JP4883311B2 - Ethylene derivatives and pest control agents - Google Patents

Description

  The present invention relates to a novel ethylene derivative and a pesticide and an underwater bioadhesive agent characterized by containing the derivative as an active ingredient. The agrochemicals in the present invention are insecticides, acaricides, nematicides, herbicides, fungicides and the like, and in particular, pesticides in the fields of agriculture, horticulture, livestock and hygiene. Underwater organism adhesion inhibitors are fishing nets, ship bottoms, buoys and other equipment placed in the sea, marine structures, condensers of thermal power or nuclear power plants, cooling water intakes for heat exchangers of chemical industries, etc. It is a chemical for preventing harmful aquatic organisms such as shellfish and algae from adhering to underwater structures or reservoirs.

  Regarding acrylonitrile derivatives, 2'-chloro-3-hydroxy-2- (4-phenyl-2-thiazolyl) -cinnamic nitrile is described as an insecticide in Japanese Patent Application Laid-Open No. 53-92769. The application publication (WO-95 / 29591) describes use as an underwater organism adhesion inhibitor. JP-A-60-11452 describes 2- (4-chlorophenyl) -3- (3-pyridinyl) -3-oxopropionitrile as a herbicide, and JP-A-60-11401. Describes the compounds as fungicides.

JP-A-53-92769 WO-95 / 29591 Japanese Unexamined Patent Publication No. 60-11452 JP 60-11401 A

  With the long-term use of insecticides and fungicides, pests have recently gained resistance, making it difficult to control with conventional insecticides and fungicides. Some insecticides are highly toxic and some are disrupting ecosystems due to persistence. Therefore, development of new insecticides and fungicides with low toxicity and low persistence is always expected.

  Moreover, in order to prevent adhesion and propagation of aquatic organisms in the sea and in fresh water, antifouling paints containing organotin compounds such as bistributyltin oxide and copper compounds such as copper sulfate and cuprous oxide are used. However, organotin compounds are effective in preventing the attachment of aquatic organisms, but they are highly toxic. In particular, fish and shellfish accumulate in the body and are currently subject to regulation because they promote environmental pollution. Although copper compounds are widely used in antifouling paints for intake channels and ship bottoms, they contain copper, which is a heavy metal as well as tin compounds. There is a need for an underwater biofouling prevention agent that has little impact on the ecosystem and less secondary pollution, not an inhibitor.

In solving the above problems, the present inventors have shown that pesticides and aquatic organisms adhere to non-target organisms such as mammals, fish and beneficial insects, and exhibit excellent pest control activity at low doses. As a result of continuing research to develop an inhibitor, the present inventors have found that the following compound group has high safety and excellent pest control activity and aquatic organism adhesion prevention activity, thereby completing the present invention.
That is, the present invention relates to the following [1] to [25].
[1] Formula (I)

［式中、Ｑは、Ｇで置換されていてもよいフェニル、Ｇで置換されていてもよいナフチルまたはＲで置換されていてもよい複素環基（但し、この複素環基は、チエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、１，２，４，５−テトラジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、イミダゾリノン、イミダゾリジンジオン、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
Ａは、Ｗで置換されていてもよいフェニル、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（但し、この複素環基は、チエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
但し、(a) Ｑが、Ｒで置換されていてもよいチエニル、Ｒで置換されていてもよいフリル、Ｒで置換されていてもよいキノリルまたはＲで置換されていてもよいイソキノリルの場合は、Ａは、Ｗで置換されていてもよいフェニル、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(b) Ｑが、Ｒで置換されていてもよい２−チアゾリルの場合は、Ａは、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はチエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テト
ラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(c) Ｑが、Ｒで置換されていてもよいピリジルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピラジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(d) Ｑが、Ｒで置換されていてもよいイソチアゾリル、Ｒで置換されていても よい１，２，３−トリアゾリルまたはＲで置換されていてもよいベンゾオキサゾリルの場合は、Ａは、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はチエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(e) Ｑが、Ｒで置換されていてもよい１，２，４−トリアゾリルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はチエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(f) Ｑが、Ｒで置換されていてもよいベンゾチアゾリルの場合は、Ａは、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はフリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(g) Ｑが、Ｒで置換されていてもよいベンゾイミダゾリルの場合は、Ａは、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピラジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(h) Ｑが、Ｇで置換されていてもよいフェニルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
(i) Ｑが、Ｇで置換されていてもよいナフチルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はチエニル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル、３（２Ｈ）−ピリダジノン、ベンゾチアゾリル、ベンゾイミダゾリル、インダゾリル、ベンゾオキサゾリル、キノリニル、イソキノリニル、キノキサリニル、フタラジニル、シンノリニルまたはキナゾリニルである。）であり、
Ｂは、Ｈ、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、ＣＨ₃ ＳＣＨ₂ 、ＣＨ₃ ＯＣ₂ Ｈ₄ ＯＣＨ₂ 、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたＣ₁ 〜Ｃ₄ アルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいベンゾイルで置換されたＣ₁ 〜Ｃ₄ アルキル、テトラヒドロピラニル、（ＣＨ₃ ）₃ Ｓｉ、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルスルホニル、−ＳＯ₂ ＣＦ₃ 、Ｃ₁ 〜Ｃ₄ モノアルキルアミノスルホニル、Ｃ₂ 〜Ｃ₈ ジアルキルアミノスルホニル、フェニルアミノスルホニル、Ｃ₂ 〜Ｃ₅ モノアルキルアミノチオカルボニル、Ｃ₃ 〜Ｃ₉ ジアルキルアミノチオカルボニル、Ｃ₂ 〜Ｃ₅ シアノアルキル、Ｃ₃ 〜Ｃ₉ アルコキシカルボニルアルキル、−Ｃ（＝Ｏ）Ｔ¹ 、−Ｐ（＝Ｏ）Ｔ² Ｔ³ 、−Ｐ（＝Ｓ）Ｔ² Ｔ³ 、アルカリ金属原子、アルカリ土類金属原子またはＮＨＴ⁴ Ｔ⁵ Ｔ⁶ であり、
但し、Ｑが２−チアゾリルおよび２−ベンゾチアゾリルの場合、ＢはＣ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、ＣＨ₃ ＳＣＨ₂ 、ＣＨ₃ ＯＣ₂ Ｈ₄ ＯＣＨ₂ 、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたＣ₁ 〜Ｃ₄ アルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいベンゾイルで置換されたＣ₁ 〜Ｃ₄ アルキル、テトラヒドロピラニル、（ＣＨ₃ ）₃ Ｓｉ、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルスルホニル、−ＳＯ₂ ＣＦ₃ 、Ｃ₁ 〜Ｃ₄ モノアルキル
アミノスルホニル、Ｃ₂ 〜Ｃ₈ ジアルキルアミノスルホニル、フェニルアミノスルホニル、Ｃ₂ 〜Ｃ₅ モノアルキルアミノチオカルボニル、Ｃ₃ 〜Ｃ₉ ジアルキルアミノチオカルボニル、Ｃ₂ 〜Ｃ₅ シアノアルキ ル、Ｃ₃ 〜Ｃ₉ アルコキシカルボニルアルキル、−Ｃ（＝Ｏ）Ｔ¹ 、−Ｐ（＝Ｏ）Ｔ² Ｔ³ または−Ｐ（＝Ｓ）Ｔ² Ｔ³ であり、
Ｅは、Ｃ₁ 〜Ｃ₄ アルキルもしくはＣ₁ 〜Ｃ₄ ハロアルキルで置換されていてもよい複素環基（但し、この複素環基は２−オキサゾリル、２−チアゾリル、２−イミダゾリル、１，２，４−トリアゾール−３−イル、１，２，４−オキサジアゾール−３−イル、１，２，４−チアジアゾール−３−イル、１，３，４−オキサジアゾール−２−イル、５−テトラゾリル、２−オキサゾリニルまたは１，２，４，５−テトラジン−３−イルである。）、ハロゲン、Ｃ₂ 〜Ｃ₄ アルキニル、Ｚで置換されていてもよいフェニルエチニル、Ｃ₁ 〜Ｃ₄ ハロアルキル、ＣＮ、イソニトリル、ＮＯ₂ 、Ｎ₃ 、ＣＨＯ、Ｃ₂ 〜Ｃ₅ アルキルカルボニル、Ｃ₂ 〜Ｃ₅ アルコキシカルボニル、Ｃ₃ 〜Ｃ₅ アルケニルオキシカルボニル、Ｃ₂ 〜Ｃ₄ アルキルアミノカルボニル、Ｃ₃ 〜Ｃ₉ ジアルキルアミノカルボニル、Ｚで置換されていてもよいベンゾイル、アミノチオカルボニル、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル基、Ｚで置換されていてもよいフェニルスルフェニル、Ｚで置換されていてもよいフェニルスルフィニル、Ｚで置換されていてもよいフェニルスルホニル、−Ｐ（＝Ｏ）Ｔ² Ｔ³ または−Ｐ（＝Ｓ）Ｔ² Ｔ³ であり、
Ｇは、ハロゲン、Ｃ₁ 〜Ｃ₁₀アルキル、Ｃ₂ 〜Ｃ₄ シアノアルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたＣ₁ 〜Ｃ₄ アルキル、Ｃ₂ 〜Ｃ₆ アルケニル、Ｃ₂ 〜Ｃ₆ アルキニル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₂ 〜Ｃ₆ ハロアルケニル、Ｃ₂ 〜Ｃ₆ ハロアルキニル、Ｃ₃ 〜Ｃ₆ ハロシクロアルキル、Ｃ₁ 〜Ｃ₃ アルキルで置換されていてもよいＣ₃ 〜Ｃ₆ シクロアルキル、Ｃ₁ 〜Ｃ₁₀アルコキシ、Ｃ₂ 〜Ｃ₆ アルケニルオキシ、Ｃ₂ 〜Ｃ₆ アルキニルオキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₂ 〜Ｃ₆ ハロアルケニルオキシ、Ｃ₂ 〜Ｃ₆ ハロアルキニルオキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルケニルスルホニル、Ｃ₂ 〜Ｃ₆ アルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ アルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルキニルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルホニル、ＣＨＯ、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、ＯＨ、ナフチル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたメトキシ、Ｃ₂ 〜Ｃ₇ アルコキシカルボニル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｃ₂ 〜Ｃ₄ アルキルカルボニル、Ｃ₂ 〜Ｃ₄ ハロアルキルカルボニル、Ｃ₂ 〜Ｃ₅ アルキルカルボニルオキシ、Ｃ₂ 〜Ｃ₅ ハロアルキルカルボニルオキシ、Ｃ₃ 〜Ｃ₇ ジアルキルアミノカルボニルオキシ、Ｚで置換されていてもよいフェニル、Ｚで置換されていてもよいフェノキシ、Ｚで置換されていてもよいベンゾイル、Ｚで置換されていてもよいピリジル、Ｚで置換されていてもよいピリジルオキシ、Ｚで置換されていてもよいチエニル、隣接した置換位置で結合したメチレンジオキシ、隣接した置換位置で結合したハロメチレンジオキシおよび−Ｎ＝ＣＴ⁷ Ｔ⁸ （但し、Ｔ⁷ 及びＴ⁸ は各々独立に、Ｈ、フェニル、ベンジルまたはＣ₁ 〜Ｃ₆ アルキルであるか、Ｔ⁷ とＴ⁸ とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよい。）の中から任意に選ばれる置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であって、その置換基の数は１、２、３または４個であるか、または隣接した置換位置で結合したアルキレン基によって形成される５員環、６員環、７員環もしくは８員環であり、
Ｒは、ハロゲン、Ｃ₁ 〜Ｃ₁₀アルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたＣ₁ 〜Ｃ₄ アルキル、Ｃ₂ 〜Ｃ₆ のアルケニル、Ｃ₂ 〜Ｃ₆ アルキニル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₂ 〜Ｃ₆ ハロアルケニル、Ｃ₂ 〜Ｃ₆
ハロアルキニル、Ｃ₃ 〜Ｃ₆ ハロシクロアルキル、Ｃ₁ 〜Ｃ₃ アルキルで置換されていてもよいＣ₃ 〜Ｃ₆ シクロアルキル、Ｃ₁ 〜Ｃ₆ アルコキシ、Ｃ₂ 〜Ｃ₆ アルケニルオキシ、Ｃ₂ 〜Ｃ₆ アルキニルオキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₂ 〜Ｃ₆ ハロアルケニルオキシ、Ｃ₂ 〜Ｃ₆ ハロアルキニルオキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルケニルスルホニル、Ｃ₂ 〜Ｃ₆ アルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ のアルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルキニルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルホニル、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、フェノキシ、ＯＨ、ナフチル、Ｃ₂ 〜Ｃ₇ アルコキシカルボニル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｃ₂ 〜Ｃ₄ アルキルカルボニル、Ｃ₂ 〜Ｃ₅ アルキルカルボニルオキシ、Ｃ₂ 〜Ｃ₅ ハロアルキルカルボニルオキシ、Ｘで置換されていてもよいベンゾイル、Ｘで置換されていてもよいフェニル、Ｘで置換されていてもよいピリジル、Ｘで置換されていてもよいチエニルおよび−Ｎ＝ＣＴ⁷ Ｔ⁸ の中から任意に選ばれる置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であって、その置換基の数は１、２、３または４個であるか、または隣接した置換位置で結合したアルキレン基によって形成される５員環、６員環、７員環もしくは８員環であり、
Ｙは、ハロゲン、Ｃ₁ 〜Ｃ₁₀アルキル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₁ 〜Ｃ₆ アルコキシ、Ｃ₂ 〜Ｃ₆ アルケニルオキシ、Ｃ₂ 〜Ｃ₆ アルキニルオキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₂ 〜Ｃ₆ ハロアルケニルオキシ、Ｃ₂ 〜Ｃ₆ ハロアルキニルオキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルケニルスルホニル、Ｃ₂ 〜Ｃ₆ アルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ アルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ アルキニルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルケニルスルホニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフェニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルフィニル、Ｃ₂ 〜Ｃ₆ ハロアルキニルスルホニル、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、ＯＨ、Ｃ₂ 〜Ｃ₇ アルコキシカルボニル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｃ₂ 〜Ｃ₅ アルキルカルボニルオキシ、Ｃ₂ 〜Ｃ₅ ハロアルキルカルボニルオキシ、Ｃ₃ 〜Ｃ₇ ジアルキルアミノカルボニルオキシ、Ｘで置換されていてもよいフェニル、および−Ｎ＝ＣＴ⁷ Ｔ⁸ （但し、Ｔ⁷ 及びＴ⁸ は各々独立に、Ｈ、フェニル、ベンジルまたはＣ₁ 〜Ｃ₆ アルキルであるか、Ｔ⁷ とＴ⁸ とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよい。）の中から任意に選ばれる置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であって、その置換基の数は１、２、３または４個であるか、または隣接した置換位置で結合したアルキレン基によって形成される５員環、６員環、７員環もしくは８員環であり、
Ｗは、ハロゲン、Ｃ₁ 〜Ｃ₆ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、Ｃ₂ 〜Ｃ₄ アルケニル、Ｃ₂ 〜Ｃ₄ ハロアルケニル、Ｃ₂ 〜Ｃ₄ アルケニルオキシ、Ｃ₂ 〜Ｃ₄ ハロアルケニルオキシ、Ｃ₂ 〜Ｃ₄ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₄ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₄ アルケニルスルホニル、Ｃ₂ 〜Ｃ₄ ハロアルケニルスルフェニル、Ｃ₂ 〜Ｃ₄ ハロアルケニルスルフィニル、Ｃ₂ 〜Ｃ₄ ハロアルケニルスルホニル、Ｃ₂ 〜Ｃ₄ アルキニル、Ｃ₂ 〜Ｃ₄ ハロアルキニル、Ｃ₂ 〜Ｃ₄ アルキニルオキシ、Ｃ₂ 〜Ｃ₄ ハロアルキニルオキシ、Ｃ₂ 〜Ｃ₄ アルキニルスルフェニル、Ｃ₂ 〜Ｃ₄ アルキニルスルフィ
ニル、Ｃ₂ 〜Ｃ₄ アルキニルスルホニル、Ｃ₂ 〜Ｃ₄ ハロアルキニルスルフェニル、Ｃ₂ 〜Ｃ₄ ハロアルキニルスルフィニル、Ｃ₂ 〜Ｃ₄ ハロアルキニルスルホニル、ＮＯ₂ 、ＣＮ、ホルミル、Ｃ₂ 〜Ｃ₆ アルコキシカルボニル、Ｃ₂ 〜Ｃ₆ アルキルカルボニル、Ｃ₂ 〜Ｃ₆ ハロアルキルカルボニル、Ｃ₂ 〜Ｃ₆ アルキルカルボニルオキシおよび-NU ¹ U ² の中から任意に選ばれる置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であって、その置換基の数は１、２、３、４または５個であり、
Ｔ¹ は、Ｃ₁ 〜Ｃ₂₀アルキル、Ｃ₂ 〜Ｃ₆ アルケニル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ−Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₃ 〜Ｃ₆ ハロシクロアルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたＣ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₃ アルキルで置換されていてもよいＣ₃ 〜Ｃ₆ シクロアルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルで置換されたシクロアルキル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキルで置換されていてもよいフェニルとＣ₁ 〜Ｃ₄ アルキルで置換されたシクロプロピル、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルコキシで置換されていてもよいフェニルとハロゲンで置換されたＣ₃ 〜Ｃ₄ シクロアルキル基、ハロゲンで置換されていてもよいＣ₂ 〜Ｃ₄ アルケニルとＣ₁ 〜Ｃ₄ アルキルで置換されたシクロプロピル基、ハロゲンもしくはＣ₁ 〜Ｃ₄ アルキル基で置換されていてもよいフェニルで置換されたＣ₂ 〜Ｃ₄ アルケニル、Ｃ₁ 〜Ｃ₁₂アルコキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₂ 〜Ｃ₅ アルケニルオキシ、Ｃ₁ 〜Ｃ₃ アルキルで置換されていてもよいＣ₃ 〜Ｃ₆ シクロアルコキシ、ベンジルオキシ、Ｃ₂ 〜Ｃ₅ アルコキシカルボニル、-NU ¹ U ² 、フェニルアミノ、Ｚで置換されていてもよいフェニル、Ｚで置換されていてもよいフェノキシ、Ｚで置換されていてもよいフェニルチオ、Ｚで置換されていてもよいナフチルまたはＺで置換されていてもよい５員環もしくは６員環の複素環基（但し、これらの複素環基はチエニル、フリル、ピロリル、オキサゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、ピラゾリル、イミダゾリル、１，３，４−オキサジアゾリル、１，２，４−オキサジアゾリル、１，３，４−チアジアゾリル、１，２，４−チアジアゾリル、１，２，４−トリアゾリル、１，２，３−チアジアゾリル、１，２，３−トリアゾリル、１，２，３，４−テトラゾリル、ピリジニル、ピリミジニル、ピラジニル、ピリダジニル、１，３，５−トリアジニル、１，２，４−トリアジニル、ピラゾリニル、イミダゾリニル、オキサゾリニル、イソキサゾリニル、チアゾリニル及び３（２Ｈ）−ピリダジノンの中から選ばれる。）であり、
Ｔ² 及びＴ³ は、各々独立に、ＯＨ、フェニル、Ｃ₁ 〜Ｃ₆ アルキル、Ｃ₁ 〜Ｃ₆ アルコキシまたはＣ₁ 〜Ｃ₄ アルキルスルフェニルであり、
Ｔ⁴ 、Ｔ⁵ 及びＴ⁶ は、各々独立に、Ｈ、Ｃ₁ 〜Ｃ₆ アルキル、Ｃ₁ 〜Ｃ₆ アルケニル、Ｃ₁ 〜Ｃ₃ アルキル基で置換されていてもよいＣ₃ 〜Ｃ₆ シクロアルキル基またはベンジルであるか、あるいはＴ⁴ 、Ｔ⁵ 及びＴ⁶ のうちの２個が、それぞれが結合している窒素原子と共に酸素原子、窒素原子もしくは硫黄原子を含有していてもよい５員環、６員環、７員環または８員環基を形成するものであり、
Ｘ及びＺは、各々独立して、ハロゲン、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₂ 〜Ｃ₅ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₅ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₅ アルケニルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、ＮＯ₂ 、ＣＮ、ＣＨＯ、ＯＨ、-NU ¹ U ² 、フェニル、フェノキシまたはＣ₂ 〜Ｃ₅ アルコキシカルボニルの中から任意に選ばれる置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であって、その置換基の数は１、２、３、４または５個であり、
Ｔ⁷ 及びＴ⁸ は、各々独立に、Ｈ、フェニル、ベンジルまたはＣ₁ 〜Ｃ₆ アルキルであるか、あるいはＴ⁷ とＴ⁸ とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよく、
U ¹ 及びU ² は、各々独立に、Ｈ、Ｃ₁ 〜Ｃ₆ アルキル、Ｃ₂ 〜Ｃ₅ アルキルカルボニ
ル、フェニルまたはベンジルを表すか、U ¹ とU ² とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよい。］
で表されるエチレン誘導体。

[Wherein Q is phenyl optionally substituted with G, naphthyl optionally substituted with G, or heterocyclic group optionally substituted with R (wherein this heterocyclic group is thienyl, furyl, , Pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2 , 4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2 , 4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxy Zoriniru, thiazolinyl, imidazolinone, imidazolidinedione, 3 (2H) - a pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  A is phenyl optionally substituted by W, naphthyl optionally substituted by W, or heterocyclic group optionally substituted by Y (provided that this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl) , Isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl , Pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H)- Ridajinon, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl.), And
    However, (a) when Q is thienyl optionally substituted with R, furyl optionally substituted with R, quinolyl optionally substituted with R, or isoquinolyl optionally substituted with R , A is phenyl optionally substituted with W, naphthyl optionally substituted with W, or heterocyclic group optionally substituted with Y (this heterocyclic group is pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl) , Pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3 -Thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-tri Azinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzoimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl. Yes,
  (b) When Q is 2-thiazolyl which may be substituted with R, A is a naphthyl which may be substituted with W or a heterocyclic group which may be substituted with Y (this heterocyclic group) Is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-teto
Razolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzoimidazolyl, indazolyl, benzoyl Oxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl. ) And
  (c) When Q is pyridyl optionally substituted with R, A is a heterocyclic group optionally substituted with Y (this heterocyclic group is pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl) Imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H ) -Pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, Noxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  (d) When Q is isothiazolyl optionally substituted with R, 1,2,3-triazolyl optionally substituted with R, or benzooxazolyl optionally substituted with R, A is , Naphthyl optionally substituted with W or heterocyclic group optionally substituted with Y (this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3, 4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3- Triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1 2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzoimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinazolinyl or quinolinyl). Yes,
  (e) When Q is 1,2,4-triazolyl which may be substituted with R, A is a heterocyclic group which may be substituted with Y (this heterocyclic group is thienyl, furyl, pyrrolyl). , Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4 -Triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl , Pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazo , Benzimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  (f) When Q is benzothiazolyl optionally substituted with R, A is a naphthyl optionally substituted with W or a heterocyclic group optionally substituted with Y (this heterocyclic group is furyl , Pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2 , 4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2 , 4-Triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2 H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl.
  (g) When Q is benzoimidazolyl optionally substituted with R, A is a naphthyl optionally substituted with W or a heterocyclic group optionally substituted with Y (this heterocyclic group is pyrrolyl) , Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4 -Triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl , Oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzoy Midazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  (h) When Q is phenyl which may be substituted with G, A is a heterocyclic group which may be substituted with Y (this heterocyclic group is pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl) 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1 , 2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H ) -Pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, Noxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  (i) when Q is naphthyl optionally substituted with G, A is a heterocyclic group optionally substituted with Y (this heterocyclic group is thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl) , Pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3 -Thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl , Isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzo Imidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl).
  B is H, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₂~ C_FourAlkoxyalkyl, CH_ThreeSCH₂, CH_ThreeOC₂H_FourOCH₂, Halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl₁~ C_FourAlkyl, halogen or C₁~ C_FourC substituted with benzoyl optionally substituted with alkyl₁~ C_FourAlkyl, tetrahydropyranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfonyl, halogen or C₁~ C_FourPhenylsulfonyl optionally substituted with alkyl, -SO₂CF_Three, C₁~ C_FourMonoalkylaminosulfonyl, C₂~ C₈Dialkylaminosulfonyl, phenylaminosulfonyl, C₂~ C_FiveMonoalkylaminothiocarbonyl, C_Three~ C₉Dialkylaminothiocarbonyl, C₂~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonylalkyl, -C (= O) T¹, -P (= O) T²T^Three, -P (= S) T²T^Three, Alkali metal atoms, alkaline earth metal atoms or NHT^FourT^FiveT⁶And
    However, when Q is 2-thiazolyl and 2-benzothiazolyl, B is C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₂~ C_FourAlkoxyalkyl, CH_ThreeSCH₂, CH_ThreeOC₂H_FourOCH₂, Halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl₁~ C_FourAlkyl, halogen or C₁~ C_FourC substituted with benzoyl optionally substituted with alkyl₁~ C_FourAlkyl, tetrahydropyranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfonyl, halogen or C₁~ C_FourPhenylsulfonyl optionally substituted with alkyl, -SO₂CF_Three, C₁~ C_FourMonoalkyl
Aminosulfonyl, C₂~ C₈Dialkylaminosulfonyl, phenylaminosulfonyl, C₂~ C_FiveMonoalkylaminothiocarbonyl, C_Three~ C₉Dialkylaminothiocarbonyl, C₂~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonylalkyl, -C (= O) T¹, -P (= O) T²T^ThreeOr -P (= S) T²T^ThreeAnd
  E is C₁~ C_FourAlkyl or C₁~ C_FourHeterocyclic group optionally substituted with haloalkyl (wherein this heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxa Diazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 5-tetrazolyl, 2-oxazolinyl or 1,2,4,5-tetrazine -3-yl), halogen, C₂~ C_FourAlkynyl, phenylethynyl optionally substituted with Z, C₁~ C_FourHaloalkyl, CN, isonitrile, NO₂, N_Three, CHO, C₂~ C_FiveAlkylcarbonyl, C₂~ C_FiveAlkoxycarbonyl, C_Three~ C_FiveAlkenyloxycarbonyl, C₂~ C_FourAlkylaminocarbonyl, C_Three~ C₉Dialkylaminocarbonyl, benzoyl optionally substituted with Z, aminothiocarbonyl, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl group, phenylsulfenyl optionally substituted with Z, phenylsulfinyl optionally substituted with Z, phenylsulfonyl optionally substituted with Z, -P (= O) T²T^ThreeOr -P (= S) T²T^ThreeAnd
  G is halogen, C₁~ C_TenAlkyl, C₂~ C_FourCyanoalkyl, halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl₁~ C_FourAlkyl, C₂~ C₆Alkenyl, C₂~ C₆Alkynyl, C₁~ C₆Haloalkyl, C₂~ C₆Haloalkenyl, C₂~ C₆Haloalkynyl, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloalkyl, C₁~ C_TenAlkoxy, C₂~ C₆Alkenyloxy, C₂~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy, C₂~ C₆Haloalkenyloxy, C₂~ C₆Haloalkynyloxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl, C₂~ C₆Alkenylsulfenyl, C₂~ C₆Alkenylsulfinyl, C₂~ C₆Alkenylsulfonyl, C₂~ C₆Alkynylsulfenyl, C₂~ C₆Alkynylsulfinyl, C₂~ C₆Alkynylsulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkylsulfonyl, C₂~ C₆Haloalkenylsulfenyl, C₂~ C₆Haloalkenylsulfinyl, C₂~ C₆Haloalkenylsulfonyl, C₂~ C₆Haloalkynylsulfenyl, C₂~ C₆Haloalkynylsulfinyl, C₂~ C₆Haloalkynylsulfonyl, CHO, NO₂, CN, -NU¹U², OH, naphthyl, halogen or C₁~ C_FourMethoxy substituted with phenyl, optionally substituted with alkyl, C₂~ C₇Alkoxycarbonyl, C₂~ C_FourAlkoxyalkyl, C₂~ C_FourAlkylcarbonyl, C₂~ C_FourHaloalkylcarbonyl, C₂~ C_FiveAlkylcarbonyloxy, C₂~ C_FiveHaloalkylcarbonyloxy, C_Three~ C₇Dialkylaminocarbonyloxy, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, benzoyl optionally substituted with Z, pyridyl optionally substituted with Z, substituted with Z Optionally pyridyloxy, thienyl optionally substituted with Z, methylenedioxy bonded at adjacent substitution positions, halomethylenedioxy bonded at adjacent substitution positions, and -N = CT⁷T⁸(However, T⁷And T⁸Each independently represents H, phenyl, benzyl or C₁~ C₆Is alkyl or T⁷And T⁸A 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring may be formed together with the carbon atom to which and are bonded. ), And the number of the substituents is 1, 2, 3 or 4 (in which two or more substituents may be the same or different from each other). A 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring formed by an alkylene group which is an individual or bonded at adjacent substitution positions;
  R is halogen, C₁~ C_TenAlkyl, halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl₁~ C_FourAlkyl, C₂~ C₆Alkenyl, C₂~ C₆Alkynyl, C₁~ C₆Haloalkyl, C₂~ C₆Haloalkenyl, C₂~ C₆
Haloalkynyl, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C₂~ C₆Alkenyloxy, C₂~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy, C₂~ C₆Haloalkenyloxy, C₂~ C₆Haloalkynyloxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl, C₂~ C₆Alkenylsulfenyl, C₂~ C₆Alkenylsulfinyl, C₂~ C₆Alkenylsulfonyl, C₂~ C₆Alkynylsulfenyl, C₂~ C₆Alkynylsulfinyl, C₂~ C₆Alkynylsulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkylsulfonyl, C₂~ C₆Haloalkenylsulfenyl, C₂~ C₆Haloalkenylsulfinyl, C₂~ C₆Haloalkenylsulfonyl, C₂~ C₆Haloalkynylsulfenyl, C₂~ C₆Haloalkynylsulfinyl, C₂~ C₆Haloalkynylsulfonyl, NO₂, CN, -NU¹U², Phenoxy, OH, naphthyl, C₂~ C₇Alkoxycarbonyl, C₂~ C_FourAlkoxyalkyl, C₂~ C_FourAlkylcarbonyl, C₂~ C_FiveAlkylcarbonyloxy, C₂~ C_FiveHaloalkylcarbonyloxy, benzoyl optionally substituted with X, phenyl optionally substituted with X, pyridyl optionally substituted with X, thienyl optionally substituted with X and -N = CT⁷T⁸Substituents arbitrarily selected from the above (provided that the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2, 3 or 4 Or a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring formed by an alkylene group bonded at adjacent substitution positions;
  Y is halogen, C₁~ C_TenAlkyl, C₁~ C₆Haloalkyl, C₁~ C₆Alkoxy, C₂~ C₆Alkenyloxy, C₂~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy, C₂~ C₆Haloalkenyloxy, C₂~ C₆Haloalkynyloxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl, C₂~ C₆Alkenylsulfenyl, C₂~ C₆Alkenylsulfinyl, C₂~ C₆Alkenylsulfonyl, C₂~ C₆Alkynylsulfenyl, C₂~ C₆Alkynylsulfinyl, C₂~ C₆Alkynylsulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkylsulfonyl, C₂~ C₆Haloalkenylsulfenyl, C₂~ C₆Haloalkenylsulfinyl, C₂~ C₆Haloalkenylsulfonyl, C₂~ C₆Haloalkynylsulfenyl, C₂~ C₆Haloalkynylsulfinyl, C₂~ C₆Haloalkynylsulfonyl, NO₂, CN, -NU¹U², OH, C₂~ C₇Alkoxycarbonyl, C₂~ C_FourAlkoxyalkyl, C₂~ C_FiveAlkylcarbonyloxy, C₂~ C_FiveHaloalkylcarbonyloxy, C_Three~ C₇Dialkylaminocarbonyloxy, phenyl optionally substituted by X, and -N = CT⁷T⁸(However, T⁷And T⁸Each independently represents H, phenyl, benzyl or C₁~ C₆Is alkyl or T⁷And T⁸A 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring may be formed together with the carbon atom to which and are bonded. ), And the number of the substituents is 1, 2, 3 or 4 (in which two or more substituents may be the same or different from each other). A 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring formed by an alkylene group which is an individual or bonded at adjacent substitution positions;
  W is halogen, C₁~ C₆Alkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkylsulfonyl, C₂~ C_FourAlkenyl, C₂~ C_FourHaloalkenyl, C₂~ C_FourAlkenyloxy, C₂~ C_FourHaloalkenyloxy, C₂~ C_FourAlkenylsulfenyl, C₂~ C_FourAlkenylsulfinyl, C₂~ C_FourAlkenylsulfonyl, C₂~ C_FourHaloalkenylsulfenyl, C₂~ C_FourHaloalkenylsulfinyl, C₂~ C_FourHaloalkenylsulfonyl, C₂~ C_FourAlkynyl, C₂~ C_FourHaloalkynyl, C₂~ C_FourAlkynyloxy, C₂~ C_FourHaloalkynyloxy, C₂~ C_FourAlkynylsulfenyl, C₂~ C_FourAlkynylsulfi
Nil, C₂~ C_FourAlkynylsulfonyl, C₂~ C_FourHaloalkynylsulfenyl, C₂~ C_FourHaloalkynylsulfinyl, C₂~ C_FourHaloalkynylsulfonyl, NO₂, CN, formyl, C₂~ C₆Alkoxycarbonyl, C₂~ C₆Alkylcarbonyl, C₂~ C₆Haloalkylcarbonyl, C₂~ C₆Alkylcarbonyloxy and -NU¹U²(In which two or more substituents may be the same or different from each other), the number of the substituents is 1, 2, 3, 4 or 5
  T¹Is C₁~ C₂₀Alkyl, C₂~ C₆Alkenyl, C₁~ C₆Haloalkyl, C₁~ C_FourAlkoxy-C₁~ C_FourAlkyl, C_Three~ C₆Halocycloalkyl, halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl₁~ C_FourAlkyl, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloalkyl, halogen or C₁~ C_FourCycloalkyl substituted with phenyl, halogen or C which may be substituted with alkyl₁~ C_FourPhenyl optionally substituted with alkyl and C₁~ C_FourCyclopropyl, halogen or C substituted with alkyl₁~ C_FourC optionally substituted with phenyl and halogen optionally substituted with alkoxy_Three~ C_FourCycloalkyl group, C optionally substituted with halogen₂~ C_FourAlkenyl and C₁~ C_FourCyclopropyl group substituted with alkyl, halogen or C₁~ C_FourC substituted with phenyl which may be substituted with alkyl group₂~ C_FourAlkenyl, C₁~ C₁₂Alkoxy, C₁~ C_FourHaloalkoxy, C₂~ C_FiveAlkenyloxy, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloalkoxy, benzyloxy, C₂~ C_FiveAlkoxycarbonyl, -NU¹U², Phenylamino, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, phenylthio optionally substituted with Z, naphthyl optionally substituted with Z, or substituted with Z A 5- or 6-membered heterocyclic group (provided that these heterocyclic groups are thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2, 3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2 4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl and 3 (2H) - a chosen from among pyridazinone).
  T²And T^ThreeEach independently represents OH, phenyl, C₁~ C₆Alkyl, C₁~ C₆Alkoxy or C₁~ C_FourAlkylsulfenyl,
  T^Four, T^FiveAnd T⁶Are each independently H, C₁~ C₆Alkyl, C₁~ C₆Alkenyl, C₁~ C_ThreeC optionally substituted with an alkyl group_Three~ C₆A cycloalkyl group or benzyl, or T^Four, T^FiveAnd T⁶Two of them form a 5-membered, 6-membered, 7-membered or 8-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bonded. Is,
  X and Z are each independently halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfonyl, C₂~ C_FiveAlkenylsulfenyl, C₂~ C_FiveAlkenylsulfinyl, C₂~ C_FiveAlkenylsulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkylsulfonyl, NO₂, CN, CHO, OH, -NU¹U², Phenyl, phenoxy or C₂~ C_FiveA substituent arbitrarily selected from alkoxycarbonyl (provided that the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2, 3, 4 or 5,
  T⁷And T⁸Each independently represents H, phenyl, benzyl or C₁~ C₆Is alkyl or T⁷And T⁸And may form a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring with the carbon atom to which
  U¹And U²Are each independently H, C₁~ C₆Alkyl, C₂~ C_FiveAlkylcarboni
R, phenyl or benzyl, or U¹And U²A 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring may be formed together with the carbon atom to which and are bonded. ]
An ethylene derivative represented by

[2] Q is phenyl optionally substituted with G, naphthyl optionally substituted with G, or a heterocyclic group optionally substituted with R (provided that this heterocyclic group includes thienyl, furyl, Pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2, 4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2, 4,5-tetrazinyl, pyrazolinyl, imidazolinyl, imidazolinone, imidazolidinedione). ,
A is phenyl optionally substituted by W, naphthyl optionally substituted by W, or heterocyclic group optionally substituted by Y (provided that this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl) , Isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl , Pyrazolinyl, imidazolinyl).
B is, H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C _{4 alkoxyalkyl, CH 3 OC 2 H 4 OCH} 2, C 1 ~C 4 alkylsulfonyl, halogen or C ₁ -C ₄ phenylsulfonyl optionally substituted with alkyl, —SO ₂ CF ₃ , C _{2 to} C ₈ dialkylaminosulfonyl, C _{2 to} C ₉ dialkylaminothiocarbonyl, C _{3 to} C ₉ alkoxycarbonylalkyl, —C (= ^{O) T 1, -P (=} O) T 2 T 3, -P (= S) T 2 T 3, an alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ^6,
T ¹ is substituted with C ₁ -C ₂₀ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl substituted C ₁ in phenyl optionally -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted cycloalkyl, halogen or C ₁ -C ₄ alkyl substituted C ₁ and also phenyl optionally -C ₄ alkyl substituted cyclopropyl, halogen or C ₁ -C ₄ alkoxy substituted with phenyl and halogen substituted a C ₃ -C ₄ cycloalkyl group, an optionally C ₂ optionally substituted by halogen -C ₄ alkenyl A C ₁ -C ₄ alkyl-substituted cyclopropyl group, halogen or C ₁ -C ₄ alkyl C ₂ -C ₄ alkenyl substituted with also phenyl substituted with one, C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C ₃ optionally C ₃ be alkyl substituted -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, and Z Phenyl which may be substituted, phenoxy which may be substituted with Z, phenylthio, naphthyl or heterocyclic group which may be substituted with Z (provided that this heterocyclic group is thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl) Or an ethylene derivative according to the above [1].

である。）であり、
Ａが、Ｗで置換されていてもよいフェニル、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（但し、この複素環基は、

である。）であり、
但し、（ａ）Ｑが、Ｑ−１、Ｑ−２、Ｑ−３またはＱ−４の場合は、Ａは、Ｗで置換されていてもよいフェニル、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はＡ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−５７、Ａ−５８、Ａ−５９、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｂ）Ｑが、Ｑ−１２の場合は、Ａは、Ｗで置換されていてもよいナフチルまたはＹで置換されていてもよい複素環基（この複素環基はＡ−１、Ａ−２、Ａ−３、Ａ−４、Ａ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−５４、Ａ−５５、Ａ−５６、Ａ−５７、Ａ−５８、Ａ−５９、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｃ）Ｑが、Ｑ−５２、Ｑ−５３またはＱ−５４の場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はＡ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ
−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−６０、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｄ）Ｑが、Ｑ−２３、Ｑ−２４、Ｑ−４３、Ｑ−４４、Ｑ−４５、Ｑ−４６またはＱ−４９の場合は、Ａは、Ｗで置換されていてもよいナフチル基またはＹで置換されていてもよい複素環基（この複素環基はＡ−１、Ａ−２、Ａ−３、Ａ−４、Ａ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−５４、Ａ−５５、Ａ−５６、Ａ−５７、Ａ−５８、Ａ−５９、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｅ）Ｑが、Ｑ−３７、Ｑ−３８、Ｑ−３９、Ｑ−４０、Ｑ−４１またはＱ−４２の場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はＡ−１、Ａ−２、Ａ−３、Ａ−４、Ａ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−５７、Ａ−５８、Ａ−５９、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｆ）Ｑが、Ｇで置換されていてもよいフェニルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はＡ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
（ｇ）Ｑが、Ｇで置換されていてもよいナフチルの場合は、Ａは、Ｙで置換されていてもよい複素環基（この複素環基はＡ−１、Ａ−２、Ａ−５、Ａ−６、Ａ−７、Ａ−８、Ａ−９、Ａ−１０、Ａ−１１、Ａ−１２、Ａ−１３、Ａ−１４、Ａ−１５、Ａ−１６、Ａ−１７、Ａ−１８、Ａ−１９、Ａ−２０、Ａ−２１、Ａ−２２、Ａ−２３、Ａ−２４、Ａ−２５、Ａ−２６、Ａ−２７、Ａ−２８、Ａ−２９、Ａ−３０、Ａ−３１、Ａ−３２、Ａ−３３、Ａ−３４、Ａ−３５、Ａ−３６、Ａ−３７、Ａ−３８、Ａ−３９、Ａ−４０、Ａ−４１、Ａ−４２、Ａ−４３、Ａ−４４、Ａ−４５、Ａ−４６、Ａ−４７、Ａ−４８、Ａ−４９、Ａ−５０、Ａ−５１、Ａ−５２、Ａ−５３、Ａ−５４、Ａ−５５、Ａ−５６、Ａ−５７、Ａ−５８、Ａ−５９、Ａ−６０、Ａ−６１、Ａ−６２、Ａ−６３、Ａ−６４、Ａ−６５、Ａ−６６、Ａ−６７、Ａ−６８、Ａ−６９、Ａ−７０、Ａ−７１、Ａ−７２、Ａ−７３、Ａ−７４またはＡ−７５である。）であり、
Ｒ¹ が、ハロゲン、Ｃ₁ 〜Ｃ₁₀アルキル、Ｃ₂ 〜Ｃ₆ アルケニル、Ｃ₂ 〜Ｃ₆ アルキニ
ル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₁ 〜Ｃ₆ アルコキシ、Ｃ₂ 〜Ｃ₆ アルケニルオキシ、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、ＯＨ、Ｃ₂ 〜Ｃ₇ アルコキシカルボニル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｃ₂ 〜Ｃ₄ アルキルカルボニル、Ｘで置換されていてもよいフェニル、Ｘで置換されていてもよいピリジル、Ｘで置換されていてもよいチエニルおよび−Ｎ＝ＣＴ⁷ Ｔ⁸ （但し、Ｔ⁷ 及びＴ⁸ は各々独立に、Ｈ、フェニル、ベンジルまたはＣ₁ 〜Ｃ₆ アルキルであるか、Ｔ⁷ とＴ⁸ とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよい。）であるか、または隣接したＲと共にアルキレン鎖として５員環、６員環、７員環もしくは８員環を形成してもよく、
Ｙ¹ は、ハロゲン、Ｃ₁ 〜Ｃ₁₀アルキル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₁ 〜Ｃ₆ アルコキシ、Ｃ₂ 〜Ｃ₆ アルケニルオキシ、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、ＯＨ、Ｃ₂ 〜Ｃ₇ アルコキシカルボニル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｘで置換されていてもよいフェニルおよび−Ｎ＝ＣＴ⁷ Ｔ⁸ （但し、Ｔ⁷ 及びＴ⁸ は各々独立に、Ｈ、フェニル、ベンジルまたはＣ₁ 〜Ｃ₆ アルキルであるか、Ｔ⁷ とＴ⁸ とが結合している炭素原子と共に５員環、６員環、７員環または８員環を形成してもよい。）であるか、または隣接したＹ¹ と共にアルキレン鎖として５員環、６員環、７員環もしくは８員環を形成してもよく、
Ｘが、ハロゲン、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₂ 〜Ｃ₅ アルケニルスルフェニル、Ｃ₂ 〜Ｃ₅ アルケニルスルフィニル、Ｃ₂ 〜Ｃ₅ アルケニルスルホニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフェニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルフィニル、Ｃ₁ 〜Ｃ₄ ハロアルキルスルホニル、ＮＯ₂ 、ＣＮ、ＣＨＯ、ＯＨ、-NU ¹ U ² 、フェニル、フェノキシまたはＣ₂ 〜Ｃ₅ アルコキシカルボニルの中から任意に選ばれる１ないし４個の置換基（但し、その置換基が２個以上の場合は同一か相互に異なってもよい。）であり、
Ｚが、ハロゲン、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ、Ｃ₁ 〜Ｃ₄ ハロアルコキシ、Ｃ₁ 〜Ｃ₄ アルキルスルフェニル、Ｃ₁ 〜Ｃ₄ アルキルスルフィニル、Ｃ₁ 〜Ｃ₄ アルキルスルホニル、Ｃ₁ 〜Ｃ₄ アルケニルスルフェニル、Ｃ₁ 〜Ｃ₄ アルケニルスルフィニル、Ｃ₁ 〜Ｃ₄ アルケニルスルホニル、ＮＯ₂ 、ＣＮ、-NU ¹ U ² 、フェニル、フェノキシおよびＣ₂ 〜Ｃ₅ アルコキシカルボニルの中から任意に選ばれる１ないし４個の置換基( 但し、その置換基が２個以上の場合は同一か相互に異なってもよい) であり、
ｍは、置換基の数を表し、０、１、２または３であり、
ｎは、置換基の数を表し、０、１、２、３または４であり、
ｐは、置換基の数を表し、０、１または２であり、
ｑは、置換基の数を表し、０または１（但し、ｍ、ｎ及びｐが２以上の整数を表す場合は、その置換基は同一でも異なっていてもよい。）である上記〔２〕記載のエチレン誘導体。 [3] Q is phenyl optionally substituted with G, naphthyl optionally substituted with G, or heterocyclic group optionally substituted with R (provided that the heterocyclic group is

It is. ) And
A is phenyl optionally substituted with W, naphthyl optionally substituted with W, or heterocyclic group optionally substituted with Y (provided that this heterocyclic group is

It is. ) And
However, (a) when Q is Q-1, Q-2, Q-3 or Q-4, A is phenyl optionally substituted with W, naphthyl optionally substituted with W, or A heterocyclic group which may be substituted with Y (this heterocyclic group is A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A -13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25 A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A -38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50 , A-51, A-52, A-53 A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A- 69, A-70, A-71, A-72, A-73, A-74 or A-75).
(B) When Q is Q-12, A is a naphthyl which may be substituted with W or a heterocyclic group which may be substituted with Y (this heterocyclic group is A-1, A-2) A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A -15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27 A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A -40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52 A-53, A-54, A-55, A-56, A 57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75).
(C) When Q is Q-52, Q-53 or Q-54, A is a heterocyclic group which may be substituted with Y (this heterocyclic group is A-5, A-6, A -7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19 A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A -32, A-33, A-34, A
-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47 A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-63, A-64, A-65, A-66, A-67, A -68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75. ) And
(D) When Q is Q-23, Q-24, Q-43, Q-44, Q-45, Q-46 or Q-49, A is a naphthyl group optionally substituted with W. Or a heterocyclic group optionally substituted with Y (this heterocyclic group is A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A- 21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A- 46, A-47, A-48, A-49, A-5 A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A -63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75 And)
(E) When Q is Q-37, Q-38, Q-39, Q-40, Q-41, or Q-42, A is a heterocyclic group optionally substituted with Y (this heterocyclic group). The cyclic group is A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12. A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A -25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37 A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A -50, A-51, A-52, A-53, A-57, A-5 A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A -71, A-72, A-73, A-74 or A-75).
(F) When Q is phenyl which may be substituted with G, A is a heterocyclic group which may be substituted with Y (this heterocyclic group is A-5, A-6, A-7). A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-19, A-20, A-21, A-22, A-23, A -24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36 A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A -49, A-50, A-51, A-52, A-53, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67 A-68, A-69, A-70, A-71 An A-72, A-73, A-74 or A-75.),
(G) When Q is naphthyl which may be substituted with G, A is a heterocyclic group which may be substituted with Y (this heterocyclic group is A-1, A-2, A-5). , A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A -18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30 A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A -43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55 A-56, A-57, A-58, A-59, A 60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75).
R ¹ is halogen, C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, NO ₂ , CN, -NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted by X, substituted by X pyridyl which may have, X thienyl and -N = CT ⁷ be replaced by T ⁸ (where, T ⁷ and T ⁸ each independently is a H, phenyl, benzyl or C ₁ -C ₆ alkyl Or may form a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded.) Or an alkylene chain together with adjacent R Forms a 5-, 6-, 7- or 8-membered ring At best,
Y ¹ is halogen, C ₁ -C ₁₀ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, NO ₂ , CN, -NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, phenyl and -N be substituted by X = CT ⁷ T ⁸ (where, T ⁷ and T ⁸ are each independently, H, phenyl, benzyl or C ₁ -C ₆ alkyl, or may form a 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded. Or an adjacent Y ¹ may form a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring as an alkylene chain,
X is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl , C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl 1 to 4 substituents optionally selected from C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, CHO, OH, —NU ¹ U ² , phenyl, phenoxy or C ₂ -C ₅ alkoxycarbonyl ( However, when two or more substituents are present, they may be the same or different from each other.)
Z is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl , C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkenyl Le phenyl, C ₁ -C ₄ alkenylsulfinyl, C ₁ -C _{4 ^{alkenylsulfonyl, NO 2, CN, -NU 1}} U 2, phenyl, phenoxy and C 1 to 4 substituents arbitrarily selected from _{2 to} C ₅ alkoxycarbonyl (provided that the substituents are two or more, they may be the same or different from each other);
m represents the number of substituents and is 0, 1, 2 or 3;
n represents the number of substituents and is 0, 1, 2, 3 or 4;
p represents the number of substituents and is 0, 1 or 2;
q represents the number of substituents and is 0 or 1 (provided that when m, n and p represent an integer of 2 or more, the substituents may be the same or different) [2]. The ethylene derivatives described.

    [4] The ethylene derivative according to the above [2], wherein E is CN.

    [5] The ethylene derivative according to the above [3], wherein E is CN.

[6] E is a heterocyclic group optionally substituted by C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl (provided that this heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1 , 2,4-Triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl in a.), halogen, C ₂ -C ₄ alkynyl, phenyl ethynyl optionally substituted by Z, C ₁ -C _{4 haloalkyl, CN, NO 2, N 3} , CHO, C 2 ~C 5 alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C ₃ -C ₉ dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C ₁ -C ₄ Arukirusurufu Enyl, C ₁ -C ₄ alkylsulfinyl, C
₁ -C ₄ alkylsulfonyl group, Z good phenylsulfanyl phenyl optionally substituted, Z with optionally substituted phenylsulfinyl, phenyl sulfonyl optionally substituted by Z, -P (= O) T 2 T ³ or -P (= S) ethylene derivatives of the above-mentioned [2], wherein a T ² T ^3.

[7] E is a heterocyclic group optionally substituted by C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl (provided that this heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1 , 2,4-Triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl in a.), halogen, C ₂ -C ₄ alkynyl, phenyl ethynyl optionally substituted by Z, C ₁ -C _{4 haloalkyl, CN, NO 2, N 3} , CHO, C 2 ~C 5 alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C ₃ -C ₉ dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C ₁ -C ₄ alkylsulfamoyl Eniru, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl group, phenyl sulphenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z alkylsulfinyl, optionally substituted by Z ^{phenylsulfonyl, -P (= O) T 2} T 3 , or -P (= S) ethylene derivative described in [3] is a T ² T ^3.

    [8] Q is phenyl optionally substituted with G, oxazolyl optionally substituted with R, thiazolyl optionally substituted with R, pyrazolyl optionally substituted with R, substituted with R The ethylene derivative according to the above [4], which may be 1,2,3-triazolyl, pyridinyl optionally substituted with R, or pyrimidinyl optionally substituted with R.

    [9] The ethylene derivative according to the above [8], wherein Q is phenyl optionally substituted with G.

    [10] The ethylene derivative according to the above [8], wherein Q is oxazolyl optionally substituted with R or 1,2,3-triazolyl optionally substituted with R.

    [11] The ethylene derivative according to the above [8], wherein Q is thiazolyl optionally substituted with R.

    [12] The ethylene derivative according to the above [8], wherein Q is pyrazolyl optionally substituted with R.

    [13] Phenyl optionally substituted with G, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q- 27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56 or The ethylene derivative according to [5] above, which is Q-57.

    [14] Phenyl optionally substituted with G, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q- 27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56 or The ethylene derivative according to the above [7], which is Q-57.

    [15] The ethylene derivative according to the above [13], wherein Q is Q-10, Q-44, Q-45, Q-46, or Q-47.

    [16] The ethylene derivative according to the above [13], wherein Q is Q-12, Q-13, or Q-14.

    [17] The ethylene derivative according to the above [13], wherein Q is Q-25, Q-26, Q-27, Q-28, Q-29, or Q-30.

    [18] The ethylene derivative according to the above [13], wherein Q is phenyl optionally substituted with G.

    [19] A is phenyl optionally substituted by W, thiazolyl optionally substituted by Y, pyrazolyl optionally substituted by Y, pyridinyl optionally substituted by Y or Y substituted The ethylene derivative according to the above [2], which is pyrimidinyl which may be present.

であり、
Ａが、

であり、
Ｙ² が、ハロゲン、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₄ ハロアルキル、Ｃ₁ 〜Ｃ₄ アルコキシ、ＮＯ₂ 、ＣＮ、Ｃ₂ 〜Ｃ₅ アルコキシカルボニルであり、
Ｙ³ が、ハロゲン、Ｃ₁ 〜Ｃ₄ アルキル、Ｃ₁ 〜Ｃ₆ ハロアルキル、Ｃ₂ 〜Ｃ₄ アルコキシアルキル、Ｘで置換されていてもよいフェニルである上記〔３〕記載のエチレン誘導体。 [20] Q may be substituted with G phenyl, naphthyl, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-44, Q-45, Q-46, Q-49,

And
A is

And
Y ² is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, NO ₂ , CN, C ₂ -C ₅ alkoxycarbonyl,
The ethylene derivative according to the above [3], wherein Y ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₄ alkoxyalkyl, or phenyl optionally substituted with X.

    [21] The ethylene derivative according to the above [20], wherein E is CN.

[22] E is a heterocyclic group optionally substituted by C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl (provided that this heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1 , 2,4-Triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl in a.), halogen, C ₂ -C ₄ alkynyl may phenylethynyl optionally substituted by Z, C ₁ -C _{4 haloalkyl, CN, NO 2, N 3} , CHO, C 2 ~C 5 alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C ₃ -C ₉ dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C ₁ -C ₄ Arukirusurufu Alkylsulfonyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl group, phenyl sulphenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z alkylsulfinyl, optionally substituted by Z ^{phenylsulfonyl, -P (= O) T 2} T 3 , or -P (= S) ethylene derivatives of the above [20], wherein a T ² T ^3.

[23] The ethylene derivative according to any one of the above [1], selected from the following compound group:

    [24] An agrochemical comprising one or more ethylene derivatives according to the above [1] to [23] as active ingredients.

    [25] An underwater organism adhesion inhibitor comprising one or more acrylonitrile derivatives according to the above [1] to [23] as active ingredients.

で表される互変異性形で存在しうることは理解されるであろう。該化合物は主としてエノール形（１′）で存在すると考えられるが、或条件下では互変異性形（２）をとりうる。本発明は３つの互変異性形およびそれらの混合物を全て包含すると理解されるべきである。
次にＱ、Ａ、Ｂ、Ｅ、Ｇ、Ｒ、Ｒ¹ 、Ｙ、Ｙ¹ 、Ｙ² 、Ｗ、Ｘ、Ｚ、Ｔ¹ 、Ｔ² 、Ｔ³ 、Ｔ⁴ 、Ｔ⁵ 、Ｔ⁶ 、Ｔ⁷ 、Ｔ⁸ 、U ¹ 、U ² 、ｍ、ｎ、ｐまたはｑの好ましい範囲を説明する。 The -C (E) = C (OB)-moiety of the compound (1) of the present invention has two isomers, E-form and Z-form, both of which are included in the present invention.
When the substituent B in the formula (1) is a hydrogen atom, the compound of the present invention has the formula

It will be understood that it can exist in the tautomeric form represented by The compound is thought to exist predominantly in the enol form (1 '), but under certain conditions may take the tautomeric form (2). The present invention should be understood to include all three tautomeric forms and mixtures thereof.
Then Q, A, B, E, G, R, R 1, Y, Y 1, Y 2, W, X, Z, T 1, T 2, T 3, T 4, T 5, T 6, T The preferable range of ⁷ , T ⁸ , U ¹ , U ² , m, n, p or q will be described.

The heterocyclic group in Q, A or B has the following meaning.
That is, thienyl is thiophen-2-yl or thiophen-3-yl, furyl is furan-2-yl or furan-3-yl, and pyrrolyl is pyrrol-1-yl, pyrrol-2-yl. Oxazolyl is oxazol-2-yl, oxazol-4-yl or oxazol-5-yl and thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazole- 5-yl, imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl; Isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazolyl Is pyr-5-yl, pyrazolyl is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl, and 1,3,4-oxadiazolyl is 1,3,4 4-oxadiazol-2-yl, 1,3,4-thiadiazolyl is 1,3,4-thiadiazol-2-yl, 1,2,4-oxadiazolyl is 1,2,4-oxadiazol Azol-3-yl or 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazole- 5-yl and 1,2,4-triazolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-4-yl Yes, 1, 2, Thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl, 1,2,3-triazolyl is 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl, 1,2,3,4-tetrazolyl is 1,2,3,4-tetrazol-1-yl, , 2,3,4-tetrazol-2-yl or 1,2,3,4-tetrazol-5-yl and pyridinyl is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl , Pyrimidinyl is pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl, pyrazinyl is pyrazin-2-yl and pyridazinyl is pyridazin-3-yl or pyridazin -4-yl, 1,3,5-triazinyl is 1,3,5-triazin-2-yl, 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl, 1,2,4,5-tetrazinyl is 1,2,4,5-tetrazin-3-yl And pyrazolinyl is 3-pyrazolin-1-yl, 3-pyrazolin-3-yl, 3-pyrazolin-4-yl or 3-pyrazolin-5-yl, and imidazolinyl is 1-imidazolin-3-yl, 1- Imidazolin-2-yl, 1-imidazolin-4-yl or 4-imidazolin-2-yl, wherein oxazolinyl is 2-oxazolin-2-yl, 2-oxazolin-4-yl or 2-oxazolin-5-yl Yes, isoxazolinyl is 2-isoxazolin-3-yl, 2-isoxazolin-4-yl or 2-isoxazolin-5-yl and thiazolinyl is 2-thiazolin-2-yl, 2-thiazolin-4-yl or 3- Thiazolin-2-yl, imidazolidinone-yl is imidazolidin-2-one-1-yl, imidazolinone-yl is 2-imidazolinone-1-yl, 3 (2H) -pyridazinone- The yl is 3 (2H) -pyridazinon-2-yl, 3 (2H) -pyridazinon-4-yl, 3 (2H) -pyridazinon-5-yl or 3 (2H) -pyridazinon-6-yl.

Preferred Q ranges are the following groups.
QI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl.

  QII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4- Triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl.

  QIII: phenyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, 1,2,3-triazolyl.

  QIV: phenyl. QV: Oxazolyl. QVI: thiazolyl. QVII: Pyrazolyl. QVIII: Pyrimidinyl. QIX: 1,2,3-triazolyl.

Preferred ranges of A are the following groups.
That is, AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 3,5-triazinyl, 1,2,4-triazinyl.

  AII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.

  AIII: phenyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl.

  AIV: thiazolyl, pyrazolyl, pyridinyl.

  AV: Thiazolyl. AVI: pyrazolyl. AVII: Pyridinyl.

Preferred ranges of B are the following groups.
_{That, BI: H, C 1 ~C} 4 alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C _{4 alkoxyalkyl, CH 3 OC 2 H 4 OCH} 2, C 1 ~C 4 alkylsulfonyl, halogen or C ₁ ~ C ₄ phenyl sulfonyl optionally substituted by _{alkyl, -SO 2 CF 3, C 2} ~C 8 dialkylaminosulfonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, C ₃ -C ₉ alkoxycarbonylalkyl, -C ( = O) T ¹ , -P (= O) T ² T ³ , -P (= S) T ² T ³ , an alkali metal atom, an alkaline earth metal atom, or NHT ⁴ T ⁵ T ⁶ .

BII: H, C ₁ ~C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C _{4 alkoxyalkyl, CH 3 OC 2 H 4 OCH} 2, C 1 ~C 4 alkylsulfonyl, -SO ₂ CF _3, - C (= O) T ¹ , an alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ .

BIII: H, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkylsulfonyl, —SO ₂ CF ₃ , —C (═O) T ¹ , alkali metal atom, alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ .

BIV: C ₂ ~C ₄ alkoxyalkyl, C ₁ -C _{4 alkylsulfonyl, -SO 2 CF 3, -C (} = O) T 1, alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ^6.

Preferred ranges of E are the following groups.
That, EI: halogen, C ₂ -C ₄ alkynyl, phenyl ethynyl optionally substituted by Z, C ₁ -C _{4 haloalkyl, CN, NO 2, N 3} , CHO, C 2 ~C 5 alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C
₃ -C ₉ dialkylaminocarbonyl, optionally substituted by Z benzoyl, amino thiocarbonyl, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl group, and Z Phenylsulfenyl which may be substituted, phenylsulfinyl which may be substituted with Z, phenylsulfonyl which may be substituted with Z, -P (= O) T ² T ³ or -P (= S) T ² T ³ .

EII: halogen, C ₂ -C ₄ alkynyl, phenylethynyl optionally substituted with Z, CN, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C ₃ -C ₉ dialkylaminocarbonyl, optionally substituted by Z benzoyl, amino thiocarbonyl, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl group, and Z optionally substituted phenyl sulfenyl, Z in an optionally substituted phenylsulfinyl, phenyl sulfonyl optionally substituted by Z or ^{-P, (= O) T 2} T 3.

  EIII: CN.

Preferred G ranges are the following groups.
That, GI: halogen, C ₁ -C ₆ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ haloalkynyl, C ₁ -C ₃ alkyl substituted optionally C ₃ even though -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ halo alkoxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ Arukinirusuru Alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, C ₂ -C ₄ haloalkylene Nils Le phenyl, C ₂ -C ₄ halo alkynylsulfinyl, C ₂ -C ₄ haloalkynyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U 2, halogen or C ₁ -C ₄ alkyl methoxy substituted by phenyl optionally substituted, C ₂ -C ₆ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkylcarbonyl, C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ halo alkylcarbonyloxy, C ₃ -C ₇ dialkylamino Cal Bonyloxy, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, benzoyl optionally substituted with Z, pyridyl optionally substituted with Z and optionally substituted with Z A substituent arbitrarily selected from pyridyloxy (provided that the number of substituents is two or more, they may be the same or different from each other), and the number of substituents G is 1, 2, 3 Or a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring formed by an alkylene group which is 4 or bonded at adjacent substitution positions.

GII: halogen, C ₁ -C ₆ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl C ₃ optionally substituted by -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₁ -C ₄ alkylsulfamoyl phenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ Arukinirusuru phenyl, C ₂ ~ C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ Haloalkylsulfonyl, C ₂ -C ₄
Halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, halogen or C ₁ -C ₄ alkyl-methoxy substituted by phenyl optionally substituted, C ₂ -C ₆ alkoxycarbonyl, C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ halo alkylcarbonyloxy, substituents selected arbitrarily from among the pyridyloxy which may be substituted by optionally substituted phenoxy and Z and Z (However, when the number of the substituents is 2 or more, they may be the same or different from each other.), And the number of the substituents G is 1, 2 or 3.

GIII: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl optionally substituted C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ Haroaru Nils Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, halogen or C ₁ -C ₄ alkyl-methoxy substituted by phenyl optionally substituted, C ₂ -C ₆ alkoxy Substituents arbitrarily selected from carbonyl, C ₂ -C ₅ alkylcarbonyloxy, phenoxy optionally substituted with Z and pyridyloxy optionally substituted with Z (provided that two or more substituents are present) And the number of substituents G is 1 or 2.

Preferred ranges of R are the following groups.
That, RI: halogen, C ₁ -C ₆ alkyl, halogen or C ₁ -C ₄ alkyl C ₁ -C ₃ alkyl substituted by phenyl optionally substituted, C ₁ -C ₆ haloalkyl, C ₁ ~ C ₃ optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl , C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, alkynylsulfinyl of _{C 2 ~C 4, C 2 ~C} 4 alkynyl Ruhoniru, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U 2, naphthyl, and C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, optionally substituted with X phenyl, substituted by X A substituent arbitrarily selected from among pyridyl or thienyl optionally substituted with X (provided that the substituents are two or more, they may be the same or different from each other), The number of substituents R is 1, 2 or 3, or a 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ring formed by an alkylene group bonded at adjacent substitution positions. It is.

RII: halogen, C ₁ -C ₆ alkyl, halogen or C ₁ -C ₄ alkyl C ₁ -C ₃ alkyl substituted by phenyl optionally substituted, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ optionally substituted by alkyl C ₃ -C _{6 ^{cycloalkyl, NO 2, CN, -NU 1}} U 2, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, substituted by X A substituent arbitrarily selected from phenyl which may be substituted or pyridyl which may be substituted by X (however, when there are two or more substituents, they may be the same or different from each other), The number of substituents R is 1, 2 or 3.

RIII: halogen, C ₁ -C ₆ alkyl, halogen or C ₁ -C ₄ alkyl C ₁ -C ₃ alkyl substituted by phenyl optionally substituted, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ C ₃ -C ₆ cycloalkyl optionally substituted with alkyl, NO ₂ , CN, —NU ¹ U ² , naphthyl, C ₂ -C ₄ alkoxycarbonyl, phenyl optionally substituted with X or substituted with X A substituent arbitrarily selected from pyridyl which may be substituted (provided that when there are two or more substituents, they may be the same or different from each other), and the number of substituents R is 1 Or two.

  The number of R varies depending on the type of heterocycle substituted by R, and the heterocycle is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl. , 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, preferably 1. The heterocyclic ring is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- In the case of triazinyl or 1,2,4-triazinyl, the number of R is an integer of 0 to 2, preferably 1 or 2. When the heterocycle is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. is there. When the heterocyclic ring is a pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl group, the number of R is an integer of 0 to 4, preferably an integer of 0 to 3, more preferably 1 or 2 It is.

Preferred ranges of Y are the following groups.
That, YI: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy , C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl sulfenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkyl sulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ Halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, C ₂ -C ₄ haloalkylene Nils Le phenyl, C ₂ -C ₄ halo alkynylsulfinyl, C ₂ -C ₄ haloalkynyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U ² , C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -C ₄ haloalkylcarbonyloxy, or phenyl optionally substituted with X The substituent is selected (provided that the number of substituents may be the same or different when there are two or more substituents), and the number of substituents Y is 1, 2 or 3.

YII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, Among C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, C ₂ -C ₄ alkoxycarbonyl or phenyl optionally substituted with X An optional substituent (provided that the number of substituents is 2 or more, they may be the same or different from each other), and the number of substituents Y is 1, 2 or 3.

  The number of Y varies depending on the type of heterocycle substituted by Y, and the heterocycle is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl. In the case of 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1. The heterocyclic ring is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- In the case of triazinyl or 1,2,4-triazinyl, the number of Y is an integer of 0 to 2, preferably 1 or 2. When the heterocycle is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. is there. When the heterocycle is pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Y is an integer of 0 to 4, preferably an integer of 0 to 3, more preferably 1 or 2. is there.

Preferable W ranges are the following groups.
That, WI: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ haloalkenyl oxy, C ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, C ₂ -C ₄ alkynyloxy, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl C ₂ -C _{4 alkynylsulfonyl, NO 2, CN, C 2} ~C 4 alkoxycarbonyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkylcarbonyl, C ₂ -C ₄ alkylcarbonyloxy and -NU ¹ U ² is a substituent arbitrarily selected from ² (provided that the number of substituents may be the same or different when there are 2 or more substituents), and the number of substituents W is 1, 2, 3 or There are four.

WII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ alkenyl sulfenyl, C ₂ -C ₄ alkenyl sulfinyl, C ₂ -C ₄ alkenyl sulfonyl, C ₂ -C ₄ alkynyloxy, C ₂ -C ₄ alkynyl sulfenyl, C ₂ -C ₄ alkynyl sulfinyl, Substituents arbitrarily selected from C _{2 to} C ₄ alkynylsulfonyl, NO ₂ , CN (provided that the substituents are the same when there are two or more substituents) And the number of substituents W is 1, 2 or 3.

WIII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2, CN, optionally selected substituents from among (where When the number of the substituents is 2 or more, they may be the same or different from each other.) The number of the substituents W is 1 or 2.

Preferred T ¹ ranges are the following groups.
That is, T ¹ I: C ₁ -C ₁₈ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl substituted substituted by a phenyl C ₁ -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted cycloalkyl, halogen or C ₁ -C ₄ alkyl C ₂ -C ₄ alkenyl substituted with also phenyl substituted with groups, C ₁ -C ₁₀ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C ₃ alkyl optionally substituted C ₃ even though -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ A Job aryloxycarbonyl, -NU ¹ U ^2, which may be substituted with Z phenyl, optionally substituted by Z, phenoxy, optionally substituted by Z, phenylthio, optionally substituted naphthyl or Z Heterocyclic group (provided that this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl 1,3,5-triazinyl or 1,2,4-triazinyl).

T ¹ II: C ₁ -C ₁₈ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, halogen or phenyl optionally substituted with C ₁ -C ₄ alkyl substituted C ₁ -C ₄ alkyl, substituted by C ₁ -C ₃ optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, optionally substituted by halogen or C ₁ -C ₄ alkylphenyl cycloalkyl, halogen or C ₁ -C ₄ alkyl C ₂ -C ₄ alkenyl substituted with also phenyl substituted with one, C ₁ -C ₁₀ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ ~ C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, which may be substituted with Z phenoxazine , Phenylthio, naphthyl or Hajime Tamaki which may be substituted with Z (provided that the heterocyclic group selected from thienyl, furyl, selected oxazolyl, thiazolyl, among pyrazolyl or pyridinyl.) Is.

T ¹ III: C ₁ -C ₁₇ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkyl substituted with phenyl, C ₁ -C ₃ alkyl optionally substituted C ₃ -C ₆ cycloalkyl, cycloalkyl substituted with phenyl, C ₂ -C ₄ alkenyl substituted with phenyl, C ₁ -C ₈ alkoxy, C ₁ -C ₄ haloalkoxy C ₂ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, phenylthio, Naphthyl, pyrazolyl optionally substituted with Z, or pyridinyl optionally substituted with Z.

Preferred T ² ranges are the groups shown below.
That is, T ² I: phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkyl sulfenyl.

Preferred T ³ ranges are the following groups.
That is, T ³ I: phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkyl sulfenyl.

Preferred T ⁴ ranges are the following groups.
That is, T ⁴ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl group or benzyl, or two of T ⁴ , T ⁵ and T ⁶ are bonded to each other. A 5-membered ring, a 6-membered ring or a 7-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom.

Preferred T ⁵ ranges are the groups shown below.
That is, T ⁵ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or two of T ⁴ , T ⁵ and T ⁶ are bonded to each other. It forms a 5-membered ring, 6-membered ring or 7-membered ring group which may contain an oxygen atom, nitrogen atom or sulfur atom together with the nitrogen atom.

Preferred T ⁶ ranges are the groups shown below.
That is, T ⁶ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or two of T ⁴ , T ⁵ and T ⁶ are bonded to each other. A 5-membered ring, a 6-membered ring or a 7-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom,

Preferred X ranges are the following groups.
That, XI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkyl A substituent arbitrarily selected from sulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, —NU ¹ U ^2, or C ₂ -C ₅ alkoxycarbonyl (provided that there are two or more substituents) And the number of substituents X is 1, 2, or 3.

XII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, optionally selected from the NO ₂ And the number of the substituents X is 1, 2 and 3. However, the number of the substituents X is 1, 2 or 3.

XIII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, identical or mutually when the substituent (provided that the substituent is two or more selected arbitrarily from among And the number of substituents X is 1 or 2.

  The number of X varies depending on the ring substituted by X. When the ring is phenyl, the number of X is an integer of 0 to 5, preferably an integer of 0 to 3, more preferably an integer of 0 to 2. It is. When the ring is pyridyl, the number of X is an integer of 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1. In the case of a thienyl group, the number of X is an integer of 0 to 3, preferably 0 or 1.

Preferred Z ranges are the following groups.
That, ZI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkyl A substituent arbitrarily selected from sulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, —NU ¹ U ^2, or C ₂ -C ₅ alkoxycarbonyl (provided that there are two or more substituents) And the number of substituents Z is 1, 2, 3 or 4.

ZII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, A substituent arbitrarily selected from C ₁ -C ₄ haloalkylsulfonyl (provided that the number of substituents may be the same or different when two or more substituents are present), and the number of substituents Z is 1, 2, 3 or 4.

  The number of Z differs depending on the type of ring substituted by Z. When the ring substituted by Z is phenyl, the number of Z is an integer of 0 to 5, preferably an integer of 0 to 4, more preferably 0, 1, 2 or 3, more preferably 0, 1, or 2. When the ring substituted by Z is naphthyl, the number of Z is an integer of 0 to 7, preferably 0. When the ring substituted by Z is a heterocyclic group, the number of Z varies depending on the heterocyclic ring, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, In the case of 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z Is 0 or 1. The heterocyclic ring is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- In the case of triazinyl or 1,2,4-triazinyl, the number of Z is an integer of 0 to 2, preferably 1 or 2. When the heterocycle is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. is there. When the heterocycle is pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2. is there.

Preferred T ⁷ ranges are the following groups.
That is, it is T ⁷ I: H, phenyl, benzyl or C ₁ -C ₄ alkyl, or forms a 5- or 6-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded.

Preferred T ⁸ ranges are the groups shown below.
That is, T ⁸ I is phenyl, benzyl or C ₁ -C ₄ alkyl, or forms a 5- or 6-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded.

Preferred U ¹ ranges are the groups shown below.
That is, U ¹ I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅ alkylcarbonyl, or a 5-membered ring, 6-membered ring, 7-membered together with the carbon atom to which U ¹ and U ² are bonded. A ring may be formed.

Preferred U ² ranges are the groups shown below.
That is, U ² I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅ alkylcarbonyl, or a 5-membered ring, 6-membered ring, 7-membered together with the carbon atom to which U ¹ and U ² are bonded. A ring may be formed.

  A preferable range of m is 1, 2 or 3, more preferably 1 or 2.

  A preferable range of n is 0, 1, 2 or 3, more preferably 1 or 2.

  A preferable range of p is 1 or 2.

  Each group in the range of the above-mentioned preferred substituents can be arbitrarily combined, and each represents a preferred range of the compound of the present invention. Particularly preferred ranges are listed below.

That is, the preferred range of the substituent is QI, AI, BI, EI, GI, RI, YI, WI, T 1 I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XI, ^{ZI, T 7 I, T 8} I, a compound of the invention which is U ¹ I and U ² I.

A preferred range of the substituent is QI, AI, BI, EIII, GI, RI, YI, WI, T 1 I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XI, ZI, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QII, AII, BI, EII, GI, RI, YI, WI, T 1 I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XI, ZI, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QII, AII, BI, EIII, GI, RI, YI, WI, T 1 I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XI, ZI, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AIII, BI, EIII, GI, RI, YI, WI, T 1 I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XI, ZI, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

Preferred substituent ranges are QIII, AIII, BII, EIII, GII, RII, YII, WII, T ¹ II, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AIII, BII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AIV, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIV, AIV, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QV, AIII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QVI, AIII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QVI, AIV, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QVII, AIII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QVIII, AIII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIX, AIII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AV, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AVI, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compound of the present invention which is T ⁷ I, T ⁸ I, U ¹ I and U ² I.

A preferred range of the substituent is QIII, AVII, BIII, EIII, GIII, RIII, YII, WII, T 1 III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, The compounds of the present invention which are T ⁷ I, T ⁸ I, U ¹ I and U ² I.

Next, Q, A, B, E, G, R, R ¹ , Y, Y ¹ , Y ² , W, X, Z, T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ , T Examples of ⁷ , T ⁸ , U ¹ or U ² are shown.

The halogen atom in the definition of E, G, R, R ¹ , W, X, Y, Y ¹ , Y ² , Y ³ or Z includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably Examples thereof include fluorine atom, chlorine atom and bromine atom.

^{B, G, R, R 1} , T 1, T 2, T 3, T 4, T 5, T 5, T 7, T 8, U 1, U 2, W, X, Y, Y 1, Y 2 In the definition of Y ³ or Z, the linear or branched alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl- 2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1, 2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2 , 3-Zime Tylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2- Methylpropyl, n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl , N-icosyl and the like, and each is selected within the range of the designated carbon number.

As the alkenyl in the definition of G, R, R ¹ , T ¹ , T ⁴ , T ⁵ , T ⁶ , Y ¹ or W, ethenyl, 1-propenyl, 2-propenyl, 1- Butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl- -Pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2- Ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, etc. Selected from.

Alkynyl in the definition of E, G, R, R ¹ , Y ¹ or W includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl as linear or branched alkynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-d -2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and the like, is selected from the range of the specified number of carbon.

As the haloalkyl in the definition of B, E, G, R, R ¹ , T ¹ , W, X, Y, Y ¹ , Y ² , Y ³ or Z, fluoromethyl, chloromethyl as linear or branched haloalkyl , Bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chloro Difluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n-hexyl, fluoro-n-hexyl, etc. Each It is selected from the specified number range of carbon.

C ₃ -C ₆ cycloalkyl optionally substituted with C ₁ -C ₃ alkyl in the definition of G, R, T ¹ , T ⁴ , T ⁵ or T ⁶ includes cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, etc. It is done.

C ₁ -C ₄ alkyl substituted with a halogen atom in the definition of B, G, R or T ¹ or phenyl optionally substituted with C ₁ -C ₄ alkyl includes benzyl, 2-chlorobenzyl, 3- Bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tertiarybutylbenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3 -Phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl Pill, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4-chlorophenyl) -2-methyl-propyl, 2-methyl-2- (3-methylphenyl) propyl, etc. It is done.

C ₃ -C ₆ cycloalkyl substituted with a halogen atom in the definition of T ¹ or phenyl optionally substituted with C ₁ -C ₄ alkyl includes 1-phenylcyclopropyl, 1- (3-chlorophenyl) cyclopropyl 1- (4-chlorophenyl) cyclopropyl, 1- (4-bromophenyl) cyclopropyl, 1- (4-fluorophenyl) cyclopropyl, 1- (4-ethylphenyl) cyclopropyl, 1- (4-propyl) Phenyl) cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1- (4-chlorophenyl) cyclopentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenyl Cyclohexyl, 1- (3-fluorophene Le) cyclohexyl, 1- (4-chlorophenyl) cyclohexyl, 1- (4-tert-butylphenyl) cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenylcyclohexyl, and the like.

The cyclopropyl substituted by a halogen atom or a C ₁ -C ₄ alkyl optionally substituted good phenyl and C ₁ -C ₄ alkyl in the definition of T ^1, 2,2-dimethyl-1-phenyl-cyclopropyl, 1- (4-chlorophenyl) -2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3- (3-chlorophenyl) -2,2-dimethylcyclopropyl, (4-chlorophenyl)- 2,2-dimethyl-3-phenylcyclopropyl, (4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl, 2,2-dimethyl-3- (4-methylphenyl) cyclopropyl, (4 -Tertiary butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl and the like.

As the C ₃ -C ₄ cycloalkyl substituted with a halogen atom in the definition of T ¹ or phenyl optionally substituted with C ₁ -C ₄ alkoxy and a halogen atom, 2,2-dichloro-1-phenylcyclopropyl 2,2-dichloro-1- (3-chlorophenyl) cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-ethoxyphenyl) cyclopropyl 2,2-dichloro-1- (4-i-propyloxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-tert-butylphenyl) cyclopropyl, 2,2-dichloro-1- (4 -Methoxyphenyl) -3-phenylcyclopropyl, 1- (4-ethoxyphenyl) -2,2,3,3-tetrafluorobutyl, etc. .

Cyclopropyl substituted with C ₂ -C ₄ alkenyl optionally substituted with a halogen atom in the definition of T ¹ and C ₁ -C ₄ alkyl includes 2,2-dimethyl-3- (2,2-dimethyl). Ethenyl) cyclopropyl, 3- (2,2-dibromoethenyl) -2,2-dimethylcyclopropyl, 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropyl, 3- (2, 2-chlorotrifluoroethenyl) -2,2-dimethylcyclopropyl and the like.

Examples of C ₃ -C ₆ cycloalkoxy optionally substituted with C ₁ -C ₃ alkyl in the definition of T ¹ include cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, 1-methylcyclopropoxy and the like. It is done.

Examples of C ₂ -C ₄ alkenyl substituted with a halogen atom in the definition of T ¹ or phenyl optionally substituted with C ₁ -C ₄ alkyl include 1-phenylethenyl, 2-phenylethenyl, 2- ( 2-chlorophenyl) ethenyl, 2- (3-chlorophenyl) ethenyl, 2- (4-chlorophenyl) ethenyl, 2- (4-methylphenyl) ethenyl, 2- (2,6-difluorophenyl) ethenyl, 2- (2 , 5-dimethylphenyl) ethenyl, 1-methyl-2-phenylethenyl, 2-phenyl-1-propenyl, 2- (4-bromophenyl) -1-propenyl, 2- (2,4,6-trimethylphenyl) ) -1-propenyl and the like.

As alkoxy in the definition of G, R, T ¹ , T ² , T ³ , R ¹ , W, X, Y, Y ¹ , Y ² or Z, methoxy, ethoxy, n -Propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1 , 1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, , 2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2 -Trimethylpropyloxy, 1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc. Selected from a range of carbon numbers.

C ₃ -C ₆ halocycloalkyl in the definition of G, R or T ¹ includes fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclo Examples include butyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl, tetrafluorocyclobutyl and the like.

-NU ¹ U ² in the definition of G, R, R ¹ , T ¹ , W, X, Y, Y ¹ or Z is methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutyl Amino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutyl Amino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethyl Tilamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutyl Amino, di-n-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino, Methylpentylamino, Tylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-sec-butylamino, ethylisobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamide, N-ethylacetamide, N -Phenylacetamide, N-acetylacetamide and the like are listed, and each is selected within the range of the designated number of carbon atoms.

C ₂ -C ₅ alkoxycarbonyl in the definition of E, G, R, R ¹ , T ¹ , W, X, Y, Y ¹ , Y ² and Z include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso -Propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl, tert-butoxycarbonyl and the like.

Examples of C ₁ -C ₄ haloalkoxy in the definition of G, R, T ¹ , W, X, Y and Z include C ₁ -C ₄ linear or branched haloalkoxy, fluoromethoxy, Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy , Pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro- and iso-propoxy.

C ₁ -C ₄ alkylsulfenyl in the definition of E, G, R, T ² , T ³ , W, X, Y and Z includes methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso- Examples thereof include butylthio, sec-butylthio and tert-butylthio.

E, G, R, X, W, as C ₁ -C ₄ alkylsulfinyl in the definition of Y and Z, methylsulfinyl, ethylsulfinyl, n- propyl sulfinyl, iso- propyl sulfinyl, n- butylsulfinyl, iso- butyl Examples thereof include sulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl.

B, E, G, R, W, X, as C ₁ -C ₄ alkylsulfonyl in the definition of Y and Z are methylsulfonyl, ethylsulfonyl, n- propylsulfonyl, iso- propylsulfonyl, n- butylsulfonyl, iso -Butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl.

C ₂ -C ₄ alkoxyalkyl in the definition of B, G, R, R ¹ , T ¹ , Y, Y ¹ or Y ² includes C ₁ -C ₃ alkoxy-methyl, C ₁ -C ₂ alkoxy-ethyl, Examples include methoxyethoxymethyl and methoxypropyl.

E, G, R, as the C ₂ -C ₄ alkylcarbonyl in the definition of ^{R 1, U 1, U 2} , Y 1, Y 2 or W, acetyl, propionyl, butanoyl, iso- butanoyl and the like.

Examples of C ₂ -C ₆ haloalkylcarbonyl in the definition of G or W include chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl, pentafluoropropionyl and the like.

Examples of C ₂ -C ₅ haloalkylcarbonyloxy in the definition of G, R or Y include chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy, pentafluoropropionyloxy and the like.

Examples of C ₃ -C ₇ dialkylaminocarbonyloxy in the definition of G or Y include dimethylaminocarbonyloxy, diethylaminocarbonyloxy, di-i-propylaminocarbonyloxy and the like.

Examples of naphthyl in the definition of R, Y, Z and T ¹ include 1-naphthyl and 2-naphthyl.

As the pyridyl optionally substituted with Z in the definition of G or T ¹ , 2-pyridyl optionally substituted with Z, 3-pyridyl optionally substituted with Z, or substituted with Z 4-pyridyl which may be substituted with Z, preferably 2-pyridyl which may be substituted with Z or 3-pyridyl which may be substituted with Z, more preferably 2-pyridyl which may be substituted with Z It is.

As pyridyloxy optionally substituted with Z in the definition of G or T ¹ , 2-pyridyloxy optionally substituted with Z, 3-pyridyloxy optionally substituted with Z or substituted with Z 4-pyridyloxy which may be sufficient is mentioned.

The pyridyl which may be substituted with X in the definition of R or R ¹ may be 2-pyridyl which may be substituted with X, 3-pyridyl which may be substituted with X or X 4-pyridyl which may be substituted, preferably 2-pyridyl which may be substituted with X or 3-pyridyl which may be substituted with X, more preferably 2-pyridyl which may be substituted with X It is.

As pyridyloxy optionally substituted with X in the definition of R or R ¹ , 2-pyridyloxy optionally substituted with X, 3-pyridyloxy optionally substituted with X, or substituted with X 4-pyridyloxy which may be included is mentioned.

Examples of thienyl which may be substituted with X in the definition of R or R ¹ include 2-thienyl which may be substituted with X and 3-thienyl which may be substituted with X.

Examples of thienyl which may be substituted with Z in the definition of G or Y ¹ include 2-thienyl group which may be substituted with Z and 3-thienyl which may be substituted with Z.

—N═CT ⁷ T ⁸ in the definition of G, R, R ¹ , Y and Y ¹ means alkylideneamino, benzylideneamino, arylideneamino or cycloalkylideneamino, methylideneamino, ethylideneamino, propylideneamino, isopropylidene Amino, 4-methyl-2-pentylideneamino, cyclopentylideneamino, cyclohexylideneamino and the like.

Examples of C ₂ -C ₄ alkylaminocarbonyl in the definition of E include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl and the like.

Examples of C ₃ -C ₉ dialkylaminocarbonyl in the definition of E include dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, diisopropylaminocarbonyl, and di-n-butylaminocarbonyl.

Examples of C ₁ -C ₄ alkylaminosulfonyl in the definition of B include methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl.

Examples of C ₂ -C ₈ dialkylaminosulfonyl in the definition of B include dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, diisopropylaminosulfonyl and di-n-butylaminosulfonyl.

Examples of C ₂ -C ₅ alkylaminothiocarbonyl in the definition of B include methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl, n-butylaminothiocarbonyl and the like.

Examples of C ₃ -C ₉ dialkylaminothiocarbonyl in the definition of B include dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, diisopropylaminothiocarbonyl, and di-n-butylaminothiocarbonyl. It is done.

Examples of C ₁ -C ₄ alkyl substituted with a halogen atom in the definition of B or benzoyl optionally substituted with C ₁ -C ₄ alkyl include phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl. 2-methylphenacyl, 3-ethylphenacyl, 4-i-propylphenacyl, 4-t-butylphenacyl and the like.

As good phenylsulfonyl optionally substituted by halogen atom or C ₁ -C ₄ alkyl in the definition of B, 2-fluorophenyl sulfonyl, 4-fluorophenyl sulfonyl, 2-chlorophenyl sulfonyl, 4-chlorophenyl sulfonyl, 4-bromo Phenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2,4-dimethylphenylsulfonyl 2,4,6-trimethylphenylsulfonyl, 2,4,6-tri-i-propylphenylsulfonyl and the like.

C ₂ -C ₅ cyanoalkyl in the definition of G or B includes cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, 1-cyano-1-methylethyl and the like.

C ₃ -C ₉ alkoxycarbonylalkyl in the definition of B includes methoxycarbonylmethyl, ethoxycarbonylmethyl group, n-propoxycarbonylmethyl, i-propoxycarbonylmethyl, n-butoxycarbonyl as linear or branched alkoxycarbonylalkyl. Methyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2-methoxy Carbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, - methoxycarbonyl-1-methylethyl, 1-an iso-propoxycarbonyl-1-methylethyl, 1-ethoxycarbonyl-2-methylpropyl and the like.

  Examples of the alkali metal in the definition of B include lithium, sodium, and potassium.

  Examples of the alkaline earth metal in the definition of B include magnesium, calcium, strontium and barium, and preferably magnesium, calcium and barium.

As ammonium represented by NHT ⁴ T ⁵ T ⁶ in the definition of B, ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, diisopropylammonium, diisopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethyl ammonium, allyl methyl ammonium, two oxygen atoms together with the nitrogen atom to which each is attached one of or a carboxymethyl Le ethylammonium to benzyl methyl ammonium or 4-methylcyclohexyl, or T ^4, T ⁵ and T ^6, And a heterocyclic 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ammonium group which may contain a nitrogen atom or a sulfur atom.

The methoxy substituted in phenyl substituted with a halogen atom or a C ₁ -C ₄ alkyl in the definition of G, benzyloxy, 2-chloro-benzyloxy, 3-chloro-benzyloxy, 4-chloro-benzyloxy, Examples include 3-methylbenzyloxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy, 2-fluoro-4-chlorobenzyloxy and the like.

A heterocyclic group in which two of T ⁴ , T ⁵ and T ⁶ in the definition of T ⁴ , T ⁵ or T ⁶ may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bonded. The 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ammonium group includes pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine, heptamethyleneimine Is given.

Haloalkylsulfenyl in the definition of G, R, W, X, Y or Z includes C ₁ -C ₄ linear or branched haloalkylthio as fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio , Trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio.

Haloalkylsulfinyl in the definition of G, R, W, X, Y or Z includes C ₁ -C ₄ linear or branched haloalkylsulfinyl as fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, tri Fluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl It is done.

The haloalkylsulfonyl in the definition of G, R, W, X, Y or Z includes C ₁ -C ₄ linear or branched haloalkylsulfonyl as fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, tri Examples include fluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1, 1, 2, 2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoroethylsulfonyl, and fluoro-iso-propylsulfonyl. It is done.

Examples of haloalkenyl in the definition of G, R, T ¹ or W include 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl and the like as C ₂ -C ₄ linear or branched haloalkenyl.

^{G, R, R 1, T} 1, W, as the alkenyloxy in the definition of Y or Y ^1, C ₂ -C ₄ linear or branched allyloxy as alkenyloxy, 2-propenyloxy, 2-butenyloxy, 2 -Methyl-2-propenyloxy and the like.

As haloalkenyloxy in the definition of G, R, W or Y, C ₂ -C ₄ linear or branched haloalkenyloxy as 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy, 4,4-difluoro-3-butenyloxy and the like.

The alkenyl sulfenyl in the definition of G, R, W, X, Y or Z is C ₂ -C ₄ linear or branched alkenyl sulfenyl as allyl sulfenyl, 2-propenyl sulfenyl, 2-butenyls. And phenyl, 2-methyl-2-propenylsulfenyl and the like.

As alkenylsulfinyl in the definition of G, R, W, X, Y or Z, C ₂ -C ₄ linear or branched alkenylsulfinyl includes allylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl, 2- And methyl-2-propenylsulfinyl.

As alkenylsulfonyl in the definition of G, R, W, X, Y or Z, C ₁ -C ₄ linear or branched alkenylsulfonyl is allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methyl-2 -Propenylsulfonyl and the like.

As the haloalkenylsulfenyl in the definition of G, R, W or Y, C ₁ -C ₄ linear or branched haloalkenylsulfenyl as 3-chloro-2-propenylsulfenyl, 4-chloro-2-butyl Examples thereof include tenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl, 4,4-difluoro-3-butenylsulfenyl, and the like.

As haloalkenylsulfinyl in the definition of G, R, W or Y, C ₂ -C ₄ linear or branched haloalkenylsulfinyl as 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl, 4,4-difluoro-3-butenylsulfinyl and the like.

As the haloalkenylsulfonyl in the definition of G, R, W or Y, C ₂ -C ₄ linear or branched haloalkenylsulfonyl as 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl, and the like.

Examples of C ₂ -C ₄ haloalkynyl in the definition of G, R or W include chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl, 3-bromo-1-butynyl and the like.

Examples of the C ₂ -C ₄ alkynyloxy group in the definition of G, R, W or Y include 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and the like.

Examples of C ₂ -C ₄ haloalkynyloxy in the definition of G, R, W or Y include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-iodo-2-propynyloxy and the like. It is done.

Examples of C ₂ -C ₆ alkynylsulfenyl in the definition of G, R, W or Y include 2-propynylsulfenyl, 2-butynylsulfenyl, 1-methyl-2-propynylsulfenyl and the like.

Examples of C ₂ -C ₆ alkynylsulfinyl in the definition of G, R, W or Y include 2-propynylsulfinyl, 2-butynylsulfinyl, 1-methyl-2-propynylsulfinyl and the like.

Examples of C ₂ -C ₆ alkynylsulfonyl in the definition of G, R, W or Y include 2-propynylsulfonyl, 2-butynylsulfonyl, 1-methyl-2-propynylsulfonyl and the like.
G, R, as a C ₂ -C ₆ haloalkylene Nils Le phenyl in the definition of W, or Y is 3-chloro-2-propynyl sulfenyl, 3-bromo-2-propynyl sulfenyl, 3-iodo-2-propynyl sul And phenyl.

Examples of C ₂ -C ₆ haloalkynylsulfinyl in the definition of G, R, W or Y include 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-iodo-2-propynylsulfinyl and the like. It is done.

Examples of C ₂ -C ₆ haloalkynylsulfonyl in the definition of G, R, W or Y include 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl, 3-iodo-2-propynylsulfonyl and the like. It is done.

Examples of C ₂ -C ₄ alkylcarbonyloxy in the definition of G, R, W or Y include acetoxy, propanoyloxy, butanoyloxy, isopropylcarbonyloxy and the like.

  Benzoyl optionally substituted by X in the definition of E or G includes benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tertiarybutylbenzoyl, 3,4-dichlorobenzoyl and the like can be mentioned.

  The compounds of the present invention are stored in warehouses, so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called sanitary pests that cause various adverse effects in human living environments such as houses It is possible to effectively control low-concentration pests such as so-called stored-grain pests that damage grains and the like, and mite, nematodes, mollusks, and crustaceans that occur and damage in similar situations.

Specific examples of insects, mites, nematodes, molluscs, and crustaceans that can be controlled using the compounds of the present invention include the following, but are not limited thereto.
Nika Meiga, Kono-no-gaiga, Futabikogaga, Ichimonse-seri, Konaga, Yotoga, Monroe butterfly, Kaburagaga, Lotus japonicus, Shirochimonjiyoto, Chanokakumonmon, Chachamaki, Momoshinshii, Nashihime-Sancho, Apple, Coconut, Pepper Lepidopterous pests such as borers, fall army worms, codling moths, and white-spotted starfish,
Leafhopper leafhopper, leafhopper, peach aphid, cotton aphid, whitefly whitefly, tobacco whitefly, pearfly weevil, azalea, agaricus aphid, stag beetle, ruby rotifer, winged beetle
Nitto moth, Douganebububu, rice weevil, aphid weevil, cucumber weevil, kissing flea beetle, Colorado potato beetle, bark beetle, pine beetle beetle, corn rootworm, coconut elephant, moth pod moth
Dipteran pests such as beetle, flyfly, hessian fly, urticae, wingfly, housefly, hornfly, sheep flies, damselfly, bullfly, sheep fly, tsetse fly, mosquito, Aedes aegypti, anopheles, etc.
Hymenoptera pests such as wasps, pine bees, and wasps,
Common pests such as Southern Thrips, Thrips thrips, Thrips thrips, Thrips thrips, Thrips thrips
Reticulate pests such as black cockroaches, cockroaches, German cockroaches,
Straight-eyed pests such as Tonosama grasshopper, Cobainago, Sabaquat grasshopper,
Termite pests such as termites, Yamato termites, Thai termites
Pests such as cat fleas, human fleas, keops mud mines, etc.
White-eye pests, such as chicken lice and bovine lice,
Lice pests such as cattle lice, pig lice, cattle white lice, kelp cause lice,
Spider mites such as citrus mite, apple spider mite, spider spider mite, Kanzawa spider mite,
Fusid mites such as citrus red mite, black rust mite, tulip rust mite, chanogasabi mite,
Dust mites, such as tea dust mites and cyclamen dust mites,
Coniferous mites, such as the mite and robin mite,
Bee mites such as bees
Cucumber mites, such as ticks, spider mites,
Hymenid mites such as mites,
Nematodes such as sweet potato nematode, northern root-knot nematode, red-knot nematode, chromedes nematode, potato cyst nematode, pine wood nematode,
Molluscs such as Sukurimingai, Slug, Uskawamaimai, Misujimaimai,
Examples include crustaceans such as okadangamushi.

Moreover, as a plant disease to be controlled by the compound of the present invention,
Rice blast (Piculararia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani),
Wheat powdery mildew (Erysiphe graminis f.sp.hordei, f.sp.tritici), leafy spot (Pyrenophora teraminea), leaf spot (Pyrenophora teres), leaf blight (Gibberellainae) striiformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronetriori nipivais), naked smut (Ustilo tritici, U. nuda), eye spot (Pseudospell). seca
lis), leaf blight (Septoria tritici), blight (Leptos phaeria nodorum),
Citrus black spot (Diaporthe citri), scab (Elsinoe fawceti), fruit rot (Penicillium digitatum, P. italicum),
Apple Monilia disease (Sclerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leukotricha), spotted leaf (Alternaria maria), scab (Venturia inaequalis)
Pear black spot disease (Venturia nashicola), black spot disease (Alternaria Kikuchiana), red star disease (Gymnosporium haraeanum),
Peach blight (Sclerotinia cinerea), black scab (Cladosporium carpophilum), pomopsis spoilage (Phomopsis sp.),
Grape downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), late rot (Glomerella gingulata), powdery mildew (Uncinula necator), rust (Phakopsorais epelops)
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora)
kaki, Mycosphaerella nawae),
Downy mildew (Pseudoperenospora cubensis), anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella meloniis),
Tomato plague (Phytophthora infestans), ring rot (Alternaria solani), leaf mold (Cladosporium)
fulvam),
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracoarum), cruciferous vegetable black spot (Alternaria japonica), white spot (Cerocosporella brassicae),
Leek rust (Puccinia allii),
Soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), sunspot disease (Diaporthe phaseolum),
Bean anthracnose (Colletotrichum lindemuthianum), groundnut black rot (Mycosphaerella personatum), brown spot (Cercospora arachidicola),
Pea powdery mildew (Erysiphe pisi),
Potato summer plague (Alternaria solani),
Strawberry powdery mildew (Sphaerotheca humuli),
Tea net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco red scab (Alternaria longipes), powdery mildew (Erysiphe cichoracerum), anthracnose (Colleb) ),
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum brown spot (Septoria chrysanthemiindicii), white rust (Puccinia horiana),
Examples include gray mold disease of various crops (Botrytis cinerea), mycorrhizal disease of various crops and the like.

  In addition, the compound of the present invention is effective in preventing the adhesion of aquatic organisms at a very low concentration. Examples of the aquatic organisms include mussels, barnacles, oysters, hydroworms, hydras, serpras, squirts, bryophytes, scallops, snails, sea breams, blue sea breams, sea lions, and the like.

  That is, the compound of the present invention can effectively control the pests and plant diseases of the order Diptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites, and mites and lices at low concentrations. Furthermore, the compound of the present invention can control the adhesion of various aquatic organisms in seawater and freshwater to underwater structures. On the other hand, the compounds of the present invention include extremely useful compounds that have almost no adverse effects on mammals, fish, crustaceans and beneficial insects.

［（スキーム１）中のＱ、Ａ及びＢは前記と同じ意味を表し、Ｌは良好な脱離基例えば塩素原子、臭素原子、ヨウ素原子、炭素数１〜４のアルコキシ、フェノキシ、炭素数１〜4 のアルキルスルホニルオキシ、ベンゼンスルホニルオキシ、トルエンスルホニルオキシ、フェノキシ、１−ピラゾリルまたは１−イミダゾリル等であり、Ｌ’はハロゲン原子であり、アルキルは、好ましくは炭素数１〜４のアルキルである。］
（スキーム１）におけるＡ法は、一般式（３）で表されるアセトニトリル誘導体と一般
式（４）で表される酸クロライド類、エステル類またはアミド類あるいは一般式（５）で表される酸無水物を反応させることにより本発明化合物（１′）を合成する方法を示す。更に本発明化合物（１′）は一般式（８）で表されるアルキルハライド類、アルキルスルホネート類、トリメチルシリルハライド類、スルホニルクロライド類、スルファモイルクロライド類、チオカルバモイルクロライド類、酸クロライド類またはエステル類等と反応させることにより本発明化合物（１）に変換できる。このとき本発明化合物（１）におけるＢの種類によっては、本発明化合物（１′）にジヒドロピラン、イソシアネート類またはチオイソシアネート類を反応させて合成する。またＡ法で（４）または（５）を過剰に用いる事で、（１′）を単離せずに直接（１）を合成することもできる。 When E is CN among the compounds of the present invention, they can be synthesized by the following method (Scheme 1).

[Q, A, and B in (Scheme 1) have the same meaning as described above, and L is a good leaving group such as a chlorine atom, a bromine atom, an iodine atom, an alkoxy having 1 to 4 carbon atoms, phenoxy, 1 carbon atom. -4 alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy, phenoxy, 1-pyrazolyl or 1-imidazolyl, etc., L 'is a halogen atom, and alkyl is preferably an alkyl having 1 to 4 carbon atoms. . ]
Method A in (Scheme 1) is an acetonitrile derivative represented by the general formula (3) and an acid chloride, ester or amide represented by the general formula (4) or an acid represented by the general formula (5). A method for synthesizing the compound (1 ′) of the present invention by reacting with an anhydride is shown. Further, the compound (1 ′) of the present invention is an alkyl halide, alkyl sulfonate, trimethylsilyl halide, sulfonyl chloride, sulfamoyl chloride, thiocarbamoyl chloride, acid chloride or ester represented by the general formula (8). It can be converted to the compound (1) of the present invention by reacting with a compound. At this time, depending on the type of B in the compound (1) of the present invention, the compound (1 ′) of the present invention is synthesized by reacting dihydropyran, isocyanates or thioisocyanates. Moreover, by using (4) or (5) in excess in Method A, (1) can be directly synthesized without isolating (1 ′).

  When Q is a nitrogen atom and is bonded to an acrylonitrile moiety, it can also be synthesized by the B method. Method B shows a method for synthesizing the compound (1 ′) of the present invention by reacting the heterocyclic ring represented by the general formula (6) with the halogenocyanoketone derivative represented by the general formula (7).

  When A is a nitrogen atom and is bonded to an acrylonitrile moiety, it can also be synthesized by the C method. Method C shows a method for synthesizing the compound of the present invention from the cyanoacetic acid derivative represented by the general formula (9) and the heterocyclic compound represented by the general formula (10). In addition, the compound represented by the general formula (9) may be synthesized by reacting the acetonitrile derivative represented by the general formula (3) shown in Method A with a carbonate ester in the presence of a base.

［（スキーム２）中のＱ、Ａ、Ｅ、Ｂ、Ｌ、Ｌ’は前記と同じ意味である。］
（スキーム２）におけるＤ法は、一般式（１１）で表される化合物と一般式（４）で表される酸クロライド類、エステル類、アミド類または一般式（５）で表される酸無水物を反応させることにより本発明化合物（１′）を合成する方法を示す。更に本発明化合物（１′）は一般式（８）で表されるアルキルハライド類、アルキルスルホネート類、トリメチルシリルハライド類、スルホニルクロライド類、スルファモイルクロライド類、チオカルバモイルクロライド類、酸クロライド類またはエステル類等と反応させることにより本発明化合物（１）に変換できる。このとき本発明化合物（１）におけるＢの種類によっては、本発明化合物（１′）にジヒドロピラン、イソシアネート類またはチオイソシアネート類を反応させて合成する。またＡ法で（４）または（５）を過剰に用いる事で、（１′）を単離せずに直接（１）を合成することもできる。 When E is other than CN among the compounds of the present invention, they can be synthesized by the following method (Scheme 2).

[Q, A, E, B, L, and L ′ in (Scheme 2) have the same meaning as described above. ]
Method D in (Scheme 2) is a compound represented by general formula (11) and acid chlorides, esters, amides represented by general formula (4) or acid anhydrides represented by general formula (5). A method for synthesizing the compound (1 ′) of the present invention by reacting the product is shown. Further, the compound (1 ′) of the present invention is an alkyl halide, alkyl sulfonate, trimethylsilyl halide, sulfonyl chloride, sulfamoyl chloride, thiocarbamoyl chloride, acid chloride or ester represented by the general formula (8). It can be converted to the compound (1) of the present invention by reacting with a compound. At this time, depending on the type of B in the compound (1) of the present invention, the compound (1 ′) of the present invention is synthesized by reacting dihydropyran, isocyanates or thioisocyanates. Moreover, by using (4) or (5) in excess in Method A, (1) can be directly synthesized without isolating (1 ′).

When Q is a nitrogen atom and is bonded to the ethylene moiety, it can also be synthesized by the E method.
Method E shows a method of synthesizing the compound (1 ′) of the present invention by reacting the heterocyclic ring represented by the general formula (6) and the compound represented by the general formula (12) in the presence of a base.

  When A is a nitrogen atom and is bonded to the ethylene moiety, it can be synthesized also by the F method. Method F shows a method for synthesizing the compound of the present invention by dealcoholization reaction from the compound represented by the general formula (13) and the heterocyclic compound represented by the general formula (10). The compound represented by the general formula (13) may be synthesized by reacting the compound represented by the general formula (11) shown in Method D with a carbonate in the presence of a base.

Furthermore, after synthesizing (1 ′) in which E is alkoxycarbonyl, the compound of the present invention in which E is halogen can be synthesized by hydrolyzing and decarboxylating. Further, the compound of the present invention in which E is halogen is used as a raw material, and nucleophilic agents corresponding to E (phosphorous acid triesters, alkyl mercaptans, thiophenols, metal acetylides, metal cyanides, metal azides or In some cases, the compound of the present invention can also be synthesized by reacting nitrites and the like, and an electrophile is allowed to act on the compound obtained by decarboxylation of (1 ′) in which E is alkoxycarbonyl under basic conditions. In some cases, the compound of the present invention can be synthesized.
In the methods described in (Scheme 1) and (Scheme 2), it may be preferable to use a base. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide, and potassium butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. , Organic bases such as triethylamine, pyridine and DBU, organic lithium compounds such as butyl lithium, lithium amides such as lithium diisopropylpropylamide and lithium bistrimethylsilylamide, sodium hydride and the like.

  The reactions shown in (Scheme 1) and (Scheme 2) can be carried out in a solvent inert to the reaction. The solvent includes lower alcohols such as methanol and ethanol, and aromatic hydrocarbons such as benzene and toluene. , Ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, dimethyl Examples include amides such as formamide and dimethylacetamide, acetonitrile, dimethyl sulfoxide, and mixed solvents thereof. In some cases, a mixed solvent of these solvents and water can be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. The reaction temperature can be set to any temperature from -30 ° C to 200 ° C, and preferably from 0 ° C to 150 ° C or, when a solvent is used, from 0 ° C to the boiling point of the solvent. The base is used in an amount of 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, of the reaction substrate.

  The compound of the present invention can be obtained from the reaction solution by a conventional method. However, when it is necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization or column chromatography.

１）一般式（１４）で表されるベンジルハライド類、ベンジル アルキルスルフォネート類、ベンジル アリールスルフォネート類、ハロメチル複素環化合物、アルキルスルホニルオキシメチル複素環化合物またはアリールスルホニルオキシメチル複素環化合物を適当なシアノ化剤と反応させる事により合成できる。また、フェニル酢酸誘導体、複素環酢酸誘導体をアミド誘導体に変換した後、脱水反応を行う事によっても合成できる。
２）複素環のハロゲン化物（１５）とシアノ酢酸エステル（１６）を塩基存在下で縮合することにより得られる（１７）を原料とし、次いで加水分解、脱炭酸により化合物（３）が合成できる場合もある。
３）Ｑが窒素原子でエチレン部分と結合する場合は、その窒素が無置換である複素環誘導体（６）とハロアセトニトリル誘導体を塩基の存在下で反応させるか、シアノ酢酸エステルをハロゲン化して得られる化合物（１８）と化合物（６）を塩基存在下で反応させて化合物（１７）を合成し、次いで加水分解、脱炭酸により化合物（３）を合成できる場合もある。
また、（スキーム２）中の化合物（１１）は上述の化合物（３）の合成法に準じて合成できる。
（スキーム１）中の化合物（７）は安息香酸ハライド類または複素環カルボン酸ハライド類とシアノ酢酸エステルを塩基存在下で縮合し、次いでハロゲン化することにより合成できる。 In addition, in the case of the compound which has asymmetric carbon in the compound included by this invention, an optically active compound (+) body and (-) body are included.
A method for synthesizing the compound (3) in (Scheme 1) is described below.
That is,

1) A benzyl halide, benzyl alkyl sulfonate, benzyl aryl sulfonate, halomethyl heterocyclic compound, alkylsulfonyloxymethyl heterocyclic compound or arylsulfonyloxymethyl heterocyclic compound represented by the general formula (14) It can be synthesized by reacting with an appropriate cyanating agent. It can also be synthesized by converting a phenylacetic acid derivative or a heterocyclic acetic acid derivative into an amide derivative and then performing a dehydration reaction.
2) When compound (3) can be synthesized by starting from (17) obtained by condensing heterocyclic halide (15) and cyanoacetate (16) in the presence of a base, followed by hydrolysis and decarboxylation There is also.
3) When Q is a nitrogen atom and is bonded to the ethylene moiety, it is obtained by reacting a heterocyclic derivative (6) in which the nitrogen is unsubstituted with a haloacetonitrile derivative in the presence of a base or halogenating a cyanoacetic acid ester. In some cases, compound (18) and compound (6) are reacted in the presence of a base to synthesize compound (17), and then compound (3) can be synthesized by hydrolysis and decarboxylation.
In addition, compound (11) in (Scheme 2) can be synthesized according to the synthesis method of compound (3) described above.
Compound (7) in (Scheme 1) can be synthesized by condensing a benzoic acid halide or heterocyclic carboxylic acid halide with a cyanoacetic acid ester in the presence of a base, and then halogenating.

The above halomethyl heterocyclic compound, alkylsulfonyloxymethyl heterocyclic compound or arylsulfonyloxymethyl heterocyclic compound is prepared by a known method {Alain R.R. Alan R. katritzky, Charles W. Lease (Charles
W. Rees), Comprehensive Heterocyclic Chemistry (Volume 2, Volume 3, Volume 4, Volume 6 or Volume 6)}, synthesized from heterocyclic methane derivatives and heterocyclic carboxylic acid ester derivatives by conventional methods Can be guided. When Q is oxazol-4-yl or thiazol-4-yl, it can also be synthesized by reacting a carboxylic acid amide or thioamide with 1,3-dichloro-2-propanone.

Examples of compounds included in the present invention are shown in Tables 1 to 14. In addition, the symbol in a table | surface shows the following meaning, respectively.
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo,

  In applying the compound of the present invention as a pest control agent, generally a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or water, alcohols (isopropanol, butanol, benzyl alcohol, furfuryl alcohol). Etc.), aromatic hydrocarbons (toluene, xylene etc.), ethers (anisole etc.), ketones (cyclohexanone, isophorone etc.), esters (butyl acetate etc.), acid amides (N-methylpyrrolidone etc.) or It can be applied by mixing with liquid carriers such as halogenated hydrocarbons (such as chlorobenzene). If desired, surfactants, emulsifiers, dispersants, penetrants, spreaders, thickeners, antifreeze agents, Add anti-caking agent, stabilizer, liquid, emulsion, wettable powder, dry flowable, floor Le, powders, can be put into practical use in granules such as any dosage form.

  In addition, when the compound of the present invention is used as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, co-agents, and the like, can be used when formulated or sprayed. You may mix and apply it with a power agent, a fertilizer, a soil conditioner, etc.

  In particular, when mixed with other pesticides or plant hormones, it can be expected to reduce costs by reducing the amount of drug applied, expand the insecticidal spectrum due to the synergistic action of the mixed drugs, and achieve higher pest control effects. At this time, a combination with a plurality of known agricultural chemicals is also possible. Examples of the type of agrochemical used in combination with the compound of the present invention include compounds described in the 1994 edition of Farm Chemicals Handbook.

  The application amount of the compound of the present invention varies depending on the application scene, the application time, the application method, the cultivated crops, etc., but generally the amount of the active ingredient is suitably about 0.005 to 50 kg per hectare (ha).

Next, the formulation example of the formulation when using the compound of the present invention is shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.
[Wettable powder]
Compound of the present invention ... 5-80 parts Solid carrier ... 10-85 parts Surfactant ... ··· 1-10 parts Others ·············· 1-5 parts Other examples include anti-caking agents.
〔emulsion〕
Compound of the present invention ... 1-30 parts Liquid carrier ... 30-95 parts Surfactant ... .. 5-15 parts [flowable agent]
Compound of the present invention ... 5-70 parts Liquid carrier ... 15-65 parts Surfactant ... ··· 5 to 12 parts Other ·········· 5 to 30 parts Others include, for example, antifreezing agents and thickeners.
[Granular wettable powder (dry flowable)]
Compound of the present invention ... 20-90 parts Solid carrier ... 10-60 parts Surfactant ... .. 1-20 parts [granule]
Compound of the present invention ... 0.1-10 parts Solid carrier ... 90-99.99 parts Others ... ... 1-5 parts [powder]
Compound of the present invention ... 0.01-30 parts Solid carrier ... 67-99.5 parts Others ... .... 0-3 parts

When applying the compound of the present invention as an underwater organism adhesion inhibitor, it can be used as an aquatic organism adhesion inhibitor for a wide range of subjects by formulating it into an appropriate dosage form such as a paint, solution, emulsion, pellet or flake. Depending on the place of use, purpose, and dosage form, it can be used by appropriately selecting commonly used techniques such as coating, spraying, impregnation, addition in water, and installation in water. For the preparation of these paints, solutions, emulsions, etc., the usual formulation can be employed. Furthermore, the compound of the present invention is incorporated in the production stage of ropes or fiber materials used for fishing nets, etc., and used in other dosage forms and methods such as imparting underwater organism adhesion control performance to the ropes or fiber materials themselves. You can also The underwater organism adhesion inhibitor of the present invention may be used alone, or may be used by mixing with an underwater organism adhesion inhibitor other than the present invention.

  When the underwater organism adhesion inhibitor of the present invention is used in the form of an antifouling paint, for example, the compound of the present invention is blended with a film-forming agent to adjust the paint. As the coating film forming agent, oil varnish, synthetic resin, artificial rubber and the like are used. Furthermore, a solvent, a pigment or the like may be used as necessary. In the case of preparing a paint, the concentration of the compound of the present invention is not limited as long as a coating film can be formed, but it is 1 to 50% by weight, preferably 5 to 20% by weight, based on the weight of the antifouling paint. Blended.

  When the underwater organism adhesion inhibitor of the present invention is used in the form of a solution, for example, a solution prepared by dissolving the compound of the present invention in a solvent together with a film forming agent is used. Synthetic resins, artificial rubbers, natural resins and the like are used as the film forming agent, and xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone and the like are used as the solvent. Furthermore, an additive such as a plasticizer may be used as necessary. When preparing a solution, the compound of the present invention has no upper limit as long as the solution can be formed, but it is blended in a proportion of 1 to 50% by weight, preferably 5 to 30% by weight, based on the weight of the solution. .

  When using the underwater organism adhesion inhibitor of the present invention in the form of an emulsion, a surfactant is added to the compound of the present invention in accordance with a general method for preparing an emulsion, and a desired emulsion is prepared for use. There are no particular limitations on the type of surfactant used. When preparing an emulsion, the compound of the present invention has no upper limit as long as an emulsion can be formed, but it is blended in an amount of 1 to 50% by weight, preferably 5 to 30% by weight, based on the weight of the emulsion. .

  When using the underwater organism adhesion inhibitor of the present invention in the form of pellets or flakes, for example, based on a hydrophilic resin such as polyethylene glycol that is solid at room temperature, the compound of the present invention and optionally a plasticizer, A surfactant or the like can be blended as a constituent component and used as pellets or flakes by a method such as melt molding or compression molding. When preparing pellets or flakes, the compound of the present invention has no upper limit as long as pellets and flakes can be formed, but it is 20 to 95% by weight, preferably 30 to 90% by weight, based on the weight of the pellets and flakes. It is blended at a ratio of

The synthesis examples, formulation examples, and test examples of the compound of the present invention are specifically described below as examples, but the present invention is not limited thereto.
[Synthesis Example 1]
Synthesis of 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile (Compound No. I -40)
1) 3.0 g of 3- (2,6-difluorophenyl) pyrazole was dissolved in 20 ml of acetonitrile, 2.52 g of chloroacetonitrile and 4.61 g of potassium carbonate were added at room temperature, and the mixture was heated to reflux for 5 hours. Acetonitrile was distilled off under reduced pressure, ethyl acetate was added, and the mixture was washed with a small amount of water. The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was recrystallized from a mixed solvent of isopropyl ether and diethyl ether to obtain 1.74 g of 1-cyanomethyl-3- (2,6-difluorophenyl) pyrazole.
2) A solution prepared by dissolving 0.5 g of 1-cyanomethyl-3- (2,6-difluorophenyl) pyrazole in 10 ml of THF in a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF was added dropwise at 50 ° C. did. After stirring for 30 minutes, a solution prepared by dissolving 0.67 g of 1- (1-methyl-3,5-dichloropyrazole-4-carbonyl) pyrazole in 10 ml of THF was added dropwise at 50 ° C., and then stirred overnight at room temperature. The reaction solution was poured into water, extracted with ethyl acetate, and washed with a small amount of water. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether / ethyl acetate = 3/1 to give 2- {3- (2,6-difluorophenyl) pyrazole-1 0.52 g of -yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile was obtained.

[Synthesis Example 2]
Synthesis of 3- (1-methyl-3,5-dichloropyrazol-4-yl) -2- (2-phenylthiazol-4-yl) -3-hydroxyacrylonitrile (Compound No. II-1)
1) 2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added at room temperature, followed by heating under reflux for 1 hour. After distilling off the solvent under reduced pressure, ice water was added and neutralized with an aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform / n-hexane = 1/2.
2) 1.39 g of 4-chloromethyl-2-phenylthiazole was dissolved in 10 ml of acetonitrile, and 0.65 g of potassium cyanide and 0.05 g of dibenzo-18-crown-6-ether were added at room temperature, followed by heating under reflux for 10 hours. After returning to room temperature, ethyl acetate was added and insolubles were filtered off. The ethyl acetate solution was washed with saturated brine and water, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and 0.98 g of 4-cyanomethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform.
3) 0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of dry THF, and 4.6 ml of n-butyllithium (1.56 M hexane solution) was added dropwise at -60 ° C. or lower in an argon atmosphere. After stirring at −60 ° C. or lower for 20 minutes, 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride dissolved in 3 ml of dry THF was added dropwise at −60 ° C. or lower, and then the temperature was gradually raised. Stir at room temperature for 4 hours. The reaction mixture was poured into ice water, acidified with dilute hydrochloric acid, extracted with ethyl acetate, and washed with saturated brine. After drying with sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the desired product from the fraction eluted with chloroform, and further, the crystal was washed with diethyl ether to give 3- (1-methyl-3,5-dichloropyrazol-4-yl). There was obtained 0.86 g of 2- (2-phenylthiazol-4-yl) -3-hydroxyacrylonitrile.

[Synthesis Example 3]
Synthesis of 3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -2- (4-tertiarybutylthiazol-2-yl) -3-pivaloyloxyacrylonitrile (Compound No. III-6, III-15)
3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -2- (4-tertiarybutylthiazol-2-yl) -3-hydroxyacrylonitrile and triethylamine in 15 ml of THF 0.14 g was added at room temperature and stirred until a homogeneous solution was obtained. 0.16 g of pivaloyl chloride was added dropwise to the solution under ice-cooling, and the temperature was gradually raised and stirred at room temperature for 8 hours. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed 3 times with saturated brine. After drying with sodium sulfate, it was passed through a short column of silica gel. After distilling off the solvent under reduced pressure, 3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -2- (4-tarsha) was purified by silica gel thin layer chromatography (developing solvent: chloroform). Libutylthiazol-2-yl) -3-pivaloyloxyacrylonitrile 0.16 g (III-6) and its geometric isomer 0.35 g (III-
15) got.
Compound No.III-6
¹ H-NMR (CDCl ₃ , δ ppm); 1.18 (9H, s), 1.32 (9H, s), 3.85 (3H, s), 6.88 (1H, s)
Compound No.III-15
¹ H-NMR (CDCl ₃ , δ ppm); 1.33 (9H, s), 1.39 (9H, s), 3.94 (3H, s), 7.03 (1H, s)

[Reference example]
Synthesis of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid 1) 21.35 g of phosphorus oxychloride was dropped into 4.72 g of DMF while maintaining the temperature at 10 ° C. or lower. The reaction solution was returned to room temperature and stirred for 1 hour, and then 10.71 g of 1-methyl-3-trifluoromethyl-5-pyrazolone was added. The temperature was then raised to 110 ° C. and stirred for 7 hours. The reaction solution was brought to 70 ° C. and then poured into ice water. After adjusting the pH to about 4 with an aqueous sodium hydroxide solution, the precipitated crystals were filtered and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carbaldehyde.
2) In 0.23 g of potassium hydroxide dissolved in 85 ml of water, 8.88 g of 1-methyl-3--2- (tertiary trifluoromethyl-5-chloropyrazole-4-carbaldehyde and potassium permanganate 7 .24 g was added at room temperature, the temperature was raised to 60 ° C., and the mixture was stirred for 2 hours, after returning to room temperature, the solid was removed by filtration, the filtrate was acidified with aqueous hydrochloric acid, and the precipitated crystals were collected by filtration. After washing with water and drying, the obtained crystals were added to 150 ml of chloroform, heated and refluxed, and insolubles were removed by filtration while hot, and the chloroform was distilled off under reduced pressure. 6.24 g of fluoromethyl-5-chloropyrazole-4-carboxylic acid was obtained.

[Synthesis Example 4]
2- (2-tert-butylthiazol-4-yl) -3- (2-methyl-
Synthesis of 4-trifluoromethylthiazol-5-yl) -3-benzoyloxyacrylonitrile (Compound No. II-75)
The above compound was synthesized by the same method (viscous liquid, EZ mixture).
¹ H-NMR (CDCl ₃ , δ ppm);
1.09 (9H, s), 2.75 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): major
1.19 (9H, s), 2.70 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): minor

[Synthesis Example 5]
2- (4-Trifluoromethylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3- (1-methyl-3,5-dichloropyrazole-4-carbonyloxy) acrylonitrile Synthesis (Compound No.IV-5)
Dissolve 1.0 g of 4- (trifluoromethyl) phenylacetonitrile and 2.31 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride in 30 ml of dry THF, and add 0.61 g of potassium tert-butoxide at room temperature did. After raising the temperature and heating under reflux for 3 hours, 0.61 g of potassium tert-butoxide was added, and the mixture was further heated under reflux for 2 hours. THF was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a dilute aqueous sodium hydroxide solution and then washed with water. After drying with sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography. From the elution fraction of n-hexane: ethyl acetate = 2: 1, 3- (1-methyl-3,5-dichloropyrazol-4-yl) -2- (4- 1.92 g of trifluoromethylphenyl) -3- (1-methyl-3,5-dichloropyrazole-4-carbonyloxy) acrylonitrile was obtained.

[Synthesis Example 6]
Synthesis of 2- (4-tertiarybutylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile (Compound No. IV-18)
To a suspension of 0.22 g of dibenzo-18-crown-6-ether and 1.57 g of sodium cyanide in 20 ml of DMSO, 5.00 g of 4-tertiarybutylbenzyl bromide was added dropwise under water cooling. After stirring overnight at room temperature, the mixture was stirred at 50 ° C. for 5 hours. After returning to room temperature, water was added and the mixture was extracted with ether. The organic layer was washed with water and dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 1.19 g of 4-tert-butylphenylacetonitrile was obtained from the fraction eluted with n-hexane: ethyl acetate = 5: 1.
In a solution of 1.00 g of 4-tert-butylphenylacetonitrile and 1.23 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride in 20 ml of dry THF, 1.01 g of potassium tert-butoxide was cooled with ice. Added to. After stirring overnight at room temperature, water was added, acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, 0.38 g of potassium hydroxide was added, and the mixture was heated to reflux for 4 hours. After returning to room temperature, the solution was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 2- (4-tertiarybutylphenyl) -3- (1-methyl-3,5-dichloropyrazole was extracted from the fraction eluted with n-hexane: ethyl acetate = 2: 1. There was obtained 0.64 g of -4-yl) -3-hydroxyacrylonitrile.

[Synthesis Example 7]
Synthesis of 2- (4-tertiarybutylphenyl) -3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -3-pivaloyloxyacrylonitrile (Compound No. IV-24 )
The above compound was synthesized by the same method (viscous liquid).
¹ H-NMR (CDCl ₃ , δ ppm); 1.13 (9H, s), 1.33 (9H, s), 3.98 (3H, s), 7.48 (4H, brs)

[Synthesis Example 8]
Synthesis of 2- (4-tertiarybutylphenyl) -3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-methoxycarbonyloxyacrylonitrile (Compound No. IV-36)
The above compound was synthesized by the same method (glassy, EZ mixture).
¹ H-NMR (CDCl ₃ , δ ppm);
1.32 (9H, s), 3.75 (3H, s), 3.87 (3H, s), 7.49 (2H, d, J = 8Hz), 7.58 (2H, d, J = 8Hz): 75%
1.27 (9H, s), 3.88 (3H, s), 3.96 (3H, s), 7.49 (2H, d, J = 8Hz), 7.58 (2H, d, J = 8Hz): 25%

[Synthesis Example 9]
Synthesis of 2- {2-tertiarybutyloxazol-4-yl} -3- (3,5-dichloro-1-methyl-pyrazol-4-yl) -3-hydroxyacrylonitrile (Compound No. V-40)
1) 25 g of pivalic acid amide and 25 g of 1,3-dichloro-2-propanone were mixed and heated on an oil bath at 135 ° C. for 2.5 hours. It was cooled to ice temperature and made alkaline by adding aqueous sodium hydroxide solution. After extraction with ethyl acetate, washing with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate / n-hexane = 1/8). 17.5 g of sharybutyl-4-chloromethyloxazole was obtained.
2) Weigh 6.2 g of sodium cyanide, add 50 ml of dimethyl sulfoxide, add dropwise 16.9 g of dimethyl sulfoxide solution of 2-tert-butyl-4-chloromethyloxazole, and then add 1 on a 65 ° C. oil bath. Stir with heating for hours. After cooling to room temperature, 150 ml of dilute aqueous sodium hydroxide was added and extracted with toluene. The organic layer was sufficiently washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 14.8 g of 2-tert-butyl-4-cyanomethyloxazole.
3) 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2,5-dichloro-1 in 2.87 g of potassium tertiary carboxide suspended in 20 ml of THF
-A solution prepared by dissolving 2.37 g of methylpyrazole-4-carbonyl chloride in 10 ml of THF was added dropwise at an ice temperature, followed by stirring at room temperature overnight. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate = 4/1) to obtain 3.26 g of the objective compound.

[Synthesis Example 10]
Synthesis of 2- (2-tertiarybutyloxazol-4-yl) -3- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -3-ethoxymethoxyacrylonitrile (Compound No. V -44)
2- {2-tertiarybutyloxazol-4-yl} -3- (5-chloro-3-trifluoromethyl-1-methyl-pyrazol-4-yl) -3-hydroxyacrylonitrile (0.6 g) was dissolved in 5 ml of THF. Then, 0.07 g of 60% sodium hydride was added at ice temperature, and the mixture was stirred at room temperature for 15 minutes. 0.17 g of ethoxymethyl chloride was added and stirred at room temperature for 6 days. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel thin layer chromatography (ethyl acetate). / N-hexane = 1/4) to obtain 0.1 g of a glassy target compound.
¹ H-NMR (CDCl ₃ , δ ppm); 1.17 (3H, t), 1.41 (9H, s), 3.98 (3H, s), 5.03 (2H, s), 8.00 (1H, s)

[Synthesis Example 11]
Synthesis of ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-hydroxyacrylate (Compound No. IV-91)
8.2 g (50 mmol) of ethyl phenylacetate and 10.7 g (50 mmol) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride were dissolved in 100 ml of dry tetrahydrofuran, and 14 g of tertiary butoxy potassium was dissolved at room temperature. (125 mmol) is added. The reaction mixture was stirred at room temperature for 1 hour, 300 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the desired ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazole. 17 g of -4-yl) -3-hydroxyacrylate was obtained.
¹ H-NMR (CDCl ₃ , δ ppm); 1.1-1.5 (3H, m), 3.59 (1.5H, s), 3.73 (1.5H, s), 3.95-4.45 (2H, m), 5.58 (0.5H, s), 7.0-7.35 (5H, m), 13.21 (0.5H, s)

[Synthesis Example 12]
Synthesis of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-2-bromoethanone (Compound No. IV-90)
1) 17 g (50 mmol) of ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-hydroxyacrylate is dissolved in 50 ml of 6N hydrochloric acid and 250 ml of 1,4-dioxane. And heated to reflux for 15 hours. The reaction mixture was poured into 500 ml of ice water, and the precipitated crystals were collected by filtration to obtain 8 g of the desired 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenylethanone as white crystals. . Melting point 94-96 ° C
2) 1.38 g (20 mmol) of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenylethanone was dissolved in 50 ml of chloroform, stirred at room temperature for 1 hour, and then under reduced pressure. The solvent was distilled off to obtain 7.4 g of the target 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-2-bromoethanone as white crystals. Melting point: 74.5-75.5 ° C

[Synthesis Example 13]
Synthesis of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -1-pivaloyloxy-2-phenyl-2-bromoethylene (Compound No. IV-92)
1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-bromoethanone 0.55 g (1.58 mmol) and triethylamine 0.18 g (1.74 mmol) were dissolved in 4 ml of dry tetrahydrofuran, At room temperature, 0.19 g (1.58 mmol) of pivalic acid chloride was added. The reaction mixture was stirred at room temperature for 16 hours, 10 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain the target 1- (3,5-dichloro-1-methylpyrazol-4-yl) -1-pivaloyloxy-2-phenyl-2-bromoethylene. 23 g were obtained as a colorless liquid (EZ mixture).
¹ H-NMR (CDCl ₃ , δ ppm);
1.05 (9H, s), 3.81 (3H, s), 7.37 (5H, m): major
1.32 (9H, s), 3.62 (3H, s), 7.24 (5H, m): minor

[Synthesis Example 14]
Synthesis of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2- {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} -2-diethylphosphonoethanone (Compound No.II-156)
1) 4.15 g (18.1 mmol) of 2- (1-methyl-cyclohexane-1-yl) -4-chloromethylthiazole and 3.32 g (20 mmol) of trimethyl phosphite were mixed and heated to reflux for 16 hours. The reaction mixture was cooled to room temperature and purified by silica gel column chromatography to obtain 4.63 g of the desired diethyl {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} methylphosphonate. Obtained as a colorless liquid.
¹ H-NMR (CDCl ₃ , δppm); 1.25 (3H, t, J = 7.2Hz), 1.31 (3H, s), 1.1-2.3 (10H, m), 3.33 (2H, d, J = 20.4Hz) , 4.04 (4H, dd, J = 7.2,7.2Hz), 7.01 (1H, m)
2) 3,5-Dichloro-1-methylpyrazole-4-carboxylic acid chloride 0.85 g (4 mmol) and diethyl {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} methylphosphonate 1 .32 g (4 mmol) was dissolved in 15 ml of dry tetrahydrofuran, and 1.12 g (10 mmol) of tertiary butoxypotassium was added at room temperature. The reaction mixture was stirred at room temperature for 1 hour, 20 ml of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
The obtained residue was purified by silica gel column chromatography to obtain the desired 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2- {2- (1-methylcyclohexane-1 0.4 g of -yl) -thiazol-4-yl} -2-diethylphosphonoethanone was obtained.
¹ H-NMR (CDCl ₃ , δ ppm); 1.23 (3H, t, J = 7.2 Hz), 1.23 (3H, s), 1.1-2.3 (10H, m), 3.79 (3H, s), 4.09 (2H, dd, J = 7.2,7.2Hz), 5.90 (1H, d, J = 22.8Hz), 7.43 (1H, m)

[Synthesis Example 15]
Synthesis of allyl 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) 3-hydroxyacrylate ( Compound No.I-133)
1) Potassium carbonate (1.53 g) was added to a solution of 3- (2,6-difluorophenyl) pyrazole (1 g) and allyl 2-bromoacetate (1.49 g) in acetonitrile (10 mL) and refluxed for 3 hours. And extracted with ethyl acetate and dilute hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, concentrated and then purified by silica gel column chromatography (chloroform) to obtain allyl 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} acetate (1.5 g). It was.
¹ H-NMR (CDCl ₃ , δ ppm); 4.70 (2H, d, J = 6.0 Hz), 5.10 (2H, s), 5.30-5.60 (2H, m), 5.70-6.40 (1H, m), 6.50- 7.80 (5H, m)
2) Allyl 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} acetate (0.5 g) and 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carbonyl chloride (0 .44 g) in THF (10 mL) was added potassium t-butoxide (0.5 g) at 0 ° C. and stirred for 5 minutes. Water (5 mL) was added thereto, followed by extraction with diluted hydrochloric acid and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography (chloroform) to obtain Compound I-133 (0.89 g).
¹ H-NMR (CDCl ₃ , δ ppm); 3.95 (3H, s), 4.80 (2H, d, J = 6.0 Hz), 5.20-5.60 (2H, m), 5.60-6.40 (1H, m), 6.45 7.90 (6H, m)

[Synthesis Example 16]
2-Bromo-2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -1- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -1-hydroxy Synthesis of ethylene (Compound No.I-134)
1) Formic acid (60 mg) was added to a solution of palladium acetate (7 mg) and triphenylphosphine (17 mg) in THF (1 mL) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 minutes, and then Compound I-133 (0.32 g) in THF was added. (5 mL) solution was added and refluxed for 1 hour. The reaction mixture was returned to room temperature and concentrated, and then purified by silica gel column chromatography (chloroform) and recrystallization (chloroform-diisopropyl ether) to give 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (5-Chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) ethane-1-one (0.1 g) was obtained. mp152-154 ℃
2) 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (5-chloro-1-methyl-3-trifluoromethylpyrazole-4 at −78 ° C. in a nitrogen atmosphere To a THF solution of -yl) ethane-1-one (0.1 g), a 1M THF solution (0.27 mL) of lithium hexamethyldisilazide was added and stirred for 15 minutes at the same temperature. To this was added a solution of carbon tetrabromide (0.098 g) in THF (2 mL), the temperature was gradually raised to room temperature, water (1 mL) was added, and diluted hydrochloric acid and ethyl acetate were added for extraction. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by recrystallization (chloroform-diethyl ether) to obtain Compound I-134 (0.062 g). mp123-125 ℃

[Synthesis Example 17]
2-Bromo-2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -1- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -1-pi Synthesis of Valoyloxyethylene (Compound No.I-135)
Triethylamine (0.3 g) and pivalic acid chloride (0.23 g) were sequentially added to a solution of compound I-134 (0.47 g) in chloroform (25 mL) at 0 ° C., followed by stirring at room temperature for 1 hour. Water and chloroform were added for extraction. The organic layer was dried over anhydrous magnesium sulfate, concentrated and then purified by silica gel column chromatography (chloroform) to obtain compound I-135 (0.4 g).
¹ H-NMR (CDCl ₃ , δ ppm); 1.25 (9H, s), 3.90 (3H, s), 6.55-7.80 (5H, m)
The structures and melting points of the compounds of the present invention synthesized according to the above schemes or examples are shown in Tables 15 to 19, but those not specifically described are mixtures of E and Z isomers. In addition, the symbol in a table | surface shows the same meaning as the above.

[Formulation example]
Next, although the formulation example of the pest control agent which uses this invention compound as an active ingredient is shown, this invention is not limited to these.
In the following formulation examples, “parts” means parts by weight.
[Formulation Example 1] Wetting Agent Compound No. I -1 ..... 50 parts Sieglite PFP 43 parts (Kaolin clay: trade name of Sikleite Industrial Co., Ltd.)
Solpol 5050 2 parts (Anionic surfactant: Toho Chemical Co., Ltd. trade name)
LUNOX 1000C ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 3 parts (Anionic surfactant: Toho Chemical Co., Ltd. trade name)
Carplex # 80 (anti-caking agent) 2 parts (White carbon: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Emulsion I-1 ... 3 parts Methylnaphthalene ... 76 parts Isophorone ... 15 parts Solpol 3005X ...・ ・ ・ ・ ・ ・ ・ 6 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Flowable Agent Compound No. I-1 ... 35 parts Agrisol S-711 ... 8 parts (Nonionic surfactant: trade name of Kao Corporation)
LUNOX 1000C ............ 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
1% Rhodopol water ············ 20 parts
Ethylene glycol (antifreezing agent) ··· 8 parts Water ········································ 28.5 parts

[Formulation Example 4] Granular wettable powder (dry flowable)
This invention compound No. I-1 ... 75 parts Isoban No. 1 ······· 10 parts (Anionic surfactant: Kuraray isoprene Chemical Co., Ltd. trade name)
Vanillex N 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd.)
Product name)
Carplex # 80 ································ 10 parts
The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granule Compound No. I-1: 0.1 parts Bentonite: 55.0 parts Talc: 44.9 parts or more After uniformly mixing and pulverizing, a small amount of water is added and mixed by stirring, kneading, granulating with an extrusion granulator, and drying to form granules.

[Formulation Example 6] Powder Formula Compound No. I-1 ... 3.0 parts Carplex # 80 ... 0.5 parts (White Carbon: Shionogi & Co., Ltd. trade name)
Clay: 95 parts Diisopropyl phosphate: 1.5 parts or more uniformly mixed and pulverized into a powder.
In use, the above wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha).
Next, the formulation example of the underwater organism adhesion inhibitor of this invention is shown. However, it is not limited only to these.

[Formulation Example 7]
The active ingredient compound no. II-2 8 parts VYHH (vinyl-based synthetic resin, manufactured by UCC) 7 parts Rosin 7 parts Tricresyl phosphate 3 parts Talc 20 parts Barium sulfate 15 parts Valve handle 10 parts Xylene 20 parts Methyl isobutyl ketone 10 parts The underwater organism adhesion inhibitor of the present invention was prepared by mixing.
This underwater organism adhesion inhibitor can be used as a paint.

[Formulation Example 8]
The active ingredient compound no. II-2 5 parts CR-10 (chlorinated rubber resin, manufactured by Asahi Denka Co., Ltd.) 13 parts Zinc flower 20 parts Talc 20 parts Plasticizer 2 parts Petrole 10 parts Xylene 30 parts A biofouling inhibitor was prepared.
This underwater organism adhesion inhibitor can be used as a paint.

[Formulation Example 9]
The active ingredient compound no. II-2 8 parts VYHH (vinyl-based synthetic resin, manufactured by UCC) 7 parts Rosin 7 parts Tricresyl phosphate 3 parts Talc 20 parts Barium sulfate 15 parts Valve handle 10 parts Xylene 20 parts Methyl isobutyl ketone 10 parts The underwater organism adhesion inhibitor of the present invention was prepared by mixing.
This underwater organism adhesion inhibitor can be used as a paint.

[Formulation Example 10]
The active ingredient compound no. II-2 5 parts CR-10 (chlorinated rubber resin, manufactured by Asahi Denka Co., Ltd.) 13 parts Zinc flower 20 parts Talc 20 parts Plasticizer 2 parts Petrole 10 parts Xylene 30 parts A biofouling inhibitor was prepared.
This underwater organism adhesion inhibitor can be used as a paint.

[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples.
Test Example 1: Insecticidal test against brown planthopper A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was tested with a compound) was diluted with water containing a spreading agent to give a chemical solution having a concentration of 500 ppm. Prepared.
A sufficient amount of this chemical solution was sprayed on the stems and leaves of rice planted in a 1/20000 are pot. After air-drying, the cylinder was set up and 10 young larvae of the brown planthopper were released per pot, covered, and stored in a thermostatic chamber. The survey was conducted after 6 days, and the death rate was obtained from the following formula. The test was conducted in a two-ward system.
Death rate (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100
As a result, the following compounds showed a death rate of 80% or more.
Compound No. of the present invention: I-2, I-18, I-19, I-23, I-30, I-31, I-32, I-35, I-39, I-42, I-44, I-58, I-59, I-62, I-63, I-70, I-72, I-80, I-106, I-114, I-123, I-137, II-1, II- 2, II-3, II-5, II-6, II-12, II-15, II-23, II-25, II-26, II-28, II-33, II-34, II-36, II-37, II-38, II-39, II-43, II-44, II-46, II-53, II-54, II-55, II-61, II-66, II-73, II- 74, II-75, II-76, II-80, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-111, II-114, II-116, II-134, II-136, II-137, II-154, II-155, II-159, III- 1, III-2, III-4, III-6, III-15, III-16, III-17, III-18, III-19, III-21, IV-48, IV-58, V-2, V-12, V-13, V-28, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V- 60

Test Example 2: Insecticidal test against leafhopper leaf The rice leaflet is dipped in an emulsion of 500 ppm concentration of the compound of the present invention for about 10 seconds, and this leaflet is placed in a glass cylinder. It was released, covered with a hole, accommodated in a thermostatic chamber at 25 ° C., the number of dead insects after 6 days was examined, and the death rate was determined from the same calculation formula as in Test Example 1. The test was conducted in a two-ward system. As a result, the following compounds showed a death rate of 80% or more.
Compound No. of the present invention: I-1, I-2, I-4, I-5, I-8, I-9, I-10, I-19, I-24, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, II-39, I-40, I-41, I-42, I-43, I-44, I- 47, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-79, I-80, I-81, I-115, I-121, I-125, I-127, I-137, II-1, II-2, II- 3, II-5, II-6, II-7, II-9, II-10, II-11, II-12, II-13, II-15, II-23, II-26, II-28, II-33, II-34, II-36, II-38, II-37, II-43, II-46, II-49, II-52, II-54, II-55, II-63, II- 64, II-65, II-66, II-67, II-68, II-69, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II- 97, II-98, II-99, II-107, II-111, II-116, II-117, II-130, II-131, II-132, II-134, II-136, II-137, II-142, II-145, II-153, II-154, III-1, III-2, III-3, III-4, III-5, III-6, III-13, III-15, III- 16, III-17, III-18, III-19, III-20, III-21, IV-32, IV-58, V-2, V-12, V-13, V-14, V-38, V-41, V-43, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V- 75

Test Example 3: Insecticidal test against peach aphid A moist filter paper was laid on a glass petri dish having an inner diameter of 3 cm, and a cabbage leaf having the same diameter was placed thereon. Four adult mosquito aphids were released, and one day later, a chemical solution was sprayed (2.5 mg / cm ² ) in a rotary spray tower. As the chemical solution, a 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was tested for some compounds) was diluted with water containing a spreading agent to adjust the concentration to 500 ppm. . Six days after the treatment, the mortality of adults and larvae was determined from the following calculation formula. The test was conducted in a two ward system.
Death rate (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100
As a result, the following compounds showed a death rate of 80%.
Compound No. of the present invention: I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-24, I-25, I-26, I- 27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-51, I-52, I-53, I-54, I- 55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-85, I-86, I-89, I-90, I-92, I- 96, I-97, I-104, I-108, I-125, I-136, I-137, I-138, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-15, II-16, II-17, II-23, II-24, II-25, II-26, II- 27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-43, II-44, II-50, II-52, II-53, II-54, II-55, II-58, II-60, II-63, II-64, II-65, II-66, II-68, II-69, II-70, II- 71, II-73, II-74, II-75, II-76, II-78, II-79, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-97, II-98, II-99, II-101, II-102, II-105, II-107, II- 111, II-116, II-117, II-118, II-121, II-130, II-131, II-132, II-133, II-134, II-136, II-137, II-138, II-140, II-141, II-142, II-151, II-153, II-154, II-159, II-160, III-1, III-2, III-3, III-4, II I-5, III-6, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-10, IV-11, IV-21, IV- 23, IV-45, V-1, V-2, V-10, V-11, V-12, V-13, V-14, V-28, V-31, V-32, V-41, V-45, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-59, V- 60, V-65, V-73, V-75

Test Example 4: Contact insecticidal test for diamondback moth Orchid leaves were immersed in a 500 ppm aqueous emulsion of the compound of the present invention for about 10 seconds, air-dried and placed in a petri dish, into which ten second-order larvae per petri dish were placed. Each was released, covered with a hole, and stored in a thermostatic chamber at 25 ° C., the number of dead insects after 6 days was examined, and the death rate was calculated from the same formula as in Test Example 1. The test was conducted in a two-ward system. As a result, the following compounds showed a death rate of 80% or more.
Compound No. of the present invention: I-1, I-2, I-4, I-5, I-6, I-8, I-9, I-10, I-13, I-18, I-19, I-29, I-30, I-31, I-33, I-34, I-35, I-36, I-38, I-39, I-40, I-41, I-43, I- 44, I-45, I-46, I-47, I-51, I-52, I-53, I-56, I-57, I-58, I-59, I-62, I-63, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I- 86, I-89, I-96, I-97, I-99, I-104, I-106, I-114, I-125, I-137, II-1, II-2, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-17, II-23, II-24, II- 25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-54, II-55, II-58, II-60, II-61, II-62, II-63, II-64, II-65, II-66, II- 67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II- 93, II-94, II-97, II-98, II-99, II-100, II-101, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-121, II-122, II-155, II-159, II-161, III-1, III-2, III-3, III- 4, III-5, III-6, III-7, III-9, III-10, III-11, III-12, III-13, III-14, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-7, IV-8, IV-29, IV-47 , IV-53, IV-58, V-1, V-2, V-11, V-12, V-13, V-29, V-37, V-41, V-43, V-46, V -48, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-64 , V-75

Test Example 5: Insecticidal test against cucumber beetle A 5% emulsion of the compound of the present invention described in the specification (for some compounds, 25% wettable powder was tested) was diluted with water containing a spreading agent to give a concentration of 500 ppm. Adjust to a chemical solution, soak cucumber leaves in this chemical solution for about 10 seconds, air dry, place in a petri dish, release 10 larvae of cucurbit beetle per petri dish, cover and heat at 25 ° C. The mortality after 6 days was calculated from the same calculation formula as in Test Example 1. The test was conducted in a two-zone system.
As a result, the following compounds showed 100% mortality.
Compound No. of the present invention: I-1, I-2, I-4, I-6, I-8, I-9, I-10, I-11, I-12, I-13, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-39, I-40, I-41, I-43, I-44, I-46, I- 53, I-54, I-55, I-56, I-57, I-58,
I-59, I-61, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-76, I-77, I-78, I- 79, I-80, I-81, I-82, I-83, I-92, I-101, I-103, I-104, I-108, I-109, I-124, I-127, I-128, II-1, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-15, II- 16, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-41, II-42, II-43, II-46, II-47, II-50, II-53, II-54, II-54, II-55, II- 57, II-58, II-61, II-62, II-63, II-65, II-66, II-99, II-101, II-102, II-104, II-105, II-106, II-107, II-108, II-109, II-110, II-114, II-122, II-124, II-125, II-131, II-132, II-133, II-134, II- 136, II-137, II-139, II-140, II-141, II-142, II-153, II-154, III-1, III-2, III-3, III-4, III-5, III-6, III-9, III-10, III-11, III-12, III-14, III-15, III-16, III-17, III-20, IV-6, IV-13, IV- 33, IV-39, IV-56, IV-60, IV-61, IV-72, IV-82, V-1, V-2, V-11, V-12, V-13, V-17, V-22, V-26, V-27, V-29, V-37, V-40, V-42, V-48, V-49, V-
50, V-51, V-52, V-54, V-55, V-57, V-59, V-60, V-61, V-64, V-75

Test Example 6: Acaricidal effect test against nymph spider mites Kidney beans were cut into a circular shape with a diameter of 3.0 cm using a leaf punch and placed on wet filter paper on a styrene cup with a diameter of 7 cm. Ten nymph spider larvae were inoculated per leaf. A 5% emulsion of the compound of the present invention described in the specification (for some compounds, 25% wettable powder was tested) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. 2 ml per cup was sprayed using a rotary spray tower, housed in a thermostatic chamber at 25 ° C., and the death rate after 96 hours was determined from the same calculation formula as in Test Example 1. The test was conducted in a two-ward system. As a result, the following compounds showed a death rate of 80% or more.
Compound No. of the present invention: I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-12, I-13, I-19, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I- 35, I-36, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-50, I-51, I-52, I-55, I-56, I-57, I-58, I-59, I-60, I-61, I-62, I-63, I-70, I- 71, I-72, I-74, I-76, I-80, I-94, I-95, I-96, I-97, I-99, I-101, I-102, I-103, I-104, I-105, I-106, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-117, I- 118, I-119, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-137, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-16, II-17, II-23, II- 25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-45, II-46, II-47, II-48, II-50, II-52, II-53, II-54, II-55, II-58, II- 59, II-60, II-61, II-63, II-64, II-64, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II- 86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-95, II-97, II-98, II-99, II-101, II-102, II-103, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-133, II-134, II-136, II-137, II-151, II-153, II-154, II-155, II-159, II-160, II-161, II- 173, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-12, III-15, III-17, III-18, III-19, III- 21, IV-1, IV-2, IV-3, IV-4, IV-5, IV-7, IV-10, IV-11, IV-12, IV-13, IV- 14, IV-16, IV-17, IV-18, IV-19, IV-20, IV-21, IV-22, IV-24, IV-25, IV-26, IV-28, IV-29, IV-33, IV-35, IV-36, IV-39, IV-40, IV-41, IV-42, IV-43, IV-44, IV-45, IV-46, IV-47, IV- 48, IV-49, IV-50, IV-51, IV-54, IV-55, IV-56, IV-58, IV-59, IV-60, IV-61, IV-62, IV-63, IV-64, IV-65, IV-66, IV-67, IV-68, IV-69, IV-70, IV-71, IV-72, IV-74, IV-75, IV-76, IV- 79, IV-80, IV-82, IV-94, IV-95, IV-96, IV-99, IV-100, IV-101, IV-102, IV-109, IV-110, IV-111, IV-112, V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8, V-10, V-11, V-12, V- 13, V-14, V-15, V-16, V-17, V-19, V-23, V-24, V-25, V-26, V-28, V-31, V-36, V-37, V-38, V-40, V-41, V-42, V-43, V-44, V-46, V-47, V-48, V-49, V-50, V- 51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-73, V-75

Test Example 7: Wheat Red Rust Control Test 1.5 to 2.0 leaf wheat grown in a 5.5 cm diameter pot (variety: Norin 61) was diluted with water to 500 ppm by diluting the present compound emulsion with water. The prepared chemical solution was sprayed with 20 ml per pot using a spray gun.
On the next day after spraying, inoculation was carried out by spraying a spore suspension (2 × 10 ⁵ cells / ml) of wheat red rust fungus (Puccinia recondita). The inoculated wheat was placed in an inoculation box at a temperature of 25 ° C. and a humidity of 95% or more for a whole day and night. Then, it put in the greenhouse, the lesion area formed 7 days after inoculation was measured, and the control value was calculated according to the following formula.
Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area ratio)] × 100
As a result, the following compounds exhibited control values of 70 to 100.
Compound No. of the present invention: I-9, I-108, I-127, I-128, II-14, II-15, IV-2, IV-7, IV-15, V-10

  With the long-term use of insecticides and fungicides, pests have recently gained resistance, making it difficult to control with conventional insecticides and fungicides. Some insecticides are highly toxic and some are disrupting ecosystems due to persistence. Therefore, the present invention provides a novel insecticide or fungicide with low toxicity and low persistence, and also provides an aquatic organism adhesion inhibitor with little impact on the ecosystem and secondary contamination.

Claims (14)

Formula (1)

[In the formula, Q is a heterocyclic group which may be substituted with R (provided that the heterocyclic group is oxazolyl, thiazolyl, pyrazolyl or 1,2,3-triazolyl);
A is a heterocyclic group which may be substituted with Y (provided that this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl) , pyridinyl, pyrimidinyl or pyrazinyl.), and
B is, H, C ₁ ~C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C _{4 alkoxyalkyl, CH 3 SCH 2, CH 3} OC 2 H 4 OCH 2, halogen or C ₁ -C ₄ alkyl C ₁ -C ₄ alkyl substituted with optionally substituted phenyl, C ₁ -C ₄ alkyl substituted with halogen or benzoyl optionally substituted with C ₁ -C ₄ alkyl, tetrahydropyranyl, ( _{CH 3) 3 Si, C 1} ~C 4 alkylsulfonyl, halogen or C ₁ -C ₄ phenyl sulfonyl optionally substituted by _{alkyl, -SO 2 CF 3, C 1} ~C 4 monoalkylamino aminosulfonyl, C ₂ -C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, C ₂
-C ₅ mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkylaminothiocarbonyl,
C ₂ -C ₅ cyanoalkyl, C ₃ -C ₉ ^{alkoxycarbonylalkyl, -C (= O) T 1} ,
^{-P (= O) T 2 T} 3, -P (= S) T 2 T 3, an alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ^6,
However, when Q is 2-thiazolyl, B is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ SCH ₂ , CH ₃ OC ₂ H ₄ OCH ₂ , halogen or C ₁ ~C ₄ C ₁ substituted with phenyl optionally substituted with alkyl -C ₄ alkyl, C ₁ -C ₄ substituted with even better benzoyl optionally substituted with halogen or C ₁ -C ₄ alkyl Alkyl, tetrahydropyranyl, (CH ₃ ) ₃ Si, C ₁ -C ₄ alkylsulfonyl, halogen or phenylsulfonyl optionally substituted with C ₁ -C ₄ alkyl, —SO ₂ CF ₃ , C ₁ -C ₄ mono alkylaminosulfonyl, C ₂ -C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, C ₂ -C ₅ mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkyl Aminothiocarbonyl, C ₂ -C ₅ cyanoalkyl, C ₃ -C ₉ ^{alkoxycarbonylalkyl, -C (= O) T 1} , -P (= O) T 2 T 3 , or -P (= S) T ² T ³ and
R is halogen, C ₁ -C ₁₀ alkyl, halogen or C ₁ -C ₄ alkyl C ₁ -C ₄ alkyl substituted with phenyl optionally substituted, alkenyl of C ₂ ~C _6, C ₂ ~ C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₆ halocycloalkyl, C optionally substituted with C ₁ -C ₃ alkyl ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ ~ C ₆ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl Le phenyl, C ₂ -C ₆ alkenylsulfinyl, ₂ -C ₆ alkenylsulfonyl, C ₂ -C ₆ alkyl Nils Le phenyl, alkynylsulfinyl of _{C 2 ~C 6, C 2 ~C} 6 alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₆ halo alkenyl Le phenyl, C ₂ -C ₆ halo alkenylsulfinyl, C ₂ -C ₆ haloalkenyl sulfonyl, C ₂ -C ₆ haloalkylene Nils Le phenyl, C ₂ -C ₆ halo alkynylsulfinyl, C ₂ -C ₆ haloalkynyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U 2, phenoxy, OH
, Naphthyl, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ halo alkylcarbonyloxy, substituted by X Optional benzoyl, phenyl optionally substituted with X, pyridyl optionally substituted with X, thienyl optionally substituted with X, and —N═CT ⁷ T ⁸ A group (provided that the number of substituents may be the same or different when two or more substituents are present), and the number of the substituents is 1, 2, 3 or 4 or adjacent substitutions A 5-, 6-, 7- or 8-membered ring formed by alkylene bonded in position,
Y is halogen, C ₁ -C ₁₀ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy,
C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂
-C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl Le phenyl, C ₂ -C ₆ alkenylsulfinyl, C ₂ -C ₆ alkenylsulfonyl, C ₂ -C ₆ alkyl Nils Le phenyl, C ₂ -C ₆ alkynylsulfinyl, C ₂ -C ₆ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₆ halo alkenyl Le phenyl, C ₂ -C ₆ halo alkenylsulfinyl, C ₂ -C ₆ haloalkenyl sulfonyl, C ₂ -C ₆ halo alkyl Nils Le phenyl, C ₂ -C ₆ halo alkynylsulfinyl, C ₂ -C ₆ haloalkynyl sulfonyl ^{_{Le, NO 2, CN, -NU 1}} U 2, OH, C 2 ~C 7 alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ halo alkylcarbonyloxy, C _{3 to} C ₇ dialkylaminocarbonyloxy, phenyl optionally substituted with X, and —N═CT ⁷ T ⁸ (wherein T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C ₁ -C _six alkyl, 5-membered ring with the carbon atom to which the T ⁷ and T ⁸ are attached, chosen arbitrarily from among the 6-membered ring, may form a 7-membered ring or 8-membered ring.) A substituent (provided that the number of substituents may be the same or different when there are two or more substituents), and the number of the substituents is 1, 2, 3 or 4 or adjacent to each other 5 formed by alkylene bonded at the substitution position Ring, a 6-membered ring, 7-membered ring or 8-membered ring,
T ¹ is C ₁ -C ₂₀ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted with C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl optionally substituted with C ₁ -C ₃ alkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted cycloalkyl, halogen or C ₁
-C ₄ alkyl substituted by C ₁ and also phenyl optionally -C ₄ alkyl substituted cyclopropyl, halogen or C ₁ -C ₄ C ₃ substituted by also phenyl and halogen alkoxy substituted -C ₄ cycloalkyl, optionally substituted by halogen C ₂ -C ₄ alkenyl and C ₁ -C ₄ alkyl substituted cyclopropyl, optionally substituted by halogen or C ₁ -C ₄ alkylphenyl C ₂ -C ₄ alkenyl substituted with C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C ₃ alkyl optionally substituted with C _3- C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, -NU ¹ U ^2, phenylamino, phenyl optionally substituted by Z, substituted by Z Phenoxy, which may be substituted with Z, phenylthio which may be substituted with Z, naphthyl which may be substituted with Z, or 5- or 6-membered heterocyclic groups which may be substituted with Z (provided that these heterocyclic rings) The groups are thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4- Thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5- Triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, iso Selected from xazolinyl, thiazolinyl and 3 (2H) -pyridazinone).
T ² and T ³ are each independently OH, phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkyl sulfenyl;
T ⁴ , T ⁵ and T ⁶ are each independently H, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl optionally substituted with C ₁ -C ₃ alkyl. Or benzyl,
Alternatively, two of T ⁴ , T ⁵ and T ⁶ may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bonded, a 5-membered ring, a 6-membered ring or a 7-membered ring. Forming a ring or an 8-membered ring group,
X and Z are each independently halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C _{4 haloalkylsulfonyl, NO 2, CN, CHO,} OH, -NU 1 U 2, phenyl, optionally selected from phenoxy or C ₂ -C ₅ alkoxycarbonyl substituted A group (provided that the number of substituents may be the same or different when two or more substituents are present), and the number of the substituents is 1, 2, 3, 4 or 5 ,
T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C ₁ -C ₆ alkyl, or a 5-membered ring, 6-membered ring together with the carbon atom to which T ⁷ and T ⁸ are bonded, A 7-membered ring or an 8-membered ring may be formed,
U ¹ and U ² each independently represent H, C ₁ -C ₆ alkyl, C ₂ -C ₅ alkylcarbonyl, phenyl or benzyl, or 5 together with the carbon atom to which U ¹ and U ² are bonded. A member ring, 6-membered ring, 7-membered ring or 8-membered ring may be formed. ]
An ethylene derivative represented by Q is a heterocyclic group which may be substituted with R (provided that the heterocyclic group is oxazolyl, thiazolyl, pyrazolyl or 1,2,3-triazolyl);
A is a heterocyclic group optionally substituted with Y (provided that this heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl , imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl) , Pyridinyl, pyrimidinyl or pyrazinyl)
B is, H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl,
CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkylsulfonyl, phenylsulfonyl optionally substituted by halogen or C ₁ -C ₄ alkyl, —SO ₂ CF ₃ , C ₂ -C ₈ dialkylaminosulfonyl, C ₂ -C ₉ dialkylaminothiocarbonyl, C ₃ -C ₉ ^{alkoxycarbonylalkyl, -C (= O) T 1} , -P (= O) T 2 T 3, -P (= S) T 2 T 3, An alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ ;
T ¹ is substituted with C ₁ -C ₂₀ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl substituted C ₁ in phenyl optionally -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted cycloalkyl, halogen or C ₁
-C ₄ alkyl substituted by C ₁ and also phenyl optionally -C ₄ alkyl substituted cyclopropyl, halogen or C ₁ -C ₄ C ₃ substituted by also phenyl and halogen alkoxy substituted -C ₄ cycloalkyl, optionally substituted by halogen C ₂ -C ₄ alkenyl and C ₁ -C ₄ alkyl substituted cyclopropyl, optionally substituted by halogen or C ₁ -C ₄ alkylphenyl C ₂ -C ₄ alkenyl substituted with C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C ₃ alkyl optionally substituted with C _3- C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, which may be substituted with Z phenoxy, Feniruchi , Hajime Tamaki which may be substituted with naphthyl or Z (provided that the heterocyclic group selected from thienyl, furyl, oxazolyl, thiazolyl,. Which selected from pyrazolyl or pyridinyl) ethylene derivative according to claim 1, wherein a is. Q is an optionally substituted heterocyclic group (provided that this heterocyclic group is

It is. ) And
A is a heterocyclic group optionally substituted with Y (provided that this heterocyclic group is

It is. ), And,
R ¹ is halogen, C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, NO ₂ , CN,
^{-NU 1 U 2, OH, C} 2 ~C 7 alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂
-C ₄ alkylcarbonyl, phenyl optionally substituted by X, pyridyl optionally substituted by X, thienyl and -N be substituted by X = CT ⁷ T ⁸ (where, T ⁷ and T Each ⁸ is independently H, phenyl, benzyl or C ₁ -C ₆ alkyl, or a 5-membered, 6-membered, 7-membered or 8-membered with the carbon atom to which T ⁷ and T ⁸ are attached. Or may form a 5-membered ring, a 6-membered ring, a 7-membered ring or an 8-membered ring as an alkylene chain with the adjacent R,
Y ¹ is halogen, C ₁ -C ₁₀ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, NO ₂ , CN, -NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, phenyl and -N be substituted by X = CT ⁷ T ⁸ (where, T ⁷ and T ⁸ are each independently, H, phenyl, benzyl or C ₁ -C ₆ alkyl, or may form a 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded. Or 5 as an alkylene chain with adjacent Y ¹
May form a member ring, 6-membered ring, 7-membered ring or 8-membered ring,
X is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl , C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl , C ₁ -C ₄ haloalkylsulfonyl, NO _2, CN, C
1 to 4 substituents arbitrarily selected from HO, OH, -NU ¹ U ² , phenyl, phenoxy or C ₂ -C ₅ alkoxycarbonyl (provided that the number is the same when two or more substituents are present) May be different from each other.)
Z is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C
₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkenyl Le phenyl, C ₁ -C ₄ alkenylsulfinyl, C ₁ -C _{4 ^{alkenylsulfonyl, NO 2, CN, -NU 1}} U 2, phenyl,
1 to 4 substituents arbitrarily selected from phenoxy and C ₂ -C ₅ alkoxycarbonyl (provided that the number of substituents is 2 or more, they may be the same or different from each other);
m represents the number of substituents and is 0, 1, 2 or 3;
n represents the number of substituents and is 0, 1, 2, 3 or 4;
p represents the number of substituents and is 0, 1 or 2;
The q represents the number of substituents, and is 0 or 1 (provided that when m, n and p represent an integer of 2 or more, the substituents may be the same or different). Ethylene derivatives. The ethylene derivative according to claim 2, wherein Q is oxazolyl optionally substituted with R or 1,2,3-triazolyl optionally substituted with R. The ethylene derivative according to claim 2, wherein Q is thiazolyl optionally substituted with R. The ethylene derivative according to claim 2, wherein Q is pyrazolyl optionally substituted with R. Q is Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30 The ethylene derivative according to claim 3, which is Q-44, Q-45, Q-46 or Q-47. The ethylene derivative according to claim 7, wherein Q is Q-10, Q-44, Q-45, Q-46 or Q-47. The ethylene derivative according to claim 7, wherein Q is Q-12, Q-13 or Q-14. The ethylene derivative according to claim 7, wherein Q is Q-25, Q-26, Q-27, Q-28, Q-29 or Q-30. The ethylene derivative according to claim 2, wherein A is pyridinyl optionally substituted with Y or pyrimidinyl optionally substituted with Y. Q is Q-44, Q-45, Q-46,

And
A is

And
Y ² is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy,
NO _2, CN, a C ₂ -C ₅ alkoxycarbonyl,
The ethylene derivative according to claim 3, wherein Y ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₄ alkoxyalkyl, or phenyl optionally substituted with X. The ethylene derivative according to claim 1, which is selected from the following group of compounds.

A pest control agent comprising one or more ethylene derivatives according to any one of claims 1 to 13 as an active ingredient.