxide and 10 mL of ethanol was stirred at 60° C. for 5 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 4:1) to obtain 0.14 g of the target product (yield: 49%, 2 steps). .

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.88 (1H, d), 7.09 (1H, t), 6.96 (1H, d), 6.75 (1H, d), 6.63 (1H, d), 4.70 (4H, s)

(5) 4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 Production of (3H)-thione (compound number of the present invention: E-0280):
4-hydroxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2(3H)-thione 0.14 g (0.43 mmol), 2 A mixture of 0.08 g (0.54 mmol) of ,5-dichloropyrimidine, 0.08 g (0.58 mmol) of potassium carbonate, and 10 mL of N,N-dimethylformamide was stirred at 80° C. for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.20 g (yield: quantitative) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.54 (2H, s), 7.44 (1H, d), 7.29-7.26 (2H, m), 7. 12 (1H, d), 6.43 (1H, d), 4.70-4.65 (2H, m), 4.60-4.55 (2H, m)

[Example 9]
4-[(5-chloropyrimidin-2-yl)thio]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 (3H) Production of -one (compound number of the present invention: E-0321):
(1) Production of 3-(benzyloxy)-2-nitrobenzenethiol:
A mixture of 6.00 g (24.27 mmol) of 1-(benzyloxy)-3-fluoro-2-nitrobenzene, 3.79 g (48.56 mmol) of sodium sulfide, and 100 mL of N,N-dimethylformamide was stirred at room temperature for 18 hours. did. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 3.10 g (yield: 49%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.41-7.28 (8H, m), 5.27 (2H, s)

(2) Production of 2-{[3-(benzyloxy)-2-nitrophenyl]thio}-5-chloropyrimidine:
3-(benzyloxy)-2-nitrobenzenethiol 1.70 g (6.51 mmol), 2,5-dichloropyrimidine 1.16 g (7.79 mmol), potassium carbonate 1.80 g (13.02 mmol), N,N- A mixture of 50 mL of dimethylformamide was stirred at 80° C. for 9 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 10:1) to obtain 1.51 g (yield: 62%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.44 (2H, s), 7.45 (3H, t), 7.39-7.36 (5H, m), 7. 30 (1H, d), 7.20 (1H, d), 5.22 (2H, s)

(3) Production of 2-(benzyloxy)-6-[(5-chloropyrimidin-2-yl)thio]aniline:
A mixture of 0.82 g (2.19 mmol) of 2-{[3-(benzyloxy)-2-nitrophenyl]thio}-5-chloropyrimidine, 0.20 g of 10% Pd/C, and 30 mL of tetrahydrofuran was heated under a hydrogen atmosphere (normally pressure) and stirred at room temperature for 2 days. After the reaction was completed, it was filtered through Celite, the solvent was distilled off under reduced pressure, and the target product was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5:1) to obtain 0.58 g (yield) of the target product. 77%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.72 (2H, s), 7.52-7.50 (2H, m), 7.44-7.34 (3H, m), 7.04 (1H, d), 6.97 (1H, d), 6.58 (1H, d), 5.15 (2H, s)

(4) Production of 2-amino-3-[(5-chloropyrimidin-2-yl)thio]phenol:
Boron tribromide (1 mol/L dichloromethane solution) was added to 0.30 g (0.87 mmol) of 2-(benzyloxy)-6-[(5-chloropyrimidin-2-yl)thio]aniline and 20 mL of dichloromethane at -78°C. ) and stirred for 1 hour while maintaining the same temperature. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 2:1) to obtain 0.14 g (yield: 63%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMS δ (ppm)): 8.70 (2H, s), 6.82 (1H, d), 6.79 (1H, d), 6.45 (1H ,d)

(5) Production of 4-[(5-chloropyrimidin-2-yl)thio]benzo[d]oxazol-2(3H)-one:
A mixture of 0.13 g (0.51 mmol) of 2-amino-3-[(5-chloropyrimidin-2-yl)thio]phenol, 0.10 g (0.62 mmol) of 1,1'-carbonyldiimidazole, and 40 mL of tetrahydrofuran. was stirred at 50°C for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 4:1) to obtain 0.13 g (yield: 91%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMS δ (ppm)): 8.77 (2H, s), 7.43 (1H, d), 7.34 (1H, d), 7.18 (1H ,t)

(6) 4-[(5-chloropyrimidin-2-yl)thio]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]oxazole-2 Production of (3H)-one (compound number of the present invention: E-0321):
4-[(5-chloropyrimidin-2-yl)thio]benzo[d]oxazol-2(3H)-one 0.13 g (0.46 mmol), 1-(2-bromoethyl)-3-(trifluoromethyl A mixture of 0.17 g (0.70 mmol) of )-1H-pyrazole, 0.10 g (0.72 mmol) of potassium carbonate, and 20 mL of N,N-dimethylformamide was stirred at 60° C. for 5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 10:1) to obtain 0.19 g (yield: 93%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.45 (2H, s), 7.38 (1H, d), 7.34 (2H, d), 7.17 (1H , t), 6.45 (1H, d), 4.50 (4H, s)

[Example 10]
4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazole-2 (3H) -Production of one (compound number of the present invention: F-0018):
(1) Production of 4-methoxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazol-2(3H)-one:
4-methoxybenzo[d]thiazol-2(3H)-one 0.33 g (1.82 mmol), 1-(2-bromoethyl)-3-(trifluoromethyl)-1H-pyrazole 0.57 g (2.35 mmol) ), 0.33 g (2.39 mmol) of potassium carbonate, and 20 mL of N,N-dimethylformamide was stirred at 100° C. for 8 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.47 g (yield: 75%) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.76 (1H, d), 7.54 (1H, d), 7.03 (1H, t), 6.86 (1H, d), 6.01 (1H, d), 5.80 (2H, t), 4.11 (2H, t), 3.86 (3H, s)

(2) Production of 4-hydroxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazol-2(3H)-one:
4-methoxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazol-2(3H)-one 0.46 g (1.34 mmol), dichloromethane 6.70 mL of boron tribromide (1 mol/L dichloromethane solution) was added to 10 mL of the mixture under ice cooling, and the mixture was stirred at room temperature for 3 days. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.30 g (yield 68%) of the crude target product.

(3) 4-[(5-chloropyrimidin-2-yl)oxy]-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazole-2 Production of (3H)-one (compound number of the present invention: F-0018):
Crude 4-hydroxy-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]ethyl}benzo[d]thiazol-2(3H)-one 0.26 g (0.79 mmol) , 0.15 g (1.01 mmol) of 2,5-dichloropyrimidine, 0.15 g (1.09 mmol) of potassium carbonate, and 5 mL of N,N-dimethylformamide was stirred at 100° C. for 4 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.35 g (yield: quantitative) of the desired product.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.54 (2H, s), 7.46 (1H, d), 7.35 (1H, d), 7.21 (1H, t), 7.08 (1H, d), 6.45 (1H, d), 4.48-4.45 (4H, m)

[Example 11]
7-[(5-chloropyrimidin-2-yl)oxy]-3,3-difluoro-1-(4,4,4-trifluorobutyl)indolin-2-one (compound number of the present invention: G-0024 )Manufacturing of:
(1) Production of 7-methoxy-1-(4,4,4-trifluorobutyl)indoline-2,3-dione:
1,1,1 to a mixture of 1.00 g (5.64 mmol) of 7-methoxyindoline-2,3-dione, 1.09 g (7.89 mmol) of potassium carbonate, and 10 mL of N,N-dimethylformamide under ice cooling. 1.61 g (6.76 mmol) of -trifluoro-4-iodobutane was added, and the mixture was stirred at room temperature for 28 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 6:1 to 1:1) to obtain 1.47 g (yield: 91%) of the target product. Ta.

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 7.26 (1H, d), 7.19 (1H, d), 7.09 (1H, t), 4.04 (2H, t), 3.93 (3H, s), 2.27-2.12 (2H, m), 2.04-1.94 (2H, m)

(2) Production of 7-hydroxy-1-(4,4,4-trifluorobutyl)indoline-2,3-dione:
Boron tribromide (approximately 1 mol) was added to a mixture of 1.47 g (5.12 mmol) of 7-methoxy-1-(4,4,4-trifluorobutyl)indoline-2,3-dione and 15 mL of dichloromethane under ice cooling. 10.20 mL (10.20 mmol) of dichloromethane solution) was added thereto, and the mixture was stirred at room temperature for 22 hours. After the reaction was completed, ice water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.47 g of the crude target product (yield quantitative).

¹ H-NMR data (300 MHz, CDCl ₃ /TMSδ (ppm)): 7.27 (1H, d), 7.09-6.98 (2H, m), 4.07 (2H, t), 2. 29-2.14 (2H, m), 2.10-2.00 (2H, m)

(3) 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)indoline-2,3-dione (compound number of the present invention: G-0089) Manufacturing of:
7-hydroxy-1-(4,4,4-trifluorobutyl)indoline-2,3-dione 1.47 g (5.38 mmol), 2,5-dichloropyrimidine 0.96 g (6.44 mmol), potassium carbonate A mixture of 0.97 g (7.02 mmol) and 10 mL of N,N-dimethylformamide was stirred at 80° C. for 4.5 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 9:1 to 1:1) to obtain 1.34 g (yield: 65%) of the target product. Ta.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.55 (2H, s), 7.59 (1H, d), 7.40 (1H, d), 7.18 (1H, t), 3.88 (2H, t), 2.20-2.04 (2H, m), 1.90-1.80 (2H, m)

(4) 7-[(5-chloropyrimidin-2-yl)oxy]-3,3-difluoro-1-(4,4,4-trifluorobutyl)indolin-2-one (compound number of the present invention: Production of G-0024):
In a mixture of 0.27 g (0.70 mmol) of 7-[(5-chloropyrimidin-2-yl)oxy]-1-(4,4,4-trifluorobutyl)indoline-2,3-dione and 10 mL of dichloromethane. , 0.36 g (2.23 mmol) of (diethylamino)sulfur trifluoride was added under ice-cooling, and the mixture was stirred at room temperature for 48 hours. After the reaction was completed, ice water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 20:1 to 3:2) to obtain 0.29 g (yield quantitative) of the target product. Ta.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.55 (2H, s), 7.50 (1H, d), 7.30-7.18 (2H, m), 3. 84 (2H, t), 2.18-2.02 (2H, m), 1.89-1.78 (2H, m)

[Example 12]
4-[(5-chloropyrimidin-2-yl)oxy]-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazole-2- Production of On (compound number of the present invention: H-0003):
(1) Production of 4-methoxy-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one:
4-methoxy-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 0.60 g (3.37 mmol), 1,1,1-trifluoro-4-iodobutane 1.12 g ( A mixture of 4.71 mmol), 0.70 g (5.07 mmol) of potassium carbonate, and 10 mL of N,N-dimethylformamide was stirred at 70° C. for 4 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was used as it was in the next step without purification.

(2) Production of 4-hydroxy-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one:
A mixture of crude 4-methoxy-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one and 10 mL of dichloromethane was cooled on ice. Then, 17.0 mL of boron tribromide (1 mol/L dichloromethane solution) was added, and the mixture was stirred at room temperature for 20 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate = 3:1) to obtain 0.84 g of the target product (yield 91%, 2 steps). .

^1H -NMR data (300MHz, CDCl ₃ /TMSδ (ppm)): 8.11 (1H, d), 7.02 (1H, t), 6.83 (1H, d), 3.89 (3H, s), 3.87 (2H, t), 2.14-2.05 (2H, m), 1.91-1.83 (2H, m)

(3) 4-[(5-chloropyrimidin-2-yl)oxy]-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazole Production of -2-one (compound number of the present invention: H-0003):
4-hydroxy-1-methyl-3-(4,4,4-trifluorobutyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one 0.21 g (0.77 mmol), 2, A mixture of 0.14 g (0.94 mmol) of 5-dichloropyrimidine, 0.13 (0.94 mmol) of potassium carbonate, and 10 mL of N,N-dimethylformamide was stirred at 80° C. for 8 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 5:1) to obtain 0.29 g (yield: 98%) of the desired product.

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.52 (2H, s), 7.14 (1H, t), 6.91 (1H, d), 6.88 (1H, d), 3.95 (2H, t), 2.14-2.05 (2H, m), 1.91-1.83 (2H, m)

The physical property values of the compound [I] of the present invention synthesized according to the above examples are shown in Tables 37 to 50 below, including the values in the above examples. The compound numbers and symbols in the table have the same meanings as above.

Next, a formulation example of the herbicide of the present invention using the fused heterocyclic derivative of the present invention or an agriculturally acceptable salt thereof produced as described above will be specifically explained. However, the types and blending ratios of compounds and additives are not limited to these, and can be varied within a wide range. Furthermore, in the following description, "part" means part by mass.

[Formulation Example 1] Emulsion Each compound listed in Tables 1 to 36 and 37 to 50 10 parts Cyclohexanone 30 parts Polyoxyethylene alkylaryl ether 11 parts Calcium alkylbenzenesulfonate 4 parts Methylnaphthalene 45 parts Uniformly dissolve the above It was made into an emulsion.

[Formulation Example 2] Wettable powder Each compound listed in Tables 1 to 36 and 37 to 50 10 parts Naphthalenesulfonic acid formalin condensate sodium salt 0.5 part Polyoxyethylene alkylaryl ether 0.5 part Diatomaceous earth 24 Part Clay 65 parts The above was mixed and pulverized uniformly to prepare a wettable powder.

[Formulation Example 3] Powder 2 parts of each compound listed in Tables 1 to 36 and 37 to 50, 5 parts of diatomaceous earth, 93 parts of clay, and the above were uniformly mixed and ground to obtain a powder.

[Formulation Example 4] Granules
Each compound listed in Tables 1 to 36 and Tables 37 to 50 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethylcellulose 2 parts Clay 86 parts The above materials were uniformly mixed and ground. An amount equivalent to 20 parts of water was added to this mixture, the mixture was kneaded, processed into granules of 14 to 32 mesh using an extrusion type granulator, and then dried to form granules.

[Formulation Example 5] Flowable agent 20 parts of each compound listed in Tables 1 to 36 and 37 to 50 Polyoxyethylene styrenated phenyl ether sulfate 4 parts Ethylene glycol 7 parts Silicone AF-118N (manufactured by Asahi Kasei Corporation) ) 0.02 parts Water 68.98 parts The above ingredients were mixed for 30 minutes using a high-speed stirrer, and then ground using a wet grinder to obtain a flowable agent.

[Formulation Example 6] Granule wettable powder Each compound listed in Tables 1 to 36 and 37 to 50 10 parts Sodium lignin sulfonate 5 parts Polyoxyethylene alkylaryl ether 1 part Sodium polycarboxylate 3 parts White carbon 5 Part Pregelatinized Starch 1 part Calcium Carbonate 65 parts Water 10 parts The above ingredients were mixed, kneaded, and granulated. The obtained granules were dried in a fluidized bed dryer to obtain a granular wettable powder.

[Test Example 1] Confirmation test of herbicidal activity against goldenrod in foliage treatment:
Approximately 340 cm x ³ volume plastic pots were filled with field soil, seeds of goldenrod were sown at a seeding depth of 1 cm, and cultivated in a greenhouse. After about two weeks, the wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed on the weeds in the pot using a small sprayer in an amount equivalent to 1000 liters per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on barnyard grass in foliage treatment were compounds A-0004, B-0008, B-0152, B-0153, B-0154, B-0156, B-0157, B-0158, and B. -0162, B-0221, B-0245, B-0247, B-0303, B-0304, B-0305, B-0307, B-0309, B-0311, B-0314, B-0325, B-0327 , B-0328, B-0333, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0372, B-0376, B-0384, B-0387, B -0389, B-0399, B-0403, B-0405, B-0409, B-0441, B-0448, B-0466, B-0468, B-0469, B-0493, B-0499, B-0514 , B-0543, B-0544, B-0556, B-0561, B-0563, C-0002, E-0006, E-0007, E-0009, E-0014, E-0015, E-0031, E -0032, E-0040, E-0043, E-0045, E-0051, E-0059, E-0061, E-0105, E-0124, E-0172, E-0173, E-0174, E-0181 , E-0211, E-0212, E-0219, E-0220, E-0230, E-0231, E-0232, E-0238, E-0280, E-0403, E-0418, E-0420, F -0002, F-0018, F-0021, G-0024, G-0033, G-0051, G-0090, and H-0003.

[Test Example 2] Confirmation test of herbicidal activity against wheat in foliage treatment:
Approximately 340 cm x ³ plastic pots were filled with field soil, and the seeds of rat wheat were sown at a seeding depth of 1 cm, and cultivated in a greenhouse. After about two weeks, the wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed on the weeds in the pot using a small sprayer in an amount equivalent to 1000 liters per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on murine wheat when treated with foliage were compounds A-0032, B-0008, B-0098, B-0152, B-0153, B-0154, B-0156, B-0158, and B. -0162, B-0221, B-0245, B-0247, B-0303, B-0304, B-0309, B-0311, B-0314, B-0325, B-0327, B-0328, B-0333 , B-0338, B-0359, B-0368, B-0369, B-0370, B-0372, B-0376, B-0384, B-0387, B-0389, B-0399, B-0403, B -0405, B-0409, B-0448, B-0461, B-0466, B-0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544 , B-0556, B-0561, C-0002, E-0007, E-0015, E-0031, E-0032, E-0051, E-0061, E-0105, E-0173, E-0174, E -0181, E-0182, E-0196, E-0211, E-0219, E-0231, E-0238, E-0280, E-0419, F-0002, F-0018, F-0021, G-0024 Met.

[Test Example 3] Confirmation test of herbicidal activity against Japanese grasshopper in foliage treatment:
Approximately 340 cm x ³ plastic pots were filled with field soil, and Ichibi seeds were sown at a seeding depth of 1 cm, and cultivated in a greenhouse. After about two weeks, the wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed on the weeds in the pot using a small sprayer in an amount equivalent to 1000 liters per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on Ichibi when sprayed on leaves were compounds A-0004, A-0007, A-0032, B-0008, B-0098, B-0152, B-0153, B-0154, and B. -0156, B-0157, B-0158, B-0160, B-0162, B-0217, B-0221, B-0245, B-0247, B-0266, B-0303, B-0304, B-0305 , B-0307, B-0309, B-0311, B-0314, B-0316, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B-0350, B -0359, B-0368, B-0369, B-0370, B-0372, B-0374, B-0376, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405 , B-0409, B-0434, B-0438, B-0448, B-0451, B-0461, B-0466, B-0468, B-0469, B-0493, B-0499, B-0500, B -0514, B-0543, B-0544, B-0556, B-0557, B-0561, B-0563, C-0002, E-0006, E-0007, E-0009, E-0014, E-0015 , E-0020, E-0030, E-0031, E-0032, E-0039, E-0040, E-0042, E-0043, E-0045, E-0046, E-0048, E-0050, E -0051, E-0058, E-0059, E-0074, E-0104, E-0105, E-0106, E-0124, E-0125, E-0126, E-0127, E-0128, E-0172 , E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E-0186, E-0192, E-0196, E-0206, E-0211, E -0219, E-0220, E-0221, E-0222, E-0230, E-0231, E-0232, E-0233, E-0238, E-0272, E-0275, E-0280, E-0321 , E-0403, E-0418, E-0419, E-0420, F-0002, F-0018, F-0021, G-0024, G-0033, G-0051, and H-0002.

[Test Example 4] Confirmation test of herbicidal activity against A. japonica in foliage treatment:
Approximately 340 cm x ³ plastic pots were filled with upland soil, and seeds of Aspergillus japonica were sown at a seeding depth of 1 cm, and cultivated in a greenhouse. After about two weeks, the wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed on the weeds in the pot using a small sprayer in an amount equivalent to 1000 liters per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on Aspergillus japonica in foliage treatment were compounds A-0002, A-0004, A-0007, A-0032, B-0008, B-0098, B-0152, B-0153, and B. -0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0217, B-0221, B-0245, B-0247, B-0266, B-0303, B-0304 , B-0305, B-0307, B-0309, B-0311, B-0314, B-0316, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B -0350, B-0359, B-0362, B-0368, B-0369, B-0370, B-0372, B-0373, B-0374, B-0376, B-0384, B-0387, B-0389 , B-0399, B-0403, B-0405, B-0409, B-0434, B-0438, B-0441, B-0448, B-0451, B-0461, B-0466, B-0468, B -0469, B-0492, B-0493, B-0499, B-0500, B-0514, B-0537, B-0543, B-0544, B-0556, B-0557, B-0560, B-0561 , B-0562, B-0563, C-0002, D-0002, E-0006, E-0007, E-0009, E-0014, E-0015, E-0020, E-0029, E-0030, E -0031, E-0032, E-0039, E-0040, E-0042, E-0043, E-0045, E-0046, E-0048, E-0050, E-0051, E-0053, E-0058 , E-0059, E-0061, E-0104, E-0105, E-0106, E-0124, E-0125, E-0126, E-0127, E-0128, E-0171, E-0172, E -0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E-0186, E-0192, E-0196, E-0206, E-0211, E-0212 , E-0219, E-0220, E-0221, E-0222, E-0228, E-0229, E-0230, E-0231, E-0232, E-0233, E-0236, E-0238, E -0243, E-0247, E-0268, E-0272, E-0275, E-0280, E-0321, E-0403, E-0418, E-0419, E-0420, F-0002, F-0018 , F-0019, F-0021, F-0086, G-0024, G-0033, G-0034, G-0051, G-0071, G-0089, G-0090, and H-0002.

[Test Example 5] Confirmation test of herbicidal activity against goldenrod in soil treatment:
Approximately 340 cm ^{x 3} volume plastic pots were filled with upland soil, and goldenberry seeds were sown at a seeding depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed over the entire surface of the soil using a small sprayer in an amount equivalent to 1000 liters of water per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on barnyard grass in soil treatment were compounds A-0001, A-0004, A-0032, B-0008, B-0098, B-0152, B-0153, B-0154, and B. -0156, B-0157, B-0158, B-0160, B-0162, B-0221, B-0245, B-0247, B-0266, B-0303, B-0304, B-0305, B-0307 , B-0309, B-0311, B-0314, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B-0350, B-0359, B-0368, B -0369, B-0370, B-0372, B-0376, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0438, B-0441 , B-0448, B-0461, B-0466, B-0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B -0561, B-0563, C-0002, E-0006, E-0007, E-0009, E-0014, E-0015, E-0030, E-0031, E-0032, E-0040, E-0043 , E-0045, E-0048, E-0050, E-0051, E-0053, E-0058, E-0059, E-0061, E-0105, E-0106, E-0124, E-0125, E -0126, E-0127, E-0128, E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0192, E-0194 , E-0211, E-0212, E-0219, E-0220, E-0221, E-0230, E-0231, E-0232, E-0238, E-0272, E-0275, E-0280, E -0403, E-0418, E-0419, E-0420, F-0002, F-0018, F-0021, G-0024, G-0033, G-0051, G-0090, H-0002, H-0003 Met.

[Test Example 6] Confirmation test of herbicidal activity against rat wheat in soil treatment:
Approximately 340 cm ^{x 3} volume plastic pots were filled with upland soil, and seeds of rat wheat were sown at a seeding depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed over the entire surface of the soil using a small sprayer in an amount equivalent to 1000 liters of water per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on rat wheat in soil treatment were compounds A-0004, A-0032, B-0008, B-0098, B-0152, B-0153, B-0154, B-0156, and B. -0157, B-0158, B-0162, B-0221, B-0245, B-0247, B-0266, B-0303, B-0304, B-0305, B-0307, B-0309, B-0311 , B-0314, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B -0372, B-0374, B-0376, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0438, B-0448, B-0461 , B-0466, B-0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561, B-0562, B -0563, C-0002, E-0006, E-0007, E-0009, E-0014, E-0015, E-0030, E-0031, E-0032, E-0040, E-0043, E-0045 , E-0048, E-0050, E-0051, E-0053, E-0058, E-0059, E-0061, E-0105, E-0106, E-0124, E-0127, E-0128, E -0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E-0192, E-0194, E-0211, E-0212 , E-0219, E-0220, E-0221, E-0230, E-0231, E-0232, E-0238, E-0243, E-0280, E-0321, E-0403, E-0418, E -0419, E-0420, F-0002, F-0018, F-0019, F-0021, G-0024, G-0033, G-0051, and G-0090.

[Test Example 7] Confirmation test of herbicidal activity against Japanese grasshopper in soil treatment:
Approximately 340 cm and ³ volumes of plastic pots were filled with upland soil, and Ichibi seeds were sown at a seeding depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed over the entire surface of the soil using a small sprayer in an amount equivalent to 1000 liters of water per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on Ichibi in soil treatment were compounds B-0008, B-0098, B-0152, B-0153, B-0158, B-0221, B-0245, B-0247, and B. -0266, B-0303, B-0304, B-0309, B-0311, B-0314, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B-0350 , B-0359, B-0368, B-0369, B-0376, B-0384, B-0387, B-0389, B-0403, B-0409, B-0448, B-0461, B-0468, B -0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561, C-0002, E-0006, E-0007, E-0009 , E-0014, E-0015, E-0030, E-0031, E-0032, E-0039, E-0040, E-0043, E-0045, E-0048, E-0050, E-0051, E -0053, E-0059, E-0061, E-0105, E-0106, E-0124, E-0171, E-0172, E-0174, E-0181, E-0183, E-0211, E-0212 , E-0219, E-0220, E-0221, E-0230, E-0231, E-0238, E-0243, E-0272, E-0275, E-0280, E-0321, E-0403, E -0418, E-0420, F-0002, F-0018, F-0021, G-0024, G-0033, G-0051, and H-0002.

[Test Example 8] Confirmation test for herbicidal activity against Aspergillus in soil treatment:
Approximately 340 cm and ³ volumes of plastic pots were filled with upland soil, and seeds of Aspergillus japonica were sown at a seeding depth of 1 cm. A wettable powder prepared according to Formulation Example 2 was diluted with water and sprayed over the entire surface of the soil using a small sprayer in an amount equivalent to 1000 liters of water per hectare. Thereafter, growth was continued in a greenhouse, and the herbicidal effect was confirmed approximately 20 days after treatment.

Compounds that had a herbicidal effect on A. chinensis in soil treatment were compounds A-0004, A-0032, B-0008, B-0098, B-0152, B-0153, B-0154, B-0156, and B. -0157, B-0158, B-0160, B-0162, B-0217, B-0221, B-0245, B-0247, B-0266, B-0303, B-0304, B-0305, B-0307 , B-0309, B-0311, B-0314, B-0316, B-0325, B-0327, B-0328, B-0333, B-0338, B-0342, B-0350, B-0359, B -0362, B-0368, B-0369, B-0370, B-0372, B-0374, B-0376, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405 , B-0409, B-0438, B-0441, B-0448, B-0451, B-0461, B-0466, B-0468, B-0469, B-0492, B-0493, B-0499, B -0514, B-0537, B-0543, B-0544, B-0556, B-0561, B-0562, B-0563, C-0002, E-0006, E-0007, E-0009, E-0014 , E-0015, E-0020, E-0029, E-0030, E-0031, E-0032, E-0039, E-0040, E-0043, E-0045, E-0046, E-0048, E -0050, E-0051, E-0053, E-0059, E-0061, E-0104, E-0105, E-0106, E-0124, E-0125, E-0126, E-0127, E-0128 , E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E-0192, E-0194, E-0196, E -0206, E-0211, E-0212, E-0219, E-0220, E-0221, E-0222, E-0228, E-0229, E-0230, E-0231, E-0232, E-0233 , E-0236, E-0238, E-0243, E-0272, E-0275, E-0280, E-0321, E-0403, E-0418, E-0419, E-0420, F-0002, F -0018, F-0019, F-0021, F-0086, G-0024, G-0033, G-0034, G-0051, G-0089, G-0090, H-0002, and H-0003.

[Test Example 9] Confirmation test of herbicidal activity against goldenrod in hydroponic test:
A 60 ml plastic cup was lined with cotton, and 8 ml of a hydrating powder diluted with water prepared according to Formulation Example 2 was poured into the cup, followed by sowing goldenrod seeds on the cotton surface. After the lid was placed, growth was continued under the conditions of 12 hours light/12 hours dark under fluorescent lamp irradiation at approximately 20° C., and the herbicidal effect was confirmed approximately 7 days after treatment.

In the hydroponic test, the compounds that had a herbicidal effect on barnyard grass were compounds B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0096, E-0106, E-0108, E-0109, E-0111, E-0117, E-0213, E-0223, E-0240, E-0249, E-0257, E- 0260, E-0276, E-0403, E-0420, and G-0051.

[Test Example 10] Confirmation test of herbicidal activity against rat wheat in hydroponic test:
A 60 ml plastic cup was lined with cotton, 8 ml of a wettable powder diluted with water prepared according to Formulation Example 2 was poured into the cup, and then wheat seeds were sown on the cotton surface. After the lid was placed, growth was continued under the conditions of 12 hours light/12 hours dark under fluorescent lamp irradiation at approximately 20° C., and the herbicidal effect was confirmed approximately 7 days after treatment.

In the hydroponic test, the compounds that had a herbicidal effect on rat wheat were compounds B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0096, E-0106, E-0108, E-0109, E-0111, E-0170, E-0189, E-0197, E-0213, E-0223, E-0240, E- 0249, E-0257, E-0276, E-0403, E-0420, and G-0051.

[Test Example 11] Herbicidal activity confirmation test on lettuce in hydroponic test:
A 60 ml plastic cup was lined with cotton, and 8 ml of the wettable powder diluted with water prepared according to Formulation Example 2 was poured into the cup, and then lettuce seeds were sown on the cotton surface. After the lid was placed, growth was continued under the conditions of 12 hours light/12 hours dark under fluorescent lamp irradiation at approximately 20° C., and the herbicidal effect was confirmed approximately 7 days after treatment.

In the hydroponic test, the compounds that had a herbicidal effect on lettuce were compounds B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, They were E-0096, E-0106, E-0108, E-0109, E-0111, E-0240, E-0249, E-0257, E-0276, E-0403, E-0420, and G-0051. .

[Test Example 12] Confirmation test for herbicidal activity against A. japonica in a hydroponic test:
A 60 ml plastic cup was lined with cotton, and 8 ml of a hydrating agent prepared according to Formulation Example 2 diluted with water was poured into the cup, and seeds of Aspergillus orientalis were sown on the surface of the cotton. After the lid was placed, growth was continued under fluorescent light irradiation with a 12-hour light period and a 12-hour dark period at approximately 20° C., and the herbicidal effect was confirmed approximately 7 days after treatment.

In the hydroponic test, the compounds that had a herbicidal effect on A. japonica were compounds B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, D-0021, E-0001, E-0052, E-0074, E-0096, E-0106, E-0108, E-0109, E-0111, E-0117, E-0147, E-0189, E-0197, E-0213, E- 0223, E-0240, E-0249, E-0257, E-0260, E-0266, E-0276, E-0403, E-0420, and G-0051.

[Test Example 13] Confirmation test of herbicidal activity against dogfish in hydroponic test:
A 60 ml plastic cup was lined with cotton, and 8 ml of a hydrating powder diluted with water prepared according to Formulation Example 2 was poured into the cup, and then seeds of scallops were sown on the cotton surface. After the lid was placed, growth was continued under the conditions of 12 hours light/12 hours dark under fluorescent lamp irradiation at approximately 20° C., and the herbicidal effect was confirmed approximately 7 days after treatment.

In the hydroponic test, the compounds that had a herbicidal effect on dogfly were compounds B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0096, E-0106, E-0108, E-0109, E-0111, E-0117, E-0189, E-0213, E-0223, E-0240, E-0249, E-0257, E- 0260, E-0266, E-0276, E-0403, E-0420, and G-0051.

INDUSTRIAL APPLICABILITY The present invention provides a novel compound having excellent herbicidal activity and an intermediate for producing the same, and is useful in the fields of agrochemicals and agriculture, and has the potential for industrial application.

Claims (7)

General formula [I]

[In general formula [I],
Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8,

R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group (the group may be mono- or polysubstituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono- or polysubstituted by R ⁸ ); C ₂ -C ₆ alkynyl groups (which groups may be mono- or polysubstituted by R ⁸ ), C ₃ -C ₆ cycloalkyl groups (which groups may be mono- or polysubstituted by R 8 ), C 2 -C 6 alkynyl groups (which groups may be mono- or polysubstituted by R ⁸ a phenyl group (which may be mono- or polysubstituted by R ⁹ ) or a heteroaryl group (which may be mono- or polysubstituted by R ⁹ ); ,
R ⁸ is a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, a formyl group, a C ₁ to C ₆ Alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₃ -C ₆ cycloalkylcarbonyl group, benzoyl group (the group may be mono- or polysubstituted with R ⁹ ), -C(R ¹⁰ )= NOR ¹¹ , carboxy group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, aminocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (even if the amino group is substituted by R ¹² C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted by R ¹² ), pyrrolidin-1-ylcarbonyl group (the group may be mono- or polysubstituted by R ⁹ ) ), piperidin-1-ylcarbonyl group (which group may be mono- or polysubstituted by R ⁹ ), hydroxy group, C ₁ -C ₆ alkoxy group, C _{3 -C 6} alkenyloxy group, C ₃ - C ₆ alkynyloxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C ₃ -C ₆ halocycloalkoxy group, C ₃ -C ₆ cycloalkylC ₁ -C ₆ alkoxy group, C ₃ - _C6 halocycloalkylC1 _{- C6} alkoxy group, phenoxy group (which group may be mono- or polysubstituted with ^R9 ), _phenylC1 - _C6 alkoxy group (the phenyl group is R9 ⁾ ), thiol group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylthio group, C ₁ - C ₆ haloalkylsulfinyl group, C ₁ - C ₆ haloalkylsulfonyl group, C ₃ - C ₆ cycloalkylthio group, C ₃ - C ₆ cycloalkylsulfinyl group, C ₃ - C ₆ cycloalkylsulfonyl group, C ₃ - C ₆ halocycloalkylthio group, C ₃ to C ₆ halocycloalkylsulfinyl group, C ₃ to C ₆ halocycloalkylsulfonyl group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylthio group, C ₃ to C ₆ cyclo Alkyl C ₁ - C ₆ alkylsulfinyl group, C ₃ - C ₆ cycloalkyl C ₁ - C ₆ alkylsulfonyl group, C ₃ - C ₆ halocycloalkyl C ₁ - C ₆ alkylthio group, C ₃ - C ₆ halocycloalkyl C ₁ -C ₆ alkylsulfinyl group, C ₃ -C ₆ halocycloalkylC ₁ -C ₆ alkylsulfonyl group, phenylthio group (the group may be mono- or polysubstituted by R ⁹ ), phenylsulfinyl group ( The group may be mono- or polysubstituted by R ⁹ ), phenylsulfonyl group (the group may be mono- or polysubstituted by R ⁹ ), amino group, C ₁ -C ₆ alkylamino group ( The amino group may be substituted by R ¹² ), the C ₁ -C ₆ haloalkylamino group (the amino group may be substituted by R ¹² ), the C ₁ -C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ cycloalkylcarbonylamino group (the amino group may be substituted by R 12), ), phenylcarbonylamino group (the phenyl group may be mono- or polysubstituted with R ⁹ and the amino group may be substituted with R ¹² ), C ¹ _{-C 6} alkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ Alkylaminocarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylaminocarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ Alkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ cycloalkyl a sulfonylamino group (the amino group may be substituted by R ¹² ), a phenylsulfonylamino group (the phenyl group may be mono- or polysubstituted by R ⁹ , and the amino group may be substituted by R ¹² ); ), tri(C ₁ -C ₆ alkyl)silyl group, phenyl group (said group may be mono- or polysubstituted with R ⁹ ), 1,3-benzodioxolyl group (said group may be mono- or polysubstituted with R Heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryloxy groups (which groups may be mono- or polysubstituted by R ⁹ ), a heterocycloalkyl group (which group may be mono- or polysubstituted by R ⁹ ), a cyano group, a nitro group or a thiocyanato group;
R ⁹ is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group, formyl group, hydroxy group, C _{1 -C 6} alkoxy group, C _{1 -C 6} haloalkoxy group, thiol group, C ₁ -C ₆ alkylthio group, C 1 -C ₆ alkylsulfinyl group , C ₁ to C ₆ alkylsulfonyl group, C ₁ to C ₆ haloalkylthio group, C ₁ to C ₆ haloalkylsulfinyl group, C ₁ to C ₆ haloalkylsulfonyl group, cyano group or nitro group,
R ¹⁰ is a hydrogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a phenyl group (the group may be mono- or polysubstituted by R ⁹ ) or a heteroaryl group (the group may be mono- or polysubstituted by R ⁹ );
R ¹¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, or a C ₃ ~C ₆ halocycloalkyl group,
R ¹² is a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ Halocycloalkyl group, _C3 - _{C6cycloalkylC1} -C6alkyl group, C1 _{- C6alkoxyC1} - _{C6alkyl group , C1-C6haloalkoxyC1 - C6alkyl group , cyano} C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ haloalkoxycarbonyl group, C ₁ to C ₆ represents an alkylaminocarbonyl group, a C ₁ -C ₆ haloalkylaminocarbonyl group or a benzoyl group (which group may be mono- or polysubstituted by R ⁹ );
R ² is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group , C ₃ to C ₆ halocycloalkyl group, formyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₃ to C ₆ cycloalkylcarbonyl group, -C(R ¹⁰ )=NOR ¹¹ , carboxy group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, aminocarbonyl group, aminothiocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (the amino group is defined by R ¹² ), C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted by R ¹² ), hydroxy group, C ₁ -C ₆ alkoxy group, C ₃ -C ₆ alkenyloxy group , C ₃ -C ₆ alkynyloxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C ₃ -C ₆ halocycloalkoxy group, C ₃ -C ₆ cycloalkylC ₁ -C ₆ Alkoxy group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group, phenyl C ₁ to C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted with R ⁹ ), heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ halo Alkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ haloalkylsulfonyl group, amino group, C ₁ -C ₆ alkylamino group (the amino group may be substituted by R ¹² ), C ₁ - C ₆ haloalkylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkyl carbonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ cycloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkoxycarbonyl Amino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkylsulfonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), a C ₃ -C ₆ cycloalkylsulfonylamino group (the amino group may be substituted by R ¹² ), a phenyl group (the group may be monosubstituted by R ⁹ ), (which may be substituted or polysubstituted), a heteroaryl group (which group may be mono- or polysubstituted by R ⁹ ), a cyano group or a nitro group;
R ³ is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group , C ₃ -C ₆ halocycloalkyl group, C ₁ -C ₆ alkoxyC 1 _{-C 6} alkyl group, C _{1 -C 6} haloalkoxyC ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthioC ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkylthioC ₁ -C ₆ alkyl group, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl group, cyano C ₁ to C ₆ alkyl group, formyl group, C ₁ to C ₆ alkylcarbonyl group, C ₁ to C ₆ haloalkylcarbonyl group, C ₃ to C ₆ cycloalkylcarbonyl group, -C(R ¹⁰ )=NOR ¹¹ , carboxy group, C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ haloalkoxycarbonyl group , aminocarbonyl group, aminothiocarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ haloalkylaminocarbonyl group (the amino group may be substituted with R ¹² ) ), hydroxy group, C ₁ -C ₆ alkoxy group, C ₃ -C 6 alkenyloxy group, C ₃ -C ₆ alkynyloxy group, C _{1 -C 6 haloalkoxy} group, C ₃ -C ₆ cycloalkoxy group, C ₃ - C ₆ halocycloalkoxy group, C ₃ - C ₆ cycloalkyl C ₁ - C 6 alkoxy group, C _{3 - C 6 halocycloalkyl} C ₁ - C ₆ alkoxy group, phenyl C ₁ - C ₆ alkoxy group (the phenyl group may be mono- or polysubstituted with R ⁹ ), heteroaryloxy group (the group may be mono- or polysubstituted with R ⁹ ), C ₁ -C ₆ Alkylthio group, C ₁ - C ₆ alkylsulfinyl group, C ₁ - C 6 alkylsulfonyl group, C ₁ - C ₆ haloalkylthio group, C ₁ - _{C 6 haloalkylsulfinyl} group, C ₁ - C ₆ haloalkylsulfonyl group, amino group , C ₁ -C ₆ alkylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylamino group (the amino group may be substituted by R 12), C 1 -C 6 alkylamino group (the amino group may be substituted by R ¹² ₎ C ₆ alkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ haloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₃ -C ₆ Cycloalkylcarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkoxycarbonylamino group (the amino group may be substituted by R ¹² ), C ₁ -C ₆ alkyl Sulfonylamino group (the amino group may be substituted with R ¹² ), C ₁ -C ₆ haloalkylsulfonylamino group (the amino group may be substituted with R ¹² ), C ₃ -C ₆ cycloalkylsulfonyl an amino group (the amino group may be substituted with R ¹² ), a phenyl group (the group may be mono- or polysubstituted with R ⁹ ), a heteroaryl group (the group may be mono-substituted or polysubstituted with R ⁹ ); (which may be polysubstituted), represents a cyano group or a nitro group,
R ⁴ is independently a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a hydroxy group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, a cyano group, or a nitro group. Indicates the group,
m represents an integer of 0, 1, 2 or 3,
Y represents an oxygen atom or a sulfur atom,
R ⁵ is independently a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C _{3 -C 6} halocycloalkyl group, a hydroxy group , C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, heteroaryloxy group (which group may be mono- or polysubstituted by R ⁹ ), tri(C ₁ -C ₆ alkyl)silyloxy or a cyano group, and two R ^5s may be combined to form an oxo group (=O) or a C ₁ -C ₆ alkoxyimino group, and two R ^5s are bonded to each other. selected from a 3- to 6-membered carbon ring together with the carbon atoms to which they are bonded, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom may be substituted with one or two oxo groups (=O)) may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms,
R ⁶ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group, C ₃ - C ₆ cycloalkylC 1 -C ₆ alkyl group, C ₁ -C 6 alkoxyC _{1 -C 6} alkyl group, C _{1 -C 6 haloalkoxyC 1} -C ₆ alkyl group, a cyano C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a C ₁ -C ₆ alkylsulfonyl group,
R ⁷ is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ - C ₆ halocycloalkyl group, hydroxy group, C ₁ - C ₆ alkoxy group, C ₁ - C ₆ haloalkoxy group, C ₁ - C ₆ alkylthio group, C ₁ - C ₆ alkylsulfinyl group, C ₁ - C ₆ It represents an alkylsulfonyl group, a C ₁ -C ₆ haloalkylthio group, a C ₁ -C ₆ haloalkylsulfinyl group, a C ₁ -C ₆ haloalkylsulfonyl group, a cyano group or a nitro group,
Z represents an oxygen atom or a sulfur atom,
A represents N or CR ¹³ ,
R ¹³ represents a hydrogen atom, a halogen atom, or a cyano group]
A fused heterocyclic derivative represented by or an agriculturally acceptable salt thereof. In the general formula [I], Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8,

R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group (the group may be mono- or polysubstituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono- or polysubstituted by R ⁸ ); C ₂ -C ₆ alkynyl groups (which may be mono- or polysubstituted by R ⁸ ), phenyl groups (which may be mono- or polysubstituted by R ⁹ ) ) or a heteroaryl group (which group may be mono- or polysubstituted by R ⁹ ),
R ⁸ is a halogen atom, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, a benzoyl group (the group is mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₃ -C ₆ cycloalkoxy group, C _{3 -C 6} cycloalkylC _{1 -C 6} alkoxy group, phenoxy group (which group may be mono- or polysubstituted by R ⁹ ), C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ haloalkylsulfonyl group , a phenylthio group (the group may be mono- or polysubstituted by R ⁹ ), a phenylsulfinyl group (the group may be mono- or polysubstituted by R ⁹ ), a phenylsulfonyl group (the group may be mono- or polysubstituted by R 9 ), phenyl groups (which groups may be mono- or polysubstituted by ^{R 9} ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), heteroaryl groups (which groups may be mono- or polysubstituted by R ⁹ ), ), a heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), a heterocycloalkyl group (the group may be mono- or polysubstituted by R ⁹ ), a cyano group or represents a thiocyanato group,
R ⁹ represents a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a formyl group, a C ₁ to C ₆ alkoxy group, a C ₁ to C ₆ haloalkoxy group, or a cyano group,
R ¹⁰ represents a hydrogen atom,
R ¹¹ represents a C ₁ to C ₆ alkyl group,
R ² represents a hydrogen atom, a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group,
R ³ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxyC ₁ to C ₆ alkyl group, formyl group, -C(R ¹⁰ )=NOR ¹¹ , aminocarbonyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, heteroaryloxy group (the group is R ⁹ ), C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, phenyl group (the group may be mono-substituted or polysubstituted by R ⁹ or may be polysubstituted) or a cyano group,
R ⁴ represents a halogen atom,
m represents an integer of 0 or 1,
Y represents an oxygen atom or a sulfur atom,
R ⁵ is independently a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a heteroaryloxy group (the group may be mono- or polysubstituted by R ⁹ ), or a tri( C ₁ -C ₆ alkyl)silyloxy group, and two R ⁵ may be taken together to form an oxo group (=O) or a C ₁ -C ₆ alkoxyimino group, and two R ⁵ are mutually bonded together with these bonding carbon atoms to form a 3- to 6-membered carbon ring, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom is substituted with one or two oxo groups (=O)). may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms selected from
R ⁶ represents a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group,
R ⁷ represents a halogen atom, a C ₁ to C ₆ haloalkyl group, or a cyano group,
Z represents an oxygen atom,
A represents N or CR ¹³ ,
The fused heterocyclic derivative according to claim 1, or an agriculturally acceptable salt thereof, wherein R ¹³ represents a hydrogen atom, a halogen atom, or a cyano group. An agricultural chemical composition containing the fused heterocyclic derivative according to claim 1 or 2, or an agriculturally acceptable salt thereof as an active ingredient. The agricultural chemical composition according to claim 3, further comprising a surfactant. A herbicide containing the fused heterocyclic derivative according to claim 1 or 2, or an agriculturally acceptable salt thereof as an active ingredient. Herbicidal effect on weeds that grow in fields, paddy fields, orchards, lawns, non-agricultural lands, greenhouses, seedling facilities, or plant factories where useful plants for agricultural, horticultural, and industrial purposes are cultivated. The herbicide according to claim 5. 7. The herbicide according to claim 6, wherein the useful plant having agricultural, horticultural and industrial uses is a trait plant cultivated by a breeding method or genetic recombination technology.