JP2010254629A - Optically active azoline derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new optically active azoline derivative exhibiting excellent insecticidal effects as an insecticide. <P>SOLUTION: The optically active azoline derivative is represented by formula (I) and used as an insecticide. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an optically active azoline derivative, and further relates to its use as an insecticide.

  Patent Document 1 describes that dihydroazole-substituted benzamide compounds are useful as pest control agents.

  Patent Documents 2 to 12, 15 and 16 describe that isoxazoline derivatives are useful as pest control agents.

  Patent Document 13 describes that a 5-membered heterocyclic compound is useful as a pest control agent.

  Patent Document 14 describes that a pyrazoline compound is useful as a pest control agent.

  Patent Documents 1 to 16 all relate to racemates.

JP2007-91708 WO2005 / 085216 (International publication number) WO2007 / 026965 (International Publication Number) WO2007 / 074789 (International publication number) WO2007 / 070606 (International publication number) WO2007 / 075459 (International publication number) WO2007 / 079162 (International publication number) WO2007 / 105814 (International Publication Number) WO2007 / 125984 (International publication number) JP2007-16017A JP2007-106756 JP2007-308471A WO2007 / 123853 (International publication number) WO2007 / 123855 (International Publication Number) WO2008 / 019760 (International publication number) WO2008 / 260691 (International publication number)

  The present inventors have found that an optically active form of an azoline derivative represented by the following formula (I) has a remarkable pesticidal activity.

式中、Ｘは独立してハロゲン、置換されてもよいアルキル、置換されてもよいハロアルキル、ニトロ、シアノ、置換されてもよいアルコキシ、置換されてもよいハロアルコキシ、置換されてもよいアルキルチオ、置換されてもよいアルキルスルフィニル、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルチオ、置換されてもよいハロアルキルスルフィニル、置換されてもよいハロアルキルスルホニル、ヒドロキシ、メルカプト、アミノ、置換されてもよいアルキルアミノ、置換されてもよいジアルキルアミノ、置換されてもよいアシルアミノ、置換されてもよいアルコキシカルボニルアミノ、置換されてもよいハロアルコキシカルボニルアミノ、置換されてもよいアルキルスルホニルアミノ又は置換されてもよいハロアルキルスルホニルアミノを示し、
Ｒ^１は置換されてもよいアルキル、置換されてもよいシクロアルキル、置換されてもよいアルキルシクロアルキル、置換されてもよいシクロアルキルアルキル、置換されてもよいアルケニル、置換されてもよいアルキニル、置換されてもよいハロアルキル、置換されてもよいハロシクロアルキル又はシアノを示し、
ｍは０、１、２、３、４、５、６又は７を示し、
ＡはＯ、ＣＨ_２又はＮ−Ｒ^２を示し、
Ｒ^２は独立して水素、シアノ、ホルミル、置換されてもよいアルキル、置換されてもよいアルケニル、置換されてもよいアルキニル、置換されてもよいシクロアルキル、置換されてもよいアルキルシクロアルキル、置換されてもよいシクロアルキルアルキル、置換されてもよいハロアルキル、置換されてもよいフェニル、置換されてもよいアルキルカルボニル、置換されてもよいアルコキシカルボニル、置換されてもよいアルキルアミノカルボニル又は置換されてもよいジアルキルアミノカルボニルを示し、
Ｑはフェニル、ナフチル又は５ないし６員の芳香族複素環式基を示し、そして
Ｔは下記の基（Ｔ−１）又は基（Ｔ−２）を示す、

In which X is independently halogen, optionally substituted alkyl, optionally substituted haloalkyl, nitro, cyano, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio, Optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylthio, optionally substituted haloalkylsulfinyl, optionally substituted haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted Good alkylamino, optionally substituted dialkylamino, optionally substituted acylamino, optionally substituted alkoxycarbonylamino, optionally substituted haloalkoxycarbonylamino, optionally substituted alkylsulfonylamino or substituted Good halo It indicates Kill sulfonylamino,
R ¹ is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkylcycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, Represents optionally substituted haloalkyl, optionally substituted halocycloalkyl or cyano;
m represents 0, 1, 2, 3, 4, 5, 6 or 7,
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted alkylcycloalkyl, Optionally substituted cycloalkylalkyl, optionally substituted haloalkyl, optionally substituted phenyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, or substituted Dialkylaminocarbonyl which may be
Q represents phenyl, naphthyl or a 5- to 6-membered aromatic heterocyclic group, and T represents the following group (T-1) or group (T-2):

上記の基中、
Ｇは、置換されてもよい飽和若しくは不飽和の５員又は置換されてもよい飽和若しくは不飽和の６員の複素環式基を示し、
又は

In the above group,
G represents an optionally substituted saturated or unsaturated 5-membered or optionally substituted saturated or unsaturated 6-membered heterocyclic group;
Or

を示し、
Ｒ^３及びＲ^４は、それぞれ独立して水素、置換されてもよいアルキル、置換されてもよいシクロアルキル、置換されてもよいハロアルキル、置換されてもよいシクロハロアルキル、置換されてもよいアルケニル、置換されてもよいアルキニル、置換されてもよいハロアルケニル、置換されてもよいハロアルキニル、シアノ、アルコキシカルボニル又はアルコキシチオカルボニルを示し、
Ｒ^３とＲ^４は、一緒になってアルキレンを形成してもよく、
Ｒ^５は、水素、アミノ、ヒドロキシ、置換されてもよいアルコキシ、置換されてもよいアミノカルボニルアルキル、置換されてもよいイミノアルキル、置換されてもよいアルキル、置換されてもよいシクロアルキル、置換されてもよいハロアルキル、シアノ、置換されてもよいアルケニル、置換されてもよいアルキニル、置換されてもよいアルキルカルボニル、−ＣＨ_２−Ｒ^７、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^６は、水素、シアノ、カルボニル、チオカルボニル、置換されてもよいアルキルカルボニル、置換されてもよいアルキルチオカルボニル、置換されてもよいハロアルキルカルボニル、置換されてもよいハロアルキルチオカルボニル、置換されてもよいアルキルアミノカルボニル、置換されてもよいアルキルアミノチオカルボニル、置換されてもよいジアルキルアミノカルボニル、置換されてもよいジアルキルアミノチオカルボニル、置換されてもよいアルコキシアミノカルボニル、置換されてもよいアルコキシアミノチオカルボニル、置換されてもよいアルコキシカルボニル、置換されてもよいアルコキシチオカルボニル、置換されてもよいチオアルコキシカルボニル、置換されてもよいチオアルコキシチオカルボニル、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルスルホニル、置換されてもよいシクロアルキルカルボニル、アルケニルカルボニル、アルキニルカルボニル、シクロアルキル−アルキルカルボニル、アルキルスルフェニルアルキルカルボニル、アルキルスルフィニルアルキルカルボニル、アルキルスルホニルアルキルカルボニル、アルキルカルボニル−アルキルカルボニル、シクロアルキルアミノカルボニル、アルケニルアミノカルボニル、アルキニルアミノカルボニル、アルコキシアルキルカルボニル、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^５とＲ^６は、それらが結合する窒素原子と一緒になって、置換されてもよい３乃至６員の複素環を形成してもよく、該環は、ケト、チオケト又はニトロイミノ基で置換されていてもよく、
Ｒ^７は、置換されてもよいフェニル又は置換されてもよい飽和若しくは不飽和の複素環を示し、
Ｂ^１，Ｂ^２，Ｂ^３及びＢ^４は、それぞれ独立してＣ−Ｌ又は窒素を示し、
Ｂ^１及びＢ^２は、一緒になって炭素数６の芳香環を形成してもよく、
Ｌは、それぞれ独立して水素、ハロゲン、置換されてもよいハロアルキル、ニトロ、置換されてもよいアルキル、置換されてもよいシクロアルキル、置換されてもよいシクロハロアルキル、置換されてもよいアルコキシ、シアノ、置換されてもよいハロアルコキシ、置換されてもよいアルキルスルフェニル、置換されてもよいアルキルスルフィニル、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルスルフェニル、置換されてもよいハロアルキルスルフィニル、置換されてもよいハロアルキルスルホニル、置換されてもよいアルキルスルホニルオキシ、置換されてもよいハロアルキルスルホニルオキシ、置換されてもよいアルキルアミノスルホニル、置換されてもよいハロアルキルアミノスルホニル、置換されてもよいジアルキルアミノスルホニル、置換されてもよいジ（ハロアルキル）アミノスルホニル、ヒドロキシル、チオール、アミノ、置換されてもよいアルキルアミノ、置換されてもよいジアルキルアミノ、置換されてもよいアシルアミノ、置換されてもよいアルコキシカルボニルアミノ、置換されてもよいハロアルコキシカルボニルアミノ、置換されてもよいアルキルスルホニルアミノ、置換されてもよいハロアルキルスルホニルアミノ、置換されてもよいトリアルキルシリル、置換されてもよいアルコキシイミノ、置換されてもよいハロアルコキシイミノ、置換されてもよいアルコキシ−イミノ−置換されてもよいアルキル、置換されてもよいハロアルコキシ−イミノ−置換されてもよいアルキル、置換されてもよいアルキルスルフィニルイミノ、置換されてもよいアルキルスルフィニル−イミノ−置換されてもよいアルキル、置換されてもよいアルキルスルフィニル−イミノ−置換されてもよいアルキルカルボニル、置換されてもよいアルキルスルホキシイミノ、置換されてもよいアルキルスルホキシ−イミノ−置換されてもよいアルキル、置換されてもよいアルコキシカルボニル、置換されてもよいアルキルカルボニル、アミノカルボニル、置換されてもよいアルキルアミノカルボニル、アミノチオカルボニル、置換されてもよいアルキルアミノチオカルボニル、置換されてもよいジアルキルアミノカルボニル又は置換されてもよいジアルキルアミノチオカルボニルを示し、
ｌは、１乃至３を示し、
Ｙは独立してハロゲン、置換されてもよいアルキル、置換されてもよいハロアルキル、置換されてもよいシクロアルキル、置換されてもよいシクロハロアルキル、ニトロ、シアノ、置換されてもよいアルケニル、置換されてもよいハロアルケニル、置換されてもよいアルコキシ、置換されてもよいハロアルコキシ、置換されてもよいアルキルチオ、置換されてもよいアルキルスルフィニル、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルチオ、置換されてもよいハロアルキルスルフィニル、置換されてもよいハロアルキルスルホニル、ヒドロキシ、メルカプト、アミノ、置換されてもよいアルキルアミノ、置換されてもよいジアルキルアミノ、アミノカルボニル、置換されてもよいアルキルアミノカルボニル、置換されてもよいジアルキルアミノカルボニル、置換されてもよいアシルアミノ、置換されてもよいアルコキシカルボニルアミノ、置換されてもよいベンジルオキシカルボニルアミノ、置換されてもよいハロアルコキシカルボニルアミノ、置換されてもよいアルキルスルホニルアミノ、置換されてもよいハロアルキルスルホニルアミノまたは置換されてもよいトリアルキルシリルを示し、
ｎは０、１、２又は３を示し、
Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４は独立して単結合、ＣＨ_２、ＣＨ、Ｎ、Ｏ、Ｓ、ＣＨ−Ｒ^８、Ｃ−Ｒ^８、Ｃ（Ｒ^８）_２、Ｎ−Ｒ^９、Ｎ−Ｒ^１０、ＣＨ−Ｒ^１０、Ｃ−Ｒ^１０又はＣ＝Ｕを示し、
Ｒ^８は独立してヒドロキシ、アミノ、シアノ、ホルミル、ハロゲン、ニトロ、置換されてもよいアルキル、置換されてもよいアルケニル、置換されてもよいアルキニル、置換されてもよいシクロアルキル、置換されてもよいアルキルシクロアルキル、置換されてもよいシクロアルキルアルキル、置換されてもよいハロアルキル、置換されてもよいアルキルカルボニル、置換されてもよいアルコキシカルボニル、置換されてもよいアルキルアミノカルボニル、置換されてもよいジアルキルアミノカルボニル、置換されてもよいアルキルカルボニルアミノ、置換されてもよいアルキルチオカルボニルアミノ、置換されてもよいシクロアルキルカルボニルアミノ、置換されてもよいシクロアルキルアルキルカルボニルアミノ、置換されてもよいシクロアルキルチオカルボニルアミノ、置換されてもよいシクロアルキルアルキルチオカルボニルアミノ、置換されてもよいハロアルキルカルボニルアミノ、置換されてもよいハロアルキルチオカルボニルアミノ、置換されてもよいアルキルアミノカルボニルアミノ、置換されてもよいアルキルアミノチオカルボニルアミノ、置換されてもよいシクロアルキルアミノカルボニルアミノ、置換されてもよいシクロアルキルアルキルアミノカルボニルアミノ、置換されてもよいシクロアルキルアミノチオカルボニルアミノ、置換されてもよいシクロアルキルアルキルアミノチオカルボニルアミノ、置換されてもよいハロアルキルアミノカルボニルアミノ、置換されてもよいハロアルキルアミノチオカルボニルアミノ、置換されてもよいジアルキルアミノカルボニルアミノ、置換されてもよいジアルキルアミノチオカルボニルアミノ、置換されてもよいアルキルアミノカルボニルオキシ、置換されてもよいアルキルアミノカルボニルチオ、置換されてもよいシクロアルキルアミノカルボニルオキシ、置換されてもよいシクロアルキルアルキルアミノカルボニルオキシ、置換されてもよいシクロアルキルアミノカルボニルチオ、置換されてもよいシクロアルキルアルキルアミノカルボニルチオ、置換されてもよいハロアルキルアミノカルボニルオキシ、置換されてもよいハロアルキルアミノカルボニルチオ、置換されてもよいジアルキルアミノカルボニルオキシ、置換されてもよいジアルキルアミノカルボニルチオ、置換されてもよいアルコキシカルボニルアミノ、置換されてもよいシクロアルキルオキシカルボニルアミノ、置換されてもよいシクロアルキルアルキルオキシカルボニルアミノ、置換されてもよいハロアルコキシカルボニルアミノ、置換されてもよいアルキルスルホニルアミノ又は置換されてもよいハロアルキルスルホニルアミノを示し、上記シアノ、ホルミル、ハロゲン及びニトロ以外の置換基は後記に示すＲ^１０で置換されてよく、
Ｒ^９は水素、ヒドロキシ、アミノ、置換されてもよいアルキル、置換されてもよいハロアルキル、置換されてもよいアルケニル、置換されてもよいアルケニルオキシ、置換されてもよいアルキニル、置換されてもよいアルキニルオキシ、置換されてもよいシクロアルキル、置換されてもよいアルキルシクロアルキル、置換されてもよいシクロアルキルアルキル、置換されてもよいアルキルアミノ、置換されてもよいジアルキルアミノ、置換されてもよいアルコキシ、置換されてもよいハロアルコキシ、ホルミル、置換されてもよいアルキルカルボニル、置換されてもよいハロアルキルカルボニル、置換されてもよいアルコキシカルボニル、置換されてもよいアルキルアミノカルボニル、置換されてもよいアルキルカルボニルアミノ、置換されてもよいハロアルキルカルボニルアミノ、置換されてもよいアルコキシカルボニルアミノ、置換されてもよいアルキルアミノカルボニルアミノ、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルスルホニル、置換されてもよいフェニルスルホニル、置換されてもよいアルキルアミノカルボニル又は置換されてもよいハロアルキルアミノカルボニルであり、上記水素およびホルミル以外の置換基は後記に示すＲ^１０で置換されてもよく、
Ｒ^１０は独立してフェニル又は５ないし６員の飽和又は不飽和の複素環式基を示し、それらの基はハロゲン、置換されてもよいアルキル、置換されてもよいハロアルキル、置換されてもよいシクロアルキル、置換されてもよいハロシクロアルキル、置換されてもよいアルコキシ、置換されてもよいハロアルコキシ、置換されてもよいアルキルチオ、置換されてもよいハロアルキルチオ、置換されてもよいアルキルスルフィニル、置換されてもよいハロアルキルスルフィニル、置換されてもよいアルキルスルホニル、置換されてもよいハロアルキルスルホニル、置換されてもよいアルキルアミノ、置換されてもよいハロアルキルアミノ、シアノ、ニトロ、アミノカルボニル、置換されてもよいアルキルアミノカルボニル、置換されてもよいジアルキルアミノカルボニル、置換されてもよいアルコキシカルボニル、置換されてもよいフェニルおよび置換されてもよいピリジルからなる群より選ばれる少なくとも１ヶの基によって置換されてもよく、
ＵはＣＨ_２、Ｏ、Ｓ、Ｎ−Ｒ^９又はＮ−Ｒ^１０を示し、ここでＲ^９及びＲ^１０は独立して、上記Ｒ^９及びＲ^１０と同義を示し、
そして
ａ） Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４の内、同時に二つ以上は単結合でなく、
ｂ） Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４の内、同時に三つ以上はＯ、Ｓ、Ｎ−Ｒ^９又はＮ−Ｒ^１０でなく、
ｃ） Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４の内、同時に三つ以上はＣ＝Ｕでなく、
ｄ） Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４の内、同時に二つがＯおよび／またはＳを示すとき、それら二つは少なくとも１ヶの炭素原子を介する、また、
ｅ） Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４の内、一つがＣＨ、Ｎ、Ｃ−Ｒ^８又はＣ−Ｒ^１０であるとき、縮環内で二重結合を形成する。

Indicate
R ³ and R ⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted haloalkyl, optionally substituted cyclohaloalkyl, optionally substituted alkenyl, Represents optionally substituted alkynyl, optionally substituted haloalkenyl, optionally substituted haloalkynyl, cyano, alkoxycarbonyl or alkoxythiocarbonyl;
R ³ and R ⁴ together may form an alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted alkoxy, optionally substituted aminocarbonylalkyl, optionally substituted iminoalkyl, optionally substituted alkyl, optionally substituted cycloalkyl, substituted Optionally substituted haloalkyl, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkylcarbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S ) -R ⁷
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylthiocarbonyl, optionally substituted haloalkylcarbonyl, optionally substituted haloalkylthiocarbonyl, optionally substituted Good alkylaminocarbonyl, optionally substituted alkylaminothiocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted dialkylaminothiocarbonyl, optionally substituted alkoxyaminocarbonyl, optionally substituted alkoxyamino Thiocarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkoxythiocarbonyl, optionally substituted thioalkoxycarbonyl, optionally substituted thioalkoxythiocarbonyl, optionally substituted Alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl-alkylcarbonyl, alkylsulfenylalkylcarbonyl, alkylsulfinylalkylcarbonyl, alkylsulfonylalkylcarbonyl, alkylcarbonyl - indicates alkylcarbonyl, cycloalkyl amino carbonyl, alkenylcarbonyl aminocarbonyl, alkynylamino, alkoxycarbonyl alkylcarbonyl, a -C (O) -R ⁷ or -C (S) -R ^7,
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form an optionally substituted 3- to 6-membered heterocycle, which ring is substituted with a keto, thioketo, or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² may form an aromatic ring having 6 carbon atoms together,
L is independently hydrogen, halogen, haloalkyl which may be substituted, nitro, alkyl which may be substituted, cycloalkyl which may be substituted, cyclohaloalkyl which may be substituted, alkoxy which may be substituted, Cyano, optionally substituted haloalkoxy, optionally substituted alkylsulfenyl, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfenyl, optionally substituted haloalkyl Sulfinyl, optionally substituted haloalkylsulfonyl, optionally substituted alkylsulfonyloxy, optionally substituted haloalkylsulfonyloxy, optionally substituted alkylaminosulfonyl, optionally substituted haloalkylaminosulfonyl, optionally substituted Good Alkylaminosulfonyl, optionally substituted di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted acylamino, optionally substituted Alkoxycarbonylamino, optionally substituted haloalkoxycarbonylamino, optionally substituted alkylsulfonylamino, optionally substituted haloalkylsulfonylamino, optionally substituted trialkylsilyl, optionally substituted alkoxyimino, substituted Optionally substituted haloalkoxyimino, optionally substituted alkoxy-imino-optionally substituted alkyl, optionally substituted haloalkoxy-imino-optionally substituted alkyl, optionally substituted alkylsulfinylimino Optionally substituted alkylsulfinyl-imino-optionally substituted alkyl, optionally substituted alkylsulfinyl-imino-optionally substituted alkylcarbonyl, optionally substituted alkylsulfoxyimino, optionally substituted Alkylsulfoxy-imino-optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, aminothiocarbonyl, optionally substituted Represents alkylaminothiocarbonyl, optionally substituted dialkylaminocarbonyl or optionally substituted dialkylaminothiocarbonyl,
l represents 1 to 3,
Y is independently halogen, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted cycloalkyl, optionally substituted cyclohaloalkyl, nitro, cyano, optionally substituted alkenyl, substituted Optionally substituted haloalkenyl, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted halo Alkylthio, optionally substituted haloalkylsulfinyl, optionally substituted haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted alkylamino, optionally substituted dialkylamino, aminocarbonyl, optionally substituted alkylamino Carbonyl, substituted Dialkylaminocarbonyl which may be substituted, acylamino which may be substituted, alkoxycarbonylamino which may be substituted, benzyloxycarbonylamino which may be substituted, haloalkoxycarbonylamino which may be substituted, alkylsulfonyl which may be substituted Amino, optionally substituted haloalkylsulfonylamino or optionally substituted trialkylsilyl;
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are each independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ , C—R ⁸ , C (R ⁸ ) ₂ , N—R ^9. N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, substituted Alkylcycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted haloalkyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, substituted Dialkylaminocarbonyl which may be substituted, alkylcarbonylamino which may be substituted, alkylthiocarbonylamino which may be substituted, cycloalkylcarbonylamino which may be substituted, cycloalkylalkylcarbonylamino which may be substituted, may be substituted Siku Boroalkylthiocarbonylamino, optionally substituted cycloalkylalkylthiocarbonylamino, optionally substituted haloalkylcarbonylamino, optionally substituted haloalkylthiocarbonylamino, optionally substituted alkylaminocarbonylamino, optionally substituted Alkylaminothiocarbonylamino, optionally substituted cycloalkylaminocarbonylamino, optionally substituted cycloalkylalkylaminocarbonylamino, optionally substituted cycloalkylaminothiocarbonylamino, optionally substituted cycloalkylalkylamino Thiocarbonylamino, optionally substituted haloalkylaminocarbonylamino, optionally substituted haloalkylaminothiocarbonylamino, optionally substituted dialkylamino Carbonylamino, optionally substituted dialkylaminothiocarbonylamino, optionally substituted alkylaminocarbonyloxy, optionally substituted alkylaminocarbonylthio, optionally substituted cycloalkylaminocarbonyloxy, optionally substituted Cycloalkylalkylaminocarbonyloxy, optionally substituted cycloalkylaminocarbonylthio, optionally substituted cycloalkylalkylaminocarbonylthio, optionally substituted haloalkylaminocarbonyloxy, optionally substituted haloalkylaminocarbonylthio, Dialkylaminocarbonyloxy which may be substituted, dialkylaminocarbonylthio which may be substituted, alkoxycarbonylamino which may be substituted, cycloal which may be substituted Oxycarbonylamino, cycloalkylalkyloxycarbonylamino which may be substituted, haloalkoxycarbonylamino which may be substituted, alkylsulfonylamino which may be substituted or haloalkylsulfonylamino which may be substituted, Substituents other than formyl, halogen and nitro may be substituted with R ¹⁰ as shown below,
R ⁹ is hydrogen, hydroxy, amino, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted alkenyl, optionally substituted alkenyloxy, optionally substituted alkynyl, optionally substituted. Alkynyloxy, optionally substituted cycloalkyl, optionally substituted alkylcycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted Alkoxy, optionally substituted haloalkoxy, formyl, optionally substituted alkylcarbonyl, optionally substituted haloalkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted Alkylcarbonylamino, substituted Optionally substituted haloalkylcarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted alkylaminocarbonylamino, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted phenylsulfonyl, An alkylaminocarbonyl which may be substituted or a haloalkylaminocarbonyl which may be substituted, and the substituents other than hydrogen and formyl may be substituted with R ¹⁰ shown below,
R ¹⁰ independently represents phenyl or a 5- to 6-membered saturated or unsaturated heterocyclic group, and these groups are halogen, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted Cycloalkyl, optionally substituted halocycloalkyl, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio, optionally substituted haloalkylthio, optionally substituted alkylsulfinyl, Optionally substituted haloalkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted alkylamino, optionally substituted haloalkylamino, cyano, nitro, aminocarbonyl, substituted Alkylaminocarbonyl, optionally substituted dia May be substituted with at least one group selected from the group consisting of alkylaminocarbonyl, optionally substituted alkoxycarbonyl, optionally substituted phenyl, and optionally substituted pyridyl;
U represents CH _2, O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁹ and R ¹⁰ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and
e) When ^one of W ¹ , W ² , W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring.

  The optically active azoline derivative of the above formula (I) is fractionated by chromatography on a chiral silica gel stationary phase in the presence of an eluent or an eluent mixture, with the racemate corresponding to the optically active form as a liquid phase. Can be generated.

  The optically active azoline derivative of the formula (I) of the present invention exhibits extremely remarkable insecticidal activity, and such insecticidal activity is unexpectedly exceptionally superior as compared with the corresponding racemate.

In the present invention, the optically active azoline derivative represented by the formula (I) has a chiral center at the 5-position carbon atom of the azoline ring represented by “*” in the formula (I). In I), when T represents the group (T-2), when any one of W ¹ , W ² , W ³ and W ⁴ represents CH—R ⁸ or CH—R ¹⁰ , R ⁸ , R ¹⁰ The carbon atom to which is bonded is also a chiral center, and the optically active azoline derivative of the formula (I) of the present invention has at least two enantiomers (enantiomers).

In the compound of formula (I) of the present invention,
X is independently halogen, optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-12} haloalkyl, nitro, cyano, optionally substituted _{C 1-12} alkoxy, optionally substituted C _1-12 haloalkoxy, optionally substituted _{C 1-12} alkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally _{C 1-12} substituted haloalkylthio, optionally substituted C _1-12 haloalkylsulfinyl, optionally substituted C _1-12 haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted C _1-12 alkylamino, may be substituted C _2-24 (total carbon number) dialkylamino, optionally substituted _{C 1-12} (total carbon number) acylamino, Conversion which may C _{2-13 (total} carbon number) be alkoxycarbonylamino, optionally C _{2-13 (total} carbon number) be substituted halo alkoxycarbonylamino, optionally substituted C _1-12 alkylsulfonylamino or And represents _optionally substituted _C1-12 haloalkylsulfonylamino,
R ¹ may be substituted C _1-12 alkyl, _optionally substituted C _3-12 (total carbon number) cycloalkyl, _optionally substituted C _4-24 (total carbon number) alkyl cycloalkyl, substituted C _4-24 (total carbon number) cycloalkylalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted C _1-12 haloalkyl, C _3-12 (total carbon number) halocycloalkyl, or cyano, which may be substituted,
m represents 0, 1, 2, 3, 4 or 5;
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted C _1-12 alkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted. C _3-12 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, _optionally substituted C _4-24 (total carbon number) cycloalkyl alkyl, substituted which may be _{C 1-12} haloalkyl, optionally substituted phenyl, optionally substituted _{C 2-13} (total carbon number) even alkylcarbonyl, optionally substituted _{C 2-13} (total carbon number) alkoxycarbonyl, C _2-13 (total carbon number) alkylaminocarbonyl which may be substituted or C _3-25 (total carbon number) dialkylaminocarbonyl which may be substituted;
Q represents the following Q-1 to Q-54 phenyl, naphthyl and heterocyclic groups,

そして
Ｔが下記の基（Ｔ−１）又は基（Ｔ−２）を示す、

And T represents the following group (T-1) or group (T-2),

上記の基中、
Ｇが、下記Ｇ１〜Ｇ９の複素環式基を示し、

In the above group,
G represents a heterocyclic group of G1 to G9 below,

又は

Or

を示し、
Ｒ^３及びＲ^４が、それぞれ独立して水素、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_３−８シクロアルキル、置換されてもよいＣ_１−１２ハロアルキル、置換されてもよいＣ_３−８シクロハロアルキル、置換されてもよいＣ_２−１２アルケニル、置換されてもよいＣ_２−１２アルキニル、置換されてもよいＣ_２−１２ハロアルケニル、置換されてもよいＣ_２−１２ハロアルキニル、シアノ、Ｃ_１−１２アルコキシ−カルボニル又はＣ_１−１２アルコキシ−チオカルボニルを示し、
Ｒ^３とＲ^４が、一緒になってＣ_３−６アルキレンを形成してもよく、
Ｒ^５が、水素、アミノ、ヒドロキシ、置換されてもよいＣ_１−１２アルコキシ、置換されてもよいアミノ−カルボニル−Ｃ_１−１２アルキル、置換されてもよいイミノ−Ｃ_１−１２アルキル、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_３−８シクロアルキル、置換されてもよいＣ_１−１２ハロアルキル、シアノ、置換されてもよいＣ_２−１２アルケニル、置換されてもよいＣ_２−１２アルキニル、置換されてもよいＣ_１−１２アルキル−カルボニル、−ＣＨ_２−Ｒ^７、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^６が、水素、シアノ、カルボニル、チオカルボニル、置換されてもよいＣ_１−１２アルキル−カルボニル、置換されてもよいＣ_１−１２アルキル−チオカルボニル、置換されてもよいＣ_１−１２ハロアルキル−カルボニル、置換されてもよいＣ_１−１２ハロアルキル−チオカルボニル、置換されてもよいＣ_１−１２アルキルアミノ−カルボニル、置換されてもよいＣ_１−１２アルキルアミノ−チオカルボニル、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノ−カルボニル、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノ−チオカルボニル、置換されてもよいＣ_１−１２アルコキシアミノ−カルボニル、置換されてもよいＣ_１−１２アルコキシアミノ−チオカルボニル、置換されてもよいＣ_１−１２アルコキシ−カルボニル、置換されてもよいＣ_１−１２アルコキシ−チオカルボニル、置換されてもよいＣ_１−１２チオアルコキシ−カルボニル、置換されてもよいＣ_１−１２チオアルコキシ−チオカルボニル、置換されてもよいＣ_１−１２アルキルスルホニル、置換されてもよいＣ_１−１２ハロアルキルスルホニル、置換されてもよいＣ_３−８シクロアルキルカルボニル、Ｃ_２−１２アルケニルカルボニル、Ｃ_２−１２アルキニルカルボニル、Ｃ_３−８シクロアルキル−Ｃ_１−１２アルキルカルボニル、Ｃ_１−１２アルキルスルフェニル−Ｃ_１−１２アルキルカルボニル、Ｃ_１−１２アルキルスルフィニル−Ｃ_１−１２アルキルカルボニル、Ｃ_１−１２アルキルスルホニル−Ｃ_１−１２アルキルカルボニル、Ｃ_１−１２アルキルカルボニル−Ｃ_１−１２アルキルカルボニル、Ｃ_３−８シクロアルキルアミノカルボニル、Ｃ_２−１２アルケニルアミノカルボニル、Ｃ_２−１２アルキニルアミノカルボニル、Ｃ_１−１２アルコキシ−Ｃ_１−１２アルキルカルボニル、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^５とＲ^６が、それらが結合する窒素原子と一緒になって、置換されてもよい３乃至６員の複素環を形成してもよく、該環は、ケト、チオケト又はニトロイミノ基で置換されていてもよく、
Ｒ^７が、置換されてもよいフェニル又は置換されてもよい飽和若しくは不飽和の複素環を示し、
Ｚが、同一でも異なってもよいハロゲン、置換されてもよいＣ_１−１２ハロアルキル、ニトロ、置換されてもよいＣ_１−１２アルコキシ、シアノ、置換されてもよいＣ_１−１２ハロアルコキシ、置換されてもよいＣ_１−１２アルキルスルフェニル、置換されてもよいＣ_１−１２アルキルスルフィニル、置換されてもよいＣ_１−１２アルキルスルホニル、置換されてもよいＣ_１−１２ハロアルキルスルフェニル、置換されてもよいＣ_１−１２ハロアルキルスルフィニル、置換されてもよいＣ_１−１２ハロアルキルスルホニル、ヒドロキシル又はチオールを示し、
ｋが、０乃至４を示し、
Ｂ^１，Ｂ^２，Ｂ^３及びＢ^４が、それぞれ独立してＣ−Ｌ又は窒素を示し、
Ｂ^１及びＢ^２が、一緒になって炭素数６の芳香環を形成してもよく、
Ｌが、それぞれ独立して水素、ハロゲン、置換されてもよいＣ_１−１２ハロアルキル、ニトロ、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_３−８シクロアルキル、置換されてもよいＣ_３−８シクロハロアルキル、置換されてもよいＣ_１−１２アルコキシ、シアノ、置換されてもよいＣ_１−１２ハロアルコキシ、置換されてもよいＣ_１−１２アルキルスルフェニル、置換されてもよいＣ_１−１２アルキルスルフィニル、置換されてもよいＣ_１−１２アルキルスルホニル、置換されてもよいＣ_１−１２ハロアルキルスルフェニル、置換されてもよいＣ_１−１２ハロアルキルスルフィニル、置換されてもよいＣ_１−１２ハロアルキルスルホニル、置換されてもよいＣ_１−１２アルキルスルホニルオキシ、置換されてもよいＣ_１−１２ハロアルキルスルホニルオキシ、置換されてもよいＣ_１−１２アルキルアミノスルホニル、置換されてもよいＣ_１−１２ハロアルキルアミノスルホニル、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノスルホニル、置換されてもよいＣ_２−２４（総炭素数）ジ（ハロアルキル）アミノスルホニル、ヒドロキシル、チオール、アミノ、置換されてもよいＣ_１−１２アルキルアミノ基、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノ、置換されてもよいＣ_１−１２アシルアミノ、置換されてもよいＣ_１−１２アルコキシ−カルボニルアミノ、置換されてもよいＣ_１−１２ハロアルコキシ−カルボニルアミノ、置換されてもよいＣ_１−１２アルキルスルホニルアミノ、置換されてもよいＣ_１−１２ハロアルキルスルホニルアミノ、置換されてもよいＣ_１−１２トリアルキルシリル、置換されてもよいＣ_１−１２アルコキシイミノ、置換されてもよいＣ_１−１２ハロアルコキシイミノ、置換されてもよいＣ_１−１２アルコキシ−イミノ−置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_１−１２ハロアルコキシ−イミノ−置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_１−４アルキルスルフィニルイミノ、置換されてもよいＣ_１−４アルキルスルフィニル−イミノ−置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_１−４アルキルスルフィニル−イミノ−置換されてもよいＣ_１−５アルキル−カルボニル、置換されてもよいＣ_１−４アルキル−スルホキシイミノ、置換されてもよいＣ_１−４アルキルスルホキシ−イミノ−置換されてもよいＣ_１−４アルキル、置換されてもよいＣ_１−６アルコキシ−カルボニル、置換されてもよいＣ_１−６アルキル−カルボニル、アミノカルボニル、置換されてもよいＣ_１−６アルキルアミノカルボニル、アミノチオカルボニル、置換されてもよいＣ_１−６アルキルアミノ−チオカルボニル、置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノカルボニル基又は置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノチオカルボニルを示し、
ｌが、１乃至３を示し、
Ｙが独立してハロゲン、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_１−１２ハロアルキル、置換されてもよいＣ_３−１２シクロアルキル、置換されてもよいＣ_３−１２シクロハロアルキル、ニトロ、シアノ、置換されてもよいＣ_２−１２アルケニル、置換されてもよいＣ_２−１２ハロアルケニル、置換されてもよいＣ_１−１２アルコキシ、置換されてもよいＣ_１−１２ハロアルコキシ、置換されてもよいＣ_１−１２アルキルチオ、置換されてもよいＣ_１−１２アルキルスルフィニル、置換されてもよいＣ_１−１２アルキルスルホニル、置換されてもよいＣ_１−１２ハロアルキルチオ、置換されてもよいＣ_１−１２ハロアルキルスルフィニル、置換されてもよいＣ_１−１２ハロアルキルスルホニル、ヒドロキシ、メルカプト、アミノ、置換されてもよいＣ_１−１２アルキルアミノ、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノ、アミノカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_３−２５（総炭素数）ジアルキルアミノカルボニル、置換されてもよいＣ_１−１２（総炭素数）アシルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルコキシカルボニルアミノ、置換されてもよいベンジルオキシカルボニルアミノ、置換されてもよいＣ_２−１３ハロアルコキシカルボニルアミノ、置換されてもよいＣ_１−１２アルキルスルホニルアミノ、置換されてもよいＣ_１−１２ハロアルキルスルホニルアミノまたは置換されてもよいＣ_３−２６（総炭素数）トリアルキルシリルを示し、
ｎが０、１、２又は３を示し、
Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４が独立して単結合、ＣＨ_２、ＣＨ、Ｎ、Ｏ、Ｓ、ＣＨ−Ｒ^８、Ｃ−Ｒ^８、Ｃ（Ｒ^８）_２、Ｎ−Ｒ^９、Ｎ−Ｒ^１０、ＣＨ−Ｒ^１０、Ｃ−Ｒ^１０又はＣ＝Ｕを示し、
Ｒ^８は独立してヒドロキシ、アミノ、シアノ、ホルミル、ハロゲン、ニトロ、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_２−１２アルケニル、置換されてもよいＣ_２−１２アルキニル、置換されてもよいＣ_３−１２シクロアルキル、置換されてもよいＣ_４−２４アルキルシクロアルキル、置換されてもよいＣ_４−２４シクロアルキルアルキル、置換されてもよいＣ_１−１２ハロアルキル、置換されてもよいＣ_２−１３（総炭素数）アルキルカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルコキシカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_３−２５（総炭素数）ジアルキルアミノカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルキルカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルキルチオカルボニルアミノ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルカルボニルアミノ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルカルボニルアミノ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルチオカルボニルアミノ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルチオカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルチオカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノチオカルボニルアミノ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルアミノカルボニルアミノ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルアミノカルボニルアミノ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルアミノカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_３−２５（総炭素数）ジアルキルアミノカルボニルアミノ、置換されてもよいＣ_２−２５（総炭素数）ジアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニルオキシ、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニルチオ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルアミノカルボニルオキシ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルアミノカルボニルオキシ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルアミノカルボニルチオ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルアミノカルボニルチオ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルアミノカルボニルオキシ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルアミノカルボニルチオ、置換されてもよいＣ_３−２５（総炭素数）ジアルキルアミノカルボニルオキシ、置換されてもよいＣ_３−２５（総炭素数）ジアルキルアミノカルボニルチオ、置換されてもよいＣ_２−１３（総炭素数）アルコキシカルボニルアミノ、置換されてもよいＣ_４−１３（総炭素数）シクロアルキルオキシカルボニルアミノ、置換されてもよいＣ_５−２５（総炭素数）シクロアルキルアルキルオキシカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルコキシカルボニルアミノ、置換されてもよいＣ_１−１２アルキルスルホニルアミノ又は置換されてもよいＣ_１−１２ハロアルキルスルホニルアミノを示し、上記シアノ、ホルミル、ハロゲン及びニトロ以外の置換基は後記に示すＲ^１０で置換されてよく、
Ｒ^９は水素、ヒドロキシ、アミノ、置換されてもよいＣ_１−１２アルキル、置換されてもよいＣ_１−１２ハロアルキル、置換されてもよいＣ_２−１２アルケニル、置換されてもよいＣ_２−１２アルケニルオキシ、置換されてもよいＣ_２−１２アルキニル、置換されてもよいＣ_２−１２アルキニルオキシ、置換されてもよいＣ_３−１２シクロアルキル、置換されてもよいＣ_４−２４アルキルシクロアルキル、置換されてもよいＣ_４−２４シクロアルキルアルキル、置換されてもよいＣ_１−１２アルキルアミノ、置換されてもよいＣ_２−２４（総炭素数）ジアルキルアミノ、置換されてもよいＣ_１−１２アルコキシ、置換されてもよいＣ_１−１２ハロアルコキシ、ホルミル、置換されてもよいＣ_２−１３（総炭素数）アルキルカルボニル、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルコキシカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_２−１３（総炭素数）アルキルカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルコキシカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニルアミノ、置換されてもよいＣ_１−１２（総炭素数）アルキルスルホニル、置換されてもよいＣ_１−１２（総炭素数）ハロアルキルスルホニル、置換されてもよいフェニルスルホニル、置換されてもよいＣ_２−１３（総炭素数）アルキルアミノカルボニル又は置換されてもよいＣ_２−１３（総炭素数）ハロアルキルアミノカルボニルであり、上記水素およびホルミル以外の置換基は後記に示すＲ^１０で置換されてもよく、
Ｒ^１０は、下記Ｒ^１０−１〜Ｒ^１０−８３のフェニル及び複素環式基を示し、

Indicate
R ³ and R ⁴ are each independently hydrogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, optionally substituted C _1-12 haloalkyl, substituted C _3-8 cyclohaloalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted C _2-12 haloalkenyl, _optionally substituted C _{2 -12} haloalkynyl, cyano, C _1-12 alkoxy-carbonyl or C _1-12 alkoxy-thiocarbonyl,
R ³ and R ⁴ together may form a C _3-6 alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted C _1-12 alkoxy, optionally substituted amino-carbonyl-C _1-12 alkyl, optionally substituted imino-C _1-12 alkyl, substituted _Optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, _optionally substituted C _1-12 haloalkyl, cyano, _optionally substituted C _2-12 alkenyl, _optionally substituted Good C _2-12 alkynyl, _optionally substituted C _1-12 alkyl-carbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S) —R ⁷ ,
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted C _1-12 alkyl-carbonyl, _optionally substituted C _1-12 alkyl-thiocarbonyl, optionally substituted C _1-12 haloalkyl -Carbonyl, optionally substituted C _1-12 haloalkyl-thiocarbonyl, optionally substituted C _1-12 alkylamino-carbonyl, _optionally substituted C _1-12 alkylamino-thiocarbonyl, optionally substituted Good C _2-24 (total carbon number) dialkylamino-carbonyl, optionally substituted C _2-24 (total carbon number) dialkylamino-thiocarbonyl, optionally substituted C _1-12 alkoxyamino-carbonyl, substituted which may be _{C 1-12} alkoxy amino - thiocarbonyl, optionally substituted _{C 1-12} aralkyl Carboxy - carbonyl, optionally substituted _{C 1-12} alkoxy - thiocarbonyl, optionally substituted _{C 1-12} thioalkoxy - carbonyl, optionally substituted _{C 1-12} thioalkoxy - thiocarbonyl, optionally substituted C _1-12 alkylsulfonyl, optionally substituted C _1-12 haloalkylsulfonyl, optionally substituted C _3-8 cycloalkylcarbonyl, C _2-12 alkenylcarbonyl, C _2-12 alkynylcarbonyl, C _{3 -8} cycloalkyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfenyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfinyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfonyl-C _{1 -12 alkylcarbonyl, C 1-12} alkyl Cal Cycloalkenyl _{-C 1-12 alkylcarbonyl, C 3-8} cycloalkyl amino _{carbonyl, C 2-12} alkenyl _{aminocarbonyl, C 2-12 alkynyl-aminocarbonyl, C 1-12} alkoxy _{-C 1-12} alkylcarbonyl, -C ( O) -R ⁷ or -C (S) -R ⁷
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form a 3-6 membered heterocyclic ring which may be substituted, which ring is substituted with a keto, thioketo or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
Z may be the same or different halogen, optionally substituted C _1-12 haloalkyl, nitro, optionally substituted C _1-12 alkoxy, cyano, optionally substituted C _1-12 haloalkoxy, substituted which may be _{C 1-12} alkyl sulphenyl, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkyl sulfenyl, substituted which may be C _1-12 haloalkylsulfinyl, optionally substituted C _1-12 haloalkylsulfonyl, a hydroxyl or thiol,
k represents 0 to 4,
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² together may form an aromatic ring having 6 carbon atoms,
L is independently hydrogen, halogen, optionally substituted C _1-12 haloalkyl, nitro, _optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, substituted C _3-8 cyclohaloalkyl, optionally substituted C _1-12 alkoxy, cyano, optionally substituted C _1-12 haloalkoxy, optionally substituted C _1-12 alkylsulfenyl, substituted which may _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkylsulfenyl, optionally substituted _{C 1-12} haloalkylsulfinyl, be substituted Good C _1-12 haloalkylsulfonyl, optionally substituted C _1-12 alkylsulfonyloxy, optionally substituted C _1-12 haloalkylsulfonyloxy, optionally substituted C _1-12 alkylaminosulfonyl, optionally substituted C _1-12 haloalkylaminosulfonyl, optionally substituted C _2-24 (total carbon number) dialkylamino Sulfonyl, optionally substituted C _2-24 (total carbon number) di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted C _1-12 alkylamino group, _optionally substituted C _{2− 24} (total carbon number) dialkylamino, optionally substituted C _1-12 acylamino, optionally substituted C _1-12 alkoxy-carbonylamino, optionally substituted C _1-12 haloalkoxy-carbonylamino, substituted and which may be _{C 1-12} alkylsulfonylamino, optionally substituted _{C 1-12} Ha Alkylsulfonylamino, optionally substituted _{C 1-12} trialkylsilyl, optionally substituted _{C 1-12} alkoxyimino, optionally substituted _{C 1-12} halo alkoxyiminoalkyl, optionally substituted _{C 1- 12} alkoxy - imino - optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-12} haloalkoxy - imino - optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-4} alkyl sulfinyl amino, optionally substituted C _1-4 alkylsulfinyl - imino - optionally substituted C _1-12 alkyl, optionally substituted C _1-4 alkylsulfinyl - imino - optionally substituted C _{1 -5} alkyl-carbonyl, optionally substituted C _1-4 alkyl-sulfoxyimino, optionally substituted C _1-4 alkyl Rusuruhokishi - imino - optionally substituted C _1-4 alkyl optionally, an optionally substituted C _1-6 alkoxy - carbonyl, optionally substituted C _1-6 alkyl -, aminocarbonyl, optionally substituted C _1-6 alkylaminocarbonyl, aminothiocarbonyl, optionally substituted C _1-6 alkylamino-thiocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminocarbonyl group or optionally substituted Good C _2-12 (total carbon number) dialkyl-aminothiocarbonyl,
l represents 1 to 3,
Y is independently halogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl, optionally substituted C _3-12 cycloalkyl, _optionally substituted C _3-12 cycloalkyl haloalkyl, nitro, cyano, optionally substituted _{C 2-12} alkenyl, optionally substituted _{C 2-12} haloalkenyl, optionally substituted _{C 1-12} alkoxy, optionally _{C 1-12} substituted haloalkoxy, optionally substituted _{C 1-12} alkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkylthio, optionally substituted _{C 1-12} haloalkylsulfinyl, optionally substituted _{C 1-12} haloalkylsulfonyl, hydroxy, main Mercapto, amino, optionally substituted _{C 1-12} alkylamino, optionally substituted _{C 2-24} (total carbon number) dialkylamino, aminocarbonyl, optionally substituted _{C 2-13} (total carbon number) Alkylaminocarbonyl, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonyl, _optionally substituted C _1-12 (total carbon number) acylamino, optionally substituted C _2-13 (total carbon number) Number) alkoxycarbonylamino, optionally substituted benzyloxycarbonylamino, optionally substituted C _2-13 haloalkoxycarbonylamino, optionally substituted C _1-12 alkylsulfonylamino, optionally substituted C _{1 -12} haloalkylsulfonyl amino or optionally substituted _{C 3-26} (total carbon number) trialkylsilyl Shows,
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ , C—R ⁸ , C (R ⁸ ) _2, N—R ^9. N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, _optionally substituted C _1-12 alkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl. _Optionally substituted C _3-12 cycloalkyl, _optionally substituted C _4-24 alkyl cycloalkyl, _optionally substituted C _4-24 cycloalkylalkyl, _optionally substituted C _1-12 haloalkyl, C _2-13 (total carbon number) alkylcarbonyl which may be substituted, C _2-13 (total carbon number) alkoxycarbonyl which may be substituted, C _2-13 (total carbon number) alkylamino which may be substituted carbonyl, optionally substituted _{C 3-25} (total carbon number) dialkylaminocarbonyl, optionally substituted _{C 2-13} (total carbon number) Al Le carbonylamino, optionally substituted _{C 2-13} (total carbon number) be alkylthiocarbonyl amino, optionally substituted _{C 4-13} (total carbon number) be a cycloalkyl carbonyl amino, optionally substituted _{C 5-25} (Total carbon number) cycloalkylalkylcarbonylamino, optionally substituted C _4-13 (total carbon number) cycloalkylthiocarbonylamino, optionally substituted C _5-25 (total carbon number) cycloalkylalkylthiocarbonylamino, optionally substituted _{C 2-13} (total carbon number) be halo alkylcarbonylamino, optionally substituted _{C 2-13} (total carbon number) haloalkylthio alkylcarbonylamino, optionally substituted _{C 2-13} (the total number of carbon atoms ) alkylaminocarbonyl amino, optionally substituted _{C 2-13} (total carbon number) alkylamino Thiocarbonylamino, optionally substituted C _{4-13 (total} carbon number) be a cycloalkyl aminocarbonylamino, optionally substituted C _{5-25 (total} carbon number) cycloalkylalkyl aminocarbonylamino, may be substituted C _4-13 (total carbon number) cycloalkylaminothiocarbonylamino, _optionally substituted C _5-25 (total carbon number) cycloalkylalkylaminothiocarbonylamino, _optionally substituted C _2-13 (total carbon number) Number) haloalkylaminocarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkylaminothiocarbonylamino, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonylamino, _optionally substituted good _{C 2-25} (total number of carbon atoms) dialkylaminothiocarbonyl amino, substituted Which may _{C 2-13} (total carbon number) be alkylaminocarbonyloxy, optionally substituted _{C 2-13} (total carbon number) alkylaminocarbonyl thio, optionally substituted _{C 4-13} (the total number of carbon atoms ) Cycloalkylaminocarbonyloxy, _optionally substituted C _5-25 (total carbon number) cycloalkylalkylaminocarbonyloxy, _optionally substituted C _4-13 (total carbon number) cycloalkylaminocarbonylthio, substituted which may be _{C 5-25} (total carbon number) cycloalkylalkyl aminocarbonylthio, optionally substituted _{C 2-13} (total carbon number) be halo alkylaminocarbonyloxy, optionally substituted _{C 2-13} (total carbon Number) haloalkylaminocarbonylthio, C _{3-25 optionally} substituted (total carbon number) dialkylaminocarbo Nyloxy, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonylthio, optionally substituted C _2-13 (total carbon number) alkoxycarbonylamino, optionally substituted C _4-13 (total Carbon number) cycloalkyloxycarbonylamino, optionally substituted C _5-25 (total carbon number) cycloalkylalkyloxycarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkoxycarbonylamino, substituted C _1-12 alkylsulfonylamino which may be substituted or C _1-12 haloalkylsulfonylamino which may be substituted, and substituents other than the above cyano, formyl, halogen and nitro may be substituted with R ¹⁰ shown below ,
R ⁹ is hydrogen, hydroxy, amino, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _{2- 12} alkenyloxy, optionally substituted _{C 2-12} alkynyl, optionally substituted _{C 2-12} alkynyloxy, optionally substituted _{C 3-12} cycloalkyl, optionally _{C 4-24} alkylcycloalkyl substituted Alkyl, _optionally substituted C _4-24 cycloalkylalkyl, _optionally substituted C _1-12 alkylamino, _optionally substituted C _2-24 (total carbon number) dialkylamino, optionally substituted C _1-12 alkoxy, optionally substituted _{C 1-12} haloalkoxy, formyl, optionally substituted _{C 2-13} (total carbon number) alkylcarbonyl Le, optionally substituted _{C 2-13} (total carbon number) haloalkylcarbonyl, optionally substituted _{C 2-13} (total carbon number) alkoxycarbonyl, optionally substituted _{C 2-13} (total carbon number) Alkylaminocarbonyl, optionally substituted C _2-13 (total carbon number) alkylcarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-13 ( (Total carbon number) alkoxycarbonylamino, optionally substituted C _2-13 (total carbon number) alkylaminocarbonylamino, optionally substituted C _1-12 (total carbon number) alkylsulfonyl, optionally substituted C _1-12 (total carbon number) haloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally substituted _{C 2-13} (total carbon number) Le Kill aminocarbonyl or optionally substituted C _{2-13 (total} carbon number) halo alkylaminocarbonyl, the substituents other than the hydrogen and formyl may be substituted with R ¹⁰ shown in the following,
R ¹⁰ represents phenyl and heterocyclic groups the following ^R 10 ^-1~R 10 -83,

E represents O, S or N, and each group is hydrogen, halogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl in the above phenyl and heterocyclic groups, _Optionally substituted C _3-12 cycloalkyl, optionally substituted C _{3-12 halocycloalkyl,} optionally substituted C _1-12 alkoxy, optionally substituted C _1-12 haloalkoxy, substituted which may be _{C 1-12} alkylthio, optionally substituted _{C 1-12} haloalkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} haloalkylsulfinyl, it may be substituted C _1-12 alkylsulfonyl, optionally substituted _{C 1-12} haloalkylsulfonyl, optionally substituted _{C 1-12} alkylamino, substituted C _1-12 haloalkylamino, cyano, nitro, aminocarbonyl, optionally substituted C _2-13 (total carbon number) alkylaminocarbonyl, optionally substituted C _2-25 (total carbon number) dialkylamino May be substituted with at least one group selected from the group consisting of carbonyl, optionally substituted C _1-13 alkoxycarbonyl, optionally substituted phenyl, and optionally substituted pyridyl;
U represents CH ₂ , O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁹ and R ¹⁰ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and e) W ¹ , W ² , When one of W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring.
The optically active substance of the case can be mentioned as a suitable thing.

Among them, in the compound of formula (I)
X is independently halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl, nitro, cyano, optionally substituted C _1-6 alkoxy, optionally substituted C _1-6 haloalkoxy, optionally substituted _{C 1-6} alkylthio, optionally substituted _{C 1-6} alkylsulfinyl, optionally substituted _{C 1-6} alkylsulfonyl, optionally substituted _{C 1-6} haloalkylthio, optionally substituted C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted C _1-6 alkyl amino, optionally substituted C _2-12 (total carbon number) dialkylamino, optionally substituted C _1-6 (total carbon number) acylamino, optionally substituted C _2-7 (Total carbon number) alkoxycarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino or optionally substituted C _1-6 Represents haloalkylsulfonylamino;
R ¹ is optionally substituted C _1-6 alkyl, optionally substituted C _3-6 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, substituted _Optionally substituted C _4-12 (total carbon number) cycloalkylalkyl, _optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _1-6 haloalkyl, C _3-6 (total carbon number) halocycloalkyl, or cyano, which may be substituted,
m represents 0, 1, 2, 3, 4 or 5;
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted C _1-6 alkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _3-6 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, optionally substituted C _4-12 (total carbon number) cycloalkyl alkyl, substituted It is a C _1-6 haloalkyl, optionally substituted phenyl, optionally substituted C _{2-7 (total} carbon number) even alkylcarbonyl, optionally substituted C _{2-7 (total} carbon number) alkoxycarbonyl, C _2-7 (total carbon number) alkylaminocarbonyl which may be substituted or C _3-13 (total carbon number) dialkylaminocarbonyl which may be substituted;
Q represents the following Q-1 to Q-54 phenyl, naphthyl and heterocyclic groups,

  T represents the following group (T-1) or group (T-2),

上記の基中、
Ｇが、下記Ｇ１〜Ｇ９の複素環式基を示し、

In the above group,
G represents a heterocyclic group of G1 to G9 below,

又は

Or

を示し、
Ｒ^３及びＲ^４が、それぞれ独立して水素、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_１−６ハロアルキル、置換されてもよいＣ_３−６シクロハロアルキル、置換されてもよいＣ_２−６アルケニル、置換されてもよいＣ_２−６アルキニル、置換されてもよいＣ_２−６ハロアルケニル、置換されてもよいＣ_２−６ハロアルキニル、シアノ、Ｃ_１−６アルコキシ−カルボニル又はＣ_１−６アルコキシ−チオカルボニルを示し、
Ｒ^３とＲ^４が、一緒になってＣ_３−６アルキレンを形成してもよく、
Ｒ^５が、水素、アミノ、ヒドロキシ、置換されてもよいＣ_１−６アルコキシ、置換されてもよいアミノカルボニル−Ｃ_１−６アルキル、置換されてもよいイミノ−Ｃ_１−６アルキル、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_１−６ハロアルキル、シアノ、置換されてもよいＣ_２−６アルケニル、置換されてもよいＣ_２−６アルキニル、置換されてもよいＣ_１−６アルキル−カルボニル、−ＣＨ_２−Ｒ^７、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^６が、水素、シアノ、カルボニル、チオカルボニル、置換されてもよいＣ_１−６アルキル−カルボニル、置換されてもよいＣ_１−６アルキル−チオカルボニル、置換されてもよいＣ_１−６ハロアルキル−カルボニル、置換されてもよいＣ_１−６ハロアルキル−チオカルボニル、置換されてもよいＣ_１−６アルキルアミノ−カルボニル、置換されてもよいＣ_１−６アルキルアミノ−チオカルボニル、置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノカルボニル、置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノチオカルボニル、置換されてもよいＣ_１−６アルコキシ−アミノカルボニル、置換されてもよいＣ_１−６アルコキシ−アミノチオカルボニル、置換されてもよいＣ_１−６アルコキシ−カルボニル、置換されてもよいＣ_１−６アルコキシ−チオカルボニル、置換されてもよいＣ_１−６チオアルコキシ−カルボニル、置換されてもよいＣ_１−６チオアルコキシ−チオカルボニル、置換されてもよいＣ_１−６アルキルスルホニル、置換されてもよいＣ_１−６ハロアルキルスルホニル、置換されてもよいＣ_３−６シクロアルキルカルボニル、Ｃ_２−６アルケニルカルボニル、Ｃ_２−６アルキニルカルボニル、Ｃ_３−６シクロアルキル−Ｃ_１−６アルキルカルボニル、Ｃ_１−６アルキルスルフェニル−Ｃ_１−６アルキルカルボニル、Ｃ_１−６アルキルスルフィニル−Ｃ_１−６アルキルカルボニル、Ｃ_１−６アルキルスルホニル−Ｃ_１−６アルキルカルボニル、Ｃ_１−６アルキルカルボニル−Ｃ_１−６アルキルカルボニル、Ｃ_３−６シクロアルキルアミノカルボニル、Ｃ_２−６アルケニルアミノカルボニル、Ｃ_２−６アルキニルアミノカルボニル、Ｃ_１−６アルコキシ−Ｃ_１−６アルキルカルボニル、−Ｃ（Ｏ）−Ｒ^７又は−Ｃ（Ｓ）−Ｒ^７を示し、
Ｒ^５とＲ^６が、それらが結合する窒素原子と一緒になって、置換されてもよい３乃至６員の複素環を形成してもよく、該環は、ケト、チオケト又はニトロイミノ基で置換されていてもよく、
Ｒ^７が、置換されてもよいフェニル又は置換されてもよい飽和若しくは不飽和の複素環を示し、
Ｚが、同一でも異なってもよいハロゲン、置換されてもよいＣ_１−６ハロアルキル、ニトロ、置換されてもよいＣ_１−６アルコキシ、シアノ、置換されてもよいＣ_１−６ハロアルコキシ、置換されてもよいＣ_１−６アルキルスルフェニル、置換されてもよいＣ_１−６アルキルスルフィニル、置換されてもよいＣ_１−６アルキルスルホニル、置換されてもよいＣ_１−６ハロアルキルスルフェニル、置換されてもよいＣ_１−６ハロアルキルスルフィニル、置換されてもよいＣ_１−６ハロアルキルスルホニル、ヒドロキシル又はチオールを示し、
ｋが、０乃至４を示し、
Ｂ^１，Ｂ^２，Ｂ^３及びＢ^４が、それぞれ独立してＣ−Ｌ又は窒素を示し、
Ｂ^１及びＢ^２が、一緒になって炭素数６の芳香環を形成してもよく、
Ｌが、それぞれ独立して水素、ハロゲン、置換されてもよいＣ_１−６ハロアルキル、ニトロ、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_３−６シクロハロアルキル、置換されてもよいＣ_１−６アルコキシ、シアノ、置換されてもよいＣ_１−６ハロアルコキシ、置換されてもよいＣ_１−６アルキルスルフェニル、置換されてもよいＣ_１−６アルキルスルフィニル、置換されてもよいＣ_１−６アルキルスルホニル、置換されてもよいＣ_１−６ハロアルキルスルフェニル、置換されてもよいＣ_１−６ハロアルキルスルフィニル、置換されてもよいＣ_１−６ハロアルキルスルホニル、置換されてもよいＣ_１−６アルキルスルホニルオキシ、置換されてもよいＣ_１−６ハロアルキルスルホニルオキシ、置換されてもよいＣ_１−６アルキルアミノスルホニル、置換されてもよいＣ_１−６ハロアルキルアミノスルホニル、置換されてもよいＣ_２−１２（総炭素数）ジアルキルアミノスルホニル基、置換されてもよいＣ_２−１２（総炭素数）ジ（ハロアルキル）アミノスルホニル、ヒドロキシル、チオール、アミノ、置換されてもよいＣ_１−６アルキルアミノ、置換されてもよいＣ_２−１２（総炭素数）ジアルキルアミノ、置換されてもよいＣ_１−６アシルアミノ、置換されてもよいＣ_１−６アルコキシ−カルボニルアミノ、置換されてもよいＣ_１−６ハロアルコキシ−カルボニルアミノ、置換されてもよいＣ_１−６アルキルスルホニルアミノ、置換されてもよいＣ_１−６ハロアルキルスルホニルアミノ、置換されてもよいＣ_１−６トリアルキルシリル、置換されてもよいＣ_１−６アルコキシイミノ、置換されてもよいＣ_１−６ハロアルコキシイミノ、置換されてもよいＣ_１−６アルコキシ−イミノ−置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_１−６ハロアルコキシ−イミノ−置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_１−４アルキルスルフィニルイミノ、置換されてもよいＣ_１−４アルキルスルフィニル−イミノ−置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_１−４アルキルスルフィニル−イミノ−置換されてもよいＣ_１−５アルキル−カルボニル、置換されてもよいＣ_１−４アルキル−スルホキシイミノ、置換されてもよいＣ_１−４アルキルスルホキシ−イミノ−置換されてもよいＣ_１−４アルキル、置換されてもよいＣ_１−６アルコキシ−カルボニル、置換されてもよいＣ_１−６アルキル−カルボニル、アミノカルボニル、置換されてもよいＣ_１−６アルキルアミノカルボニル、アミノチオカルボニル、置換されてもよいＣ_１−６アルキルアミノ−チオカルボニル、置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノカルボニル又は置換されてもよいＣ_２−１２（総炭素数）ジアルキル−アミノチオカルボニルを示し、
ｌが、１乃至３を示し、
Ｙが独立してハロゲン、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_１−６ハロアルキル、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_３−６シクロハロアルキル、ニトロ、シアノ、置換されてもよいＣ_２−６アルケニル、置換されてもよいＣ_２−６ハロアルケニル、置換されてもよいＣ_１−６アルコキシ、置換されてもよいＣ_１−６ハロアルコキシ、置換されてもよいＣ_１−６アルキルチオ、置換されてもよいＣ_１−６アルキルスルフィニル、置換されてもよいＣ_１−６アルキルスルホニル、置換されてもよいＣ_１−６ハロアルキルチオ、置換されてもよいＣ_１−６ハロアルキルスルフィニル、置換されてもよいＣ_１−６ハロアルキルスルホニル、ヒドロキシ、メルカプト、アミノ、置換されてもよいＣ_１−６アルキルアミノ、置換されてもよいＣ_２−１２（総炭素数）ジアルキルアミノ、アミノカルボニル、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_２−１３（総炭素数）ジアルキルアミノカルボニル、置換されてもよいＣ_１−６（総炭素数）アシルアミノ、置換されてもよいＣ_２−７（総炭素数）アルコキシカルボニルアミノ、置換されてもよいベンジルオキシカルボニルアミノ、置換されてもよいＣ_２−７ハロアルコキシカルボニルアミノ、置換されてもよいＣ_１−６アルキルスルホニルアミノ、置換されてもよいＣ_１−６ハロアルキルスルホニルアミノまたは置換されてもよいＣ_３−２６（総炭素数）トリアルキルシリルを示し、
ｎが０、１、２又は３を示し、
Ｗ^１、Ｗ^２、Ｗ^３およびＷ^４が独立して単結合、ＣＨ_２、ＣＨ、Ｎ、Ｏ、Ｓ、ＣＨ−Ｒ^８、Ｃ−Ｒ^８、Ｃ（Ｒ^８）_２、Ｎ−Ｒ^９、Ｎ−Ｒ^１０、ＣＨ−Ｒ^１０、Ｃ−Ｒ^１０又はＣ＝Ｕを示し、
Ｒ^８は独立してヒドロキシ、アミノ、シアノ、ホルミル、ハロゲン、ニトロ、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_２−６アルケニル、置換されてもよいＣ_２−６アルキニル、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_４−１２アルキルシクロアルキル、置換されてもよいＣ_４−１２シクロアルキルアルキル、置換されてもよいＣ_１−６ハロアルキル、置換されてもよいＣ_２−７（総炭素数）アルキルカルボニル、置換されてもよいＣ_２−７（総炭素数）アルコキシカルボニル、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_３−１３（総炭素数）ジアルキルアミノカルボニル、置換されてもよいＣ_２−７（総炭素数）アルキルカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルキルチオカルボニルアミノ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルカルボニルアミノ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルカルボニルアミノ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルチオカルボニルアミノ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルチオカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ハロアルキルカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルチオカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルキルアミノチオカルボニルアミノ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルアミノカルボニルアミノ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルアミノカルボニルアミノ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルアミノカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_３−１３（総炭素数）ジアルキルアミノカルボニルアミノ、置換されてもよいＣ_２−１３（総炭素数）ジアルキルアミノチオカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニルオキシ、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニルチオ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルアミノカルボニルオキシ、置換されてもよいＣ_５−７（総炭素数）シクロアルキルアルキルアミノカルボニルオキシ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルアミノカルボニルチオ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルアミノカルボニルチオ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルアミノカルボニルオキシ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルアミノカルボニルチオ、置換されてもよいＣ_３−１３（総炭素数）ジアルキルアミノカルボニルオキシ、置換されてもよいＣ_３−１３（総炭素数）ジアルキルアミノカルボニルチオ、置換されてもよいＣ_２−７（総炭素数）アルコキシカルボニルアミノ、置換されてもよいＣ_４−７（総炭素数）シクロアルキルオキシカルボニルアミノ、置換されてもよいＣ_５−１３（総炭素数）シクロアルキルアルキルオキシカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）ハロアルコキシカルボニルアミノ、置換されてもよいＣ_１−６アルキルスルホニルアミノ又は置換されてもよいＣ_１−６ハロアルキルスルホニルアミノを示し、上記シアノ、ホルミル、ハロゲン及びニトロ以外の置換基はＲ^１０で置換されてよく、
Ｒ^９は水素、ヒドロキシ、アミノ、置換されてもよいＣ_１−６アルキル、置換されてもよいＣ_１−６ハロアルキル、置換されてもよいＣ_２−６アルケニル、置換されてもよいＣ_２−６アルケニルオキシ、置換されてもよいＣ_２−６アルキニル、置換されてもよいＣ_２−６アルキニルオキシ、置換されてもよいＣ_３−６シクロアルキル、置換されてもよいＣ_４−１２アルキルシクロアルキル、置換されてもよいＣ_４−１２シクロアルキルアルキル、置換されてもよいＣ_１−６アルキルアミノ、置換されてもよいＣ_２−１２（総炭素数）ジアルキルアミノ、置換されてもよいＣ_１−６アルコキシ、置換されてもよいＣ_１−６ハロアルコキシ、ホルミル、置換されてもよいＣ_２−７（総炭素数）アルキルカルボニル、置換されてもよいＣ_２−７（総炭素数）ハロアルキルカルボニル、置換されてもよいＣ_２−７（総炭素数）アルコキシカルボニル、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニル、置換されてもよいＣ_２−７（総炭素数）アルキルカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）ハロアルキルカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルコキシカルボニルアミノ、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニルアミノ、置換されてもよいＣ_１−６（総炭素数）アルキルスルホニル、置換されてもよいＣ_１−６（総炭素数）ハロアルキルスルホニル、置換されてもよいフェニルスルホニル、置換されてもよいＣ_２−７（総炭素数）アルキルアミノカルボニル又は置換されてもよいＣ_２−７（総炭素数）ハロアルキルアミノカルボニルであり、上記水素およびホルミル以外の置換基はＲ^１０で置換されてもよく、
Ｒ^１０は、下記Ｒ^１０−１〜Ｒ^１０−８３のフェニル及び複素環式基を示し、

Indicate
R ³ and R ⁴ are each independently hydrogen, optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _1-6 haloalkyl, substituted C _3-6 cyclohaloalkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _2-6 haloalkenyl, optionally substituted C _{2 -6} haloalkynyl, _{cyano, C 1-6} alkoxy - carbonyl or _{C 1-6} alkoxy - indicates thiocarbonyl,
R ³ and R ⁴ together may form a C _3-6 alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted C _1-6 alkoxy, optionally substituted aminocarbonyl-C _1-6 alkyl, optionally substituted imino-C _1-6 alkyl, substituted _Optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _1-6 haloalkyl, cyano, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _1-6 alkyl-carbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S) —R ⁷ ,
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted C _1-6 alkyl-carbonyl, optionally substituted C _1-6 alkyl-thiocarbonyl, optionally substituted C _1-6 haloalkyl -Carbonyl, optionally substituted C _1-6 haloalkyl-thiocarbonyl, optionally substituted C _1-6 alkylamino-carbonyl, optionally substituted C _1-6 alkylamino-thiocarbonyl, optionally substituted Good C _2-12 (total carbon number) dialkyl-aminocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminothiocarbonyl, optionally substituted C _1-6 alkoxy-aminocarbonyl, substituted It is a _{C 1-6} alkoxy optionally - aminothiocarbonyl, optionally substituted _{C 1-6} alkoxy - carbonyl Optionally substituted C _1-6 alkoxy - thiocarbonyl, optionally substituted C _1-6 thioalkoxy - carbonyl, optionally substituted C _1-6 thioalkoxy - thiocarbonyl, optionally C ₁ substituted _-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfonyl, optionally substituted C _3-6 cycloalkylcarbonyl, C _2-6 alkenylcarbonyl, C _2-6 alkynylcarbonyl, C _3-6 cycloalkyl -C _{1-6 alkylcarbonyl, C 1-6} alkylsulfenyl _{-C 1-6 alkylcarbonyl, C 1-6} alkylsulfinyl _{-C 1-6 alkylcarbonyl, C 1-6} alkylsulfonyl _{-C 1-6} alkylcarbonyl , _{C 1-6} alkylcarbonyl _{-C 1-6 alkylcarbonyl, C 3-6} Shi B _{alkylaminocarbonyl, C 2-6} alkenyl _{aminocarbonyl, C 2-6} alkynyl _{aminocarbonyl, C 1-6} alkoxy _{-C 1-6} alkylcarbonyl, -C (O) -R ⁷ or -C (S) -R ⁷
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form a 3-6 membered heterocyclic ring which may be substituted, which ring is substituted with a keto, thioketo or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
Z may be the same or different halogen, optionally substituted C _1-6 haloalkyl, nitro, optionally substituted C _1-6 alkoxy, cyano, optionally substituted C _1-6 haloalkoxy, substituted which may be C _1-6 alkylsulfenyl, optionally substituted C _1-6 alkylsulfinyl, optionally substituted C _1-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfenyl, substituted which may be C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, a hydroxyl or thiol,
k represents 0 to 4,
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² together may form an aromatic ring having 6 carbon atoms,
L is independently hydrogen, halogen, optionally substituted C _1-6 haloalkyl, nitro, optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, substituted C _3-6 cyclohaloalkyl, optionally substituted C _1-6 alkoxy, cyano, optionally substituted C _1-6 haloalkoxy, optionally substituted C _1-6 alkylsulfenyl, substituted also a C _1-6 alkylsulfinyl, optionally substituted C _1-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfenyl, optionally substituted C _1-6 haloalkylsulfinyl, be substituted a _{C 1-6} haloalkylsulfonyl, optionally substituted _{C 1-6} alkylsulfonyloxy, a _{C 1-6} haloalkyl optionally substituted Ruhoniruokishi, optionally substituted C _1-6 alkylaminosulfonyl, optionally substituted C _1-6 haloalkylsulfonyl, aminosulfonyl, optionally substituted C _{2-12 (total} carbon number) dialkylamino sulfonyl group, optionally substituted C _2-12 (total carbon number) di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted C _1-6 alkylamino, optionally substituted C _2-12 (total carbon number) Dialkylamino, optionally substituted C _1-6 acylamino, optionally substituted C _1-6 alkoxy-carbonylamino, optionally substituted C _1-6 haloalkoxy-carbonylamino, optionally substituted C _{1 -6} alkylsulfonylamino, optionally substituted C _1-6 haloalkylsulfonyl amino, optionally substituted There _{C 1-6} trialkylsilyl, optionally substituted _{C 1-6} alkoxyimino, optionally substituted _{C 1-6} halo alkoxyiminoalkyl, optionally substituted _{C 1-6} alkoxyimino - substituted also _{C 1-6} alkyl, optionally substituted _{C 1-6} haloalkoxy - imino - optionally substituted _{C 1-6} alkyl, optionally substituted _{C 1-4} alkyl sulfinyl amino, substituted Good C _1-4 alkylsulfinyl-imino-optionally substituted C _1-6 alkyl, optionally substituted C _1-4 alkylsulfinyl-imino-optionally substituted C _1-5 alkyl-carbonyl, substituted which may be _{C 1-4} alkyl - Suruhokishiimino, optionally substituted _{C 1-4} alkylsulfoxy - imino - optionally substituted _{C 1-4} alkyl Optionally substituted C _1-6 alkoxy - carbonyl, optionally substituted C _1-6 alkyl -, aminocarbonyl, optionally substituted C _1-6 alkylaminocarbonyl, amino thiocarbonyl, optionally substituted Good C _1-6 alkylamino-thiocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminocarbonyl or _optionally substituted C _2-12 (total carbon number) dialkyl-aminothiocarbonyl Show
l represents 1 to 3,
Y is independently halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _3-6 cycloalkyl haloalkyl, nitro, cyano, optionally substituted _{C 2-6} alkenyl, optionally substituted _{C 2-6} haloalkenyl, optionally substituted _{C 1-6} alkoxy, optionally substituted _{C 1-6} haloalkoxy, optionally substituted _{C 1-6} alkylthio, optionally substituted _{C 1-6} alkylsulfinyl, optionally substituted _{C 1-6} alkylsulfonyl, optionally substituted _{C 1-6} haloalkylthio, optionally substituted C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, hydroxy, mercapto, amino, substituted _{C 1-6} alkyl amino, optionally substituted _{C 2-12} (total carbon number) dialkylamino, aminocarbonyl, optionally substituted _{C 2-7} (total carbon number) alkylaminocarbonyl, optionally substituted Good C _2-13 (total carbon number) dialkylaminocarbonyl, optionally substituted C _1-6 (total carbon number) acylamino, optionally substituted C _2-7 (total carbon number) alkoxycarbonylamino, substituted Optionally substituted benzyloxycarbonylamino, optionally substituted C _2-7 haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino, optionally substituted C _1-6 haloalkylsulfonylamino or substituted _{May represent C3-26} (total carbon number) trialkylsilyl,
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are each independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ , C—R ⁸ , C (R ⁸ ) ₂ , N—R ^9. , N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, optionally substituted C _1-6 alkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl _Optionally substituted C _3-6 cycloalkyl, _optionally substituted C _4-12 alkyl cycloalkyl, _optionally substituted C _4-12 cycloalkylalkyl, _optionally substituted C _1-6 haloalkyl, C _2-7 (total carbon number) alkylcarbonyl which may be substituted, C _2-7 (total carbon number) alkoxycarbonyl which may be substituted, C _2-7 (total carbon number) alkylamino which may be substituted carbonyl, optionally substituted _{C 3-13} (total carbon number) dialkylaminocarbonyl, optionally substituted _{C 2-7} (total carbon number) alkylcarbonyl amino , Optionally substituted _{C 2-7} (total carbon number) alkyl thiocarbonyl amino, optionally substituted _{C 4-7} (total carbon number) cycloalkyl carbonyl amino, optionally substituted _{C 5-13} (total carbon Number) Cycloalkylalkylcarbonylamino, optionally substituted C _4-7 (total carbon number) cycloalkylthiocarbonylamino, optionally substituted C _5-13 (total carbon number) cycloalkylalkylthiocarbonylamino, substituted C _2-13 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkylthiocarbonylamino, optionally substituted C _2-7 (total carbon number) alkylamino carbonylamino, optionally substituted C _{2-7 (total} carbon number) alkylamino thiocarbonyl amino, it is substituted Which may be _{C 4-7} (total carbon number) cycloalkyl aminocarbonylamino, optionally substituted _{C 5-13} (total carbon number) be cycloalkylalkyl aminocarbonylamino, optionally substituted _{C 4-7} (total Carbon number) cycloalkylaminothiocarbonylamino, _optionally substituted C _5-13 (total carbon number) cycloalkylalkylaminothiocarbonylamino, _optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonylamino _Optionally substituted C _2-7 (total carbon number) haloalkylaminothiocarbonylamino, optionally substituted C _3-13 (total carbon number) dialkylaminocarbonylamino, optionally substituted C _2-13 ( Total carbon number) Dialkylaminothiocarbonylamino, C _2-7 (total carbon number) optionally substituted C _2-7 (total carbon number) alkylaminocarbonylthio, optionally substituted C _4-7 (total carbon number) cycloalkylaminocarbonyloxy, optionally substituted C 2 _5-7 (total carbon number) cycloalkylalkylaminocarbonyloxy, optionally substituted C _4-7 (total carbon number) cycloalkylaminocarbonylthio, optionally substituted C _5-13 (total carbon number) cyclo Alkylalkylaminocarbonylthio, optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonyloxy, optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonylthio, optionally substituted C _3-13 (total carbon number) dialkylamino carbonyloxy, optionally _{C 3-13} substituted (total carbon number) Alkylaminocarbonyl thio, optionally substituted C _{2-7 (total} carbon number) alkoxycarbonylamino, optionally substituted C _{4-7 (total} carbon number) be cycloalkyloxycarbonyl amino, optionally substituted C _{5 -13} (total carbon number) cycloalkylalkyloxycarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino or optionally substituted Good C _1-6 haloalkylsulfonylamino, wherein the substituents other than cyano, formyl, halogen and nitro may be substituted with R ¹⁰ ;
R ⁹ is hydrogen, hydroxy, amino, optionally substituted _{C 1-6} alkyl, optionally substituted _{C 1-6} haloalkyl also, optionally substituted _{C 2-6} alkenyl, optionally substituted _{C 2- 6} alkenyloxy, optionally substituted _{C 2-6} alkynyl, optionally substituted _{C 2-6} alkynyloxy, optionally substituted _{C 3-6} cycloalkyl, optionally _{C 4-12} alkylcycloalkyl substituted Alkyl, _optionally substituted C _4-12 cycloalkylalkyl, _optionally substituted C _1-6 alkylamino, optionally substituted C _2-12 (total carbon number) dialkylamino, optionally substituted C _C1-6 alkoxy, optionally substituted _{C 1-6} haloalkoxy, formyl, optionally substituted _{C 2-7} (total carbon number) even alkylcarbonyl may be substituted _{2-7 (total} carbon number) haloalkylcarbonyl, optionally substituted C _{2-7 (total} carbon number) be alkoxycarbonyl, optionally substituted C _{2-7 (total} carbon number) be alkylaminocarbonyl, optionally substituted Good C _2-7 (total carbon number) alkylcarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-7 (total carbon number) alkoxycarbonylamino, It is optionally substituted C _{2-7 (total} carbon number) alkylaminocarbonyl amino, optionally substituted C _{1-6 (total} carbon number) alkylsulfonyl, optionally substituted C _{1-6 (total} carbon number) haloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally C _{2-7 (total} carbon number) be substituted be alkylaminocarbonyl or substituted A C _{2-7 (total} carbon number) halo alkylaminocarbonyl, the substituents other than the hydrogen and formyl may be substituted with R ^10,
R ¹⁰ represents phenyl and heterocyclic groups the following ^R 10 ^-1~R 10 -83,

E represents O, S or N, and each group is hydrogen, halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl in the above phenyl and heterocyclic groups, Optionally substituted C _3-6 cycloalkyl, optionally substituted C _3-6 halocycloalkyl, optionally substituted C _1-6 alkoxy, optionally substituted C _1-6 haloalkoxy, substituted be a C _1-6 alkylthio, optionally substituted C _1-6 haloalkylthio, optionally substituted C _1-6 alkylsulfinyl, optionally substituted C _1-6 haloalkylsulfinyl, it may be substituted C _1-6 alkylsulfonyl, optionally substituted _{C 1-6} haloalkylsulfonyl, optionally substituted _{C 1-6} alkylamino, optionally substituted _{C 1-6} Haroaruki Amino, cyano, nitro, aminocarbonyl, optionally substituted C _{2-7 (total} carbon number) alkylaminocarbonyl, optionally substituted C _{2-13 (total} carbon number) be dialkylaminocarbonyl, optionally substituted C _1-7 alkoxycarbonyl may be substituted by at least 1 month group selected from the group consisting of optionally substituted pyridyl are also substituted phenyl and substituted,
U represents CH ₂ , O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁴ and R ⁵ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and e) W ¹ , W ² , When one of W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring.
The optically active substance in this case is particularly suitable.

  In the method for obtaining the optically active azoline derivative of the formula (I) of the present invention, the racemate corresponding as the starting material is WO2008 / 019760, WO2008 / 260691, Japanese Patent Application No. 2008-208394 and Japanese Patent Application No. 2008-. It can be obtained by the method described in each specification of No. 143120.

  Specific examples of the racemic compound include all compounds disclosed in the WO publication and the patent application.

  In carrying out the above method, preparative chromatography, preferably high performance liquid chromatography (HPLC) is used.

  As the stationary phase, chiral silica gel can be used. In particular, Chiracel OD (trade name) and Chiral Pack AD (trade name) are separation agents suitable for the operation of separating racemic compounds into enantiomers. It is.

  When the racemate is separated into multiple individual optically active forms by fractional recrystallization, all optically active acids are suitable for the formation of diastereomeric salts. For example, (1S)-(+)-camphor-10-sulfonic acid, (1R)-(-)-camphor-10-sulfonic acid, S, S-(-)-tartaric acid, R, R-(+)- Tartaric acid, R-lactic acid, S-lactic acid or an optically active amino acid, preferably a natural optically active amino acid.

  The above process can be carried out over a wide temperature range, usually in the range of about 10 ° C to about 60 ° C, preferably about 10 ° C to about 40 ° C, more preferably about 15 ° C to about 25 ° C.

  When carrying out the above method, usually about 1% solution of the racemate can be used for chromatographic separation. The general procedure is to concentrate the extract highly, remove the solids by filtration, wash with n-heptane and then dry. The residue in some cases removes impurities that may still be present by chromatography. Although n-hexane or cyclohexane or a mixture of cyclohexane and ethyl acetate is used as the eluent, the composition must be adjusted for each compound to be purified.

  The optically active azoline derivatives of the present invention are all optically active substances included in the above formula (I). Specifically, WO2008 / 019760, WO2008 / 260691, Japanese Patent Application No. 2008-208394 and Japanese Patent Application No. 2008- It is an optically active substance corresponding to the racemate which is the final product described in each specification of No. 143120.

  The compounds of the present invention include, for example, harmful sucking insects, chewable insects and other plant parasite pests, stored grain pests, pests that destroy industrial materials, hygiene pests, and pests including those in the veterinary field. It can be used to control a wide range of pests, including, and can be applied to control such as, for example, eradication and eradication. Therefore, the present invention also includes a method for controlling harmful pests.

Examples of such pests include the following pests.
As insects,
Coleoptera, for example,
Adzuki bean weevil (Callosobruchus Chinensis), maize weevil (Sitophilus zeamais), red flour beetle (Tribolium castaneum), the giant beetle, Epilachna vigintioctopunctata (Epilachna vigintioctomaculata), Tobii Lom Na tailed click beetle (Agriotes ogurae fuscicollis), rufocuprea (Anomala rufocuprea), Colorado potato beetle (Leptinotarsa decemlineata), corn root worms (Diabrotica spp.), Japanese pine beetle (Monochumal alternatus endai), rice weevil (Lissohoptrus oryzoph) lus), Hirata beetle (Lyctus brunneus);
Lepidoptera pests, for example
Gypsy moth (Lymantria dispar), lackey moth (Malacosoma neustria), cabbage butterfly (Pieris rapae crucivora), common cutworm (Spodoptera litura), cabbage armyworm (Mamestra brassicae), rice stem borer (Chilo suppressalis), the European corn borer (Ostrinia nubilalis), streaks moth (Cadra cautella ), Chamodium spider oyster (Adoxophys honmai), Codlinga (Cydia pomonella), Kaburayaga (Agrotis segetum), Hachinotsutsu Riga (Galleria melonella), Konaga (Plutella x tella), fake American tobacco budworm (Heliothis virescens), mandarin orange leafminer (Phyllocnistis citrella);
Hemiptera pests, for example
Leafhopper (Nepotettix cinticices), Green planthopper (Nilaparvata lugens), Aphid isp (Pseudococcus comstuscki), Mushroom aphid (Unaspis yanone niss) ), Yellow pea aphids (Lipophis erysimi), pearfish (Stephanitis nashi), blue stink bugs (Nezara spp.), White-tailed whitefly (Trialeurodes vaporariorum), pheasant larvae (P);
Thrips pests, for example
Southern palm thrips (Trips palmi), Citrus thrips (Franklinella occidentalis);
Direct insect pests, for example
German cockroach (Blatella germanica), American cockroach (Periplaneta americana), African foliage (Gryllotalpa africana), Tosama locust (Locusta migratoria);
Isopods, for example,
Yamato termites (Reticulites speratus), termites termites (Copttermes formosanus);
Diptera pests, for example
House fly (Musca domestica), Aedes aegypti, Panax fly (Delia platula), Culex pipiens pallens (Cinex pipens pellens), Cyprus pistol
Etc. Also,
As mites, for example,
Tetanychus cinnabarinus, Tetanychus urticae, Pannychus citri, Acrops pelekassi, Tarsonemus spp.
Etc. further,
As nematodes, for example,
Melodygyne incognita, pinewood nematode (Bursaphelenchus xylophilus), rice stalk nematode (Aphelenchoides besseyii), soybean cyst nephu
Etc.

  In the veterinary field, ie in veterinary medicine, the active compounds according to the invention are effective against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths (such as tapeworms, nematodes or flukes) and protozoa (such as coccidium). Ectoparasites are usually and preferably arthropods, in particular insects (fly (stab and lick flies), parasitic fly larvae, lice, whitefly, whitefly, fleas, etc.) or conifer mites (eg ticks, eg hard mites) Or soft mites) or ticks (such as mites, tsutsugamushi and birdmite).

These parasites are
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtyrus sp. spp.); particularly representative examples include Linognus setosus, Linognus bitus (Linognus tus), Linognus vis, (Linognusus vilus) ), Rinogunatsu Ste Nopushisu (Linognathus stenopsis), Haematopinusu - Asini macro cell Fars (Haematopinus asini macrocephalus), Haematopinusu-Yurisu Ternes (Haematopinus eurysternus), Haematopinusu, Switzerland (Haematopinus suis), Pedikurusu-Fumanusu-Kapitisu (Pediculus humanus capitis), Pedikurusu-Fumanusu・ Corpolis (Pediculus humanus corpis), Philoela vastatorix (Phyllora evastatix), Phyllus pubis (Phtilus pubis), Solenopotes capilats (Solenopotes capilats) There in s);
From the order of Mallophagida and Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Menopon spt. ), Bobicola spp., Wernekiella spp., Lepikentron spp., Damarina spp., Trichodectes spp., Trichodectes sp. Genus species (Felicola spp.); Particularly representative examples include Bovicola bovis, Bovicola ovis, Bovicola limbata, Damarina bovis, Trichodictes canis (Trichodictes canis), Felicola sbrostras Levikentron ovis, Wernekiella equi;
From the order of the Diptera and Nematocerina and Brachycerina, for example, Aedes spp., Anopheles ssp., Crex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomia spp., Clicoides spp., Clicoides spp. Chrysops spp.), Odagmia spp., Wilhelmia spp., Hybomitra spp. , Atyrotus spp., Tabanus spp., Haematopota spp., Phillipomia spp., Braula sp. Musca spp.), Hydrotaea spp., Stomoxys spp., Haematobia spp., Morelia spp., Fannia a. Grossina spp., Califora spp., Lucilia spp., Chrysomya sp. ia spp.), Wolfalthia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gastrospter ph ), Hippobosca spp., Lipoptena spp., Melophagas spp., Rhinoestrus spp., Tipula, Spul; Representative examples include Aedes aegypti, Aedes albopictus, Aedes taeni. Orinkusu (Aedes taeniorhynchus), Anopheles-Ganbiae (Anopheles gambiae), Anopheles-Makuripen'nisu (Anopheles maculipennis), Karifora-Eritorosefara (Calliphora erythrocephala), Kurisozona pluvialis (Chrysozona pluvialis), Kurekusu Quinn query fascia Tsusu (Culex quinquefasciatus), Kurekusu • Pilex (Culex pipiens), Crex tarsalis (Culex tarsalis), Fania canicularis (Fannia canicularis), Sarcophaga carnaria (Sarcophaga carnaria), Tomochi Cis calcitrans (Stomoxys calcitrans), Tipula paludosa (Lucilia cuprina), Lucilia sericata (Simulus reputas) Phlebotomus longipalpis, Odagmia ornate, Wilhelmia equina, Buchthra ertrocephala us), Tabanusu-Supodoputerusu (Tabanus spodopterus), Tabanusu-Atoratsusu (Tabanus atratus), Tabanusu-Sudechikusu (Tabanus sudeticus), Hibomitora-Shiurea (Hybomitra ciurea), Kurisopusu-Kaekuchiensu (Chrysops caecutiens), Kurisopusu-Rerikutsusu (Chrysops relictus) , Haematopota pluvialis, Haematopota italica, Musca autumalis, Musca domestica, Musca domestica matobia irritans irritans), Haematobia-Iritansu exigua (Haematobia irritans exigua), Haematobia-Suchimuransu (Haematobia stimulans), Hidorotaea-Iritansu (Hydrotaea irritans), Hidorotaea-Arubipunkuta (Hydrotaea albipuncta), Kurisomia-Kuroropiga (Chrysomya chloropyga), Kurisomia - Brydgeana (Chrysomya bezziana), Oestrus ovis, Hippoderma bovis (Hypoderma bovis), Hypoderma lineatum Shirenusu (Przhevalskiana silenus), Derumatobia hominis (Dermatobia hominis), Merofagusu-Obinusu (Melophagus ovinus), Ripoputena-Kapureori (Lipoptena capreoli), Ripoputena-Serbia (Lipoptena cervi), Hippobosuka-Bariegata (Hippobosca variegata), Hippobosuka-Ekuina ( Hippobosca equina), Gasterophilus intestinalis, Gastrophilus haemoroidalis, Gasterophilus internis s interrnis), Gas terrorism Filth-Nazarisu (Gasterophilus nasalis), Gas terrorism Filth-Nigurikorunisu (Gasterophilus nigricornis), Gas terrorism Filth-Pekorumu (Gasterophilus pecorum), located in Buraura-Koeka (Braula coeca);
From the order of Siphonaptida, for example, Plexex spp., Ctenocephalides spp., Tunga spp., Xenopsilla spp., Seratophylla spp. Species (Ceratophyllus spp.); Particularly representative examples include Ctenocephalides canis, Ctenocephalides felis, Plex irritans (Pulex irritans) penetrans), Xenopsilla cheopes;
From the order of the Heteroptera, for example, Simex spp., Triatoma spp., Rhodnius spp., Panstrungylus spp. From the order of the Blattida, for example, Blatta orientalis, Periplaneta americana, Bratella germanica, Superella spp. ));
From the order of the mites (Acari (Acarina)) and the subspecies (Megastigmata) and Mestigmatata, for example, Argas spp., Ornithodorus spp., Otobius sp. .), Ixodes spp., Amblyomma spp., Ripicephalus (Boufilus) spp., Dermacentor spp., Dermacentor spp. Species (Haemophysalis spp.), Hyalomma spp., Dermanys (Dermanysu) spp.), Lipipephalus spp. (original genus of multi-host mites), Ornithnis spp., Pneumonysus spp., Railietia spp. Species (Pneumonyssus spp.), Sternostoma spp., Barroa spp., Acarapis spp .; particularly representative examples include Argas persicus, Argas reflexus, Ornithodorus moutata, Otobius megu Nini (Otobius megnini), Lipisephalus (Boufilus) microplus (Rhipicephalus (Boophilus) microplus, Lipisephalus (Buophilus) decoloratus (Rhopicephalus (Boophilus) decolortus (Boophilus) decolortus (Boophilus) (Buophilus) Calcerats, Hyaluma anatomicum, Hyaloma aegypticum, Hyalonma marginatum (Hyalomma marginatum), Hyalomma transiens, Lipicephalus eusti (Rhipicephalus evertis), Ixodes ixonus (Ixodes ricinus) Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holoculus, Haemaphysalis conc. Haemafisarisu-Punkutata (Haemaphysalis punctata), Haemafisarisu-Shin'nabarina (Haemaphysalis cinnabarina), Haemafisarisu-Otofira (Haemaphysalis otophila), Haemafisarisu Leach (Haemaphysalis leachi), Haemafisarisu-Rongikoruni (Haemaphysalis longicorni), Dermacentor marginatus, Dermacentor reticulatas, Dermacentor pictus, Dermacentor albictus bipictus), Delmas Sentoru-Anderusoni (Dermacentor andersoni), Delmas Sentoru variabilis (Dermacentor variabilis), Hiaronma-Mauritanikumu (Hyalomma mauritanicum), Rhipicephalus-sanguineus (Rhipicephalus sanguineus), Rhipicephalus, Bursa (Rhipicephalus bursa), Rhipicephalus-Appenjikura Rhipicephalus appendiculatus, Ripicephalus capensis, Rhipicephalus turnicus, Ripicephalus zambezien Cis (Rhipicephalus zambeziensis), Anburionma America-Num (Amblyomma americanum), Anburionma-Bariegatsumu (Amblyomma variegatum), Anburionma-Makuratsumu (Amblyomma maculatum), Anburionma-Heburaeumu (Amblyomma hebraeum), Anburionma-Kajenensu (Amblyomma cajennense), Derumanisusu-Garinae (Dermanyssus gallinae), Ornithnissus bursa, Ornithonysus sylviarum, Barroa Jacob soni (Varroa ja) cobsconi);
From the order of the subspecies (Actinedida (Prostigmata)) and the subfamily Acaridida (Astigmata), for example, the species of Acarapis spp., Cheytilella spp. .), Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus sp. Acarus spp., Tyrophagus spp., Caloglyphus spp. phys spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Choropoptes spp., Otodex Sarcoptes spp., Notoderes spp., Knemidocoptes spp., Cytodites spp., Laminosoptes sp. Keiletiella yasuguri, Cheyletiella b. lakei), demodex canis, demodex bovis, demodex ovis, demodex capraie, demodex equide (Demodex edem) , Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleli, Neoschengasia xerothermvia Mushi), Otodictes cynotis, Notoderes cati, Sarcoptis canis, Scoptes bovis, Sarcoptes bovis, Sarcoptes bovis = S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes vis, ps ), Psoergates ovis, Pneumonysoidic mange, Pneumonysoides caninum, and Acarapis woody.

  The active compounds according to the invention are also suitable for combating arthropods, helminths and protozoa that attack animals. Animals include, for example, agricultural animals such as cows, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees and the like. Furthermore, animals include those known as companion animals, known as companion animals, such as dogs, cats, caged birds, ornamental fish and laboratory animals (eg, hamsters, guinea pigs, rats and mice).

  By controlling these arthropods, helminths and / or protozoa by using the active compounds according to the invention, the mortality of the host animals is reduced and the productivity (meat, milk, wool, leather, eggs, honey etc.) In this case, it is intended to improve health and, as a result, allow for more economical and simple animal breeding.

  For example, it may be desirable to prevent or prevent blood uptake from the host by parasites (when applicable). Exterminating parasites can also help to prevent transmission of infectious pathogens.

  As used herein with respect to the veterinary field, the term “disinfect” is effective in reducing the incidence of each parasite in an animal infected with such parasites to an innocuous level. It means that. More specifically, “disinfecting” as used herein means that the active compound is effective in killing the respective parasite, inhibiting its growth or inhibiting its proliferation. .

  When used as an insecticide, the active compounds of the present invention can be in the form of conventional preparations. Formulation forms include, for example, liquids, emulsions, wettable powders, granular wettable powders, suspensions, powders, foams, pastes, tablets, granules, aerosols, active compound infiltration-natural and synthetic, microcapsules, Seed coatings, preparations with combustion devices (for example, combustion devices include fumigation and fumigation cartridges, cans, coils, etc.), ULV [cold mist, warm mist], etc. .

  These preparations can be produced in a manner known per se. For example, the active compound may be a developing agent, ie a liquid diluent or carrier; a liquid gas diluent or carrier; a solid diluent or carrier, and optionally a surfactant, ie an emulsifier and / or a dispersant and And / or by mixing with a foam former.

  When water is used as a developing agent, for example, an organic solvent can also be used as an auxiliary solvent.

  Examples of the liquid diluent or carrier include aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chloride, chloride) Methylenes), aliphatic hydrocarbons (for example, cyclohexane, paraffins (for example, mineral oil classification), alcohols (for example, butanol, glycol and their ethers, esters, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl) Isobutyl ketone, cyclohexanone, etc.), strong polar solvents (eg, dimethylformamide, dimethyl sulfoxide, etc.), water and the like.

  Examples of the liquefied gas diluent or carrier include those which are gases at room temperature and normal pressure, for example, aerosol propellants such as bran, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons.

  Examples of the solid diluent include ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (for example, highly dispersed silicic acid, alumina, silicate, etc.) And so on.

  Solid carriers for granules include, for example, crushed and fractionated rocks (eg calcite, marble, pumice, gabbro, dolomite, etc.), synthetic particles of inorganic or organic powders, organic substances (eg sawdust) , Coconuts, corn cobs, tobacco stems, etc.).

  Examples of emulsifiers and / or foam-forming goods include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ethers), alkyl sulfonates, and alkyl sulfates. Salts, aryl sulfonates, etc.], albumin hydrolysis products, and the like.

  Examples of the dispersant include lignin sulfite waste liquid and methylcellulose.

  Fixing agents can also be used in preparations (powder, granules, emulsions), and examples of the fixing agent include carboxymethyl cellulose, natural or synthetic polymers (for example, gum arabic, polyvinyl alcohol, and polyvinyl acetate). Can be mentioned.

  Colorants can also be used, for example, inorganic pigments (eg iron oxide, titanium oxide, Prussian blue, etc.), alizarin dyes, organic dyes such as azo dyes or metal phthalocyanine dyes, and further And trace elements such as iron, manganese, boron, copper, cobalt, molybdenum, and zinc salts.

  The formulation generally can contain the active ingredient in an amount in the range of 0.1 to 95% by weight, preferably 0.5 to 90% by weight.

  The active compounds of the formula (I) according to the invention are in the form of their commercially useful preparations and in the use forms prepared from these preparations, other active compounds such as insecticides, baits, fungicides, acaricides. It can also be present as a mixture with nematocides, fungicides, growth regulators, herbicides and the like. Here, examples of the insecticide include organophosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, insecticides produced from microorganisms, and the like.

  Furthermore, the active compounds of the formula (I) according to the invention can also be present as admixtures with synergists, such formulations and use forms being those that are commercially useful. The synergist is not necessarily active per se, but is a compound that enhances the action of the active compound.

  The content of the active compounds of the formula (I) according to the invention in commercially useful forms of use can be varied within wide limits.

  The practical use concentration of the active compounds of the formula (I) according to the invention can be, for example, in the range of 0.0000001 to 100% by weight, preferably 0.00001 to 1% by weight.

  The compound of the formula (I) of the present invention can be used in a usual manner adapted to the use form.

  The active compound of the present invention has effective stability against alkalis on lime substances when used for sanitary pests and pests against stored products, and also exhibits excellent residual effects in wood and soil.

  In general, when the active compounds according to the invention are used for the treatment of animals, they can be applied directly to animals. Preferably they are applied as pharmaceutical compositions that may contain pharmaceutically acceptable excipients and adjuvants or both known in the art.

  In the veterinary field and in animal husbandry, the active compounds are known in the manner known, for example in the form of tablets, capsules, drinks, drinks, granules, pastes, bolus, feedthrough, suppositories. By enteral administration; for example, in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation, intranasal application, eg, bathing or dipping, spraying, pouring and instillation, washing, spraying It is applied (administered) by parenteral administration by skin application and using active compound-containing molded articles such as collars, ear tags, tail tags, leg rings, end ropes, marking devices and the like. The active compound can be formulated as a shampoo or in a suitable dosage form that can be used in aerosols, non-pressurized sprays such as pump sprays and nebulizer sprays.

  When used for livestock, poultry, pets, etc., the active compound according to the invention comprises a dosage form containing the active compound in an amount of 1 to 80% by weight (eg powder, wettable powder [“WP”], Emulsions, emulsifiable concentrates [“EC”], fluids, homogeneous solutions, and suspension concentrates [“SC”])) either directly or after dilution (eg, 100 to 10,000 fold dilution), Or it can be applied as a chemical bath in another way.

  When used in the veterinary field, the active compounds according to the invention can be used in combination with suitable synergists or other active compounds, such as acaricides, insecticides, anthelmintics, antiprotozoal drugs.

  The active compounds of the present invention are low toxic to warm-blooded animals and can be used safely.

  Next, the present invention will be described more specifically with reference to examples.

Biological Test Example 1: Preparation of Test Reagent Solution for Larvae of Spodoptera litura Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether 1 part by weight was mixed with the above amount of solvent containing the above amount of emulsifier and the mixture was diluted with water to a predetermined concentration.

Test method Immerse the sweet potato leaves in a reagent solution diluted with water at a predetermined concentration, air-dry the chemical solution, place it in a petri dish with a diameter of 9 cm, release 10 third-instar larvae and place them in a constant temperature room at 25 ° C for 2 days. And after 4 days, sweet potato leaves were added, and after 7 days, the number of dead insects was examined to calculate the insecticidal rate.

In this test, the results of 2 dishes in 1 ward were averaged.
The optically active azoline derivative obtained by the above-described fraction generation showed a very high insecticidal effect as compared with the racemate.

Biological Test Example 2: Test against Taninychus urticae (dispersion test)
Test method 50 to 100 adults of the spider mite were inoculated on 2 leaves of green leaves grown in a 6 cm diameter pot, and after 1 day, a diluted solution of water with a predetermined concentration of the active compound prepared above was used. A sufficient amount was sprayed using a spray gun. After spraying, the miticide rate was calculated after 7 days in the greenhouse.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Biological test example 3: Test against cucumber leaf beetle (Alacophora femorialis) (dispersion test)
Test method The cucumber leaves were immersed in a dilute solution of the active compound prepared above in the prescribed concentration, air-dried, then placed in a plastic cup containing sterilized black soil, and 5 larvae of the leaf beetle were released. . Seven days later, the number of dead insects was examined and the insecticidal rate was calculated.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Biological test example 4: Preparation of test reagent solution for cat flea (Ctenocephalides felis) Solvent: Dimethyl sulfoxide To make a formulation of a suitable active compound, 10 mg of the active compound is dissolved in 0.5 ml of the above solvent and the mixture is dissolved in livestock. Dilute to predetermined concentration with blood.

Test method Approximately 10 to 15 cat flea adults are prepared in a container. A dedicated container containing the blood solution containing the compound prepared above is covered with parafilm, and the parafilm surface is placed on the flea container. Keep the blood solution at 37 degrees and the flea container at room temperature. After a certain period of time, the cat lethality is determined. In that case, 100% means that all cat fleas have died, and 0% means that all are alive.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Biological Test Example 5: Test on Boobius tick (Boophilus microplus) Test Method A compound solution prepared in the same manner as in Biological Test Example 4 is injected into the abdomen of five male tick-saturated female adults. The mite is transferred to a petri dish and kept in a cage for a certain period.
After a certain period of time, the lethality rate of the tick was determined. At that time, 100% means that all eggs laid were not hatched, and 0% means that all eggs were hatched.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Biological Test Example 6: Test on Sheep Flies (Lucilliacuprina) Test Method About 20 to 30 sheep in a test tube containing 1 cubic centimeter of ground beef and 0.5 ml of an aqueous compound solution prepared in the same manner as in Biological Test Example 4. Put the fly larvae.
After a certain period of time, the proportion of mortality of sheep fly is measured. In that case, 100% means that all sheep flies have died and 0% means that they are all alive.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Biological Test Example 7: Test for housefly (Muscadomestica) As a preparatory stage of the test method test, a sponge of a certain size is impregnated with a mixture of sugar and an aqueous compound solution prepared in the same manner as in Biotest Example 4 and placed in a test container. Put on. Ten adult houseflies are placed in a container and covered with a hole for ventilation.
After a certain period of time, the percentage of housefly mortality is measured. In that case, 100% means that all house flies have died and 0% means that they are all alive.

  The optically active azoline derivative showed a very high insecticidal effect as compared with the racemate.

Formulation Example 1 (Granule)
25 parts of water is added to a mixture of 10 parts of the present compound, 30 parts of bentonite (montmorillonite), 58 parts of talc (talc) and 2 parts of lignin sulfonate, and well hatched, and 10 to 40 mesh by an extrusion granulator. And granulated by drying at 40-50 ° C.

Formulation Example 2 (Granule)
95 parts of clay mineral particles having a particle size distribution in the range of 0.2 to 2 mm are placed in a rotary mixer and, under rotation, 5 parts of the compound of the present invention are sprayed together with a liquid diluent to make it uniform, and then 40 to 50 Dry at ℃ to make granules.

Formulation Example 3 (Emulsion)
30 parts of the compound of the present invention, 55 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to obtain an emulsion.

Formulation Example 4 (wettable powder)
15 parts of the compound of the present invention, 80 parts of a mixture of white carbon (hydrous amorphous silicon oxide fine powder) and powdered clay (1: 5), 2 parts of sodium alkylbenzenesulfonate and 3 parts of alkylnaphthalenesulfonate sodium formalin condensate Mix to make wettable powder.

Formulation Example 5 (hydrated granules)
20 parts of the compound of the present invention, 30 parts of lignin sulfonic acid sodium salt and 15 parts of bentonite and 35 parts of calcined diatomaceous earth powder are thoroughly mixed, added with water, extruded and dried with a 0.3 mm screen to obtain hydrated granules. .

  As shown in the Examples, the optically active azoline derivative of the present invention has extremely excellent insecticidal activity as an insecticide.

Claims (5)

The following formula (I):

Wherein X is independently halogen, optionally substituted alkyl, optionally substituted haloalkyl, nitro, cyano, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio. Optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylthio, optionally substituted haloalkylsulfinyl, optionally substituted haloalkylsulfonyl, hydroxy, mercapto, amino, substituted May be substituted alkylamino, optionally substituted dialkylamino, optionally substituted acylamino, optionally substituted alkoxycarbonylamino, optionally substituted haloalkoxycarbonylamino, optionally substituted alkylsulfonylamino or substituted May be halo It indicates Le kills sulfonylamino,
R ¹ is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkylcycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, Represents optionally substituted haloalkyl, optionally substituted halocycloalkyl or cyano;
m represents 0, 1, 2, 3, 4, 5, 6 or 7,
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted alkylcycloalkyl, Optionally substituted cycloalkylalkyl, optionally substituted haloalkyl, optionally substituted phenyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, or substituted Dialkylaminocarbonyl which may be
Q represents phenyl, naphthyl or a 5- to 6-membered aromatic heterocyclic group, and T represents the following group (T-1) or group (T-2):

In the above group,
G represents an optionally substituted saturated or unsaturated 5-membered or optionally substituted saturated or unsaturated 6-membered heterocyclic group;
Or

Indicate
R ³ and R ⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted haloalkyl, optionally substituted cyclohaloalkyl, optionally substituted alkenyl, Represents optionally substituted alkynyl, optionally substituted haloalkenyl, optionally substituted haloalkynyl, cyano, alkoxycarbonyl or alkoxythiocarbonyl;
R ³ and R ⁴ together may form an alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted alkoxy, optionally substituted aminocarbonylalkyl, optionally substituted iminoalkyl, optionally substituted alkyl, optionally substituted cycloalkyl, substituted Optionally substituted haloalkyl, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkylcarbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S ) -R ⁷
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylthiocarbonyl, optionally substituted haloalkylcarbonyl, optionally substituted haloalkylthiocarbonyl, optionally substituted Good alkylaminocarbonyl, optionally substituted alkylaminothiocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted dialkylaminothiocarbonyl, optionally substituted alkoxyaminocarbonyl, optionally substituted alkoxyamino Thiocarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkoxythiocarbonyl, optionally substituted thioalkoxycarbonyl, optionally substituted thioalkoxythiocarbonyl, optionally substituted Alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl-alkylcarbonyl, alkylsulfenylalkylcarbonyl, alkylsulfinylalkylcarbonyl, alkylsulfonylalkylcarbonyl, alkylcarbonyl - indicates alkylcarbonyl, cycloalkyl amino carbonyl, alkenylcarbonyl aminocarbonyl, alkynylamino, alkoxycarbonyl alkylcarbonyl, a -C (O) -R ⁷ or -C (S) -R ^7,
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form an optionally substituted 3- to 6-membered heterocycle, which ring is substituted with a keto, thioketo, or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² may form an aromatic ring having 6 carbon atoms together,
L is independently hydrogen, halogen, haloalkyl which may be substituted, nitro, alkyl which may be substituted, cycloalkyl which may be substituted, cyclohaloalkyl which may be substituted, alkoxy which may be substituted, Cyano, optionally substituted haloalkoxy, optionally substituted alkylsulfenyl, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfenyl, optionally substituted haloalkyl Sulfinyl, optionally substituted haloalkylsulfonyl, optionally substituted alkylsulfonyloxy, optionally substituted haloalkylsulfonyloxy, optionally substituted alkylaminosulfonyl, optionally substituted haloalkylaminosulfonyl, optionally substituted Good Alkylaminosulfonyl, optionally substituted di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted acylamino, optionally substituted Alkoxycarbonylamino, optionally substituted haloalkoxycarbonylamino, optionally substituted alkylsulfonylamino, optionally substituted haloalkylsulfonylamino, optionally substituted trialkylsilyl, optionally substituted alkoxyimino, substituted Optionally substituted haloalkoxyimino, optionally substituted alkoxy-imino-optionally substituted alkyl, optionally substituted haloalkoxy-imino-optionally substituted alkyl, optionally substituted alkylsulfinylimino Optionally substituted alkylsulfinyl-imino-optionally substituted alkyl, optionally substituted alkylsulfinyl-imino-optionally substituted alkylcarbonyl, optionally substituted alkylsulfoxyimino, optionally substituted Alkylsulfoxy-imino-optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, aminothiocarbonyl, optionally substituted Represents alkylaminothiocarbonyl, optionally substituted dialkylaminocarbonyl or optionally substituted dialkylaminothiocarbonyl,
l represents 1 to 3,
Y is independently halogen, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted cycloalkyl, optionally substituted cyclohaloalkyl, nitro, cyano, optionally substituted alkenyl, substituted Optionally substituted haloalkenyl, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted halo Alkylthio, optionally substituted haloalkylsulfinyl, optionally substituted haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted alkylamino, optionally substituted dialkylamino, aminocarbonyl, optionally substituted alkylamino Carbonyl, substituted Dialkylaminocarbonyl which may be substituted, acylamino which may be substituted, alkoxycarbonylamino which may be substituted, benzyloxycarbonylamino which may be substituted, haloalkoxycarbonylamino which may be substituted, alkylsulfonyl which may be substituted Amino, optionally substituted haloalkylsulfonylamino or optionally substituted trialkylsilyl;
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are each independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ , C—R ⁸ , C (R ⁸ ) ₂ , N—R ^9. N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, substituted Alkylcycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted haloalkyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, substituted Dialkylaminocarbonyl which may be substituted, alkylcarbonylamino which may be substituted, alkylthiocarbonylamino which may be substituted, cycloalkylcarbonylamino which may be substituted, cycloalkylalkylcarbonylamino which may be substituted, may be substituted Siku Boroalkylthiocarbonylamino, optionally substituted cycloalkylalkylthiocarbonylamino, optionally substituted haloalkylcarbonylamino, optionally substituted haloalkylthiocarbonylamino, optionally substituted alkylaminocarbonylamino, optionally substituted Alkylaminothiocarbonylamino, optionally substituted cycloalkylaminocarbonylamino, optionally substituted cycloalkylalkylaminocarbonylamino, optionally substituted cycloalkylaminothiocarbonylamino, optionally substituted cycloalkylalkylamino Thiocarbonylamino, optionally substituted haloalkylaminocarbonylamino, optionally substituted haloalkylaminothiocarbonylamino, optionally substituted dialkylamino Carbonylamino, optionally substituted dialkylaminothiocarbonylamino, optionally substituted alkylaminocarbonyloxy, optionally substituted alkylaminocarbonylthio, optionally substituted cycloalkylaminocarbonyloxy, optionally substituted Cycloalkylalkylaminocarbonyloxy, optionally substituted cycloalkylaminocarbonylthio, optionally substituted cycloalkylalkylaminocarbonylthio, optionally substituted haloalkylaminocarbonyloxy, optionally substituted haloalkylaminocarbonylthio, Dialkylaminocarbonyloxy which may be substituted, dialkylaminocarbonylthio which may be substituted, alkoxycarbonylamino which may be substituted, cycloal which may be substituted Oxycarbonylamino, cycloalkylalkyloxycarbonylamino which may be substituted, haloalkoxycarbonylamino which may be substituted, alkylsulfonylamino which may be substituted or haloalkylsulfonylamino which may be substituted, Substituents other than formyl, halogen and nitro may be substituted with R ¹⁰ as shown below,
R ⁹ is hydrogen, hydroxy, amino, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted alkenyl, optionally substituted alkenyloxy, optionally substituted alkynyl, optionally substituted. Alkynyloxy, optionally substituted cycloalkyl, optionally substituted alkylcycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted Alkoxy, optionally substituted haloalkoxy, formyl, optionally substituted alkylcarbonyl, optionally substituted haloalkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted Alkylcarbonylamino, substituted Optionally substituted haloalkylcarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted alkylaminocarbonylamino, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted phenylsulfonyl, An alkylaminocarbonyl which may be substituted or a haloalkylaminocarbonyl which may be substituted, and the substituents other than hydrogen and formyl may be substituted with R ¹⁰ shown below,
R ¹⁰ independently represents phenyl or a 5- to 6-membered saturated or unsaturated heterocyclic group, and these groups are halogen, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted Cycloalkyl, optionally substituted halocycloalkyl, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted alkylthio, optionally substituted haloalkylthio, optionally substituted alkylsulfinyl, Optionally substituted haloalkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted haloalkylsulfonyl, optionally substituted alkylamino, optionally substituted haloalkylamino, cyano, nitro, aminocarbonyl, substituted Alkylaminocarbonyl, optionally substituted dia May be substituted with at least one group selected from the group consisting of alkylaminocarbonyl, optionally substituted alkoxycarbonyl, optionally substituted phenyl, and optionally substituted pyridyl;
U represents CH ₂ , O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁹ and R ¹⁰ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and
e) When ^one of W ¹ , W ² , W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring)
An optically active azoline derivative represented by: X is independently halogen, optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-12} haloalkyl, nitro, cyano, optionally substituted _{C 1-12} alkoxy, optionally substituted C _1-12 haloalkoxy, optionally substituted _{C 1-12} alkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally _{C 1-12} substituted haloalkylthio, optionally substituted C _1-12 haloalkylsulfinyl, optionally substituted C _1-12 haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted C _1-12 alkylamino, may be substituted C _2-24 (total carbon number) dialkylamino, optionally substituted _{C 1-12} (total carbon number) acylamino, Conversion which may C _{2-13 (total} carbon number) be alkoxycarbonylamino, optionally C _{2-13 (total} carbon number) be substituted halo alkoxycarbonylamino, optionally substituted C _1-12 alkylsulfonylamino or And represents _optionally substituted _C1-12 haloalkylsulfonylamino,
R ¹ may be substituted C _1-12 alkyl, _optionally substituted C _3-12 (total carbon number) cycloalkyl, _optionally substituted C _4-24 (total carbon number) alkyl cycloalkyl, substituted C _4-24 (total carbon number) cycloalkylalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted C _1-12 haloalkyl, C _3-12 (total carbon number) halocycloalkyl, or cyano, which may be substituted,
m represents 0, 1, 2, 3, 4 or 5;
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted C _1-12 alkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted. C _3-12 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, _optionally substituted C _4-24 (total carbon number) cycloalkyl alkyl, substituted which may be _{C 1-12} haloalkyl, optionally substituted phenyl, optionally substituted _{C 2-13} (total carbon number) even alkylcarbonyl, optionally substituted _{C 2-13} (total carbon number) alkoxycarbonyl, C _2-13 (total carbon number) alkylaminocarbonyl which may be substituted or C _3-25 (total carbon number) dialkylaminocarbonyl which may be substituted;
Q represents the following Q-1 to Q-54 phenyl, naphthyl and heterocyclic groups,

And T represents the following group (T-1) or group (T-2),

In the above group,
G represents a heterocyclic group of G1 to G9 below,

Or

Indicate
R ³ and R ⁴ are each independently hydrogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, optionally substituted C _1-12 haloalkyl, substituted C _3-8 cyclohaloalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl, _optionally substituted C _2-12 haloalkenyl, _optionally substituted C _{2 -12} haloalkynyl, cyano, C _1-12 alkoxy-carbonyl or C _1-12 alkoxy-thiocarbonyl,
R ³ and R ⁴ together may form a C _3-6 alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted C _1-12 alkoxy, optionally substituted amino-carbonyl-C _1-12 alkyl, optionally substituted imino-C _1-12 alkyl, substituted _Optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, _optionally substituted C _1-12 haloalkyl, cyano, _optionally substituted C _2-12 alkenyl, _optionally substituted Good C _2-12 alkynyl, _optionally substituted C _1-12 alkyl-carbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S) —R ⁷ ,
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted C _1-12 alkyl-carbonyl, _optionally substituted C _1-12 alkyl-thiocarbonyl, optionally substituted C _1-12 haloalkyl -Carbonyl, optionally substituted C _1-12 haloalkyl-thiocarbonyl, optionally substituted C _1-12 alkylamino-carbonyl, _optionally substituted C _1-12 alkylamino-thiocarbonyl, optionally substituted Good C _2-24 (total carbon number) dialkylamino-carbonyl, optionally substituted C _2-24 (total carbon number) dialkylamino-thiocarbonyl, optionally substituted C _1-12 alkoxyamino-carbonyl, substituted which may be _{C 1-12} alkoxy amino - thiocarbonyl, optionally substituted _{C 1-12} aralkyl Carboxy - carbonyl, optionally substituted _{C 1-12} alkoxy - thiocarbonyl, optionally substituted _{C 1-12} thioalkoxy - carbonyl, optionally substituted _{C 1-12} thioalkoxy - thiocarbonyl, optionally substituted C _1-12 alkylsulfonyl, optionally substituted C _1-12 haloalkylsulfonyl, optionally substituted C _3-8 cycloalkylcarbonyl, C _2-12 alkenylcarbonyl, C _2-12 alkynylcarbonyl, C _{3 -8} cycloalkyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfenyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfinyl-C _1-12 alkylcarbonyl, C _1-12 alkylsulfonyl-C _{1 -12 alkylcarbonyl, C 1-12} alkyl Cal Cycloalkenyl _{-C 1-12 alkylcarbonyl, C 3-8} cycloalkyl amino _{carbonyl, C 2-12} alkenyl _{aminocarbonyl, C 2-12 alkynyl-aminocarbonyl, C 1-12} alkoxy _{-C 1-12} alkylcarbonyl, -C ( O) -R ⁷ or -C (S) -R ⁷
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form a 3-6 membered heterocyclic ring which may be substituted, which ring is substituted with a keto, thioketo or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
Z may be the same or different halogen, optionally substituted C _1-12 haloalkyl, nitro, optionally substituted C _1-12 alkoxy, cyano, optionally substituted C _1-12 haloalkoxy, substituted which may be _{C 1-12} alkyl sulphenyl, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkyl sulfenyl, substituted which may be C _1-12 haloalkylsulfinyl, optionally substituted C _1-12 haloalkylsulfonyl, a hydroxyl or thiol,
k represents 0 to 4,
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² together may form an aromatic ring having 6 carbon atoms,
L is independently hydrogen, halogen, optionally substituted C _1-12 haloalkyl, nitro, _optionally substituted C _1-12 alkyl, _optionally substituted C _3-8 cycloalkyl, substituted C _3-8 cyclohaloalkyl, optionally substituted C _1-12 alkoxy, cyano, optionally substituted C _1-12 haloalkoxy, optionally substituted C _1-12 alkylsulfenyl, substituted which may _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkylsulfenyl, optionally substituted _{C 1-12} haloalkylsulfinyl, be substituted Good C _1-12 haloalkylsulfonyl, optionally substituted C _1-12 alkylsulfonyloxy, optionally substituted C _1-12 haloalkylsulfonyloxy, optionally substituted C _1-12 alkylaminosulfonyl, optionally substituted C _1-12 haloalkylaminosulfonyl, optionally substituted C _2-24 (total carbon number) dialkylamino Sulfonyl, optionally substituted C _2-24 (total carbon number) di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted C _1-12 alkylamino group, _optionally substituted C _{2− 24} (total carbon number) dialkylamino, optionally substituted C _1-12 acylamino, optionally substituted C _1-12 alkoxy-carbonylamino, optionally substituted C _1-12 haloalkoxy-carbonylamino, substituted and which may be _{C 1-12} alkylsulfonylamino, optionally substituted _{C 1-12} Ha Alkylsulfonylamino, optionally substituted _{C 1-12} trialkylsilyl, optionally substituted _{C 1-12} alkoxyimino, optionally substituted _{C 1-12} halo alkoxyiminoalkyl, optionally substituted _{C 1- 12} alkoxy - imino - optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-12} haloalkoxy - imino - optionally substituted _{C 1-12} alkyl, optionally substituted _{C 1-4} alkyl sulfinyl amino, optionally substituted C _1-4 alkylsulfinyl - imino - optionally substituted C _1-12 alkyl, optionally substituted C _1-4 alkylsulfinyl - imino - optionally substituted C _{1 -5} alkyl-carbonyl, optionally substituted C _1-4 alkyl-sulfoxyimino, optionally substituted C _1-4 alkyl Rusuruhokishi - imino - optionally substituted C _1-4 alkyl optionally, an optionally substituted C _1-6 alkoxy - carbonyl, optionally substituted C _1-6 alkyl -, aminocarbonyl, optionally substituted C _1-6 alkylaminocarbonyl, aminothiocarbonyl, optionally substituted C _1-6 alkylamino-thiocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminocarbonyl group or optionally substituted Good C _2-12 (total carbon number) dialkyl-aminothiocarbonyl,
l represents 1 to 3,
Y is independently halogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl, optionally substituted C _3-12 cycloalkyl, _optionally substituted C _3-12 cycloalkyl haloalkyl, nitro, cyano, optionally substituted _{C 2-12} alkenyl, optionally substituted _{C 2-12} haloalkenyl, optionally substituted _{C 1-12} alkoxy, optionally _{C 1-12} substituted haloalkoxy, optionally substituted _{C 1-12} alkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} alkylsulfonyl, optionally substituted _{C 1-12} haloalkylthio, optionally substituted _{C 1-12} haloalkylsulfinyl, optionally substituted _{C 1-12} haloalkylsulfonyl, hydroxy, main Mercapto, amino, optionally substituted _{C 1-12} alkylamino, optionally substituted _{C 2-24} (total carbon number) dialkylamino, aminocarbonyl, optionally substituted _{C 2-13} (total carbon number) Alkylaminocarbonyl, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonyl, _optionally substituted C _1-12 (total carbon number) acylamino, optionally substituted C _2-13 (total carbon number) Number) alkoxycarbonylamino, optionally substituted benzyloxycarbonylamino, optionally substituted C _2-13 haloalkoxycarbonylamino, optionally substituted C _1-12 alkylsulfonylamino, optionally substituted C _{1 -12} haloalkylsulfonyl amino or optionally substituted _{C 3-26} (total carbon number) trialkylsilyl Shows,
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are each independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ _, C—R ⁸ , C (R ⁸ ) ₂ , N—R ^9. N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, _optionally substituted C _1-12 alkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _2-12 alkynyl. _Optionally substituted C _3-12 cycloalkyl, _optionally substituted C _4-24 alkyl cycloalkyl, _optionally substituted C _4-24 cycloalkylalkyl, _optionally substituted C _1-12 haloalkyl, C _2-13 (total carbon number) alkylcarbonyl which may be substituted, C _2-13 (total carbon number) alkoxycarbonyl which may be substituted, C _2-13 (total carbon number) alkylamino which may be substituted carbonyl, optionally substituted _{C 3-25} (total carbon number) dialkylaminocarbonyl, optionally substituted _{C 2-13} (total carbon number) Al Le carbonylamino, optionally substituted _{C 2-13} (total carbon number) be alkylthiocarbonyl amino, optionally substituted _{C 4-13} (total carbon number) be a cycloalkyl carbonyl amino, optionally substituted _{C 5-25} (Total carbon number) cycloalkylalkylcarbonylamino, optionally substituted C _4-13 (total carbon number) cycloalkylthiocarbonylamino, optionally substituted C _5-25 (total carbon number) cycloalkylalkylthiocarbonylamino, optionally substituted _{C 2-13} (total carbon number) be halo alkylcarbonylamino, optionally substituted _{C 2-13} (total carbon number) haloalkylthio alkylcarbonylamino, optionally substituted _{C 2-13} (the total number of carbon atoms ) alkylaminocarbonyl amino, optionally substituted _{C 2-13} (total carbon number) alkylamino Thiocarbonylamino, optionally substituted C _{4-13 (total} carbon number) be a cycloalkyl aminocarbonylamino, optionally substituted C _{5-25 (total} carbon number) cycloalkylalkyl aminocarbonylamino, may be substituted C _4-13 (total carbon number) cycloalkylaminothiocarbonylamino, _optionally substituted C _5-25 (total carbon number) cycloalkylalkylaminothiocarbonylamino, _optionally substituted C _2-13 (total carbon number) Number) haloalkylaminocarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkylaminothiocarbonylamino, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonylamino, _optionally substituted good _{C 2-25} (total number of carbon atoms) dialkylaminothiocarbonyl amino, substituted Which may _{C 2-13} (total carbon number) be alkylaminocarbonyloxy, optionally substituted _{C 2-13} (total carbon number) alkylaminocarbonyl thio, optionally substituted _{C 4-13} (the total number of carbon atoms ) Cycloalkylaminocarbonyloxy, _optionally substituted C _5-25 (total carbon number) cycloalkylalkylaminocarbonyloxy, _optionally substituted C _4-13 (total carbon number) cycloalkylaminocarbonylthio, substituted which may be _{C 5-25} (total carbon number) cycloalkylalkyl aminocarbonylthio, optionally substituted _{C 2-13} (total carbon number) be halo alkylaminocarbonyloxy, optionally substituted _{C 2-13} (total carbon Number) haloalkylaminocarbonylthio, C _{3-25 optionally} substituted (total carbon number) dialkylaminocarbo Nyloxy, optionally substituted C _3-25 (total carbon number) dialkylaminocarbonylthio, optionally substituted C _2-13 (total carbon number) alkoxycarbonylamino, optionally substituted C _4-13 (total Carbon number) cycloalkyloxycarbonylamino, optionally substituted C _5-25 (total carbon number) cycloalkylalkyloxycarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkoxycarbonylamino, substituted C _1-12 alkylsulfonylamino which may be substituted or C _1-12 haloalkylsulfonylamino which may be substituted, and substituents other than the above cyano, formyl, halogen and nitro may be substituted with R ¹⁰ shown below ,
R ⁹ is hydrogen, hydroxy, amino, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl, _optionally substituted C _2-12 alkenyl, _optionally substituted C _{2- 12} alkenyloxy, optionally substituted _{C 2-12} alkynyl, optionally substituted _{C 2-12} alkynyloxy, optionally substituted _{C 3-12} cycloalkyl, optionally _{C 4-24} alkylcycloalkyl substituted Alkyl, _optionally substituted C _4-24 cycloalkylalkyl, _optionally substituted C _1-12 alkylamino, _optionally substituted C _2-24 (total carbon number) dialkylamino, optionally substituted C _1-12 alkoxy, optionally substituted _{C 1-12} haloalkoxy, formyl, optionally substituted _{C 2-13} (total carbon number) alkylcarbonyl Le, optionally substituted _{C 2-13} (total carbon number) haloalkylcarbonyl, optionally substituted _{C 2-13} (total carbon number) alkoxycarbonyl, optionally substituted _{C 2-13} (total carbon number) Alkylaminocarbonyl, optionally substituted C _2-13 (total carbon number) alkylcarbonylamino, optionally substituted C _2-13 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-13 ( (Total carbon number) alkoxycarbonylamino, optionally substituted C _2-13 (total carbon number) alkylaminocarbonylamino, optionally substituted C _1-12 (total carbon number) alkylsulfonyl, optionally substituted C _1-12 (total carbon number) haloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally substituted _{C 2-13} (total carbon number) Le Kill aminocarbonyl or optionally substituted C _{2-13 (total} carbon number) halo alkylaminocarbonyl, the substituents other than the hydrogen and formyl may be substituted with R ¹⁰ shown in the following,
R ¹⁰ represents phenyl and heterocyclic groups the following ^R 10 ^-1~R 10 -83,

E represents O, S or N, and each group is hydrogen, halogen, _optionally substituted C _1-12 alkyl, _optionally substituted C _1-12 haloalkyl in the above phenyl and heterocyclic groups, _Optionally substituted C _3-12 cycloalkyl, optionally substituted C _{3-12 halocycloalkyl,} optionally substituted C _1-12 alkoxy, optionally substituted C _1-12 haloalkoxy, substituted which may be _{C 1-12} alkylthio, optionally substituted _{C 1-12} haloalkylthio, optionally substituted _{C 1-12} alkylsulfinyl, optionally substituted _{C 1-12} haloalkylsulfinyl, it may be substituted C _1-12 alkylsulfonyl, optionally substituted _{C 1-12} haloalkylsulfonyl, optionally substituted _{C 1-12} alkylamino, substituted C _1-12 haloalkylamino, cyano, nitro, aminocarbonyl, optionally substituted C _2-13 (total carbon number) alkylaminocarbonyl, optionally substituted C _2-25 (total carbon number) dialkylamino May be substituted with at least one group selected from the group consisting of carbonyl, optionally substituted C _1-13 alkoxycarbonyl, optionally substituted phenyl, and optionally substituted pyridyl;
U represents CH ₂ , O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁹ and R ¹⁰ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and e) W ¹ , W ² , When one of W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring.
The compound of Claim 1 represented by these. X is independently halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl, nitro, cyano, optionally substituted C _1-6 alkoxy, optionally substituted C _1-6 haloalkoxy, optionally substituted _{C 1-6} alkylthio, optionally substituted _{C 1-6} alkylsulfinyl, optionally substituted _{C 1-6} alkylsulfonyl, optionally substituted _{C 1-6} haloalkylthio, optionally substituted C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, hydroxy, mercapto, amino, optionally substituted C _1-6 alkyl amino, optionally substituted C _2-12 (total carbon number) dialkylamino, optionally substituted C _1-6 (total carbon number) acylamino, optionally substituted C _2-7 (Total carbon number) alkoxycarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino or optionally substituted C _1-6 Represents haloalkylsulfonylamino;
R ¹ is optionally substituted C _1-6 alkyl, optionally substituted C _3-6 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, substituted _Optionally substituted C _4-12 (total carbon number) cycloalkylalkyl, _optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _1-6 haloalkyl, C _3-6 (total carbon number) halocycloalkyl, or cyano, which may be substituted,
m represents 0, 1, 2, 3, 4 or 5;
A represents O, CH ₂ or N—R ² ;
R ² is independently hydrogen, cyano, formyl, optionally substituted C _1-6 alkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _3-6 (total carbon number) cycloalkyl, optionally substituted C _4-12 (total carbon number) alkyl cycloalkyl, optionally substituted C _4-12 (total carbon number) cycloalkyl alkyl, substituted It is a C _1-6 haloalkyl, optionally substituted phenyl, optionally substituted C _{2-7 (total} carbon number) even alkylcarbonyl, optionally substituted C _{2-7 (total} carbon number) alkoxycarbonyl, C _2-7 (total carbon number) alkylaminocarbonyl which may be substituted or C _3-13 (total carbon number) dialkylaminocarbonyl which may be substituted;
Q represents the following Q-1 to Q-54 phenyl, naphthyl and heterocyclic groups,

T represents the following group (T-1) or group (T-2),

In the above group,
G represents a heterocyclic group of G1 to G9 below,

Or

Indicate
R ³ and R ⁴ are each independently hydrogen, optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _1-6 haloalkyl, substituted C _3-6 cyclohaloalkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _2-6 haloalkenyl, optionally substituted C _{2 -6} haloalkynyl, _{cyano, C 1-6} alkoxy - carbonyl or _{C 1-6} alkoxy - indicates thiocarbonyl,
R ³ and R ⁴ together may form a C _3-6 alkylene,
R ⁵ is hydrogen, amino, hydroxy, optionally substituted C _1-6 alkoxy, optionally substituted aminocarbonyl-C _1-6 alkyl, optionally substituted imino-C _1-6 alkyl, substituted _Optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _1-6 haloalkyl, cyano, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl, optionally substituted C _1-6 alkyl-carbonyl, —CH ₂ —R ⁷ , —C (O) —R ⁷ or —C (S) —R ⁷ ,
R ⁶ is hydrogen, cyano, carbonyl, thiocarbonyl, optionally substituted C _1-6 alkyl-carbonyl, optionally substituted C _1-6 alkyl-thiocarbonyl, optionally substituted C _1-6 haloalkyl -Carbonyl, optionally substituted C _1-6 haloalkyl-thiocarbonyl, optionally substituted C _1-6 alkylamino-carbonyl, optionally substituted C _1-6 alkylamino-thiocarbonyl, optionally substituted Good C _2-12 (total carbon number) dialkyl-aminocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminothiocarbonyl, optionally substituted C _1-6 alkoxy-aminocarbonyl, substituted It is a _{C 1-6} alkoxy optionally - aminothiocarbonyl, optionally substituted _{C 1-6} alkoxy - carbonyl Optionally substituted C _1-6 alkoxy - thiocarbonyl, optionally substituted C _1-6 thioalkoxy - carbonyl, optionally substituted C _1-6 thioalkoxy - thiocarbonyl, optionally C ₁ substituted _-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfonyl, optionally substituted C _3-6 cycloalkylcarbonyl, C _2-6 alkenylcarbonyl, C _2-6 alkynylcarbonyl, C _3-6 cycloalkyl -C _{1-6 alkylcarbonyl, C 1-6} alkylsulfenyl _{-C 1-6 alkylcarbonyl, C 1-6} alkylsulfinyl _{-C 1-6 alkylcarbonyl, C 1-6} alkylsulfonyl _{-C 1-6} alkylcarbonyl , _{C 1-6} alkylcarbonyl _{-C 1-6 alkylcarbonyl, C 3-6} Shi B _{alkylaminocarbonyl, C 2-6} alkenyl _{aminocarbonyl, C 2-6} alkynyl _{aminocarbonyl, C 1-6} alkoxy _{-C 1-6} alkylcarbonyl, -C (O) -R ⁷ or -C (S) -R ⁷
R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may form a 3-6 membered heterocyclic ring which may be substituted, which ring is substituted with a keto, thioketo or nitroimino group May have been
R ⁷ represents an optionally substituted phenyl or an optionally substituted saturated or unsaturated heterocycle;
Z may be the same or different halogen, optionally substituted C _1-6 haloalkyl, nitro, optionally substituted C _1-6 alkoxy, cyano, optionally substituted C _1-6 haloalkoxy, substituted which may be C _1-6 alkylsulfenyl, optionally substituted C _1-6 alkylsulfinyl, optionally substituted C _1-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfenyl, substituted which may be C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, a hydroxyl or thiol,
k represents 0 to 4,
B ¹ , B ² , B ³ and B ⁴ each independently represent C—L or nitrogen,
B ¹ and B ² together may form an aromatic ring having 6 carbon atoms,
L is independently hydrogen, halogen, optionally substituted C _1-6 haloalkyl, nitro, optionally substituted C _1-6 alkyl, optionally substituted C _3-6 cycloalkyl, substituted C _3-6 cyclohaloalkyl, optionally substituted C _1-6 alkoxy, cyano, optionally substituted C _1-6 haloalkoxy, optionally substituted C _1-6 alkylsulfenyl, substituted also a C _1-6 alkylsulfinyl, optionally substituted C _1-6 alkylsulfonyl, optionally substituted C _1-6 haloalkylsulfenyl, optionally substituted C _1-6 haloalkylsulfinyl, be substituted a _{C 1-6} haloalkylsulfonyl, optionally substituted _{C 1-6} alkylsulfonyloxy, a _{C 1-6} haloalkyl optionally substituted Ruhoniruokishi, optionally substituted C _1-6 alkylaminosulfonyl, optionally substituted C _1-6 haloalkylsulfonyl, aminosulfonyl, optionally substituted C _{2-12 (total} carbon number) dialkylamino sulfonyl group, optionally substituted C _2-12 (total carbon number) di (haloalkyl) aminosulfonyl, hydroxyl, thiol, amino, optionally substituted C _1-6 alkylamino, optionally substituted C _2-12 (total carbon number) Dialkylamino, optionally substituted C _1-6 acylamino, optionally substituted C _1-6 alkoxy-carbonylamino, optionally substituted C _1-6 haloalkoxy-carbonylamino, optionally substituted C _{1 -6} alkylsulfonylamino, optionally substituted C _1-6 haloalkylsulfonyl amino, optionally substituted There _{C 1-6} trialkylsilyl, optionally substituted _{C 1-6} alkoxyimino, optionally substituted _{C 1-6} halo alkoxyiminoalkyl, optionally substituted _{C 1-6} alkoxyimino - substituted also _{C 1-6} alkyl, optionally substituted _{C 1-6} haloalkoxy - imino - optionally substituted _{C 1-6} alkyl, optionally substituted _{C 1-4} alkyl sulfinyl amino, substituted Good C _1-4 alkylsulfinyl-imino-optionally substituted C _1-6 alkyl, optionally substituted C _1-4 alkylsulfinyl-imino-optionally substituted C _1-5 alkyl-carbonyl, substituted which may be _{C 1-4} alkyl - Suruhokishiimino, optionally substituted _{C 1-4} alkylsulfoxy - imino - optionally substituted _{C 1-4} alkyl Optionally substituted C _1-6 alkoxy - carbonyl, optionally substituted C _1-6 alkyl -, aminocarbonyl, optionally substituted C _1-6 alkylaminocarbonyl, amino thiocarbonyl, optionally substituted Good C _1-6 alkylamino-thiocarbonyl, optionally substituted C _2-12 (total carbon number) dialkyl-aminocarbonyl or _optionally substituted C _2-12 (total carbon number) dialkyl-aminothiocarbonyl Show
l represents 1 to 3,
Y is independently halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted C _3-6 cycloalkyl haloalkyl, nitro, cyano, optionally substituted _{C 2-6} alkenyl, optionally substituted _{C 2-6} haloalkenyl, optionally substituted _{C 1-6} alkoxy, optionally substituted _{C 1-6} haloalkoxy, optionally substituted _{C 1-6} alkylthio, optionally substituted _{C 1-6} alkylsulfinyl, optionally substituted _{C 1-6} alkylsulfonyl, optionally substituted _{C 1-6} haloalkylthio, optionally substituted C _1-6 haloalkylsulfinyl, optionally substituted C _1-6 haloalkylsulfonyl, hydroxy, mercapto, amino, substituted _{C 1-6} alkyl amino, optionally substituted _{C 2-12} (total carbon number) dialkylamino, aminocarbonyl, optionally substituted _{C 2-7} (total carbon number) alkylaminocarbonyl, optionally substituted Good C _2-13 (total carbon number) dialkylaminocarbonyl, optionally substituted C _1-6 (total carbon number) acylamino, optionally substituted C _2-7 (total carbon number) alkoxycarbonylamino, substituted Optionally substituted benzyloxycarbonylamino, optionally substituted C _2-7 haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino, optionally substituted C _1-6 haloalkylsulfonylamino or substituted _{May represent C3-26} (total carbon number) trialkylsilyl,
n represents 0, 1, 2 or 3,
W ¹ , W ² , W ³ and W ⁴ are each independently a single bond, CH ₂ , CH, N, O, S, CH—R ⁸ , C—R ⁸ , C (R ⁸ ) ₂ , N—R ^9. , N—R ¹⁰ , CH—R ¹⁰ , C—R ¹⁰ or C═U,
R ⁸ is independently hydroxy, amino, cyano, formyl, halogen, nitro, optionally substituted C _1-6 alkyl, optionally substituted C _2-6 alkenyl, optionally substituted C _2-6 alkynyl _Optionally substituted C _3-6 cycloalkyl, _optionally substituted C _4-12 alkyl cycloalkyl, _optionally substituted C _4-12 cycloalkylalkyl, _optionally substituted C _1-6 haloalkyl, C _2-7 (total carbon number) alkylcarbonyl which may be substituted, C _2-7 (total carbon number) alkoxycarbonyl which may be substituted, C _2-7 (total carbon number) alkylamino which may be substituted carbonyl, optionally substituted _{C 3-13} (total carbon number) dialkylaminocarbonyl, optionally substituted _{C 2-7} (total carbon number) alkylcarbonyl amino , Optionally substituted _{C 2-7} (total carbon number) alkyl thiocarbonyl amino, optionally substituted _{C 4-7} (total carbon number) cycloalkyl carbonyl amino, optionally substituted _{C 5-13} (total carbon Number) Cycloalkylalkylcarbonylamino, optionally substituted C _4-7 (total carbon number) cycloalkylthiocarbonylamino, optionally substituted C _5-13 (total carbon number) cycloalkylalkylthiocarbonylamino, substituted C _2-13 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkylthiocarbonylamino, optionally substituted C _2-7 (total carbon number) alkylamino carbonylamino, optionally substituted C _{2-7 (total} carbon number) alkylamino thiocarbonyl amino, it is substituted Which may be _{C 4-7} (total carbon number) cycloalkyl aminocarbonylamino, optionally substituted _{C 5-13} (total carbon number) be cycloalkylalkyl aminocarbonylamino, optionally substituted _{C 4-7} (total Carbon number) cycloalkylaminothiocarbonylamino, _optionally substituted C _5-13 (total carbon number) cycloalkylalkylaminothiocarbonylamino, _optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonylamino _Optionally substituted C _2-7 (total carbon number) haloalkylaminothiocarbonylamino, optionally substituted C _3-13 (total carbon number) dialkylaminocarbonylamino, optionally substituted C _2-13 ( Total carbon number) Dialkylaminothiocarbonylamino, C _2-7 (total carbon number) optionally substituted C _2-7 (total carbon number) alkylaminocarbonylthio, optionally substituted C _4-7 (total carbon number) cycloalkylaminocarbonyloxy, optionally substituted C 2 _5-7 (total carbon number) cycloalkylalkylaminocarbonyloxy, optionally substituted C _4-7 (total carbon number) cycloalkylaminocarbonylthio, optionally substituted C _5-13 (total carbon number) cyclo Alkylalkylaminocarbonylthio, optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonyloxy, optionally substituted C _2-7 (total carbon number) haloalkylaminocarbonylthio, optionally substituted C _3-13 (total carbon number) dialkylamino carbonyloxy, optionally _{C 3-13} substituted (total carbon number) Alkylaminocarbonyl thio, optionally substituted C _{2-7 (total} carbon number) alkoxycarbonylamino, optionally substituted C _{4-7 (total} carbon number) be cycloalkyloxycarbonyl amino, optionally substituted C _{5 -13} (total carbon number) cycloalkylalkyloxycarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkoxycarbonylamino, optionally substituted C _1-6 alkylsulfonylamino or optionally substituted Good C _1-6 haloalkylsulfonylamino, wherein the substituents other than cyano, formyl, halogen and nitro may be substituted with R ¹⁰ ;
R ⁹ is hydrogen, hydroxy, amino, optionally substituted _{C 1-6} alkyl, optionally substituted _{C 1-6} haloalkyl also, optionally substituted _{C 2-6} alkenyl, optionally substituted _{C 2- 6} alkenyloxy, optionally substituted _{C 2-6} alkynyl, optionally substituted _{C 2-6} alkynyloxy, optionally substituted _{C 3-6} cycloalkyl, optionally _{C 4-12} alkylcycloalkyl substituted Alkyl, _optionally substituted C _4-12 cycloalkylalkyl, _optionally substituted C _1-6 alkylamino, optionally substituted C _2-12 (total carbon number) dialkylamino, optionally substituted C _C1-6 alkoxy, optionally substituted _{C 1-6} haloalkoxy, formyl, optionally substituted _{C 2-7} (total carbon number) even alkylcarbonyl may be substituted _{2-7 (total} carbon number) haloalkylcarbonyl, optionally substituted C _{2-7 (total} carbon number) be alkoxycarbonyl, optionally substituted C _{2-7 (total} carbon number) be alkylaminocarbonyl, optionally substituted Good C _2-7 (total carbon number) alkylcarbonylamino, optionally substituted C _2-7 (total carbon number) haloalkylcarbonylamino, optionally substituted C _2-7 (total carbon number) alkoxycarbonylamino, It is optionally substituted C _{2-7 (total} carbon number) alkylaminocarbonyl amino, optionally substituted C _{1-6 (total} carbon number) alkylsulfonyl, optionally substituted C _{1-6 (total} carbon number) haloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally C _{2-7 (total} carbon number) be substituted be alkylaminocarbonyl or substituted A C _{2-7 (total} carbon number) halo alkylaminocarbonyl, the substituents other than the hydrogen and formyl may be substituted with R ^10,
R ¹⁰ represents phenyl and heterocyclic groups the following ^R 10 ^-1~R 10 -83,

E represents O, S or N, and each group is hydrogen, halogen, optionally substituted C _1-6 alkyl, optionally substituted C _1-6 haloalkyl in the above phenyl and heterocyclic groups, Optionally substituted C _3-6 cycloalkyl, optionally substituted C _3-6 halocycloalkyl, optionally substituted C _1-6 alkoxy, optionally substituted C _1-6 haloalkoxy, substituted be a C _1-6 alkylthio, optionally substituted C _1-6 haloalkylthio, optionally substituted C _1-6 alkylsulfinyl, optionally substituted C _1-6 haloalkylsulfinyl, it may be substituted C _1-6 alkylsulfonyl, optionally substituted _{C 1-6} haloalkylsulfonyl, optionally substituted _{C 1-6} alkylamino, optionally substituted _{C 1-6} Haroaruki Amino, cyano, nitro, aminocarbonyl, optionally substituted C _{2-7 (total} carbon number) alkylaminocarbonyl, optionally substituted C _{2-13 (total} carbon number) be dialkylaminocarbonyl, optionally substituted C _1-7 alkoxycarbonyl may be substituted by at least 1 month group selected from the group consisting of optionally substituted pyridyl are also substituted phenyl and substituted,
U represents CH ₂ , O, S, N—R ⁹ or N—R ¹⁰ , wherein R ⁹ and R ¹⁰ independently represent the same as R ⁴ and R ⁵ above;
And a) two or more of W ¹ , W ² , W ³ and W ⁴ are not single bonds at the same time,
b) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not O, S, N—R ⁹ or N—R ¹⁰ ,
c) At least three of W ¹ , W ² , W ³ and W ⁴ at the same time are not C = U,
d) when ^{two of} W ¹ , W ² , W ³ and W ⁴ simultaneously represent O and / or S, they are via at least one carbon atom, and e) W ¹ , W ² , When one of W ³ and W ⁴ is CH, N, C—R ⁸ or C—R ¹⁰ , a double bond is formed in the condensed ring.
The compound of Claim 1 represented by these.   An insecticide containing the compound according to any one of claims 1 to 3 as an active ingredient.   The animal parasite control agent which contains the compound in any one of Claims 1-3 as an active ingredient.