JP2012017289A - Pesticidal pyrroline derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel pyrroline derivative showing excellent insecticidal effect as a pesticide.SOLUTION: This invention relates to pyrroline derivatives represented by Formula (I) and the use thereof as the pesticide and animal parasite-controlling agent, wherein each substituent is as defined in the specification.

Description

  The present invention relates to a novel insecticidal pyrroline derivative and its use as an insecticide.

  Patent Documents 1 to 5 describe that insecticidal pyrroline compounds are useful as pest control agents, but do not describe the insecticidal pyrroline derivatives of the present invention.

International Publication No. 2009/022746 International Publication No. 2009/072621 International Publication No. 2009/097992 International Publication No. 2009/112275 International Publication No. 2010/020521

As a result of intensive studies to create a novel compound having a higher effect and a broad spectrum as an insecticide, the present inventors have exhibited a high activity, a broad spectrum, and safety. The present inventors have found a novel pyrroline derivative represented by the following formula (I) which is rapidly decomposed in nature and has high environmental safety.
Formula (I):

式中、
次式

Where
Next formula

で表される部分は次式：

The part represented by the following formula:

を示すか、
又は、Ｒ^２がヒドロキシ−カルボニル、Ｃ_１−１２アルコキシ−カルボニル又はシアノの場合、
次式

Or
Or when R ² is hydroxy-carbonyl, C _1-12 alkoxy-carbonyl or cyano,
Next formula

で表される部分は次式：

The part represented by the following formula:

（式中、Ｒ^１は水素を示す。）
若しくは

(In the formula, R ¹ represents hydrogen.)
Or

（式中、Ｒ^１は非存在である。）
又はそれら位置異性体の混合物を示し、
Ｔは、次式（Ｔ−１）、（Ｔ−２）、（Ｔ−３）、（Ｔ−４）又は（Ｔ−５）のいずれかを示し、

(Wherein R ¹ is absent)
Or a mixture of these positional isomers,
T represents one of the following formulas (T-1), (T-2), (T-3), (T-4) or (T-5),

Ｂは、Ｎ又はＣ−Ｘ^３を示し、
Ｘ^１、Ｘ^２、Ｘ^３、Ｘ^４及びＸ^５は、それぞれ独立して水素、ハロゲン、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ、シアノ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、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、Ｃ_１−１２アシルアミノ、Ｃ_１−１２アルコキシ−カルボニルアミノ、Ｃ_１−１２ハロアルコキシ−カルボニルアミノ、Ｃ_１−１２アルコキシ−イミノ、Ｃ_１−１２ハロアルコキシ−イミノ、Ｃ_１−１２アルキルスルホニルアミノ又は５フッ化硫黄を示し、
Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４及びＹ^５は、それぞれ独立して水素、ハロゲン、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_３−８シクロアルキル、Ｃ_３−８シクロハロアルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ、シアノ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、Ｃ_１−１２ハロアルキルスルホニル、Ｃ_１−１２アルキルスルホニルオキシ、Ｃ_１−１２アルキルアミノスルホニル、Ｃ_１−１２ハロアルキルアミノスルホニル、ジ（Ｃ_１−１２アルキル）アミノスルホニル、ジ（Ｃ_１−１２ハロアルキル）アミノスルホニル、ヒドロキシ、メルカプト、アミノ、Ｃ_１−１２アルキルアミノ、ジ（Ｃ_１−１２アルキル）アミノ、Ｃ_１−１２アシルアミノ、Ｃ_１−１２アルコキシ−カルボニルアミノ、Ｃ_１−１２ハロアルコキシ−カルボニルアミノ、Ｃ_１−１２アルキルスルホニルアミノ、Ｃ_１−１２ハロアルキルスルホニルアミノ、トリ（Ｃ_１−１２アルキル）シリル、Ｃ_１−１２アルコキシ−イミノ、Ｃ_１−１２ハロアルコキシ−イミノ、Ｃ_１−１２アルコキシ−イミノ−Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルコキシ−イミノ−Ｃ_１−１２アルキル、Ｃ_１−１２アルキルスルフィニルイミノ、Ｃ_１−１２アルキルスルフィニルイミノ−Ｃ_１−１２アルキル、Ｃ_１−１２アルキルスルフィニルイミノ−Ｃ_１−１２アルキル−カルボニル、Ｃ_１−１２アルキルスルホキシイミノ、Ｃ_１−１２アルキルスルホキシイミノ−Ｃ_１−１２アルキル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２アルキル−カルボニル、アミノカルボニル、Ｃ_１−１２アルキル−アミノカルボニル、アミノ−チオカルボニル、Ｃ_１−１２アルキルアミノ−チオカルボニル、ジ（Ｃ_１−１２アルキル）アミノ−カルボニル、ジ（Ｃ_１−１２アルキル）アミノ−チオカルボニル又はヒドロキシカルボニルを示し、
Ｇは、次式Ｇ１からＧ９のいずれかを示し、

B represents N or C—X ³ ;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _1-12 alkoxy, C _1-12 haloalkoxy , _{cyano, C 1-12} alkyl _{sulphenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, hydroxy, mercapto , Amino, C _1-12 acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkoxy-imino, C _1-12 haloalkoxy-imino, C _1-12 alkyl Represents sulfonylamino or sulfur pentafluoride,
Y ¹ , Y ² , Y ³ , Y ⁴ and Y ⁵ are each independently hydrogen, halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _3-8 cycloalkyl, C _3-8 cyclo _{haloalkyl, C 1-12 alkoxy, C 1-12} haloalkoxy, _{cyano, C 1-12} alkyl _{sulphenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1- 12} haloalkylsulfinyl, C _1-12 haloalkylsulfonyl, C _1-12 alkylsulfonyloxy, C _1-12 alkylaminosulfonyl, C _1-12 haloalkylaminosulfonyl, di (C _1-12 alkyl) aminosulfonyl, di (C _{1 -12} haloalkyl) aminosulfonyl, hydroxy, mercapto, Amino, C _1-12 alkylamino, di (C _1-12 alkyl) amino, C _1-12 acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkylsulfonyl Amino, C _1-12 haloalkylsulfonylamino, tri (C _1-12 alkyl) silyl, C _1-12 alkoxy-imino, C _1-12 haloalkoxy-imino, C _1-12 alkoxy-imino-C _1-12 alkyl C _1-12 haloalkoxy-imino-C _1-12 alkyl, C _1-12 alkylsulfinylimino, C _1-12 alkylsulfinylimino-C _1-12 alkyl, C _1-12 alkylsulfinylimino-C _1-12 alkyl - _{carbonyl, C 1-12} alkylsulfonyl alkoximinoalkyl Mino C _1-12 alkylsulfonyl alkoximinoalkyl amino _{-C 1-12 alkyl, C 1-12} alkoxy - _{carbonyl, C 1-12} alkyl - carbonyl, _{aminocarbonyl, C 1-12} alkyl - amino, aminocarbonyl, - thiocarbonyl, _{C 1 -12 represents} alkylamino-thiocarbonyl, di ( _C1-12alkyl ) amino-carbonyl, di ( _C1-12alkyl ) amino-thiocarbonyl or hydroxycarbonyl;
G represents any of the following formulas G1 to G9,

Ｚは、水素、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_１−１２アルコキシ、シアノ、Ｃ_１−１２ハロアルコキシ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、Ｃ_１−１２ハロアルキルスルホニル、ヒドロキシ又はチオールを示し、
ｋは、０、１、２、３又は４を示し、
Ｒは、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^１及びＲ^２は非存在であるか、それぞれ独立して水素、ハロゲン、シアノ、アミノ、アジド、ヒドロキシ、メルカプト、ヒドロキシ−カルボニル、Ｃ_１−１２アルキルアミノ−カルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２アルコキシ、Ｃ_１−１２アルキル、Ｃ_２−１２アルケニル、Ｃ_２−１２アルキニル、Ｃ_１−１２アルキルチオ、Ｃ_１−１２アルキルスルフィニル又はＣ_１−１２アルキルスルホニルを示し、ただしＲ^１及びＲ^２は同時に非存在であることはなく、Ｒ^１及びＲ^２は同時に水素ではなく、
Ｒ^３は、水素、アミノ、ヒドロキシ、シアノ、Ｒ^８−ＣＨ_２−、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ、Ｃ_２−１２アルケニル、Ｃ_２−１２アルキニル、Ｃ_１−１２アルキル−カルボニル又はＣ_１−１２アルキル−カルボニルアミノを示し、
Ｒ^４は、水素、シアノ、カルボニル、チオカルボニル、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−１２アルキル−カルボニル、Ｃ_１−１２アルキル−チオカルボニル、Ｃ_１−１２ハロアルキル−カルボニル、Ｃ_１−１２ハロアルキル−チオカルボニル、Ｃ_１−１２アルキルアミノ−カルボニル、Ｃ_１−１２アルキルアミノ−チオカルボニル、ジ（Ｃ_１−１２アルキル）アミノ−カルボニル、ジ（Ｃ_１−１２アルキル）アミノ−チオカルボニル、Ｃ_１−１２アルコキシアミノ−カルボニル、Ｃ_１−１２アルコキシアミノ−チオカルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２アルコキシ−チオカルボニル、Ｃ_１−１２チオアルコキシ−カルボニル、Ｃ_１−１２チオアルコキシ−チオカルボニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルホニル、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−カルボニル又はＣ_２−１２アルキニアミノ−カルボニルを示し、
また、Ｒ^３とＲ^４は、それが結合する窒素原子と一緒になって３，４，５又は６員の、飽和又は不飽和の複素環を形成してもよく、該複素環はオキソ、チオキソ又はニトロで置換されてもよく、
Ｒ^５は、水素、シアノ、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^６は、水素、Ｃ_１−１２アルキル、Ｃ_１−１２アルキルカルボニル又はＣ_１−１２アルコキシカルボニルを示し、
Ｒ^７は、水素又はＣ_１−１２アルキルを示し
Ｒ^８は、フェニル、又は３、４、５若しくは６員の、飽和又は不飽和の複素環を示し、
Ｚ^１、Ｚ^２及びＺ^３は、それぞれ独立して−Ｃ（Ｒ^９）（Ｒ^１０）−、−Ｃ（＝Ｏ）−、−Ｃ（＝Ｎ−ＯＲ^１１）−、−Ｎ（Ｒ^１１）−、−Ｓ−、−Ｓ（＝Ｏ）−、−Ｓ（＝Ｏ）_２−又は−Ｓ（Ｏ）（＝Ｎ−Ｒ^１１）−を示し、
Ｒ^９及びＲ^１０は、それぞれ独立して水素、ハロゲン、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^１１は、水素、シアノ、ニトロ、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_３−８シクロアルキル−Ｃ_１−１２アルキル、Ｃ_１−１２アルキル−カルボニル、Ｃ_１−１２ハロアルキル−カルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２ハロアルコキシ−カルボニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルホニル、アリール部が１、２又は３のＲ^１２で置換されてよいアリール−Ｃ_１−１２アルキル、又は複素環部が１、２又は３のＲ^１２で置換されてよい複素環−Ｃ_１−１２アルキルを示し、
Ｒ^１２は、水素、ハロゲン、シアノ、ニトロ、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ又はＣ_１−１２アルコキシ−カルボニルを示し、
ｍは、１又は２を示し、
上記で定義した基は更にハロゲン、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_１−１２アルコキシ、シアノ、Ｃ_１−１２ハロアルコキシ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、Ｃ_１−１２ハロアルキルスルホニル、ヒドロキシ又はメルカプトからなる任意の置換基で置換されてもよい。

Z is _{hydrogen, C 1-12} haloalkyl, _{nitro, C 1-12} alkoxy, _{cyano, C 1-12 haloalkoxy, C 1-12 alkylsulfenyl, C 1-12 alkylsulfinyl, C 1-12} alkylsulfonyl, C _1-12 haloalkylsulfenyl, C _1-12 haloalkylsulfinyl, C _1-12 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-12 alkyl or C _1-12 haloalkyl;
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkoxy-carbonyl , C _1-12 alkoxy, C _1-12 alkyl, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkylthio, C _1-12 alkylsulfinyl or C _1-12 alkylsulfonyl, provided that R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkyl-carbonyl or C _1-12 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl-carbonyl, C _1-12 alkyl-thiocarbonyl, C _1-12 haloalkyl-carbonyl, C _1-12 haloalkyl-thiocarbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkylamino-thiocarbonyl, di (C _1-12 alkyl) amino-carbonyl, di (C _1-12 alkyl) amino- Thiocarbonyl, C _1-12 alkoxyamino-carbonyl, C _1-12 alkoxyamino-thiocarbonyl, C _1-12 alkoxy-carbonyl, C _1-12 alkoxy-thiocarbonyl, C _1-12 thioalkoxy-carbonyl, C _{1 -12} thioalkoxy - _{thiocarbonyl, C 1-12} alkylsulfamoyl _{Alkylsulfonyl, C 1-12 haloalkylsulfonyl, C 3-8} cycloalkyl - _{carbonyl, C 2-12} alkenyl - _{carbonyl, C 2-12} alkynyl - _{carbonyl, C 3-8} cycloalkyl _{-C 1-12} alkyl - carbonyl, C _1-12 alkylsulfenyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfinyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfonyl-C _1-12 alkyl-carbonyl, C _1-12 alkyl - carbonyl _{-C 1-12} alkyl - _{carbonyl, C 3-8} cycloalkylamino - _{carbonyl, C 2-12} alkenylamino - carbonyl or _{C 2-12} Arukiniamino - indicates a carbonyl,
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, the heterocycle being oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-12 alkyl or C _1-12 haloalkyl,
R ⁶ represents hydrogen, C _1-12 alkyl, C _1-12 alkylcarbonyl or C _1-12 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-12 alkyl R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently -C (R ⁹ ) (R ¹⁰ )-, -C (= O)-, -C (= N-OR ¹¹ )-, -N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-12 alkyl or C _1-12 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl-C _1-12 alkyl, C _1-12 alkyl-carbonyl, C _1-12 haloalkyl-carbonyl , C _1-12 alkoxy-carbonyl, C _1-12 haloalkoxy-carbonyl, C _1-12 alkylsulfonyl, C _1-12 haloalkylsulfonyl, aryl wherein aryl may be substituted with 1, 2 or 3 R ¹² C _1-12 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-12} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy or C _1-12 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _1-12 alkoxy, cyano, C _1-12 haloalkoxy, C _1-12 alkylsulfenyl, C _{1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, it may be substituted with any substituent consisting of hydroxy or mercapto.

In the compound of formula (I) of the present invention,
Next formula

で表される部分が次式：

The part represented by the following formula:

を示すか、
又は、Ｒ^２がヒドロキシ−カルボニル、Ｃ_１−６アルコキシ−カルボニル又はシアノの場合、
次式

Or
Or when R ² is hydroxy-carbonyl, C _1-6 alkoxy-carbonyl or cyano,
Next formula

で表される部分は次式：

The part represented by the following formula:

（式中、Ｒ^１は水素を示す。）
若しくは

(In the formula, R ¹ represents hydrogen.)
Or

（式中、Ｒ^１は非存在である。）
又はそれら位置異性体の混合物を示し、
Ｔが、次式（Ｔ−１）、（Ｔ−２）、（Ｔ−３）、（Ｔ−４）又は（Ｔ−５）のいずれかを示し、

(Wherein R ¹ is absent)
Or a mixture of these positional isomers,
T represents any one of the following formulas (T-1), (T-2), (T-3), (T-4) or (T-5),

Ｂが、Ｎ又はＣ−Ｘ^３を示し、
Ｘ^１、Ｘ^２、Ｘ^３、Ｘ^４及びＸ^５が、それぞれ独立して水素、ハロゲン、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ、シアノ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、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、Ｃ_１−６アシルアミノ、Ｃ_１−６アルコキシ−カルボニルアミノ、Ｃ_１−６ハロアルコキシ−カルボニルアミノ、Ｃ_１−６アルコキシ−イミノ、Ｃ_１−６ハロアルコキシ−イミノ、Ｃ_１−６アルキルスルホニルアミノ又は５フッ化硫黄を示し、
Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４及びＹ^５が、それぞれ独立して水素、ハロゲン、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_３−７シクロアルキル、Ｃ_３−７シクロハロアルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ、シアノ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、Ｃ_１−６ハロアルキルスルホニル、Ｃ_１−６アルキルスルホニルオキシ、Ｃ_１−６アルキルアミノスルホニル、Ｃ_１−６ハロアルキルアミノスルホニル、ジ（Ｃ_１−６アルキル）アミノスルホニル、ジ（Ｃ_１−６ハロアルキル）アミノスルホニル、ヒドロキシ、メルカプト、アミノ、Ｃ_１−６アルキルアミノ、ジ（Ｃ_１−６アルキル）アミノ、Ｃ_１−６アシルアミノ、Ｃ_１−６アルコキシ−カルボニルアミノ、Ｃ_１−６ハロアルコキシ−カルボニルアミノ、Ｃ_１−６アルキルスルホニルアミノ、Ｃ_１−６ハロアルキルスルホニルアミノ、トリ（Ｃ_１−６アルキル）シリル、Ｃ_１−６アルコキシ−イミノ、Ｃ_１−６ハロアルコキシ−イミノ、Ｃ_１−６アルコキシ−イミノ−Ｃ_１−６アルキル、Ｃ_１−６ハロアルコキシ−イミノ−Ｃ_１−６アルキル、Ｃ_１−６アルキルスルフィニルイミノ、Ｃ_１−６アルキルスルフィニルイミノ−Ｃ_１−６アルキル、Ｃ_１−６アルキルスルフィニルイミノ−Ｃ_１−６アルキル−カルボニル、Ｃ_１−６アルキルスルホキシイミノ、Ｃ_１−６アルキルスルホキシイミノ−Ｃ_１−６アルキル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６アルキル−カルボニル、アミノカルボニル、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、Ｃ_１−６アルキルアミノ−チオカルボニル、ジ（Ｃ_１−６アルキル）アミノ−カルボニル、ジ（Ｃ_１−６アルキル）アミノ−チオカルボニル又はヒドロキシカルボニルを示し、
Ｇが、次式Ｇ１からＧ９のいずれかを示し、

B represents N or C—X ³ ;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _1-6 alkoxy, C _1-6 haloalkoxy , _{cyano, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6} haloalkylsulfonyl, hydroxy, mercapto , Amino, C _1-6 acylamino, C _1-6 alkoxy-carbonylamino, C _1-6 haloalkoxy-carbonylamino, C _1-6 alkoxy-imino, C _1-6 haloalkoxy-imino, C _1-6 alkyl Represents sulfonylamino or sulfur pentafluoride,
Y ¹ , Y ² , Y ³ , Y ⁴ and Y ⁵ are each independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _3-7 cycloalkyl, C _3-7 cyclo _{haloalkyl, C 1-6 alkoxy, C 1-6} haloalkoxy, _{cyano, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1- 6} haloalkylsulfinyl, C _1-6 haloalkylsulfonyl, C _1-6 alkylsulfonyloxy, C _1-6 alkylaminosulfonyl, C _1-6 haloalkylaminosulfonyl, di (C _1-6 alkyl) aminosulfonyl, di (C _{1 -6} haloalkyl) aminosulfonyl, hydroxy, mercapto, _{amino, C 1-6} alkylamino , Di _{(C 1-6} alkyl) _{amino, C 1-6 acylamino, C 1-6} alkoxy - carbonyl _{amino, C 1-6} haloalkoxy - _{carbonylamino, C 1-6 alkylsulfonylamino, C 1-6} haloalkylsulfonyl Amino, tri (C _1-6 alkyl) silyl, C _1-6 alkoxy-imino, C _1-6 haloalkoxy-imino, C _1-6 alkoxy-imino-C _1-6 alkyl, C _1-6 haloalkoxy- Imino-C _1-6 alkyl, C _1-6 alkylsulfinylimino, C _1-6 alkylsulfinylimino-C _1-6 alkyl, C _1-6 alkylsulfinylimino-C _1-6 alkyl-carbonyl, C _1-6 alkylsulfonyl alkoximinoalkyl _{amino, C 1-6} alkylsulfonyl alkoximinoalkyl Mino _{-C 1-6 alkyl, C 1-6} alkoxy Sheet - _{carbonyl, C 1-6} alkyl -, _{aminocarbonyl, C 1-6} alkyl - amino, aminocarbonyl, - _{thiocarbonyl, C 1-6} alkylaminocarbonyl - thiocarbonyl, di _{(C 1-6} alkyl) amino - carbonyl Di (C _1-6 alkyl) amino-thiocarbonyl or hydroxycarbonyl,
G represents any of the following formulas G1 to G9,

Ｚが、水素、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_１−６アルコキシ、シアノ、Ｃ_１−６ハロアルコキシ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、Ｃ_１−６ハロアルキルスルホニル、ヒドロキシ又はチオールを示し、
ｋが、０、１、２、３又は４を示し、
Ｒが、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^１及びＲ^２が非存在であるか、それぞれ独立して水素、ハロゲン、シアノ、アミノ、アジド、ヒドロキシ、メルカプト、ヒドロキシ−カルボニル、Ｃ_１−６アルキルアミノ−カルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６アルコキシ、Ｃ_１−６アルキル、Ｃ_２−６アルケニル、Ｃ_２−６アルキニル、Ｃ_１−６アルキルチオ、Ｃ_１−６アルキルスルフィニル又はＣ_１−６アルキルスルホニルを示し、ただしＲ^１及びＲ^２は同時に非存在であることはなく、Ｒ^１及びＲ^２は同時に水素ではなく、
Ｒ^３が、水素、アミノ、ヒドロキシ、シアノ、Ｒ^８−ＣＨ_２−、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ、Ｃ_２−６アルケニル、Ｃ_２−６アルキニル、Ｃ_１−６アルキル−カルボニル又はＣ_１−６アルキル−カルボニルアミノを示し、
Ｒ^４が、水素、シアノ、カルボニル、チオカルボニル、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−６アルキル−カルボニル、Ｃ_１−６アルキル−チオカルボニル、Ｃ_１−６ハロアルキル−カルボニル、Ｃ_１−６ハロアルキル−チオカルボニル、Ｃ_１−６アルキルアミノ−カルボニル、Ｃ_１−６アルキルアミノ−チオカルボニル、ジ（Ｃ_１−６アルキル）アミノ−カルボニル、ジ（Ｃ_１−６アルキル）アミノ−チオカルボニル、Ｃ_１−６アルコキシアミノ−カルボニル、Ｃ_１−６アルコキシアミノ−チオカルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６アルコキシ−チオカルボニル、Ｃ_１−６チオアルコキシ−カルボニル、Ｃ_１−６チオアルコキシ−チオカルボニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルホニル、Ｃ_３−７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_３−７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_３−７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−カルボニル又はＣ_２−６アルキニアミノ−カルボニルを示し、
また、Ｒ^３とＲ^４が、それが結合する窒素原子と一緒になって３，４，５又は６員の、飽和又は不飽和の複素環を形成してもよく、該複素環はオキソ、チオキソ又はニトロで置換されてもよく、
Ｒ^５が、水素、シアノ、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^６が、水素、Ｃ_１−６アルキル、Ｃ_１−６アルキルカルボニル又はＣ_１−６アルコキシカルボニルを示し、
Ｒ^７が、水素又はＣ_１−６アルキルを示し
Ｒ^８が、フェニル、又は３、４、５若しくは６員の、飽和又は不飽和の複素環を示し、
Ｚ^１、Ｚ^２及びＺ^３が、それぞれ独立して−Ｃ（Ｒ^９）（Ｒ^１０）−、−Ｃ（＝Ｏ）−、−Ｃ（＝Ｎ−ＯＲ^１１）−、−Ｎ（Ｒ^１１）−、−Ｓ−、−Ｓ（＝Ｏ）−、−Ｓ（＝Ｏ）_２−又は−Ｓ（Ｏ）（＝Ｎ−Ｒ^１１）−を示し、
Ｒ^９及びＲ^１０が、それぞれ独立して水素、ハロゲン、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^１１が、水素、シアノ、ニトロ、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_３−７シクロアルキル−Ｃ_１−６アルキル、Ｃ_１−６アルキル−カルボニル、Ｃ_１−６ハロアルキル−カルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６ハロアルコキシ−カルボニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルホニル、アリール部が１、２又は３のＲ^１２で置換されてよいアリール−Ｃ_１−６アルキル、又は複素環部が１、２又は３のＲ^１２で置換されてよい複素環−Ｃ_１−６アルキルを示し、
Ｒ^１２が、水素、ハロゲン、シアノ、ニトロ、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ又はＣ_１−６アルコキシ−カルボニルを示し、
ｍが、１又は２を示し、
上記で定義した基は更にハロゲン、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_１−６アルコキシ、シアノ、Ｃ_１−６ハロアルコキシ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、Ｃ_１−６ハロアルキルスルホニル、ヒドロキシ又はメルカプトからなる任意の置換基で置換されてもよい、を示す場合の化合物を好適なものとして挙げることができる。

Z is _{hydrogen, C 1-6} haloalkyl, _{nitro, C 1-6} alkoxy, _{cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6} alkylsulfonyl, C _1-6 haloalkylsulfenyl, C _1-6 haloalkylsulfinyl, C _1-6 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-6 alkyl or C _1-6 haloalkyl,
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkoxy-carbonyl , C _1-6 alkoxy, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkylthio, C _1-6 alkylsulfinyl or C _1-6 alkylsulfonyl, wherein R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkyl-carbonyl or C _1-6 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl-carbonyl, C _1-6 alkyl-thiocarbonyl, C _1-6 haloalkyl-carbonyl, C _1-6 haloalkyl-thiocarbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkylamino-thiocarbonyl, di (C _1-6 alkyl) amino-carbonyl, di (C _1-6 alkyl) amino- Thiocarbonyl, C _1-6 alkoxyamino-carbonyl, C _1-6 alkoxyamino-thiocarbonyl, C _1-6 alkoxy-carbonyl, C _1-6 alkoxy-thiocarbonyl, C _1-6 thioalkoxy-carbonyl, C _{1 -6} thioalkoxy - _{thiocarbonyl, C 1-6 alkylsulfonyl, C 1-6} Haroarukirusu _{Honiru, C 3-7} cycloalkyl - _{carbonyl, C 2-6} alkenyl - _{carbonyl, C 2-6} alkynyl - _{carbonyl, C 3-7} cycloalkyl _{-C 1-6} alkyl - _{carbonyl, C 1-6} alkylsulfenyl - C _1-6 alkyl-carbonyl, C _1-6 alkylsulfinyl-C _1-6 alkyl-carbonyl, C _1-6 alkylsulfonyl-C _1-6 alkyl-carbonyl, C _1-6 alkyl-carbonyl-C _1-6 Represents alkyl-carbonyl, C _3-7 cycloalkylamino-carbonyl, C _2-6 alkenylamino-carbonyl or C _2-6 alkynamino-carbonyl,
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, which is oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-6 alkyl or C _1-6 haloalkyl,
R ⁶ represents hydrogen, C _1-6 alkyl, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-6 alkyl and R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently —C (R ⁹ ) (R ¹⁰ ) —, —C (═O) —, —C (= N—OR ¹¹ ) —, —N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-6 alkyl or C _1-6 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _3-7 cycloalkyl-C _1-6 alkyl, C _1-6 alkyl-carbonyl, C _1-6 haloalkyl-carbonyl , _{C 1-6} alkoxy - _{carbonyl, C 1-6} haloalkoxy - _{carbonyl, C 1-6 alkylsulfonyl, C 1-6} haloalkylsulfonyl, aryl aryl portion may be substituted with ^{R 12} in 1, 2 or 3 - C _1-6 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-6} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy or C _1-6 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _1-6 alkoxy, cyano, C _1-6 haloalkoxy, C _1-6 alkylsulfenyl, C _1-6 shown _{alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6} haloalkylsulfonyl, and it may also be substituted with any substituent consisting of hydroxy or mercapto The compounds of the case can be mentioned as suitable.

The following groups of novel pyrroline derivatives are preferred, which are in each case understood as a subgroup of compounds of the formula (I) described above.
Group 1:

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｒ、Ｂ及びＴは前記と同義を示し、Ｈａｌはフッ素、塩素、臭素又はヨウ素示す。）
群２：

(In the formula, X ¹ , X ² , X ⁴ , X ⁵ , R, B and T are as defined above, and Hal represents fluorine, chlorine, bromine or iodine.)
Group 2:

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５及びＲ、Ｂ及びＴは前記と同義を示し、Ｒ^２０は水素又はＣ_１−６アルキルを示し、
次式

Wherein X ¹ , X ² , X ⁴ , X ⁵ and R, B and T are as defined above, R ²⁰ is hydrogen or C _1-6 alkyl,
Next formula

で表される部分は
式：

The part represented by is the formula:

若しくは
式：

Or the formula:

又は、それら位置異性体の混合物を示す）
本明細書において、「アルキル」は、例えば、メチル、エチル、ｎ−もしくはｉｓｏ−プロピル、ｎ−、ｉｓｏ−、ｓｅｃ−もしくはｔｅｒｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、ｎ−オクチル、ｎ−ノニル、ｎ−デシル、ｎ−ウンデシル、ｎ−ドデシル等の直鎖状又は分枝状のＣ_１−１２アルキルを、好ましくはＣ_１−６アルキルを、より好ましくはＣ_１−４アルキルを示す。また、アルキルを構成の一部として有している各基における各アルキル部分は、上記「アルキル」で説明したものと同様のものを例示することができる。

Or a mixture of these positional isomers)
In the present specification, “alkyl” means, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n- Linear or branched C _1-12 alkyl such as octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc., preferably C _1-6 alkyl, more preferably C _1-4 Indicates alkyl. Further, examples of each alkyl moiety in each group having alkyl as a part of the configuration are the same as those described above for “alkyl”.

“Haloalkyl” is, for example, CH ₂ F, CHF ₂ , CF ₃ , CF ₂ Cl, CFCl ₂ , CF ₂ Br, CF ₂ CF ₃ , CFHCF ₃ , CH ₂ CF ₃ , CFClCF ₃ , CCl ₂ CF ₃ , CF ₂ CH ₃ , CF ₂ CH ₂ F, CF ₂ CHF ₂ , CF ₂ CF ₂ Cl, CF ₂ CF ₂ Br, CFHCH ₃ , CFHCHF ₂ , CFHCHF ₂ , CHFCF ₃ , CHFCF ₂ Cl, CHFCF ₂ Br, CFClCF ₃ , _{CCl 2 CF 3, CF 2 CF} 2 CF 3, CH 2 CF 2 CF 3, CF 2 CH 2 CF 3, CF 2 CF 2 CH 3, CHFCF 2 CF 3, CF 2 CHFCF 3, CF 2 CF 2 CHF 2, _{CF 2 CF 2 CH 2 F,} CF 2 CF 2 CF 2 Cl, CF 2 CF 2 CF 2 B _{, CH (CF 3) CF 3} , CF (CF 3) CF 3, CF (CF 3) CF 2 Br, CF 2 CF 2 CF 2 CF 3, CH (CF 3) CF 2 CF 3 or CF _(CF 3) CF ₂ CF ₃ represents a linear or branched C _1-12 alkyl, preferably C _1-6 alkyl, more preferably at least one hydrogen on C _1-4 alkyl is substituted with a halogen Also includes perfluoroalkyl, which represents a carbon chain and in which all substitutable hydrogens on the alkyl are replaced by fluorine. The haloalkyl may be further substituted with an optional substituent.

“Alkoxy” represents, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-, iso-, sec- or tert-butoxy, pentyloxy or hexyloxy, and is linear or branched C _{1 -12} , preferably C _1-6 , more preferably C _1-4 alkoxy. Alkoxy may be further substituted with any substituent.

  “Halogen” and each halogen moiety in each halogen-substituted group represents fluorine, chlorine, bromine and iodine, and preferably represents fluorine, chlorine and bromine.

“Cycloalkyl” refers to C _3-8 cycloalkyl of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, preferably C _3-7 cycloalkyl, more preferably C _3-6 cycloalkyl. Indicates. Further, examples of each cycloalkyl moiety in each group having cycloalkyl as a part of the configuration are the same as those described above for “cycloalkyl”.

  “Cyclohaloalkyl” refers to, for example, fluorocyclopropyl, chlorocyclopropyl, difluorocyclopropyl, dichlorocyclopropyl, undecafluorocyclohexyl.

“Alkenyl” refers to C _2-12 alkenyl, preferably C _2-6 alkenyl such as vinyl, allyl, 1-propenyl, 1- (or 2-, or 3-) butenyl, 1-pentenyl, and the like. Preferably _C2-5 alkenyl is shown, More preferably, _C2-4 alkenyl is shown.

“Alkynyl” refers to C _2-12 alkynyl, preferably C _2-6 alkynyl such as ethynyl, propargyl, 1-propynyl, butane-3-ynyl, pentane-4-ynyl, and more preferably C _{2− 5} alkynyl is shown, more preferably C _2-4 alkynyl.

“Aryl” refers to a C _6-12 aromatic hydrocarbon group, for example, phenyl, naphthyl, biphenyl, preferably a C _6-10 aromatic hydrocarbon group, more preferably a C ₆ aromatic hydrocarbon group. The group phenyl.

  “Heterocycle” refers to a 5- or 6-membered heterocyclic group containing at least one of N, O, S as a heteroatom, and the ring may be benzo-fused fused heterocyclic Or a carbon atom of the ring may be further substituted by oxo or thioxo.

Specific examples of the heterocyclic ring include pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, (saturation example)
Dihydropyrrolyl, dihydroisoxazolyl, dihydropyrazolyl, dihydrooxazolyl, dihydrothiazolyl (partially saturated examples)
List furyl, thienyl, pyrrolyl, isoxazolyl, pyrazolyl, oxazolyl, isothiazolyl, thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, benzoxazolyl, benzothiazolyl, quinolyl, etc. In addition, the heterocyclic ring may be substituted with any substituent.

Substituents “optionally substituted with any substituent” are, for example, amino, hydroxy, oxo, thioxo, halogen, nitro, cyano, isocyano, mercapto, isothiocyanate, carboxy, carboxamide, SF ₅ , aminosulfonyl, Alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkylcarbonyl-amino, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyl Oxycarbonyl, aryloxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio , Alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfenyl, alkylsulfinyl, isomers, including alkylsulfinyl, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylphosphinyl, alkylphosphonyl, isomer Alkyl phosphinyl containing, alkyl phosphonyl containing isomers, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl, N-alkylcarbonyl-aminocarbonyl, N-alkylcarbonyl-N-alkylaminocarbonyl, aryl , Aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, heterocycle, trialkylsilyl, alkoxyalkyl, alkylthioalkyl , Alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkylcarbonyl or haloalkoxyalkyl, preferably chloro , Fluoro, bromo, iodo, amino, nitro, cyano, hydroxy, thio or carboxy.

  The compound of the formula (I) of the present invention can be obtained, for example, by the following production method (a), (b) or (c).

Manufacturing method (a)
Formula (II):

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｒ、Ｂ及びＴは前記と同義を示す）
で表される化合物を必要であれば適当な希釈剤の存在下、ハロゲン化剤と反応させる方法。

(Wherein X ¹ , X ² , X ⁴ , X ⁵ , R, B, and T have the same meanings as described above)
A method of reacting a compound represented by the above with a halogenating agent in the presence of a suitable diluent if necessary.

Production method (b): When R ^{2 of} formula (I) represents hydroxy-carbonyl or C _1-6 alkoxy-carbonyl,
Step (b-1):
Formula (III):

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｂ、Ｒ及びＲ^２０は前記と同義を示す）
で表される化合物と
式（ＩＶ）：

(Wherein X ¹ , X ² , X ⁴ , X ⁵ , B, R and R ²⁰ have the same meanings as described above)
And a compound represented by formula (IV):

（式中、Ｔは前記と同義を示す）
で表される化合物を必要であれば適当な希釈剤及び／又は銅試薬の存在下で反応させ、
ステップ（ｂ−２）：
式（Ｖ）：

(Wherein T is as defined above)
If necessary, the compound represented by the above is reacted in the presence of a suitable diluent and / or copper reagent,
Step (b-2):
Formula (V):

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｒ、Ｂ、Ｔ及びＲ^２０は前記と同義を示す）
で表される化合物とし、続いて、必要であれば適当な希釈剤及び／又は塩基存在下、ピロリン環上の二重結合の位置をシフトさせ、
式（Ｉ−Ｉ）：

(Wherein, X ¹ , X ² , X ⁴ , X ⁵ , R, B, T and R ²⁰ have the same meanings as described above)
Followed by shifting the position of the double bond on the pyrroline ring in the presence of a suitable diluent and / or base, if necessary,
Formula (II):

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｒ、Ｂ、Ｔ及びＲ^２０は前記と同義を示し、
次式

(Wherein X ¹ , X ² , X ⁴ , X ⁵ , R, B, T and R ²⁰ have the same meanings as described above,
Next formula

で表される部分は
式：

The part represented by is the formula:

若しくは
式：

Or the formula:

又は、それら位置異性体の混合物を示す）
で表される本発明の式（Ｉ）に含まれる化合物を製造する方法。

Or a mixture of these positional isomers)
The method of manufacturing the compound contained in Formula (I) of this invention represented by these.

Production method (c): When R ^{2 of} formula (I) represents hydroxy-carbonyl or C _1-6 alkoxy-carbonyl, and T represents T-1,
Formula (I-II):

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４、Ｒ、Ｂ及びＲ^２０は前記と同義を示し、次式

(Wherein, X ¹ , X ² , X ⁴ , X ⁵ , Y ¹ , Y ² , Y ³ , Y ⁴ , R, B and R ²⁰ have the same meanings as described above,

で表される部分は
式：

The part represented by is the formula:

若しくは
式：

Or the formula:

又は、それら位置異性体の混合物を示す）で表される化合物と
次式：Ｈ−Ｇ
（式中、Ｈは水素を示し、Ｇは前述のＧ１からＧ９のいずれかを示す）
で表される化合物を、必要であれば適当な希釈剤及び／又は適当な塩基存在下、反応させる方法。

Or a mixture of these positional isomers) and the following formula: HG
(In the formula, H represents hydrogen and G represents any of G1 to G9 described above)
If necessary, the compound represented by the method of reacting in the presence of a suitable diluent and / or a suitable base.

  The production method (a) can be carried out according to a usual organic synthesis method.

  Examples of the halogenating agent in the production method (a) include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-hydantoin, 1 , 3-dibromo-5,5-dimethylhydantoin, benzyltrimethylammonium tetrachloroiodate, sodium hypochlorite and the like.

The reaction of the production method (a) can be carried out in a suitable diluent. Examples of the diluent used in this case are as follows:
Aliphatic hydrocarbons (hexane, cyclohexane, heptane, etc.), aliphatic halogenated hydrocarbons (dichloromethane, chloroform, carbon tetrachloride, dichloroethane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, Others), ethers (diethyl ether, dibutyl ether, dimethoxyethane (DME), tetrahydrofuran, dioxane, etc.), esters (ethyl acetate, ethyl propionate, etc.), acid amides (dimethylformamide (DMF), dimethyla Examples include cetamide (DMA), N-methylpyrrolidone, etc.), nitriles (acetonitrile, propionitrile, etc.), dimethyl sulfoxide (DMSO), water, or a mixed solvent thereof.

  The production method (a) can be carried out within a substantially wide temperature range. In general, it can be carried out between about −78 to about 200 ° C., preferably between about −10 to about 100 ° C. The reaction is preferably carried out under normal pressure, but can be operated under pressure or reduced pressure. The reaction time is 0.1 to 72 hours, preferably 1 to 24 hours.

  In carrying out the production method (a), for example, 1 mol of a compound of the formula (II) is reacted with 1 to 2 mol of a halogenating agent in a diluent such as carbon tetrachloride. The compound of I) can be obtained.

  Of the compounds of formula (II), which are raw materials in the production method (a), typical examples of known compounds and cited references are listed.

In the compound of formula (I), when (T) is (T-1),
5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazole-1 -Yl) benzonitrile, 2- (1H-1,2,4-triazol-1-yl) -5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] benzonitrile, 5- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H- Pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- {3- [3,4-dichloro-5- (trifluoromethyl) phenyl] -3 -(Trifluoromethyl) -3,4-dihy B-2H-pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- {3- [3-fluoro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- [3- ( 2,6-dichloropyridin-4-yl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazol-1- Yl) benzonitrile, 5- {3- [2-chloro-6- (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl } -2- (1H-1,2,4-triazo Ru-1-yl) benzonitrile, 5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- 5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 1- (4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (Trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-cyanophenyl) -1H-pyrazole-4-carbonitrile (cited document WO 2009/097992)
In the compound of formula (I), when (T) is (T-2),
N- {2-chloro-4- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- { 2-chloro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- { 2-Bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} acetamide, N- {2 -Bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2 -Brolomo-4 [3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} cyclopropanecarboxamide, N- {2-bromo- 4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} -2- (methylsulfanyl) acetamide, N -{2-Bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} -2- ( Methylsulfinyl) acetamide, N- {2-bromomo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- -Yl] benzyl} -2- (methylsulfonyl) acetamide, N- {4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole -5-yl] -2- (trifluoromethyl) benzyl} propanamide, N- {2-methyl-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-Dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2-nitro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-Dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2-cyano-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-Dihydride Ro-2H-pyrrol-5-yl] benzyl} propanamide, N- (2-bromo-4- {3- [3,4-dichloro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) ) -3,4-dihydro-2H-pyrrol-5-yl} benzyl) propanamide, N- (2-bromo-4- {3- [3-fluoro-5- (trifluoromethyl) phenyl] -3- (Trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} benzyl) propanamide, N- (4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- ( Trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzyl) propanamide, N- (4- {3- [2,6-bis (trifluoromethyl) pyridine-4 -Il] 3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzyl) propanamide, N- (1- {4- [3- (3,4,5-tri Chlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] phenyl} ethyl) propanamide, N- [1- (4- {3- [3,5-bis ( Trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} phenyl) ethyl] cyclopropanecarboxamide (cited document WO 2009/097992)
In the compound of formula (I), when (T) is (T-3),
N- {5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-indene-1 -Yl} propanamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2, 3-dihydro-1H-inden-1-yl} acetamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole -5-yl] -2,3-dihydro-1H-inden-1-yl} propanamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl)- 3,4-dihydro-2H-pyrrole-5 Yl] -2,3-dihydro-1H-inden-1-yl} cyclopropanecarboxamide, 3,3,3-trifluoro-N- {5- [3- (3,4,5-trichlorophenyl)- 3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} propanamide, 2- (methylsulfanyl) -N- { 5- [3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-indene-1 -Yl} acetamide, 2- (methylsulfinyl) -N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Il] -2 3-dihydro-1H-inden-1-yl} acetamide, 2- (methylsulfonyl) -N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} acetamide, N- (5- {3- [3,4-dichloro-5- (trifluoromethyl) ) Phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) propanamide, N- (5- { 3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-indene-1 -Yl) propanami N- (5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) propanamide, N- (5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) ) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) -2- (methylsulfonyl) acetamide (cited document WO 2009/112275)
In the compound of formula (I), when (T) is (T-4),
4- [3- (3,5-Dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2-methyl-N- (thietan-3-yl) benzamide 2-methyl-N- (thietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Yl] benzamide, 2-methyl-N- (1-oxidethietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4 -Dihydro-2H-pyrrol-5-yl] benzamide, 2-methyl-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-trichlorophenyl)- 3- (Trifluoromethyl) -3,4-dihy 2H-pyrrol-5-yl] benzamide, 2-chloro-N- (thietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl)- 3,4-dihydro-2H-pyrrol-5-yl] benzamide, 2-chloro-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-tri Chlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, 2-bromo-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, N- (1,1-dioxidethietane- 3-yl) -4- [3- (3,4,5 Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (toefluoromethyl) benzamide, N- (1,1-dioxidethietane-3- Yl) -2-nitro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, 4- { 3- [3,4-Dichloro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (thietane) -3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Methyl- N- (thietan-3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 Yl} -2-methyl-N- (1-oxidethietan-3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3 , 4-Dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1,1-dioxidethietan-3-yl) benzamide, 4- {3- [2,6-bis (trifluoro) ) Pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (thietan-3-yl) benzamide, 4- {3 -[2,6-bis (trifluoro) Lysin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1-oxidethietan-3-yl) benzamide, 4 -{3- [2,6-bis (trifluoro) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1,1-Dioxidethietan-3-yl) benzamide (cited document WO2009 / 080250)
In the compound of formula (I), when (T) is (T-5),
5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2-fluorobenzonitrile, 2-fluoro-5- [3 -(3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzonitrile, 5- (3-bromo-4-fluorophenyl)- 3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole, methyl 2-methyl-4- [3- (3,4,5-trichlorophenyl) ) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzoate, 2-methyl-4- [3- (3,4,5-trichlorophenyl) -3- (tri Fluoromethyl ) -3,4-dihydro-2H-pyrrol-5-yl] benzoic acid, 2-bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] benzonitrile, 4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Yl] -2- (trifluoromethyl) benzonitrile, 5- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole -5-yl} -2-fluorobenzonitrile, 3- [3,5-bis (trifluoromethyl) phenyl] -5- (3-bromo-4-fluorophenyl) -3- (trifluoromethyl) -3 , 4 Dihydro-2H-pyrrole, methyl 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Methylbenzoate, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylben Zoic acid, 4- {3- [3,5-bis (trifluoro) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzonitrile, 4- {3- [3,5-bis (trifluoro) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-chlorobenzonitrile, 4- [ 5 (3-Bromo-4-fluorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-3-yl] -2,6-bis (trifluoromethyl) pyridine, 5- {3 -[2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-fluorobenzonitrile, methyl 4 -{3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzoate; 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzo Ikua 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Bromobenzonitrile, 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} 2-Methylbenzonitrile (cited documents JP2007-91708, JP2008-133273, WO2009 / 072621, WO2009 / 097992, WO2009 / 112275)

  Step (b-1) in the production method (b) can be performed, for example, according to the method described in EP1538138 or WO2009-079992 (A1).

  The reaction of step (b-1) in the production method (b) can be carried out in a suitable diluent, and examples of the diluent used in this case are the same as those of the diluent in the production method (a). is there.

  Suitable copper reagents in step (b-1) in the production method (b) include copper oxide (I), copper oxide (II), copper acetyl acetate (II), copper acetate (II), copper cyanide (I) and the like. Is mentioned.

  Step (b-1) in the production method (b) can be carried out within a substantially wide temperature range. In general, it can be carried out between about 20 and about 200 ° C, preferably between about 40 and about 150 ° C. The reaction is preferably carried out under normal pressure, but can be operated under pressure or reduced pressure. The reaction time is 0.1 to 72 hours, preferably 1 to 24 hours.

  In carrying out step (b-1) in the production method (b), for example, from 1 mol of the compound of the formula (III) to 0.5 mol to 2 mol of the formula (IV) in a diluent such as toluene. The corresponding compound of formula (V) can be obtained by reacting the compound with 0.1 to 2 moles of a copper reagent such as copper (I) oxide.

  The starting compound of formula (III) in step (b-1) in the production method (b) is novel, and representative examples thereof include methyl 3- (3,5-dichlorophenyl) -4,4,4-trifluorobutene- 2-Enoate, methyl 4,4,4-trifluoro 3- (3,4,5-trichlorophenyl) -buten-2-enoate, ethyl 4,4,4-trifluoro 3- (3,4,5- Trichlorophenyl) -butene-2-enoate, isopropyl 4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) -butene-2-enoate, tert-butyl 4,4,4-trifluoro3 -(3,4,5-trichlorophenyl) -butene-2-enoate, benzyl 4,4,4-trifluoro 3- (3,4,5-trichlorophenyl) -butene- -Enoate, methyl [3,5-bis (trifluoromethyl) phenyl] -4,4,4-trifluorobutene-2-enoate, ethyl [3,5-bis (trifluoromethyl) phenyl] -4,4 , 4-trifluorobutene-2-enoate, isopropyl [3,5-bis (trifluoromethyl) phenyl] -4,4,4-trifluorobutene-2-enoate, methyl 3- [2,6-bis ( Trifluoromethyl) pyridin-4-yl] -4,4,4-trifluorobutene-2-enoate.

  The compound of formula (IV) as a raw material in step (b-1) in the production method (b) includes known compounds, and representative examples thereof include 3-bromo-4-fluorobenzyl isocyanide, 2-fluoro-5- (isocyano). And methyl) benzonitrile and 5- (isocyanomethyl) -2- (1H-1,2,4-triazol-1-yl) benzonitrile. The compounds are described in the literature Tetrahedron Letters 29 (27), (1988), 3343-3346; Heterocycles 31 (1990), 1855-1860; Journal of Organic Chemistry 70 (2005), 3542-3553; Organic 1 9), (2003), 1474-1479.

  Step (b-2) in the production method (b) is described in JP2007-91708, Chem. Lett. 1985, 1601-1604.

  The reaction of step (b-2) in the production method (b) can be carried out in a suitable diluent, and examples of the diluent used in this case are the same as the example of the diluent in the production method (a). is there.

  Sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc. as suitable bases in step (b-2) in the production method (b) Alkali metal base, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, 4-tert-butyl-N, N-dimethylaniline, pyridine, picoline, lutidine And organic bases such as diazabicycloundecene, diazabicyclooctane and imidazole.

  The reaction of step (b-2) in the production method (b) can be carried out within a substantially wide temperature range. In general, it can be carried out between about −78 to about 200 ° C., preferably between about −10 to about 100 ° C. In addition, the reaction is desirably performed under normal pressure, but can be operated under pressure or reduced pressure. The reaction time is 0.1 to 72 hours, preferably 1 to 24 hours.

  In carrying out step (b-2) in production method (b), for example, 1 to 0.1 mol of a base such as diazabicyclo in a diluent such as pyridine is used per 1 mol of compound of formula (V). By reacting undecene, the target compound of the formula (II) contained in the compound of the present invention can be obtained.

  The compound of the formula (V) of the raw material in step (b-2) in the production method (b) is typically methyl 2- (3-bromo-4-fluorophenyl) -4- (3,5-dichlorophenyl) -4. -(Trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, methyl 2- (3-bromo-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4 -(Trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, ethyl 2- (3-bromo-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4 -(Trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, isopropyl 2- (3-bromo-4-fluorophenyl) -4- (3,4, -Trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, tert-butyl 2- (3-bromo-4-fluorophenyl) -4- (3,4 , 5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, benzyl 2- (3-bromo-4-fluorophenyl) -4- (3,4 , 5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, methyl 2- (3-cyano-4-fluorophenyl) -4- (3,4 , 5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, ethyl 2- (3-cyano- -Fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, isopropyl 2- (3-cyano-4 -Fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate, methyl 2- [3-cyano-4 -(1H-1,2,4-triazol-1-yl) phenyl] -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- 3-carboxylate, methyl 4- [3,5-bis (trifluoromethyl) phenyl] -2- (3-bromo-4-fluorophenyl) -4- (trifluoromethyl)- , 4-Dihydro-2H-pyrrole-3-carboxylate, methyl 4- [3,5-bis (trifluoromethyl) phenyl] -2- (3-cyano-4-fluorophenyl) -4- (trifluorophenyl) ) -3,4-dihydro-2H-pyrrole-3-carboxylate, methyl 4- [2,6-bis (trifluoromethyl) pyridin-4-yl] -2- (3-bromo-4-fluorophenyl) Examples include -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate.

  The production method (c) can be carried out according to the method described in WO2009-079992 (A1).

  The reaction of the production method (c) can be carried out in a suitable diluent, and examples of the diluent used at that time are the same as those of the diluent of the production method (a).

  A representative example of the compound of formula (I-II) in the production method (c) is methyl 5- (3-bromo-4-fluorophenyl) -3- (3,5-dichlorophenyl) -3- (trifluoromethyl). -3,4-dihydro-2H-pyrrole-4-carboxylate, methyl 5- (3-bromo-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, methyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, ethyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- Trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, isopropyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- ( Trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, tert-butyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3 -(Trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, benzyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3 -(Trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, methyl 3- [3,5-bis (trifluoromethyl) fur Nyl] -5- (3-cyano-4-fluorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, methyl 5- (3-cyano-4-fluoro Phenyl) -3- [4-fluoro-3- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate, methyl 3- [2,6 -Bis (trifluoromethyl) pyridin-4-yl] -5- (3-cyano-4-fluorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate Can be mentioned.

  The reaction of the production method (c) includes lithium hydride, sodium hydride, potassium hydride, lithium amide, sodium amide, lithium diisopropylamide, butyl lithium, tert-butyl lithium, trimethylsilyl lithium, lithium hexamethyldisilazide as a base, Alkali metal bases such as sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium tert-butoxide, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N, N-dimethylaniline N, N-diethylaniline, 4-tert-butyl-N, N-dimethylaniline, pyridine, picoline, lutidine, diazabicycloundecene, diazabicyclooctane, It can be carried out using an organic base such as imidazole.

  The production method (c) can be carried out within a substantially wide temperature range. In general, it can be carried out between about −78 to about 200 ° C., preferably between about −10 to about 200 ° C. The reaction is preferably carried out under normal pressure, but can be operated under pressure or reduced pressure. The reaction time is 0.1 to 72 hours, preferably 0.1 to 48 hours.

  In carrying out the production method (c), for example, 1 mol to 3 mol in the presence of 1 mol to 3 mol of a base such as potassium carbonate in a diluent such as DMF in 1 mol of the compound of the formula (I-II) By reacting an amount of H-G, for example H-G6, the corresponding inventive compound of formula (I) can be obtained.

  The compounds of the formula (I-II-Br) and the formula (I-II-CN) included in the raw material formula (I-II) in the production method (c) can be produced by the method described in Scheme 1.

（式中、Ｘ^１、Ｘ^２、Ｘ^４、Ｘ^５、Ｙ^１、Ｙ^２、Ｙ^４、Ｒ、Ｂ及びＲ^２０は前記と同義を示し、Ｓｔｅｐ ｃ−１及びＳｔｅｐ ｃ−２は製法（ｂ）に準じて行うことができ、Ｓｔｅｐ ｃ−３で、式（Ｉ−ＩＩ−Ｂｒ）の化合物に必要であれば適当な希釈剤存在下、シアノ試薬及び／又は触媒を反応させ式（Ｉ−ＩＩ−ＣＮ）の化合物とし、Ｓｔｅｐ ｃ−３の反応は、適当な希釈剤中で実施することができ、その際使用される希釈剤の例として、製法（ａ）の希釈剤例と同様であるが、望ましくはジメチルホルムアミド（ＤＭＦ）を挙げることができ、Ｓｔｅｐ ｃ−３の反応は、適当な触媒存在下で実施することができ、その際使用される触媒の例として、
Ｐｄ（ＰＰｈ_３）_４、Ｐｄ_２（ｄｂａ）_３、Ｐｄ_２（ｄｂａ）_３ＣＨＣｌ_３、（ｄｂａ＝ジベンジリデンアセトン）、Ｐｄ（ＰＰｈ_３）_２Ｃｌ_２、Ｐｄ（ＯＡｃ）_２、ＣｕＩ、ＣｕＣＮなどの遷移金属等を用いて実施することができ、また、必要であれば、トリフェニルホスフィン、１，２−ビス（ジフェニルホスフィノ）エタン、１，３−ビス（ジフェニルホスフィノ）プロパン、１，４−ビス（ジフェニルホスフィノ）ブタン、１，１’−ビス（ジフェニルホスフィノ）フェロセン、２，２’−ビス（ジフェニルホスフィノ）−１，１’−ビナフタレン（ＢＩＮＡＰ）、４，５−ビス（ジフェニルホスフィノ）−９，９−ジメチルキサンテン（Ｘａｎｔｐｈｏｓ）、トリブチルフォスフィン等のフォスフィン系配位子を用いて実施することができ、Ｓｔｅｐ ｃ−３の反応において用いられるシアノ化試薬として、シアン化亜鉛、シアン化銅、シアン化ナトリウム、シアン化カリウム、シアン化銀（Ｉ）、シアン化銅（Ｉ）、トリメチルシリルシアニド、ヘキサシアノ鉄（ＩＩ）酸カリウム三水和物を代表例として挙げることができ、Ｓｔｅｐ ｃ−３は、実質的に広い温度範囲内において実施することができる。一般には、約０から約２００℃、好ましくは、約３０から約１８０℃の間で実施できる。また、該反応は常圧の下で行うことが望ましいが、加圧または減圧下で操作することもできる。反応時間は、０．１から７２時間であり、好ましくは、０．１から２４時間であり、Ｓｔｅｐ ｃ−３を実施するにあたっては、例えば、式（Ｉ−ＩＩ−Ｂｒ）の化合物１モルに対し、希釈剤例えばＤＭＦ中、触媒量のＰｄ（ＰＰｈ_３）_４の存在下、０．５モルから３モル量のシアノ化試薬例えばシアン化亜鉛を反応させることにより本発明の式（Ｉ−ＩＩ）の化合物に含まれる式（Ｉ−ＩＩ−ＣＮ）の化合物を得ることができる。）

(In the formula, X ¹ , X ² , X ⁴ , X ⁵ , Y ¹ , Y ² , Y ⁴ , R, B and R ²⁰ are as defined above, and Step c-1 and Step c-2 are the production methods ( b), and in Step c-3, if necessary for the compound of the formula (I-II-Br), a cyano reagent and / or a catalyst are reacted in the presence of a suitable diluent. -II-CN) and the reaction of Step c-3 can be carried out in a suitable diluent. Examples of the diluent used in this case are the same as those of the diluent in production method (a). Preferably, dimethylformamide (DMF) can be mentioned, and the reaction of Step c-3 can be carried out in the presence of a suitable catalyst. Examples of the catalyst used in this case are as follows:
Pd (PPh ₃ ) ₄ , Pd ₂ (dba) ₃ , Pd ₂ (dba) ₃ CHCl ₃ , (dba = dibenzylideneacetone), Pd (PPh ₃ ) ₂ Cl ₂ , Pd (OAc) ₂ , CuI, CuCN, etc. In addition, if necessary, triphenylphosphine, 1,2-bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) propane, 1, 4-bis (diphenylphosphino) butane, 1,1′-bis (diphenylphosphino) ferrocene, 2,2′-bis (diphenylphosphino) -1,1′-binaphthalene (BINAP), 4,5-bis Using phosphine-based ligands such as (diphenylphosphino) -9,9-dimethylxanthene (Xantphos) and tributylphosphine Examples of cyanating reagents that can be used and used in the reaction of Step c-3 include zinc cyanide, copper cyanide, sodium cyanide, potassium cyanide, silver (I) cyanide, copper (I) cyanide, trimethylsilyl cyanide. Nido and potassium hexacyanoferrate (II) trihydrate can be mentioned as representative examples, and Step c-3 can be carried out within a substantially wide temperature range. In general, it can be carried out between about 0 to about 200 ° C, preferably between about 30 to about 180 ° C. The reaction is preferably carried out under normal pressure, but can be operated under pressure or reduced pressure. The reaction time is 0.1 to 72 hours, preferably 0.1 to 24 hours. In carrying out Step c-3, for example, 1 mol of the compound of the formula (I-II-Br) is added. In contrast, by reacting 0.5 to 3 moles of a cyanating reagent such as zinc cyanide in a diluent such as DMF in the presence of a catalytic amount of Pd (PPh ₃ ) ₄ , the formula (I-II) The compound of formula (I-II-CN) contained in the compound of )

The compound of the formula (HG), which is a raw material in the production method (c), includes many compounds represented by H-G2, H-G3, H-G4, H-G5, H-G6, H-G8, and H-G9. Is a known compound, and specific examples thereof include 1H-imidazole,
1H-pyrazole,
4-methyl-1H-pyrazole,
4-fluoro-1H-pyrazole,
4-chloro-1H-pyrazole,
4-bromo-1H-pyrazole,
4-iodo-1H-pyrazole,
4-nitro-1H-pyrazole,
3-trifluoromethyl-1H-pyrazole,
4-trifluoromethyl-1H-pyrazole,
4-cyano-1H-pyrazole,
1H-1,2,3-triazole,
1H-1,2,4-triazole,
1H-tetrazole,
5-methyl-1H-tetrazole,
5- (methylthio) -1H-tetrazole and the like.

  Some of the compounds of the formula (I) of the present invention have an asymmetric carbon, and therefore the compounds include optical isomers.

  The compounds according to the invention exhibit a strong insecticidal action and can therefore be used as insecticides. Furthermore, the compounds of the present invention show a strong control effect against harmful insects without imposing any harmful side effects of the drugs on the cultivated plants. Thus, the compounds of the present invention can be used to combat a wide range of pest species such as harmful sucking insects, chewable insects as well as other plant parasitic pests, storage insects, sanitary pests, etc. These can be applied for the purpose of extermination. Examples of harmful harmful animals are as follows.

  With respect to insects, Coleoptera, for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaum, and Eraclacina cactiatum. fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp. hamus alternatus, Lissohoptrus oryzophilus, Lyctus bruneus, aracophora femoraris, Aracophora femoriris;・ Rapae, Spodoptera litura, Mamestra brassicae, Chilo supresalis, Pyrasta nuras nubilalis, Efestia cautella, Adoxophyes orana, Carpocapsa pomerella, Agrotisfucosella. ), Heliothis virescens, Phyllocnistis citrella; Hemiptera, for example, Nephotetics cinchetics, Niraparvata lugens (Niraparvata lugens) ilaparvata lugens), Pseudococcus comstocki, Unapsis yanonensis, Mizus persigos, Aphis pisgo (Rhopalosiphum pseudobrasicas), Stephanitis nashi, Nezara spp. ), Trialeurodes vaporariorum, Psylla spp .; Common order, eg, Trips palmi, Franklinella occidental; (Blatella germanica), Periplaneta americana, Grylotalpa Africana, Locusta migratria, Lacusta migratori, etc. itames speratus, Coptothermes formosanus; Diptera, eg Musca domestica, Aedes aegypti, p. ), Anopheles sinensis, Culex tritaenorinchus, Liriomyza torifoilii.

  For example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citris, and Acropus pelocus p.

  With regard to nematodes, for example, Meloidogyne incognita, Bursaferencus lignicolus mamiya e kiyohara (Bursaphelenchus lignicoles e hei seide), Aferencode ), Pratylenchus spp.

  Furthermore, the compounds of the present invention exhibit excellent plant tolerance and favorable toxicity to warm-blooded animals and are well tolerated by the environment and are therefore suitable for protecting plants and plant parts.

  Application of the compounds of the present invention can result in increased yield and improved quality of the harvested material. Furthermore, said compounds are used in the protection of stored products and in the protection of materials, and in the hygiene field, in the fields of agriculture, horticulture, veterinary medicine, forests, gardens and recreational facilities, especially harmful animals, in particular insects, spiders Suitable for combating helminths, nematodes and molluscs. The compounds according to the invention can preferably be used as plant protection agents. The compounds of the present invention have activity against normally sensitive and resistant species and against all or some stages of development. The pests include, among others:

  From the order of the Anophura (Phiraraptera), for example, Damalinia spp., Haematopinus, Linognathus spp., Pedulus spp. Species (Trichodes spp.).

  From the arachnida, for example, Acarus siro, Aceria sheldoni. Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpis al p spp.), Bryobia praetiosa, Corioptes spp., Dermanissus gallinae, Eetetranmpi spp. Species (Euttranyctus spp.), Eriofies spp. (Er Ophyes spp.), Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodictus mactanths, , Oligonychus spp., Ornithodoros spp., Panonychus spp., Phylocoptruta olistus, Polyphat oles. Seed (Psor ptes spp.), Rhipicephalus spp., Rhizoglyhus spp., Sarcoptes spp., Scorpio maurus sp., Scorpio maurus sp. , Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

  From the bivalvia, for example, Dreissena spp.

  From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.

  From the order of the Coleoptera, for example, Acanthocelides obectus, Adoretus spp., Agelastica alni, Agrilotes, Agripotes, Species of the genus Anthomonia spp., Anthomus spp., Anthomus spp., Anthomus spp. ), Atomaria s species pp.), Atagenus spp., Bruchidius obectus, Bruchus spp., Cethorhynus spp., Clemon dus us (Conoderus spp.), Cosmopolites spp., Costelitra zelandica, Curculio spp., Cryptordelstemp. , Diabrotica species (Di abrotica spp., Epilacna spp., Faustinus cubae, Gibium pylloides, Heteronychus larphe, Heteronychus larphe (Hylotrapes bajulus), Hypera postica, Hypothenemus spp., Lachnosterna consanguinea (Lachnosterna consangine) ata), Lithophorthus oryzophilus, Lixus spp. ), Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monchmus sp. (Nauactus xanthographus), Niptus hololeucus, Orycetes rhinoceros (Orycese urineus tyrus) Da (Oxycetonia jucunda), Faedon-Kokueriae (Phaedon cochleariae), Firofaga species (Phyllophaga spp.), Popiria-japonica (Popillia japonica), Puremunotoripesu species (Premnotrypes spp.), Pushiiriodesu-Kurisokefara (Psylliodes chrysocephala), Puchinusu genus Species (Ptinus spp.), Rhizobius ventralis, Rhizopersa dominica, Sitophilus spp., Sphenophorus sp. (Sternechus spp.), Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychlo sp. Genus species (Xylotrechus spp.), Zabrus spp.

  From the order of the Collembola, for example, Onychiurus armatus.

  From the order of the Dermaptera, for example, Forficula auricularia.

  From the order of the Diplopoda, for example, Blanilus guttulatus.

  From the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio horturanus, Caliphora erythrocephalitis, (Ceratitis capitata), Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, sp. Genus sp. Dacus oleae, Delmat Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hillemia spp., Hylemyia spp. Hypobosca spp.), Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezar sp. Oestrus spp., Oscinella frit, Pegomia hyosciam i), Horbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paldosa, Walphalia Genus species (Wohlfhrtia spp.).

  From Gastropoda, for example, Arion spp., Biomphalaria spp., Bullinus spp., Deroceras spp., Garba sp. Galba spp.), Limnaea spp., Oncomellania spp., Succinea spp.

  From the helminths, for example, Ankylostoma duodenale, Ankylostoma ceranicum, Asylostoma brasiliensis (Acylostoma sri s. Ascaris rubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostoma spp. Ter, sp. Genus species (Cl norchis spp.), Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria cirium, Diphyllobulum raditam. , Echinococcus granulosus, Echinococcus multioculiris, Enterobius vermicularis, Fachyola sp. Monecus spp., Heterakis spp., Hymenolepis nana, Hyostronglus spp., Loa loa, Loa loa spp.), Esophagogostom spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp. spp., Ostertagia spp. spp. ), Schithosomogen spp., Strongyloides fueleborni, Strongyroides stercoralis, Stronoides s. Thorium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nersoni (Trichinella nersoni) Kinera pseudotuberculosis Pushi Laris (Trichinella pseudopsiralis), Trico Strong Angeles species (Trichostrongulus spp.), Torikyurisu-Torikyuria (Trichuris trichuria), Bancroft yarn worms (Wuchereria bancrofti).

  Furthermore, it is possible to control protozoa such as Eimeria.

  From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylonma (Campylomma libida), Caverelius spp., Simex spp., Creontiades dilutus, Dasynus piperis, cyprus D・ Hewetti (Dicocoris hetet) ti), Disdelcus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horchilus nobrillus, Horchilus, Leptocorisa spp., Leptogrosus phyllopus, Lygus spp., Macropes excavatus, Mirida spr. Oebalus spp., Pentomidae , Piesma quadrata, Piezodorus spp., Psallus seritus, Pseudasta suritus, R. genus S. , Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

  From the order of the Homooptera, for example, Acythosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurodes sp. (Aureurobus barodensis), Aleurothrixus spp., Amrasca spp., Anuraphis cardui, (Aonidiella sp.) , Aphis spp., Alboridi Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Auracorsum solsia (Aulacorthum sulani) spp.), Brachycaudus helichrysii, Brachycorus spl., Brevicoryne brasicae, Caligipona marginata in Calfa Tobakuna-Ranigera (Ceratovacuna lanigera), Kerukopidae (Cercopidae), Keropurasutesu species (Ceroplastes spp.), Kaetoshifon-Furagaefori (Chaetosiphon fragaefolii), Kionasupisu-Tegarenshisu (Chionaspis tegalensis), Kurorita-Onuki (Chlorita onukii), Kuromafisu Ju Grandy Cola (Chromaphis juglandicola), Chrysomphalus fixus, Cicadulina mbila, Cocomitilus halli, Coccus genus Coccus species p. ), Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis sp. Doralis spp., Drosica spp., Disapis spp., Dysmicoccus spp., Empoaska spp., Eriosoma spp. (Eriosoma spp.), Erythroneura spp., Eucelis bilobus tus, Geococcus coffaee, Homarodisco coagulata, Hyalopters arundinis, Iceria spdius, Icerya spp. spp.), Laodelfax striatellus, Lecanium spp., Lepidosaphes spp., Lipapis erysimispi Mahanaruva-Fimuburiorata (Mahanarva fimbriolata), Meranafisu-Sakkari (Melanaphis sacchari), Metokarufiera species (Metcalfiella spp.), Metoporofiumu-Dirodzumu (Metopolophium dirhodum), Moneria-Kosutarisu (Monellia costalis), Moneriopushisu-Pekanisu (Monelliopsis pecanis), Myzus Genus species (Myzus spp.), Nasonovia rivisnigri, Nehotetix spp., Nilaparvata lugens, Oncometia species opia spp. ), Orthezia praelonga, Parabemisia myricae, Paratriosa spp., P. purimai sp. Maidis), Phenacoccus spp., Phloeomysus passerini, Phorodon spiridi, Phyllospira spi. Planococcus spp., Protopulvinaria pyriformis, Pseudouracus spis pentagona, Pseudococcus spp. , Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesda gigas, Rasprococcus, Rasprococcus, Rasprococcus, Species (Rhopalosiphum spp.), Sythete Saissetia spp., Schaphoides titanus, Schizophis graminum, Selena spidus artigasso, Ferrata sp. furcifera), Sugatodes spp., Stictocephala festina, Tenaraphala maleaensis, Tinocaralis eolia tocina efoliae. (Tomaspis spp. ), Toxoptera spp., Trialureodes vaporariorum, Triosa spp., Typlocyba spp., Unaspius sp. Viteus vitifolii).

  From the order of the Hymenoptera, for example, a Diprion spp., A Hoplocampa spp., A Lasius spp., A Monomorium pharaonis (Monomomori phalaonis) Vespa spp.).

  From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

  From the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.

  From the order of the Lepidoptera, for example, Acronica major, Aedia leucomelas, Agrotis spp., Alabama argiacea, Alabama arsp. .), Barathra brassicae, Buculatrix thurberiella, Bupalus pinialus, Cacoecia podana, Cacoecia podanaca Pomonella (Carpocapsa pomonella), Keimatobia burumata (Chimatobia burumata), Chiro spp. Insulana (Earias insulana), Ephestia kuehniella, Euprotis chrysorhoea, Euxoa spp., Feltiera sp. (Galleria melonella), Helicoverpa spp., Heliothis spp., Hofmannophira pseudopapretella, Homomana magnap. Genus species (Laphygma spp.), Lysocolletis blanccardella, lithophane antennata, genus Loxagrotis albicostia (Loxogrotis albicosta) ria spp. ), Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythima espora, Olya sp. ), Panolis flammea, Pectinophora gossypiella, Phylocnistis citrolla, Pieris spt. odenia spp.), Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera sp. Tinea pelionella, Tineola bisselliella, Tortricix viridana, Trichoplusia spp.

  From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Bratella germanica, Grylotalpa de M. , Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.

  From the order of Siphonaptera, for example, Ceratophyllus spp., Xenopsila cheopes.

  From the order of the Symphyla, for example, Scutigerella immaculata.

  From the order of the Thysanoptera, for example, Variotrips biformis, Enneotrips flavens, Sp. Hercinothrips femorialis, Kakotrips spp., Ripiforotrips cruentats, Scirtopripus spp. damoni), Thrips species (Thrips spp.).

  From the order of the Thysanura, for example, Lepisma saccharina.

  Plant parasitic nematodes include, for example, Anguina spp., Apherenchoides spp., Belonoaimus spp., Bursaphelenchus spp. Dityrenchus dipsasi, Globodera spp., Heliocotylencus spp., Heterodera spp., Longidor spr. Meloidogyne spp.), Platylencus spp., Radfo Radophorus similis, Rotylenchus spp., Trichodorus spp., Tylenchorinchus spp., Tylenculus spp. Trans (Thlenchulus semipenetrans), Xifinema spp.

  Any plant and plant part can be treated according to the invention. In the context of the present invention, plants should be understood as meaning all plants and plant populations such as desirable and undesirable wild plants or cereal plants (including naturally occurring cereal plants). A cereal plant can be a plant obtainable by conventional plant breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including transgenic plants, depending on the rights of the plant breeder Plant varieties that can or cannot be protected are included. Plant parts are to be understood as meaning all parts and organs of the plant above and below the ground, such as buds, leaves, flowers and roots, for example leaves, needles. Stalks, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include collected material, as well as materials that grow asexually and reproductively, such as cuttings, tubers, rhizomes, side branches and seeds.

  The treatment of plants and plant parts with active compounds according to the invention can be carried out directly or grown by conventional treatment methods such as immersion, spraying, evaporation, atomization, scattering, application, injection. In the case of substances, in particular in the case of seeds, it is carried out by allowing the compounds to act on their surroundings, habitat or storage area by providing one or more coatings.

  The compounds of the present invention exhibit an osmotic effect, meaning that the compounds can penetrate the plant body and migrate from the underground part of the plant to the aerial part of the plant.

  As already mentioned above, it is possible to treat all plants and their parts according to the invention. In preferred embodiments, wild plant species and plant varieties, or those obtained by traditional biological breeding methods, such as cross-breeding or protoplast fusion, and portions thereof are treated. In a further preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) and parts thereof obtained by combining genetic engineering methods with conventional methods, as appropriate, are treated. The terms “part”, “part of plant” and “plant part” are as described above.

  Particularly preferably, in each case, plants of plant varieties that are commercially available or used are treated according to the invention. Plant varieties are understood to mean plants with new properties ("traits") obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These can be plant varieties, biotypes or genotypes.

  Depending on the plant species or plant varieties, their location and growth conditions (soil, weather, growth period, nutrients), the treatment according to the invention can lead to superadditive (“synergistic”) effects. Thus, for example, beyond the expected effect, the rate of application is reduced and / or the spectrum of activity is expanded and / or the activity of substances and compositions that can be used according to the invention is increased, the growth of plants is improved, the temperature is increased. Or increased tolerance to low temperatures, increased tolerance to drought or salt in water or soil, improved flowering ability, simplified harvesting, accelerated maturation, increased yield, improved quality of harvested products And / or increased nutritional value, storage stability and / or improved processability of the harvested product may occur.

Preferred transgenic plants or plant varieties (obtained by genetic engineering) to be treated according to the present invention are all provided with genetic material that uses genetic modification to confer a very advantageous and useful trait to these plants. Of plants. Examples of such characteristics are improved plant growth, increased tolerance to high or low temperatures, increased tolerance to straw or salt in water or soil, improved flowering ability, simplified harvesting, accelerated maturation Increasing the yield, improving the quality of the harvested product and / or increasing the nutritional value, improving the storage stability and / or processability of the harvested product. Further examples of particularly emphasized such traits have improved plant defense against harmful animals and microorganisms such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and certain herbicidal activities An increase in the tolerance of plants to compounds. Examples of transgenic plants include cereals (wheat, rice), corn, soybeans, straw, sugar beet, tomatoes, beans and other plant varieties, cotton, tobacco, rapeseed and other important cereal and fruit plants (apples, Pears, fruits of citrus fruits and grapes), among which corn, soybeans, straw, cotton, tobacco and rapeseed are important. Important traits are in particular the toxins formed in the plant, in particular by genetic material from Bacillus thuringiensis (for example the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, Increased plant defense against insects, arachnids, nematodes, slugs and snails by toxins formed in plants (by CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof) (hereinafter " Referred to as "Bt plant"). Also particularly important traits are increased plant defense against fungi, bacteria and viruses by whole body acquired resistance (SAR), cystemin, phytoalexin, elicitor and resistance genes and the corresponding proteins and toxins expressed. . A trait of particular importance is the increased tolerance of plants to certain active compounds with herbicidal activity, such as imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg the “PTA” gene). Genes that impart a desired target trait can also be present in combination with each other in the transgenic plant. Examples of “Bt plants” include YIELD GARD ^(R) (eg, corn, cotton, soybean), KnockOut ^(R) (eg, corn), StarLink ^(R) (eg, corn), Bollgard ^(R) (cotton), Nucotn Mention may be made of corn varieties, cotton varieties, soybean varieties and varieties of potatoes sold under the trade names of ^(R) (cotton) and NewLeaf ^(R) (芋). Examples of herbicide-tolerant plants include Roundup Ready ^(R) (resistance to glyphosate, eg corn, cotton, soybean), Liberty Link ^(R) (resistance to phosphinotricin, eg rapeseed), IMI ^(R) ( mention may be made resistant to resistance) and STS ^{(R) (sulfonylurea} to imidazolinones, such variants of corn sold by the trade name of corn), a variant of varieties and soy cotton. Which may be mentioned as a plant that is resistant to herbicides (plants bred in a conventional manner for herbicide tolerance) is sold under the name Clearfield (R) ^(for example maize) varieties Is included. Of course, these statements also apply to plant varieties having these genetic traits or those developed in the future, and such plant varieties will be developed and / or marketed in the future.

  The listed plants can be treated particularly advantageously with a suitable concentration of the compounds according to the invention.

  Furthermore, in the field of veterinary medicine, the novel compounds of the present invention can be used effectively against a variety of harmful parasitic pests (internal and ectoparasites) such as insects and helminths. Examples of such parasitic toxic animals include the pests described below. Examples of insects include Gastrophilus spp., Stomoxys spp., Trichodictes spp., Rhodonius spp., Ctenocephalides sp. (Ctenocephalides canis), Simx lecturius, Ctenocephalides felis, Lucilia cuprina and the like. Examples of the order of the mite include Ornithodoros spp., Ixodes spp., Boophilus spp. And the like.

  In the field of veterinary medicine, ie in the field of veterinary medicine, the active compounds according to the invention are active against parasitic animals, in particular ectoparasites or endoparasites. The term endoparasite includes, in particular, helminths such as tapeworms, nematodes or flukes and protozoa such as coccidia. In vitro parasites typically and preferably include arthropods, in particular flies (biting and licking flies), parasitic fly larvae, insects such as lice, hair lice, feather lice, fleas, or tick or It is a mite such as a soft mite or mites such as cypress mites, tsutsugamushi, and bird mites.

  These parasites include the following:

  From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phitrus spp., Phtyrus spp. (Solenopotes spp.). Examples are Rinogunasasu-Setosasu (Linognathus setosus), Rinogunasasu-Bitsuri (Linognathus vituli), Rinogunasasu-Obirasu (Linognathus ovillus), Rinogunasasu-Obiforumisu (Linognathus oviformis), Rinogunasasu-Pedarisu (Linognathus pedalis), Rinogunasasu-Sutenopushisu (Linognathus stenopsis ), Haematopinus asini macrocephalus, Haematopinus eurosternus, Haematopinus suis, Haematopinus suis, Dikyurasu-Fumanusu-Kyapitisu (Pediculus humanus capitis), Pedikyurasu-Fumanusu-Koruporisu (Pediculus humanus corporis), Firoera-Busta Tricks (Phylloera vastatrix), Fusuirusu-Pyubisu (Phthirus pubis), Sorenopotesu-Kyapiratasu (Solenopotes capillatus).

  From the order of Mallophagida, Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Menopon spt. Bobicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes sp. Felicola spp. Specific examples are: Bobicola bovis, Bobicola ovis, Bobicola limbata, Lamarina bovis (Damarina bovis), Trichodetic sco subtrostratus, Bobicola caprae, Lepikentron ovis, Wernekiella equi.

From the order of the Diptera and Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Curex genus ( Culex spp.), Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomia spp., Curicoides sp. Chrysops spp., Odagmia spp., Wilhelmia spp., Hibomitra Species (Hybomitora spp.), Atyllotus spp., Tabanus spp., Haematopota spp., Philipipia spp., Philippomyra sp. ), Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morelia spp., Morelia spp. (Fannia spp.), Grossina spp., Calliphora spp., Lucilia spp., Chrysomi Genus Chrysomya spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hippoderma spp., Hypoderma spp. Genus species (Gasterophilus spp.), Hippobosca spp., Lipoptena spp., Melophagas spp., Rinoestrus spp., Rinoestrus spp. .). Specific examples are Aedes aegypti, Aedes albopictus, Aedes taeniohynchus, Anopheles gambiae, Anopelis gambiale A Phala (Calliphora erythrocephala), Chrysozona pluviaris, Curex quinquefasciatus, Culex pipiexars, Culex pipiens sul lis), Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipura palicide, Tipura palisula Lucilia sericata, Simulium reptans, Frebotos papatasi, Phlebotus longipalpis, Phdagomus longipalpis lhelmia equina), Boofthora erythrocephala, Tabanus burus (Tabanus bromius), Tabanus spodopter (Tabanus spodopterus), Tabanus Hybomitra ciurea), Chrysops caecutiens, Chrysopus relictus, Haematoporita plutalis, Haematopota plutavito , Musca Autumn Naris (Musca autumnalis), Musca domestica (Musca domestica), Hematobia-Iritansu-Iritansu (Haematobia irritans irritans), Hematobia-Iritansu exigua (Haematobia irritans exigua), Hematobia-stimulation lance (Haematobia stimulans), Hydrotaea iritans, Hydrotaea albipunta, Chrysomya chloropyga, Chrysomia veziana (Chrys) us ovis), hypoderma bovis, hypoderma lineatum, phzhevalskiana sirenus, przhevalskiana silenus, dermatvia hominito b. (Lipoptena capreoli), Lipoptena cervi, Hippobosca variegata, Hippobosca equilina, Gastello intestrus ), Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus cirgospirus gastrophilus , Braula coeca,
From the order of Siphonaptida, for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsilla spp., Xenopsilla spp. Genus species (Ceratophyllus spp.), Specific examples include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans ns Xenopsila cheopsis.

  From the order of the Heteropterida, for example, Chimex spp., Triatoma spp., Rhodnius spp., Panstromylus spp.

  From the order of the cockroach (Blatartida), for example, Blata orientalis, Periplaneta americana, Brattala germanica, Spella sp. (Supella sp.). )).

From the order of the Acari (Acarina) and the Metastigmatidae (Mestastigmata) and the Mesostigmatidae (Argas spp.), Ornithodus spp. ), Ixodes spp., Amblyomma spp., Rhipicephalus (Bopophilus) (spp.), Dermacentor spp. Haemophysalis spp.), Hyalomma spp., Delmanissus spp. (Derm) nyssus spp.), Rhipicephalus spp. (original genus of multi-host mites), Ornithonysus spp., Pneumonysus spp., Laurisia spp., Raspilis spp. Species (Pneumonysus spp.), Sternostoma spp., Barroa spp., Acarapis spp. Specific examples are Argas persicus, Argas persicus Regas (Argas reflexus), Ornithodras moubata, Otobius megu Nini (Otobius megnini), Lipicephalas (Buophilus) microplus (Rhipicephalus (Boophilus) microplus, Lipissephalus (Buophilus) decoloratas (Rhipicephalus (Boophilus) lacholas (Buphyrus) Calceratas (Rhipicephalus (Boophilus) calceratus), Hyaloma anatolicum, Hyaloma aegypticum, Hyaloma margina Hyaluma marginatum, Hyalomma transiens, Lipipephalus esussi, Ixodes riusus, Ixodes ixus (Ixodes pilosus), Ixodes rubicundus, Ixodes scapularis, Ixodes holoculus, and Haematis cincina a), Hemafisarisu-Pankutata (Haemaphysalis punctata), Hemafisarisu-Shin'abarina (Haemaphysalis cinnabarina), Hemafisarisu-Otofira (Haemaphysalis otophila), Hemafisarisu-Reachi (Haemaphysalis leachi), Hemafisarisu-Rongikoruni (Haemaphysalis longicorni), Delmas Centaur-Maruginatasu (Dermacentor marginatus ), Dermacentor reticulatus, Dermacentor pictus, Dermacentor albictus tor albipictus), Delmas Centaur-Anderusoni (Dermacentor andersoni), Delmas Centaur variabilis (Dermacentor variabilis), Hiaronma-Mauritanikamu (Hyalomma mauritanicum), Ripisefarasu-sanguineus (Rhipicephalus sanguineus), Ripisefarasu - Bursa (Rhipicephalus bursa), Ripisefarasu - Appen Diculatus (Rhipicephalus appendiculatus), Ripecephalus capensis, Rhipicephalus turnicus, Ripicef Arasu, Zanbejienshisu (Rhipicephalus zambeziensis), Anburioma America Nam (Amblyomma americanum), Anburioma-Bariegatamu (Amblyomma variegatum), Anburioma-Makyuratamu (Amblyomma maculatum), Anburioma-Heburaeumu (Amblyomma hebraeum), Anburioma-Kajenensu (Amblyomma cajennense), Dermanissus gallinae, Ornisonysus bursa, Ornisonysus sylviarum, Valois Jacobsoni (V) rroa jacobsoni);
From the order of Actinida (Prostigmata) and Acariida (Astigmata), for example, Acarapis spp., Cheeletia, Genus species (Ornithocheyletia spp.), Myobia species (Myobia spp.), Psorergates spp., Demodex spp. spp.), Acarus spp., Tyrophagus spp. ), Caloglyphas spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Corioptes sp. (Otofectes spp.), Sarcoptes spp., Notoderes spp., Knemidopoptes spp., Cytodites spp. Os, p. . Specific examples are Cheyretiella yasguri, Cheyretiella blackei, Demodex canis, Demodex bovis, Demodex visde, Demodex v Demodex caprae, Demodex equi, Demodex cavalli, Demodex suis, Neotrombicula neumbulumula Destroelli (Netrombicula desaleri), Oschoengastia xerothermobia, Trombicula akamushi, bis cos, te te sti, c Sarcoptes ovis, Sarcoptes rupicaprae (= S. Caprae), Sarcoptes sequi, Sarcoptes supe, Sarcoptes sup oroptes ovis), Psoroptes cuniculi, Psoroptes equi (Psoroptes equi), Corioptes bovis, Psoergates Ovis・ Pneumonysoides caninum, Acarapis woody.

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

  Exterminating these arthropods, helminths and / or protozoa reduces mortality and improves productivity (in the case of meat, milk, wool, skin, eggs, honey, etc.) and host animal health Thus, the use of the active compound of the present invention makes it possible to raise animals more economically and simply.

  For example, it may be desirable to inhibit or interrupt blood uptake from the host by parasites (where applicable). Also, parasite control can help to suppress transmission of infectious agents.

  As used herein with respect to the veterinary field, the term “disinfect” means that the active compound is effective in reducing the occurrence of such parasites in infectious animals to harmless levels. It means that. More specifically, “disinfect” as used herein means that an active compound is effective in killing, inhibiting its growth, or inhibiting its growth. Means.

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

  For example, intestinal administration in the form of a tablet, capsule, beverage, liquid medicine, granule, paste, bolus, feed or in the form of a suppository, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) By parenteral administration, such as implants, nasal administration, etc., for example by use of the skin in the form of immersion or immersion, spraying, pouring on and spotting on, irrigation and powder spraying, and collars With the aid of articles containing active compounds, such as ear tags, tail tags, foot rings, end ropes, marking tools, etc., the active compounds are applied in a known manner in the veterinary medicine sector and in animal husbandry (= Administration). The active compounds can be formulated as shampoos or as suitable formulations that can be used in aerosols or as pressureless sprays such as pump sprays and nebulizer sprays.

  When used on livestock, poultry, pets, etc., the active compound of the present invention comprises a formulation (eg, powder, wettable powder [“WP”]) containing the active compound in an amount of 1 to 80% by weight. Can be applied as an emulsion, emulsion [“EC”], flowable, homogeneous solution and suspension concentrate [“SC”], either directly or after dilution (eg, 100-10,000 fold dilution). It is possible or they can be used as a medicinal bath.

  When used in the veterinary field, the active compounds of the invention may be used in combination with a suitable synergist such as an acaricide, insecticide, rodenticide or protozoan or other active compounds.

  In the present invention, a substance having an insecticidal action against pests including all of these is called an insecticide.

  When used as insecticides, the active compounds according to the invention can be prepared in customary dosage forms. Examples of formulation forms include solutions, emulsions, wettable powders, water dispersible granules, suspensions, powders, foams, pastes, tablets, granules, aerosols, natural and synthetic substances impregnated with active compounds, microcapsules, Seed coatings, formulations used with combustion devices (eg, fumigation and smoke cartridges, cans, coils, etc. as combustion devices) or ULVs (cold mists, warm mists) and the like.

  These preparations can be produced by methods known per se. Formulations, for example, mix an active compound with a developing agent, ie a liquid diluent or carrier, a liquefied gaseous diluent or carrier, or a solid diluent or carrier, and a surfactant, ie an emulsifier and / or Or it can manufacture by mixing with a dispersing agent and / or a foaming agent by the case.

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

  Examples of liquid diluents or carriers include aromatic hydrocarbons (eg xylene, toluene, alkylnaphthalene), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg chlorobenzene, ethylene chloride or methylene chloride) ), Aliphatic hydrocarbons (eg, cyclohexane), paraffins (eg, mineral oil fractions), alcohols (eg, butanol or glycol and their ethers, esters, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone) Etc.), strong polar solvents (for example, dimethylformamide, dimethyl sulfoxide, etc.), water and the like.

  The liquefied gaseous diluent or carrier can be one that is a gas at normal temperature and evaporation, such as an aerosol propellant such as butane, propane, nitrogen gas, carbon dioxide and halogenated hydrocarbons.

  Examples of solid diluents include finely divided natural minerals (kaolin, clay, talc, cucumber, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), finely divided synthetic minerals (eg, highly dispersed silicic acid, Alumina, silicate, etc.).

  Examples of solid carriers for granules include finely divided and sieved rocks (eg calcite, marble, pumice, ganolite, dolomite, etc.), synthetic granules of inorganic and organic powders, fine particles of organic materials (For example, sawdust, coconut, corn cob, tobacco stem, etc.).

  Examples of emulsifiers and / or blowing agents include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (eg, alkylaryl polyglycol ethers), alkyl sulfonates, alkyl sulfates. , Aryl sulfonates, etc.], albumin hydrolysates, and the like.

  Examples of dispersants include lignin-sulfite waste liquor and methylcellulose.

  Fixatives can also be used in the formulation (powder, granules or emulsions), examples of fixatives include carboxymethylcellulose, natural and synthetic polymers (eg gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.) Is included.

  Colorants can also be used, and examples of colorants include inorganic pigments (eg, iron oxide, titanium oxide, Prussian blue, etc.), organic dyes (eg, alizarin dyes, azo dyes or metal phthalocyanine dyes), Furthermore, trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts are included.

  The formulations can generally contain the active ingredient in an amount ranging from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight.

  The compounds of the present invention can be used in commercially useful formulations and in application forms prepared from the formulations, in addition to other active compounds such as insecticides, toxic baits, fungicides, acaricides, nematicides. It can also be present as a mixture with fungicides, growth regulators, herbicides and the like.

  The content of the compounds of the invention in commercially useful application forms can be varied within a wide range.

  The concentration of the active compounds according to the invention in practical applications can be, for example, in the range from 0.0000001 to 100% by weight, preferably from 0.00001 to 1% by weight.

  The compounds of the present invention can be used through conventional methods appropriate to the use forms.

  The compounds of the present invention have effective stability against alkalis on lime materials when used against sanitary pests and pests associated with stored products, and against wood and soil. Excellent residual effect.

  Further, the active compound of the present invention is low toxic to warm-blooded animals and can be used safely.

  EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention should not be limited only to these examples.

<Synthesis Example 1>
Synthesis of 5- [4-chloro-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2-fluorobenzonitrile .

２−フルオロ−５−［３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−５−イル］ベンゾニトリル（０．３ｇ）を四塩化炭素（１０ｍＬ）に溶解し、Ｎ−クロロこはく酸イミド（０．３ｇ）を加え、４０℃で３時間攪拌した。反応混合液をろ過し、ろ液を塩化メチレン（２０ｍＬ）で希釈した。釈液したろ液を水、次いで飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。ろ過後、溶媒を減圧下留去し、残渣をシリカゲルクロマトグラフィーで精製して５−［４−クロロ−３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−５−イル］−２−フルオロベンゾニトリル（０．２６ｇ）を収率８０％で得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ： ４．５８（１Ｈ，ｄ），４．９０（１Ｈ，ｄ），５．５１（１Ｈ，ｓ），７．３３−７．３８（３Ｈ，ｍ），８．２０−８．３５（２Ｈ，ｍ）．

2-Fluoro-5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzonitrile (0.3 g). It melt | dissolved in carbon tetrachloride (10 mL), N-chloro succinimide (0.3g) was added, and it stirred at 40 degreeC for 3 hours. The reaction mixture was filtered and the filtrate was diluted with methylene chloride (20 mL). The filtrate thus obtained was washed with water and then with a saturated saline solution and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to give 5- [4-chloro-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] -2-fluorobenzonitrile (0.26 g) was obtained in 80% yield.
¹ H-NMR (CDCl ₃ ) δ: 4.58 (1H, d), 4.90 (1H, d), 5.51 (1H, s), 7.33-7.38 (3H, m), 8.20-8.35 (2H, m).

<Synthesis Example 2>
5- [4-Chloro-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1, Synthesis of 2,4-triazol-1-yl) benzonitrile (Compound No. 5-2).

２−（１Ｈ−１，２，４−トリアゾール−１−イル）−５−［３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−５−イル］ベンゾニトリル（０．２５ｇ）を四塩化炭素（１０ｍＬ）に溶解し、Ｎ−クロロこはく酸イミド（０．３ｇ）を加え、４０℃で３時間攪拌した。反応混合液をろ過し、ろ液を塩化メチレン（２０ｍＬ）で希釈した。釈液したろ液を水、次いで飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。ろ過後、溶媒を減圧下留去し、残渣をシリカゲルクロマトグラフィーで精製して５−［４−クロロ−３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−５−イル］−２−（１Ｈ−１，２，４−トリアゾール−１−イル）ベンゾニトリル（０．２５ｇ）を収率８６％で得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：４．６３（１Ｈ，ｄ），４．９６（１Ｈ，ｄ），５．５９（１Ｈ，ｓ），７．４１（２Ｈ，ｓ），７．９８（１Ｈ，ｄ），８．２３（１Ｈ，ｓ），８．３５（１Ｈ，ｄ），８．４５（１Ｈ，ｓ），８．９２（１Ｈ，ｓ）．

2- (1H-1,2,4-triazol-1-yl) -5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H- Pyrrole-5-yl] benzonitrile (0.25 g) was dissolved in carbon tetrachloride (10 mL), N-chlorosuccinimide (0.3 g) was added, and the mixture was stirred at 40 ° C. for 3 hr. The reaction mixture was filtered and the filtrate was diluted with methylene chloride (20 mL). The filtrate thus obtained was washed with water and then with a saturated saline solution and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to give 5- [4-chloro-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazol-1-yl) benzonitrile (0.25 g) was obtained in a yield of 86%.
¹ H-NMR (CDCl ₃ ) δ: 4.63 (1H, d), 4.96 (1H, d), 5.59 (1H, s), 7.41 (2H, s), 7.98 ( 1H, d), 8.23 (1H, s), 8.35 (1H, d), 8.45 (1H, s), 8.92 (1H, s).

<Synthesis Example 3>
N- (4- {3- [3,5-bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Bromobenzyl) cyclopropanecarboxamide (Compound No. 6-3)

  Step 3-1: tert-butyl (4- {3- [3,5-bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- Synthesis of 5-yl} -2-bromobenzyl) carbamate

ｔｅｒｔ‐ブチル（４‐｛３‐［３，５‐ビス（トリルオロメチル）フェニル］‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモベンジル）カルバメート（４７０ｍｇ，０．７４ｍｍｏｌ）を四塩化炭素（１００ｍＬ）に溶解し、Ｎ‐クロロスクシンイミド（９９．１ｍｇ，０．７４ｍｍｏｌ）を加え、室温にて終夜撹拌した。反応混合物を減圧濃縮し、残渣をｔｅｒｔ‐ブチルメチルエーテルに溶解し、水、飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮し、カラムクロマトグラフィーにて精製し目的物を得た（３６０ｍｇ）。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：１．４６（９Ｈ，ｓ），４．４４（２Ｈ，ｄ），４．６４（１Ｈ，ｄ），５．０９−４．９８（２Ｈ，ｍ），５．６４（１Ｈ，ｓ），７．５１（１Ｈ，ｄ），７．８１（２Ｈ，ｓ），７．８８（１Ｈ，ｄｄ），７．９６（１Ｈ，ｓ），８．１９（１Ｈ，ｄ）．

tert-Butyl (4- {3- [3,5-Bis (tolyloromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzyl ) Carbamate (470 mg, 0.74 mmol) was dissolved in carbon tetrachloride (100 mL), N-chlorosuccinimide (99.1 mg, 0.74 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tert-butyl methyl ether and washed with water and saturated brine. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography to obtain the desired product (360 mg).
¹ H-NMR (CDCl ₃ ) δ: 1.46 (9H, s), 4.44 (2H, d), 4.64 (1H, d), 5.09-4.98 (2H, m), 5.64 (1H, s), 7.51 (1H, d), 7.81 (2H, s), 7.88 (1H, dd), 7.96 (1H, s), 8.19 (1H , D).

  Step 3-2: 1- (4- {3- [3,5-bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Yl} -2-bromophenyl) methanamine

ｔｅｒｔ‐ブチル（４‐｛３‐［３，５‐ビス（トリルオロメチル）フェニル］‐４‐クロロ‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモベンジル）カルバメート（３００ｍｇ，０．４４ｍｍｏｌ）を１，２‐ジクロロメタン（３０ｍＬ）に溶解し、トリフルオロ酢酸（２５６ｍｇ，２２．４ｍｍｏｌ）を加え、室温にて１時間撹拌した。反応混合物を減圧濃縮した後、残渣をｔｅｒｔ‐ブチルメチルエーテルに溶解し、飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮した（２１２ｍｇ）。なお、目的物は精製することなく次の反応に用いた。

tert-butyl (4- {3- [3,5-bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl}- 2-Bromobenzyl) carbamate (300 mg, 0.44 mmol) was dissolved in 1,2-dichloromethane (30 mL), trifluoroacetic acid (256 mg, 22.4 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in tert-butyl methyl ether, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure (212 mg). . The target product was used in the next reaction without purification.

  Step 3-3: N- (4- {3- [3,5-bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 Synthesis of -yl} -2-bromobenzyl) cyclopropanecarboxamide

１‐（４‐｛３‐［３，５‐ビス（トリルオロメチル）フェニル］‐４‐クロロ‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモフェニル）メタンアミン（１００ｍｇ，０．１７ｍｍｏｌ）をテトラヒドロフラン（５ｍＬ）に溶解し、ピリジン（１３９ｍｇ，１．７６ｍｍｏｌ）、シクロプロパンカルボニルクロリド（２２ｍｇ，０．２１ｍｍｏｌ）を加え、終夜撹拌した。反応混合物をｔｅｒｔ‐ブチルメチルエーテルで希釈した後、２Ｎ塩酸、水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮した。得られた残渣をカラムクロマトグラフィーで精製し、目的物を得た（１００ｍｇ）。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：０．７５‐０．８１（２Ｈ，ｍ），０．９８‐１．０４（２Ｈ，ｍ），１．３７‐１．４３（１Ｈ，ｍ），４．５７‐４．６７（３Ｈ，ｍ）， ５．０１（１Ｈ，ｄ），５．６４（１Ｈ，ｓ），６．２１（１Ｈ，ｂｒ ｓ），７．５３（１Ｈ，ｄ），７．８１（２Ｈ，ｓ），７．８６（１Ｈ，ｄｄ），７．９６（１Ｈ，ｓ），８．２０（１Ｈ，ｄ）．

1- (4- {3- [3,5-Bis (tolyloromethyl) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Bromophenyl) methanamine (100 mg, 0.17 mmol) was dissolved in tetrahydrofuran (5 mL), pyridine (139 mg, 1.76 mmol) and cyclopropanecarbonyl chloride (22 mg, 0.21 mmol) were added, and the mixture was stirred overnight. The reaction mixture was diluted with tert-butyl methyl ether, washed with 2N hydrochloric acid, water and saturated brine, and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography to obtain the desired product (100 mg).
¹ H-NMR (CDCl ₃ ) δ: 0.75-0.81 (2H, m), 0.98-1.04 (2H, m), 1.37-1.43 (1H, m), 4 .57-4.67 (3H, m), 5.01 (1H, d), 5.64 (1H, s), 6.21 (1H, br s), 7.53 (1H, d), 7 .81 (2H, s), 7.86 (1H, dd), 7.96 (1H, s), 8.20 (1H, d).

<Synthesis Example 4>
4- {3- [3,5-bis (trifluoromethyl) phenyl] -4-bromo-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromo- Synthesis of N- (thietan-3-yl) benzeneamide (Compound No. 7-7)

  Step 4-1: 4- {3- [3,5-Bis (trifluoromethyl) phenyl] -4-bromo-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-Bromobenzoic acid

４‐｛３‐［３，５‐ビス（トリフルオロメチル）フェニル］‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモ安息香酸（１００ｍｇ，０．１８ｍｍｏｌ）を四塩化炭素（５ｍＬ）に溶解し、Ｎ‐ブロモスクシンイミド（３２．５ｍｇ，０．１８ｍｍｏｌ）を加え、終夜撹拌した。反応混合物を減圧濃縮し、残渣をｔｅｒｔ‐ブチルメチルエーテルに溶解し、水、飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥、ろ過した後、目的物を得た（１１０ｍｇ）。なお、目的物は精製することなく次の反応に用いた。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：４．６２（１Ｈ，ｄ），５．０５（１Ｈ，ｄ），５．６９（１Ｈ，ｓ），７．８１（２Ｈ，ｓ），８．００‐７．９７（２Ｈ，ｍ），８．０８（１Ｈ，ｄ），８．３３（１Ｈ，ｄ）．

4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzoic acid (100 mg, 0.18 mmol) was dissolved in carbon tetrachloride (5 mL), N-bromosuccinimide (32.5 mg, 0.18 mmol) was added, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tert-butyl methyl ether and washed with water and saturated brine. The organic layer was dried over magnesium sulfate and filtered, and the target product was obtained (110 mg). The target product was used in the next reaction without purification.
¹ H-NMR (CDCl ₃ ) δ: 4.62 (1H, d), 5.05 (1H, d), 5.69 (1H, s), 7.81 (2H, s), 8.00- 7.97 (2H, m), 8.08 (1H, d), 8.33 (1H, d).

  Step 4-2: 4- {3- [3,5-bis (trifluoromethyl) phenyl] -4-bromo-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} Of -2-bromo-N- (thietan-3-yl) benzeneamide

チエタン‐３‐アミン臭酸塩（３４ｍｇ，０．１９ｍｍｏｌ）をＮ，Ｎ‐ジメチルホルムアミド（５ｍＬ）に溶解し、０℃にてトリエチルアミン（５０ｍｇ，０．４９ｍｍｏｌ）を加え、室温にて３０分撹拌した。この溶液に対し、１‐（３‐ジメチルアミノプロピル）‐３‐エチルカルボジイミド塩酸塩（４５ｍｇ，０．１９ｍｍｏｌ）、１‐ヒドロキシベンゾトリアゾール（２７ｍｇ，０．１９ｍｍｏｌ）、４‐｛３‐［３，５‐ビス（トリフルオロメチル）フェニル］‐４‐ブロモ‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモ安息香酸（１１０ｍｇ，０．１９ｍｍｏｌ）を０℃にて加え、室温にて終夜撹拌した。反応混合物をｔｅｒｔ‐ブチルメチルエーテルで希釈した後、２Ｎ塩酸、水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮した。得られた残渣をカラムクロマトグラフィーで精製し、目的物を得た（３０ｍｇ）。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５２‐３．４１（４Ｈ，ｍ），４．５９（１Ｈ，ｄ），５．０１（１Ｈ，ｄ），５．３５‐５．５１（１Ｈ，ｍ），５．６８（１Ｈ，ｓ），６．６４（１Ｈ，ｄ），７．６３（１Ｈ，ｄ），７．８０（２Ｈ，ｓ），７．９２‐７．９７（２Ｈ，ｍ），８．２３（１Ｈ，ｄ）．

Thietane-3-amine bromide (34 mg, 0.19 mmol) was dissolved in N, N-dimethylformamide (5 mL), triethylamine (50 mg, 0.49 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 30 minutes. did. To this solution, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (45 mg, 0.19 mmol), 1-hydroxybenzotriazole (27 mg, 0.19 mmol), 4- {3- [3, 5-Bis (trifluoromethyl) phenyl] -4-bromo-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzoic acid (110 mg, 0.19 mmol) Was added at 0 ° C. and stirred at room temperature overnight. The reaction mixture was diluted with tert-butyl methyl ether, washed with 2N hydrochloric acid, water and saturated brine, and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain the desired product (30 mg).
¹ H-NMR (CDCl ₃ ) δ: 3.52-3.41 (4H, m), 4.59 (1H, d), 5.01 (1H, d), 5.35-5.51 (1H M), 5.68 (1H, s), 6.64 (1H, d), 7.63 (1H, d), 7.80 (2H, s), 7.92-7.97 (2H, m), 8.23 (1H, d).

<Synthesis Example 5>
Of methyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate Composition

  Step 5-1: Synthesis of (2E) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) but-2-enoic acid

２，２，２−トリフルオロ−１−（３，４，５−トリクロロフェニル）エタノン（２０ｇ，７２ｍｍｏｌ）、無水酢酸（１００ｍｌ）及び、酢酸ナトリウム（１１．８ｇ，１４４ｍｍｏｌ）の混合物を１００℃で５時間加熱攪拌した。放冷後、反応混合物を氷水浴中で攪拌しながら、水（２００ｍｌ）を約３０分かけて加えた後、室温にて２時間攪拌した。生成物をｔ−ブチルメチルエーテルを用いて抽出、有機層を水洗したのち無水硫酸マグネシウムで乾燥後、溶媒を減圧下溜去した、残存した酢酸は、トルエンを加え溜去する事によって取り除き、粗生成物３０ｇを得た。粗生成物をヘキサンを用いて再結晶し表記の化合物を得た。収量１７．９ｇ、収率８５．５％。再結晶母液を減圧溜去し同様の操作を行って、２番晶として２．６ｇの表記化合物を得た。^１Ｈ−ＮＭＲ（ＣＤＣｌ_３＋ＤＭＳＯ−ｄ６） δ：６．６７（１Ｈ，ｓ），７．３５（２Ｈ，ｓ）

A mixture of 2,2,2-trifluoro-1- (3,4,5-trichlorophenyl) ethanone (20 g, 72 mmol), acetic anhydride (100 ml) and sodium acetate (11.8 g, 144 mmol) at 100 ° C. The mixture was heated and stirred for 5 hours. After allowing to cool, water (200 ml) was added over about 30 minutes while stirring the reaction mixture in an ice-water bath, and then stirred at room temperature for 2 hours. The product was extracted with t-butyl methyl ether, the organic layer was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The remaining acetic acid was removed by adding toluene and distilled off. 30 g of product was obtained. The crude product was recrystallized from hexane to obtain the title compound. Yield 17.9 g, Yield 85.5%. The recrystallized mother liquor was distilled off under reduced pressure and the same operation was performed to obtain 2.6 g of the title compound as the second crystal. ¹ H-NMR (CDCl ₃ + DMSO-d6) δ: 6.67 (1H, s), 7.35 (2H, s)

  Step 5-2: Synthesis of methyl (2E) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) but-2-enoate

（２Ｅ）−４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）ブタ−２−エノイックアシッド（５．０ｇ，１５．６ｍｍｏｌ）及び４−トルエンスルホン酸１水和物（０．３ｇ、１．５６ｍｍｏｌ）を１００ｍｌのメチルアルコールと共に、１２時間、加熱還流した。反応終了後溶媒を減圧溜去し、残渣を酢酸エチルに溶解した後、飽和炭酸水素ナトリウム水溶液、次いで飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥後、溶媒を減圧下溜去した。残渣をシリカゲルクロマトグラフィー（溶媒ヘキサン／酢酸エチル＝９５／５）にて精製し、表記化合物３．８ｇを得た。収率７３％。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．６９（３Ｈ，ｓ），６．６６（１Ｈ，ｓ），７．３１（２Ｈ，ｓ）

(2E) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) but-2-enoic acid (5.0 g, 15.6 mmol) and 4-toluenesulfonic acid monohydrate The product (0.3 g, 1.56 mmol) was heated to reflux with 100 ml of methyl alcohol for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and then with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (solvent hexane / ethyl acetate = 95/5) to obtain 3.8 g of the title compound. Yield 73%.
¹ H-NMR (CDCl ₃ ) δ: 3.69 (3H, s), 6.66 (1H, s), 7.31 (2H, s)

  Step 5-3: Methyl 2- (3-bromo-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole Synthesis of 3-carboxylate

（２Ｅ）−４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）−ブタ−２−エノン（５００ｍｇ，１．５０ｍｍｏｌ）、２−ブロモ−１−フルオロ−４−（イソシアノメチル）ベンゼン（３３１ｍｇ，１．５０ｍｍｏｌ）及び、酸化第一銅（２１ｍｇ，０．１５ｍｍｏｌ）をトルエン（５ｍｌ）と共に１０時間加熱還流した。反応終了後、反応混合物を５０ｍｌの水に注ぎ、酢酸エチルで抽出した（３０ｍｌｘ３）。有機層を飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した後、減圧下溶媒を溜去し、残渣をシリカゲルカラムクロマトグラフィーを用いて精製して目的化合物を得た。（溶媒 ヘキサン：酢酸エチル＝９８／２次いで９５／５）、収量５００ｍｇ、収率６１％。^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．２１（ｄ）＆３．４１（ｄ）（１Ｈ），３．５４（ｓ）＆３．８８（ｓ）（３Ｈ），４．０８−４．１６（ｍ，１Ｈ），５．６７−５．７１（ｍ，１Ｈ），７．０５−７．８７（ｍ，６Ｈ）

(2E) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) -but-2-enone (500 mg, 1.50 mmol), 2-bromo-1-fluoro-4- ( Isocyanomethyl) benzene (331 mg, 1.50 mmol) and cuprous oxide (21 mg, 0.15 mmol) were heated to reflux with toluene (5 ml) for 10 hours. After completion of the reaction, the reaction mixture was poured into 50 ml of water and extracted with ethyl acetate (30 ml × 3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane: ethyl acetate = 98/2 then 95/5), yield 500 mg, yield 61%. ¹ H-NMR (CDCl ₃ ) δ: 3.21 (d) & 3.41 (d) (1H), 3.54 (s) & 3.88 (s) (3H), 4.08-4.16 ( m, 1H), 5.67-5.71 (m, 1H), 7.05-7.87 (m, 6H)

  Step 5-4: Methyl 5- (3-bromo-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole Synthesis of 4-carboxylate

メチル ２−（３−ブロモ−４−フルオロフェニル）−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−３−カルボキシレート（４５０ｍｇ、０．８２ｍｍｏｌ）、１，８−ジアザビシクロ（５，４，０）ウンデセ−７−エン（２５ｍｇ，０．１６ｍｍｏｌ）をピリジン（１０ｍｌ）と共に２時間加熱還流した。溶媒を減圧溜去下のち、残渣を酢酸エチルに溶解、水、次いで飽和食塩水にて洗浄した。有機層を無水硫酸マグネシウムで乾燥し、溶媒を減圧溜去した。残渣をシリカゲルカラムクロマトグラフィーを用いて精製して目的化合物を得た。（溶媒 ヘキサン：酢酸エチル＝９８／２次いで９５／５）、収量３１０ｍｇ、収率６９％。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５０（３Ｈ，ｓ），４．６６−４．９１（３Ｈ，ｍ），７．１７−８．２２（５Ｈ，ｍ）

Methyl 2- (3-bromo-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate ( 450 mg, 0.82 mmol), 1,8-diazabicyclo (5,4,0) undec-7-ene (25 mg, 0.16 mmol) was heated to reflux with pyridine (10 ml) for 2 hours. After removing the solvent under reduced pressure, the residue was dissolved in ethyl acetate and washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane: ethyl acetate = 98/2 then 95/5), yield 310 mg, yield 69%.
¹ H-NMR (CDCl ₃ ) δ: 3.50 (3H, s), 4.66-4.91 (3H, m), 7.17-8.22 (5H, m)

  Step 5-5: Methyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole Synthesis of 4-carboxylate

メチル ５−（３−ブロモ−４−フルオロフェニル）−３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−４−カルボキシレート（２５０ｍｇ，０．４７５ｍｍｏｌ）、シアン化亜鉛（１１２ｍｇ，０．９５ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（１１０ｍｇ，０．０９５ｍｍｏｌ）をＤＭＦ（１５ｍｌ）と共にアルゴン気流下、１００℃、２時間反応させた。反応終了後、反応混合物を水に注ぎ、酢酸エチルで抽出、有機層を水、次いで食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧溜去し、残渣をシリカゲルカラムクロマトグラフィーを用いて精製して目的化合物を得た。（溶媒 ヘキサン：酢酸エチル＝９０／１０）、収量８５ｍｇ、収率３６％。^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５１（３Ｈ，ｓ），４．６７−４．９３（３Ｈ，ｍ），７．２９−８．２３（５Ｈ，ｍ）

Methyl 5- (3-bromo-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate ( 250 mg, 0.475 mmol), zinc cyanide (112 mg, 0.95 mmol), tetrakis (triphenylphosphine) palladium (110 mg, 0.095 mmol) were reacted with DMF (15 ml) at 100 ° C. for 2 hours in an argon stream. . After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then with brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane: ethyl acetate = 90/10), yield 85 mg, yield 36%. ¹ H-NMR (CDCl ₃ ) δ: 3.51 (3H, s), 4.67-4.93 (3H, m), 7.29-8.23 (5H, m)

<Synthesis Example 6>
Of methyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-4-carboxylate Composition

  Step 6-1: Methyl 2- (3-cyano-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- Synthesis of 3-carboxylate

（２Ｅ）−４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）−ブタ−２−エノン（７００ｍｇ，２．１０ｍｍｏｌ）、２−フルオロ−５−イソシアノメチル−ベンゾニトリル（３３６ｍｇ、２．１０ｍｍｏｌ）及び、酸化第一銅（２１ｍｇ，０．１５ｍｍｏｌ）をトルエン（１０ｍｌ）と共に８時間、加熱還流した。反応終了後、反応混合物を５０ｍｌの水に注ぎ、酢酸エチルで抽出した（３０ｍｌｘ３）。有機層を飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した後、減圧下溶媒を溜去し、残渣をシリカゲルカラムクロマトグラフィーを用いて精製して目的化合物を得た。（溶媒 ヘキサン：酢酸エチル＝９０／１０）、収量４１０ｍｇ、収率４０％。^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．３７（１Ｈ、ｄ），３．６１（３Ｈ，ｓ），４．１１−４．１８（１Ｈ，ｍ），５．７３−５．７８（１Ｈ，ｍ），７．０７−７．７２（６Ｈ，ｍ）

(2E) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) -but-2-enone (700 mg, 2.10 mmol), 2-fluoro-5-isocyanomethyl-benzo Nitrile (336 mg, 2.10 mmol) and cuprous oxide (21 mg, 0.15 mmol) were heated to reflux with toluene (10 ml) for 8 hours. After completion of the reaction, the reaction mixture was poured into 50 ml of water and extracted with ethyl acetate (30 ml × 3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane: ethyl acetate = 90/10), yield 410 mg, yield 40%. ¹ H-NMR (CDCl ₃ ) δ: 3.37 (1H, d), 3.61 (3H, s), 4.11-4.18 (1H, m), 5.73-5.78 (1H , M), 7.07-7.72 (6H, m)

  Step 6-2: Methyl 5- (3-cyano-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- Synthesis of 4-carboxylate

メチル ２−（３−シアノ−４−フルオロフェニル）−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−３−カルボキシレート（１００ｍｇ、０．２０ｍｍｏｌ）、１，８−ジアザビシクロ（５，４，０）ウンデセ−７−エン（６ｍｇ，０．０４ｍｍｏｌ）をピリジン（４ｍｌ）と共に１時間加熱還流した。溶媒を減圧溜去したのち、残渣を酢酸エチルに溶解、水、次いで飽和食塩水にて洗浄した。有機層を無水硫酸マグネシウムで乾燥し、溶媒を減圧溜去した。残渣をシリカゲルカラムクロマトグラフィーを用いて精製して目的化合物を得た。（溶媒 ヘキサン：酢酸エチル＝８５／１５）、収量４０ｍｇ、収率４０％。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５１（３Ｈ，ｓ），４．６７−４．９３（３Ｈ，ｍ），７．２９−８．２３（５Ｈ，ｍ）

Methyl 2- (3-cyano-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate ( 100 mg, 0.20 mmol), 1,8-diazabicyclo (5,4,0) undec-7-ene (6 mg, 0.04 mmol) was heated to reflux with pyridine (4 ml) for 1 hour. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethyl acetate and washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane: ethyl acetate = 85/15), yield 40 mg, yield 40%.
¹ H-NMR (CDCl ₃ ) δ: 3.51 (3H, s), 4.67-4.93 (3H, m), 7.29-8.23 (5H, m)

<Synthesis Example 7>
Methyl 5- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-Dihydro-2H-pyrrole-4-carboxylate and methyl 2- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -4- (3,4, Synthesis of 5-trichlorophenyl) -4- (trifluoromethyl) -4,5-dihydro-1H-pyrrole-3-carboxylate (Compound No. 5-6)

メチル ２−（３−シアノ−４−フルオロフェニル）−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−３−カルボキシレート（１８０ｍｇ，０．３７ｍｍｏｌ）、１Ｈ−１，２，４−トリアゾール（３３ｍｇ，０．４７ｍｍｏｌ）、及び炭酸カリウム（７６ｍｇ，０．５５ｍｍｏｌ）をＤＭＦ（１０ｍｌ）と共に１００℃で２時間反応させた。反応混合物をの水に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した後、減圧下溶媒を溜去し、残渣をシリカゲルカラムクロマトグラフィーを用いて精製した。（溶媒 ヘキサン／酢酸エチル６０／４０から０／１００まで酢酸エチルの比率を増していった）。メチル ５−［３−シアノ−４−（１Ｈ−１，２，４−トリアゾロ−１−イル）フェニル］−３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−４−カルボキシレート ^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５２（３Ｈ，ｓ），４．７２−４．９９（３Ｈ，ｍ），７．４１−８．９３（７Ｈ，ｍ）、及びメチル ２−［３−シアノ−４−（１Ｈ−１，２，４−トリアゾロ−１−イル）フェニル］−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−４，５−ジヒドロ−１Ｈ−ピロール−３−カルボキシレート ^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．４６（３Ｈ，ｓ），３．８０（１Ｈ，ｄｄ），４．３４（１Ｈ，ｄｄ），４．４８（１Ｈ，ｓ），７．２５−８．８９（８Ｈ，ｍ）の混合物１１０ｍｇ、収率５５％、を得た。

Methyl 2- (3-cyano-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate ( 180 mg, 0.37 mmol), 1H-1,2,4-triazole (33 mg, 0.47 mmol), and potassium carbonate (76 mg, 0.55 mmol) were reacted with DMF (10 ml) at 100 ° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography. (Solvent increased the ratio of ethyl acetate from hexane / ethyl acetate 60/40 to 0/100). Methyl 5- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-dihydro-2H-pyrrole-4-carboxylate ¹ H-NMR (CDCl ₃ ) δ: 3.52 (3H, s), 4.72-4.99 (3H, m), 7.41-8 .93 (7H, m), and methyl 2- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -4- (3,4,5-trichlorophenyl)- 4- (trifluoromethyl) -4,5-dihydro-1H-pyrrole-3-carboxylate ¹ H-NMR (CDCl ₃ ) δ: 3.46 (3H, s), 3.80 (1H, dd), 4.34 (1H, dd), 4.48 (1H, s), 7.25- .89 (8H, m) mixture 110 mg, 55% yield, was obtained.

Synthesis example of benzonitrile intermediate Synthesis of 2-fluoro-5- (isothianomethyl) benzonitrile

Ｎ−（３−シアノ−４−フルオロベンジル）フォルムアミド（５５０ｍｇ，３．０９ｍｍｏｌ）、Ｎ，Ｎ−ジイソプロピルエチルアミン（１．８０ｇ，１３．９ｍｍｏｌ）をジクロロメタン（２０ｍｌ）と共に氷冷水浴中攪拌した中に、フォスフォラスオキシクロライド（７１０ｍｇ，４．６３ｍｍｏｌ）のジクロロメタン（１０ｍｌ）溶液を滴下した。滴下終了後０．５時間攪拌した後、室温で更に２時間攪拌した。反応混合物にジクロロメタンを加えた後、水、炭酸水素ナトリウム水溶液、飽和食塩水で順次洗浄した。有機層を無水硫酸マグネシウムを用いて乾燥した後、溶媒を減圧溜去した。残渣をシリカゲルカラムクロマトグラフィーを用いて精製し、目的化合物を得た。（溶媒 ヘキサン／酢酸エチル８０／２０）、収量３３０ｍｇ、収率６７％。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：４．６７（２Ｈ，ｓ），７．２５−７．６５（３Ｈ，ｍ）

While stirring N- (3-cyano-4-fluorobenzyl) formamide (550 mg, 3.09 mmol) and N, N-diisopropylethylamine (1.80 g, 13.9 mmol) in an ice-cold water bath with dichloromethane (20 ml) A solution of phosphorous oxychloride (710 mg, 4.63 mmol) in dichloromethane (10 ml) was added dropwise. After completion of the dropwise addition, the mixture was stirred for 0.5 hours, and further stirred at room temperature for 2 hours. Dichloromethane was added to the reaction mixture, and the mixture was washed successively with water, aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried using anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain the target compound. (Solvent Hexane / Ethyl acetate 80/20), Yield 330 mg, Yield 67%.
¹ H-NMR (CDCl ₃ ) δ: 4.67 (2H, s), 7.25-7.65 (3H, m)

  Synthesis of 2-bromo-1-fluoro-4- (isocyanomethyl) benzene

Ｎ−（３−ブロモ−４−フルオロベンジル）フォルムアミド（２８０ｍｇ，１．２１ｍｍｏｌ）、Ｎ，Ｎ−ジイソプロピルエチルアミン（７０２ｍｇ，５．４３ｍｍｏｌ）をジクロロメタン（１０ｍｌ）と共に氷冷水浴中攪拌した中に、フォスフォラスオキシクロライド（２７８ｍｇ，１．８１ｍｍｏｌ）のジクロロメタン（５ｍｌ）溶液を滴下した。滴下終了後０．５時間攪拌した後、室温で更に２時間攪拌した。反応混合物にジクロロメタンを加えた後、水、炭酸水素ナトリウム水溶液、飽和食塩水で順次洗浄した。有機層を無水硫酸マグネシウムを用いて乾燥した後、溶媒を減圧溜去した。残渣をシリカゲルカラムクロマトグラフィーを用いて精製し、目的化合物を得た。（溶媒 ヘキサン／酢酸エチル９５／５次いで９０／１０）、収量１５０ｍｇ、収率５８％
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：４．６１（２Ｈ，ｓ），７．１３−７．５８（３Ｈ，ｍ）

While stirring N- (3-bromo-4-fluorobenzyl) formamide (280 mg, 1.21 mmol), N, N-diisopropylethylamine (702 mg, 5.43 mmol) with dichloromethane (10 ml) in an ice-cold water bath, A solution of phosphorous oxychloride (278 mg, 1.81 mmol) in dichloromethane (5 ml) was added dropwise. After completion of the dropwise addition, the mixture was stirred for 0.5 hours, and further stirred at room temperature for 2 hours. Dichloromethane was added to the reaction mixture, and the mixture was washed successively with water, aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried using anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain the target compound. (Solvent hexane / ethyl acetate 95/5 then 90/10), yield 150 mg, yield 58%
¹ H-NMR (CDCl ₃ ) δ: 4.61 (2H, s), 7.13-7.58 (3H, m)

  The compounds of formula (I) and intermediates of the present invention obtained by the same methods as in the above synthesis examples and according to the methods described in detail above are shown in combinations of Table a and Tables 1 to 4. Tables 5 to 7 and Table NMR show the respective compounds and physical property values obtained in the above synthesis examples.

The abbreviations in the table are as follows.
Me: methyl, Et: ethyl, tert-Bu and Bu-t: tertiary butyl, cyclo-Pr: cyclo-propyl

ここで、式中、次式：

Where in the formula:

で表される部分は表ａのＡ１からＡ１０のうちの一つを示す。

The part represented by is one of A1 to A10 in Table a.

ここで、式中、次式：

Where in the formula:

で表される部分は表ａのＡ１からＡ１０のうちの一つを示す。

The part represented by is one of A1 to A10 in Table a.

ここで、式中、次式：

Where in the formula:

で表される部分は表ａのＡ１からＡ１０のうちの一つを示す。

The part represented by is one of A1 to A10 in Table a.

ここで、式中、次式：

Where in the formula:

で表される部分は表ａのＡ１からＡ１０のうちの一つを示す。

The part represented by is one of A1 to A10 in Table a.

別の方法を言及しない限り、供試薬剤は以下のとおり調整した。
溶剤：ジメチルホルムアミド ３重量部
乳化剤：ポリオキシエチレンアルキルフェニルエーテル １重量部

Unless stated otherwise, the reagents were prepared as follows.
Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether

  In order to produce a suitable active compound formulation, 1 part by weight of the active compound 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.

Biological Test Example 1: Tests for Spodoptera litura larvae Sweet potato leaves were immersed in a test solution having an appropriate concentration, air-dried with a chemical solution, placed in a petri dish having a diameter of 9 cm, and 10 third-spotted larvae were released. Placed in a constant temperature room at 25 ° C., sweet potato leaves were added after 2 and 4 days, and the number of dead insects was examined after 7 days to calculate the insecticidal rate. An insecticidal rate of 100% means that all larvae have died. On the other hand, an insecticidal rate of 0% means that no larvae died. In this test, the results of 2 dishes in 1 ward were averaged.

  In the above biological test example 1, as a representative example, the compound No. 1 was used. 5-2, 5-3, 5-4, 5-6, 6-2, 6-3, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5, 7- Compounds 6 and 7-7 exhibited a controlling effect with an insecticidal rate of 100% at an active compound concentration of 100 ppm.

Biological Test Example 2: Tests against Nite spider mites (Tetranychus urticae) 50 to 100 adults of Nite spider mites were inoculated on the leaves of two real leaves grown in a 6 cm diameter pot and tested at an appropriate concentration one day later A sufficient amount of the solution was sprayed using a spray gun. After spraying, the miticide rate was calculated after 7 days in the greenhouse. A miticide rate of 100% means that all ticks have died. On the other hand, a miticide rate of 0% means that there were no dead mites.

  In the above biological test example 2, as a representative example, the compound No. 1 5-2, 5-3, 5-6, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5, 7-6 and 7-7 are active compound concentrations. The control effect of 100% miticide rate was exhibited at 100 ppm.

Biological Test Example 3: Tests against cucumber leaf beetle (Alacophora femorialis) Cucumber leaves are immersed in a test solution of an appropriate concentration, air-dried with a chemical solution, placed in a plastic cup containing sterilized black soil, and 5 larvae of cucurbit beetle I released it. Placed in a constant temperature room at 25 ° C., the number of dead insects was examined after 7 days, and the insecticidal rate was calculated. An insecticidal rate of 100% means that all larvae have died. On the other hand, an insecticidal rate of 0% means that no larvae died.

  In the biological test 3, as a representative example, the compound No. 1 was used. 5-2, 5-3, 5-6, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5, 7-6 and 7-7 are active compound concentrations. The control effect of 100% insecticidal rate was exhibited at 100 ppm.

Biological Test Example 4: Test solvent for cat flea (CTECFE): 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 concentrate is brought to a predetermined concentration with bovine blood. Dilute.

  About 20 adult unsucked cat fleas (Ctenocepahrides felis) are prepared in a flea container. A blood container sealed at the bottom with parafilm is filled with bovine blood provided with a compound solution and placed on a flea container so that the flea can suck blood. Keep the blood container at 37 ° C. and the flea container at room temperature. After 2 days, find the mortality rate. 100% means that all cat fleas have died and 0% means that all are alive.

  In the above biological test, as a representative example, Compound No. 5-2, 6-3, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5, 7-6 and 7-7 are 100% at an applied concentration of 100 ppm. It showed good activity.

Biological Test Example 5: Test species for sheep flies (Lucilia cuprina): sheep flies 1st instar larvae (age 24 hours)
Solvent: dimethyl sulfoxide 10 mg of the active compound is dissolved in 0.5 ml of dimethyl sulfoxide and diluted successively to obtain the desired concentration.

  Approximately 20 sheep wing fly first larvae are placed in a test tube containing 1 ml of ground cubes of meat and 0.5 ml of an aqueous dilution of the test compound. After 48 hours, larval mortality is recorded. 100% means that all larvae have died, 0% means that the larvae have developed normally after 48 hours.

  In the above biological test, as a representative example, Compound No. 5-2, 6-2, 6-3, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5 and 7-6 are 100% at an applied concentration of 100 ppm. It showed good activity.

Biological Test Example 6: Test solvent for Musca domestica Solvent: Dimethyl sulfoxide To make a formulation of the appropriate active compound, 10 mg of the active compound is dissolved in 0.5 ml of solvent and the concentrate is diluted with water to a predetermined concentration. To do.

  As a test preparation step, a sponge of a certain size is impregnated with a mixture of sugar and compound solution and placed in a test container. Ten adult houseflies (Musca domestica) are placed in a container and covered with a vented hole. Two days later, the rate of mortality is measured. 100% means that all house flies have died and 0% means that they are all alive.

  In the above biological test, as a representative example, Compound No. 6-3 showed 90% good activity at an applied concentration of 100 ppm. In the above biological test, as a representative example, Compound No. Compounds 5-2, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5 and 7-6 showed 100% good activity at an applied concentration of 100 ppm.

Biological Test Example 7: Immersion test for Boophilus microplus Solvent: Dimethyl sulfoxide To make a suitable active compound formulation, 10 mg of active compound is dissolved in 0.5 ml of solvent and the concentrate is dissolved in water to a predetermined concentration. Dilute.

  Eight to ten adult ticks are placed in a plastic beaker with holes and immersed in an aqueous compound solution for 1 minute. Transfer the mites to a plastic petri dish with filter paper and examine the eggs that have hatching ability. After 7 days, find the mortality rate. 100% means that all ticks have died, 0% means that all have survived.

  In the above biological test, as a representative example, Compound No. The compounds 5-2, 6-4, 7-1, 7-2, 7-3, 7-4, 7-5 and 7-6 showed 100% good activity at an applied concentration of 100 ppm.

Biological Test Example 8: Injection solvent for Boophilus microplus: Dimethyl sulfoxide 10 mg of active compound is dissolved in 0.5 ml of solvent to make a suitable active compound formulation, and the concentrate is diluted with solvent to a predetermined concentration. To do.

  Five Boo ticks (Boophilus microplus) 1 μL of compound solution is injected into the abdomen of a saturated female adult. Move the mites to the petri dish and keep them in the incubator for a certain period. Investigate laying eggs with hatching ability. After 7 days, find the mortality rate. 100% means that all eggs laid have not hatched and 0% means that all eggs have hatched.

  In the above biological test, as a representative example, Compound No. 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 6-2, 6-3, 6-4, 7-1, 7-2, 7-3, 7- 4, 7-5 and 7-6 compounds showed 100% good activity at an applied concentration of 20 μg / head.

Biological Test Example 9: Test solvent for Amblyoma hebraeum: Dimethyl sulfoxide To make a suitable active compound formulation, 10 mg of the active compound is dissolved in 0.5 ml of solvent and the concentrate is dissolved in the solvent at a predetermined concentration. Dilute to

  Amblyoma hebraeum nymphs are placed in a perforated plastic beaker and immersed in an aqueous compound solution for 1 minute. Transfer the mites to a plastic petri dish with filter paper and keep them in the incubator for 42 days. After 42 days, find the mortality rate. 100% means that all ticks have died, 0% means that all have survived.

  In the above biological test, as a representative example, Compound No. Compounds 7-4 and 7-5 showed 100% good activity at an applied concentration of 100 ppm.

Formulation Example 1 (Granule)
25 parts of water is added to a mixture of 10 parts of the present compound (No. 5-2), 30 parts of bentonite (montmorillonite), 58 parts of talc (talc) and 2 parts of lignin sulfonate, and then hatched well, and extruded. It is made into 10-40 mesh granules with a granulator and dried at 40-50 ° C. to give granules.

Formulation Example 2 (Granule)
95 parts of clay mineral particles having a particle size distribution within the range of 0.2 to 2 mm are placed in a rotary mixer, and under rotation, 5 parts of the present compound (No. 5-2) is sprayed together with the liquid diluent and evenly distributed. After squeezing, it is dried at 40-50 ° C. to give granules.

Formulation Example 3 (Emulsion)
30 parts of the present compound (No. 5-2), 55 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to prepare an emulsion.

Formulation Example 4 (wettable powder)
15 parts of the present compound (No. 5-2), 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 sodium alkylnaphthalenesulfonate 3 parts of formalin condensate is pulverized and mixed to obtain a wettable powder.

Formulation Example 5 (hydrated granules)
20 parts of the present compound (No. 5-2), 30 parts of sodium lignin sulfonate and 15 parts of bentonite and 35 parts of calcined diatomaceous earth powder are thoroughly mixed, water is added, and the mixture is extruded and dried with a 0.3 mm screen. To obtain hydrated granules.

  The novel insecticidal pyrroline derivative of the present invention has an excellent insecticidal action as an insecticide, as shown in the above examples.

Ｚは、水素、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_１−１２アルコキシ、シアノ、Ｃ_１−１２ハロアルコキシ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、Ｃ_１−１２ハロアルキルスルホニル、ヒドロキシ又はチオールを示し、
ｋは、０、１、２、３又は４を示し、
Ｒは、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^１及びＲ^２は非存在であるか、それぞれ独立して水素、ハロゲン、シアノ、アミノ、アジド、ヒドロキシ、メルカプト、ヒドロキシ−カルボニル、Ｃ_１−１２アルキルアミノ−カルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２アルコキシ、Ｃ_１−１２アルキル、Ｃ_２−１２アルケニル、Ｃ_２−１２アルキニル、Ｃ_１−１２アルキルチオ、Ｃ_１−１２アルキルスルフィニル又はＣ_１−１２アルキルスルホニルを示し、ただしＲ^１及びＲ^２は同時に非存在であることはなく、Ｒ^１及びＲ^２は同時に水素ではなく、
Ｒ^３は、水素、アミノ、ヒドロキシ、シアノ、Ｒ^８−ＣＨ_２−、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ、Ｃ_２−１２アルケニル、Ｃ_２−１２アルキニル、Ｃ_１−１２アルキル−カルボニル又はＣ_１−１２アルキル−カルボニルアミノを示し、
Ｒ^４は、水素、シアノ、カルボニル、チオカルボニル、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−１２アルキル−カルボニル、Ｃ_１−１２アルキル−チオカルボニル、Ｃ_１−１２ハロアルキル−カルボニル、Ｃ_１−１２ハロアルキル−チオカルボニル、Ｃ_１−１２アルキルアミノ−カルボニル、Ｃ_１−１２アルキルアミノ−チオカルボニル、ジ（Ｃ_１−１２アルキル）アミノ−カルボニル、ジ（Ｃ_１−１２アルキル）アミノ−チオカルボニル、Ｃ_１−１２アルコキシアミノ−カルボニル、Ｃ_１−１２アルコキシアミノ−チオカルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２アルコキシ−チオカルボニル、Ｃ_１−１２チオアルコキシ−カルボニル、Ｃ_１−１２チオアルコキシ−チオカルボニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルホニル、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−カルボニル又はＣ_２−１２アルキニルアミノ−カルボニルを示し、
また、Ｒ^３とＲ^４は、それが結合する窒素原子と一緒になって３，４，５又は６員の、飽和又は不飽和の複素環を形成してもよく、該複素環はオキソ、チオキソ又はニトロで置換されてもよく、
Ｒ^５は、水素、シアノ、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^６は、水素、Ｃ_１−１２アルキル、Ｃ_１−１２アルキルカルボニル又はＣ_１−１２アルコキシカルボニルを示し、
Ｒ^７は、水素又はＣ_１−１２アルキルを示し
Ｒ^８は、フェニル、又は３、４、５若しくは６員の、飽和又は不飽和の複素環を示し、
Ｚ^１、Ｚ^２及びＺ^３は、それぞれ独立して−Ｃ（Ｒ^９）（Ｒ^１０）−、−Ｃ（＝Ｏ）−、−Ｃ（＝Ｎ−ＯＲ^１１）−、−Ｎ（Ｒ^１１）−、−Ｓ−、−Ｓ（＝Ｏ）−、−Ｓ（＝Ｏ）_２−又は−Ｓ（Ｏ）（＝Ｎ−Ｒ^１１）−を示し、
Ｒ^９及びＲ^１０は、それぞれ独立して水素、ハロゲン、Ｃ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^１１は、水素、シアノ、ニトロ、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_３−８シクロアルキル−Ｃ_１−１２アルキル、Ｃ_１−１２アルキル−カルボニル、Ｃ_１−１２ハロアルキル−カルボニル、Ｃ_１−１２アルコキシ−カルボニル、Ｃ_１−１２ハロアルコキシ−カルボニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルホニル、アリール部が１、２又は３のＲ^１２で置換されてよいアリール−Ｃ_１−１２アルキル、又は複素環部が１、２又は３のＲ^１２で置換されてよい複素環−Ｃ_１−１２アルキルを示し、
Ｒ^１２は、水素、ハロゲン、シアノ、ニトロ、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルコキシ又はＣ_１−１２アルコキシ−カルボニルを示し、
ｍは、１又は２を示し、
上記で定義した基は更にハロゲン、Ｃ_１−１２アルキル、Ｃ_１−１２ハロアルキル、ニトロ、Ｃ_１−１２アルコキシ、シアノ、Ｃ_１−１２ハロアルコキシ、Ｃ_１−１２アルキルスルフェニル、Ｃ_１−１２アルキルスルフィニル、Ｃ_１−１２アルキルスルホニル、Ｃ_１−１２ハロアルキルスルフェニル、Ｃ_１−１２ハロアルキルスルフィニル、Ｃ_１−１２ハロアルキルスルホニル、ヒドロキシ又はメルカプトからなる任意の置換基で置換されてもよい。
か１項に記載の使用。

Z is _{hydrogen, C 1-12} haloalkyl, _{nitro, C 1-12} alkoxy, _{cyano, C 1-12 haloalkoxy, C 1-12 alkylsulfenyl, C 1-12 alkylsulfinyl, C 1-12} alkylsulfonyl, C _1-12 haloalkylsulfenyl, C _1-12 haloalkylsulfinyl, C _1-12 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-12 alkyl or C _1-12 haloalkyl;
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkoxy-carbonyl , C _1-12 alkoxy, C _1-12 alkyl, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkylthio, C _1-12 alkylsulfinyl or C _1-12 alkylsulfonyl, provided that R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkyl-carbonyl or C _1-12 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl-carbonyl, C _1-12 alkyl-thiocarbonyl, C _1-12 haloalkyl-carbonyl, C _1-12 haloalkyl-thiocarbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkylamino-thiocarbonyl, di (C _1-12 alkyl) amino-carbonyl, di (C _1-12 alkyl) amino- Thiocarbonyl, C _1-12 alkoxyamino-carbonyl, C _1-12 alkoxyamino-thiocarbonyl, C _1-12 alkoxy-carbonyl, C _1-12 alkoxy-thiocarbonyl, C _1-12 thioalkoxy-carbonyl, C _{1 -12} thioalkoxy - _{thiocarbonyl, C 1-12} alkylsulfamoyl _{Alkylsulfonyl, C 1-12 haloalkylsulfonyl, C 3-8} cycloalkyl - _{carbonyl, C 2-12} alkenyl - _{carbonyl, C 2-12} alkynyl - _{carbonyl, C 3-8} cycloalkyl _{-C 1-12} alkyl - carbonyl, C _1-12 alkylsulfenyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfinyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfonyl-C _1-12 alkyl-carbonyl, C _1-12 alkyl - carbonyl _{-C 1-12} alkyl - _{carbonyl, C 3-8} cycloalkylamino - indicates a carbonyl, - _{carbonyl, C 2-12} alkenylamino - carbonyl or _{C 2-12} Arukini Le amino
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, the heterocycle being oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-12 alkyl or C _1-12 haloalkyl,
R ⁶ represents hydrogen, C _1-12 alkyl, C _1-12 alkylcarbonyl or C _1-12 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-12 alkyl R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently -C (R ⁹ ) (R ¹⁰ )-, -C (= O)-, -C (= N-OR ¹¹ )-, -N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-12 alkyl or C _1-12 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl-C _1-12 alkyl, C _1-12 alkyl-carbonyl, C _1-12 haloalkyl-carbonyl , C _1-12 alkoxy-carbonyl, C _1-12 haloalkoxy-carbonyl, C _1-12 alkylsulfonyl, C _1-12 haloalkylsulfonyl, aryl wherein aryl may be substituted with 1, 2 or 3 R ¹² C _1-12 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-12} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy or C _1-12 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _1-12 alkoxy, cyano, C _1-12 haloalkoxy, C _1-12 alkylsulfenyl, C _{1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, it may be substituted with any substituent consisting of hydroxy or mercapto.
Or use according to item 1.

Ｚが、水素、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_１−６アルコキシ、シアノ、Ｃ_１−６ハロアルコキシ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、Ｃ_１−６ハロアルキルスルホニル、ヒドロキシ又はチオールを示し、
ｋが、０、１、２、３又は４を示し、
Ｒが、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^１及びＲ^２が非存在であるか、それぞれ独立して水素、ハロゲン、シアノ、アミノ、アジド、ヒドロキシ、メルカプト、ヒドロキシ−カルボニル、Ｃ_１−６アルキルアミノ−カルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６アルコキシ、Ｃ_１−６アルキル、Ｃ_２−６アルケニル、Ｃ_２−６アルキニル、Ｃ_１−６アルキルチオ、Ｃ_１−６アルキルスルフィニル又はＣ_１−６アルキルスルホニルを示し、ただしＲ^１及びＲ^２は同時に非存在であることはなく、Ｒ^１及びＲ^２は同時に水素ではなく、
Ｒ^３が、水素、アミノ、ヒドロキシ、シアノ、Ｒ^８−ＣＨ_２−、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ、Ｃ_２−６アルケニル、Ｃ_２−６アルキニル、Ｃ_１−６アルキル−カルボニル又はＣ_１−６アルキル−カルボニルアミノを示し、
Ｒ^４が、水素、シアノ、カルボニル、チオカルボニル、Ｒ^８−ＣＯ−、Ｒ^８−ＣＳ−、Ｃ_１−６アルキル−カルボニル、Ｃ_１−６アルキル−チオカルボニル、Ｃ_１−６ハロアルキル−カルボニル、Ｃ_１−６ハロアルキル−チオカルボニル、Ｃ_１−６アルキルアミノ−カルボニル、Ｃ_１−６アルキルアミノ−チオカルボニル、ジ（Ｃ_１−６アルキル）アミノ−カルボニル、ジ（Ｃ_１−６アルキル）アミノ−チオカルボニル、Ｃ_１−６アルコキシアミノ−カルボニル、Ｃ_１−６アルコキシアミノ−チオカルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６アルコキシ−チオカルボニル、Ｃ_１−６チオアルコキシ−カルボニル、Ｃ_１−６チオアルコキシ−チオカルボニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルホニル、Ｃ_３−７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_３−７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_３−７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−カルボニル又はＣ_２−６アルキニルアミノ−カルボニルを示し、
また、Ｒ^３とＲ^４が、それが結合する窒素原子と一緒になって３，４，５又は６員の、飽和又は不飽和の複素環を形成してもよく、該複素環はオキソ、チオキソ又はニトロで置換されてもよく、
Ｒ^５が、水素、シアノ、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^６が、水素、Ｃ_１−６アルキル、Ｃ_１−６アルキルカルボニル又はＣ_１−６アルコキシカルボニルを示し、
Ｒ^７が、水素又はＣ_１−６アルキルを示し
Ｒ^８が、フェニル、又は３、４、５若しくは６員の、飽和又は不飽和の複素環を示し、
Ｚ^１、Ｚ^２及びＺ^３が、それぞれ独立して−Ｃ（Ｒ^９）（Ｒ^１０）−、−Ｃ（＝Ｏ）−、−Ｃ（＝Ｎ−ＯＲ^１１）−、−Ｎ（Ｒ^１１）−、−Ｓ−、−Ｓ（＝Ｏ）−、−Ｓ（＝Ｏ）_２−又は−Ｓ（Ｏ）（＝Ｎ−Ｒ^１１）−を示し、
Ｒ^９及びＲ^１０が、それぞれ独立して水素、ハロゲン、Ｃ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^１１が、水素、シアノ、ニトロ、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_３−７シクロアルキル−Ｃ_１−６アルキル、Ｃ_１−６アルキル−カルボニル、Ｃ_１−６ハロアルキル−カルボニル、Ｃ_１−６アルコキシ−カルボニル、Ｃ_１−６ハロアルコキシ−カルボニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルホニル、アリール部が１、２又は３のＲ^１２で置換されてよいアリール−Ｃ_１−６アルキル、又は複素環部が１、２又は３のＲ^１２で置換されてよい複素環−Ｃ_１−６アルキルを示し、
Ｒ^１２が、水素、ハロゲン、シアノ、ニトロ、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルコキシ又はＣ_１−６アルコキシ−カルボニルを示し、
ｍが、１又は２を示し、
上記で定義した基は更にハロゲン、Ｃ_１−６アルキル、Ｃ_１−６ハロアルキル、ニトロ、Ｃ_１−６アルコキシ、シアノ、Ｃ_１−６ハロアルコキシ、Ｃ_１−６アルキルスルフェニル、Ｃ_１−６アルキルスルフィニル、Ｃ_１−６アルキルスルホニル、Ｃ_１−６ハロアルキルスルフェニル、Ｃ_１−６ハロアルキルスルフィニル、Ｃ_１−６ハロアルキルスルホニル、ヒドロキシ又はメルカプトからなる任意の置換基で置換されてもよい、を示す場合の化合物を好適なものとして挙げることができる。

Z is _{hydrogen, C 1-6} haloalkyl, _{nitro, C 1-6} alkoxy, _{cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6} alkylsulfonyl, C _1-6 haloalkylsulfenyl, C _1-6 haloalkylsulfinyl, C _1-6 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-6 alkyl or C _1-6 haloalkyl,
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkoxy-carbonyl , C _1-6 alkoxy, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkylthio, C _1-6 alkylsulfinyl or C _1-6 alkylsulfonyl, wherein R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkyl-carbonyl or C _1-6 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl-carbonyl, C _1-6 alkyl-thiocarbonyl, C _1-6 haloalkyl-carbonyl, C _1-6 haloalkyl-thiocarbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkylamino-thiocarbonyl, di (C _1-6 alkyl) amino-carbonyl, di (C _1-6 alkyl) amino- Thiocarbonyl, C _1-6 alkoxyamino-carbonyl, C _1-6 alkoxyamino-thiocarbonyl, C _1-6 alkoxy-carbonyl, C _1-6 alkoxy-thiocarbonyl, C _1-6 thioalkoxy-carbonyl, C _{1 -6} thioalkoxy - _{thiocarbonyl, C 1-6 alkylsulfonyl, C 1-6} Haroarukirusu _{Honiru, C 3-7} cycloalkyl - _{carbonyl, C 2-6} alkenyl - _{carbonyl, C 2-6} alkynyl - _{carbonyl, C 3-7} cycloalkyl _{-C 1-6} alkyl - _{carbonyl, C 1-6} alkylsulfenyl - C _1-6 alkyl-carbonyl, C _1-6 alkylsulfinyl-C _1-6 alkyl-carbonyl, C _1-6 alkylsulfonyl-C _1-6 alkyl-carbonyl, C _1-6 alkyl-carbonyl-C _1-6 alkyl - _{carbonyl, C 3-7} cycloalkylamino - _{carbonyl, C 2-6} alkenyl amino - carbonyl or _{C 2-6} Arukini Le amino - indicates a carbonyl,
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, which is oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-6 alkyl or C _1-6 haloalkyl,
R ⁶ represents hydrogen, C _1-6 alkyl, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-6 alkyl and R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently —C (R ⁹ ) (R ¹⁰ ) —, —C (═O) —, —C (= N—OR ¹¹ ) —, —N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-6 alkyl or C _1-6 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _3-7 cycloalkyl-C _1-6 alkyl, C _1-6 alkyl-carbonyl, C _1-6 haloalkyl-carbonyl , _{C 1-6} alkoxy - _{carbonyl, C 1-6} haloalkoxy - _{carbonyl, C 1-6 alkylsulfonyl, C 1-6} haloalkylsulfonyl, aryl aryl portion may be substituted with ^{R 12} in 1, 2 or 3 - C _1-6 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-6} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy or C _1-6 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _1-6 alkoxy, cyano, C _1-6 haloalkoxy, C _1-6 alkylsulfenyl, C _1-6 shown _{alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6} haloalkylsulfonyl, and it may also be substituted with any substituent consisting of hydroxy or mercapto The compounds of the case can be mentioned as suitable.

Substituents “optionally substituted with any substituent” are, for example, amino, hydroxy, oxo, thioxo, halogen, nitro, cyano, isocyano, mercapto, isothiocyanate, carboxy, carboxamide, SF ₅ , aminosulfonyl, Alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkylcarbonyl-amino, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyl Oxycarbonyl, aryloxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio , Alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfenyl, alkylsulfinyl, A Le Kirusurufiniru including isomers, alkylsulfonyl, mono-alkylaminosulfonyl, dialkylaminosulfonyl, alkyl phosphinyl, alkylphosphonyl, isomer Alkyl phosphinyl containing, isomer containing alkyl phosphonyl, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl, N-alkylcarbonyl-aminocarbonyl, N-alkylcarbonyl-N-alkylaminocarbonyl, Aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, heterocycle, trialkylsilyl, alkoxyalkyl, alkylthioalkyl , Alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkylcarbonyl or haloalkoxyalkyl, preferably chloro , Fluoro, bromo, iodo, amino, nitro, cyano, hydroxy, thio or carboxy.

In the compound of formula (I), when (T) is (T-1),
5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazole-1 -Yl) benzonitrile, 2- (1H-1,2,4-triazol-1-yl) -5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] benzonitrile, 5- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H- Pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- {3- [3,4-dichloro-5- (trifluoromethyl) phenyl] -3 -(Trifluoromethyl) -3,4-dihy B-2H-pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- {3- [3-fluoro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 5- [3- ( 2,6-dichloropyridin-4-yl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazol-1- Yl) benzonitrile, 5- {3- [2-chloro-6- (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl } -2- (1H-1,2,4-triazo Ru-1-yl) benzonitrile, 5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole- 5-yl} -2- (1H-1,2,4-triazol-1-yl) benzonitrile, 1- (4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (Trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-cyanophenyl) -1H-pyrazole-4-carbonitrile (cited document WO 2009/097992)
In the compound of formula (I), when (T) is (T-2),
N- {2-chloro-4- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- { 2-chloro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- { 2 -bromo -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} acetamide, N- {2 -Bromo - 4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2 - bromo-4- [3 (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl] benzyl} cyclopropanecarboxamide, N-{2-bromo-4- [ 3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} -2- (methylsulfanyl) acetamide, N- {2 -Bromo - 4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzyl} -2- (methylsulfinyl) acetamide, N-{2-bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl] Baie Dil} -2- (methylsulfonyl) acetamide, N- {4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 Yl] -2- (trifluoromethyl) benzyl} propanamide, N- {2-methyl-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4- Dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2-nitro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4- Dihydro-2H-pyrrol-5-yl] benzyl} propanamide, N- {2-cyano-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4- Dihydro-2H-pi Roll-5-yl] benzyl} propanamide, N- (2-bromo-4- {3- [3,4-dichloro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3, 4-dihydro-2H-pyrrol-5-yl} benzyl) propanamide, N- (2-bromo-4- {3- [3-fluoro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) ) -3,4-dihydro-2H-pyrrol-5-yl} benzyl) propanamide, N- (4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzyl) propanamide, N- (4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl]- 3- (Tri Fluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-bromobenzyl) propanamide, N- (1- {4- [3- (3,4,5-trichlorophenyl) -3- (Trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] phenyl} ethyl) propanamide, N- [1- (4- {3- [3,5-bis (trifluoromethyl) phenyl] ] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} phenyl) ethyl] cyclopropanecarboxamide (cited document WO2009 / 097992)
In the compound of formula (I), when (T) is (T-3),
N- {5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-indene-1 -Yl} propanamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2, 3-dihydro-1H-inden-1-yl} acetamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole -5-yl] -2,3-dihydro-1H-inden-1-yl} propanamide, N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl)- 3,4-dihydro-2H-pyrrole-5 Yl] -2,3-dihydro-1H-inden-1-yl} cyclopropanecarboxamide, 3,3,3-trifluoro-N- {5- [3- (3,4,5-trichlorophenyl)- 3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} propanamide, 2- (methylsulfanyl) -N- { 5- [3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-indene-1 -Yl} acetamide, 2- (methylsulfinyl) -N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Il] -2 3-dihydro-1H-inden-1-yl} acetamide, 2- (methylsulfonyl) -N- {5- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} acetamide, N- (5- {3- [3,4-dichloro-5- (trifluoromethyl) ) Phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) propanamide, N- (5- { 3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-indene-1 -Yl) propanami N- (5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) propanamide, N- (5- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) ) -3,4-dihydro-2H-pyrrol-5-yl} -2,3-dihydro-1H-inden-1-yl) -2- (methylsulfonyl) acetamide (cited document WO 2009/112275)
In the compound of formula (I), when (T) is (T-4),
4- [3- (3,5-Dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2-methyl-N- (thietan-3-yl) benzamide 2-methyl-N- (thietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Yl] benzamide, 2-methyl-N- (1-oxidethietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4 -Dihydro-2H-pyrrol-5-yl] benzamide, 2-methyl-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-trichlorophenyl)- 3- (Trifluoromethyl) -3,4-dihy 2H-pyrrol-5-yl] benzamide, 2-chloro-N- (thietan-3-yl) -4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl)- 3,4-dihydro-2H-pyrrol-5-yl] benzamide, 2-chloro-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-tri Chlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, 2-bromo-N- (1,1-dioxidethietan-3-yl) -4- [3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, N- (1,1-dioxidethietane- 3-yl) -4- [3- (3,4,5 Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl] -2- (trifluoromethyl) benzamide, N-(1,1-di-oxide Chie Tan 3- Yl) -2-nitro-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzamide, 4- { 3- [3,4-Dichloro-5- (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (thietane) -3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Methyl-N -(Thietan-3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl } -2-Methyl-N- (1-oxidethietan-3-yl) benzamide, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3, 4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1,1-dioxidethietan-3-yl) benzamide, 4- {3- [2,6-bis (trifluoro) Pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (thietan-3-yl) benzamide, 4- {3- [2,6-bis (trifluoro) pi Gin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1-oxidethietan-3-yl) benzamide, 4 -{3- [2,6-bis (trifluoro) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methyl-N- (1,1-Dioxidethietan-3-yl) benzamide (cited document WO2009 / 080250)
In the compound of formula (I), when (T) is (T-5),
5- [3- (3,5-dichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2-fluorobenzonitrile, 2-fluoro-5- [3 -(3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzonitrile, 5- (3-bromo-4-fluorophenyl)- 3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole, methyl 2-methyl-4- [3- (3,4,5-trichlorophenyl) ) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] benzoate, 2-methyl-4- [3- (3,4,5-trichlorophenyl) -3- (tri Fluoromethyl ) -3,4-dihydro-2H-pyrrol-5-yl] benzoic acid, 2-bromo-4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3, 4-Dihydro-2H-pyrrol-5-yl] benzonitrile, 4- [3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 -Yl] -2- (trifluoromethyl) benzonitrile, 5- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole -5-yl} -2-fluorobenzonitrile, 3- [3,5-bis (trifluoromethyl) phenyl] -5- (3-bromo-4-fluorophenyl) -3- (trifluoromethyl) -3 , 4 Dihydro-2H-pyrrole, methyl 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Methylbenzoate, 4- {3- [3,5-bis (trifluoromethyl) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylben Zoic acid, 4- {3- [3,5-bis (trifluoro) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzonitrile, 4- {3- [3,5-bis (trifluoro) phenyl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-chlorobenzonitrile, 4- [ 5 (3-Bromo-4-fluorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-3-yl] -2,6-bis (trifluoromethyl) pyridine, 5- {3 -[2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-fluorobenzonitrile, methyl 4 -{3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzoate; 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2-methylbenzo Ikua 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} -2 -Bromobenzonitrile, 4- {3- [2,6-bis (trifluoromethyl) pyridin-4-yl] -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} 2-Methylbenzonitrile (cited documents JP2007-91708, JP2008-133273, WO2009 / 072621, WO2009 / 097992, WO2009 / 112275)

The starting compound of formula (III) in step (b-1) in the production method (b) is novel, and representative examples thereof include methyl 3- (3,5-dichlorophenyl) -4,4,4-trifluorobutene- 2-Enoate, methyl 4,4,4-trifluoro - 3- (3,4,5-trichlorophenyl) -butene-2-enoate, ethyl 4,4,4-trifluoro - 3- (3,4, 5-trichlorophenyl) -butene-2-enoate, isopropyl 4,4,4-trifluoro - 3- (3,4,5-trichlorophenyl) -butene-2-enoate, tert-butyl 4,4,4- trifluoro - 3- (3,4,5-trichlorophenyl) - butene-2-enoate, benzyl 4,4,4-trifluoro - 3- (3,4,5-trichlorophenyl) Butene-2-enoate, methyl [3,5-bis (trifluoromethyl) phenyl] -4,4,4-trifluorobutene-2-enoate, ethyl [3,5-bis (trifluoromethyl) phenyl]- 4,4,4-trifluorobuten-2-enoate, isopropyl [3,5-bis (trifluoromethyl) phenyl] -4,4,4-trifluorobutene-2-enoate, methyl 3- [2,6 -Bis (trifluoromethyl) pyridin-4-yl] -4,4,4-trifluorobutene-2-enoate.

Any plant and plant part can be treated according to the invention. In the context of the present invention, plants should be understood as meaning all plants and plant populations such as desirable and undesirable wild plants or cereal plants (including naturally occurring cereal plants). A cereal plant can be a plant obtainable by conventional plant breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including transgenic plants, depending on the rights of the plant breeder Plant varieties that can or cannot be protected are included. Plant parts are to be understood as meaning all parts and organs of the plant above and below the ground, such as buds, leaves, flowers and roots, for example leaves, needles. Stalks, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include collected material and materials that grow by asexual and sexual reproduction, such as cuttings, tubers, rhizomes, side branches and seeds.

When used as insecticides, the active compounds according to the invention can be prepared in customary dosage forms. Examples of formulation forms include solutions, emulsions, wettable powders, water dispersible granules, suspensions, powders, foams, pastes, tablets, granules, aerosols, natural and synthetic substances impregnated with active compounds, microcapsules, Seed coatings, formulations used with combustion devices (eg, fumigation and smoke cartridges, cans, coils, etc. as combustion devices) or ULVs (cold mists, warm mists) and the like.

The liquefied gaseous diluent or carrier may be one that is gaseous at ambient temperature and pressure , such as aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide and halogenated hydrocarbons.

The compounds of the present invention may be used in commercially useful formulations and in application forms prepared from the formulations in addition to other active compounds such as insecticides, toxic baits, fungicides, acaricides, nematicides. It can also be present as a mixture with fungicides, growth regulators, herbicides and the like.

<Synthesis Example 3>
N- (4- {3- [3,5- bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl} -2 -Bromobenzyl) cyclopropanecarboxamide (Compound No. 6-3)

Step 3-1: tert-butyl (4- {3- [3,5-bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol - Synthesis of 5-yl} -2-bromobenzyl) carbamate

ｔｅｒｔ‐ブチル（４‐｛３‐［３，５‐ビス（トリフルオロメチル）フェニル］‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモベンジル）カルバメート（４７０ｍｇ，０．７４ｍｍｏｌ）を四塩化炭素（１００ｍＬ）に溶解し、Ｎ‐クロロスクシンイミド（９９．１ｍｇ，０．７４ｍｍｏｌ）を加え、室温にて終夜撹拌した。反応混合物を減圧濃縮し、残渣をｔｅｒｔ‐ブチルメチルエーテルに溶解し、水、飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮し、カラムクロマトグラフィーにて精製し目的物を得た（３６０ｍｇ）。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δ：１．４６（９Ｈ，ｓ），４．４４（２Ｈ，ｄ），４．６４（１Ｈ，ｄ），５．０９−４．９８（２Ｈ，ｍ），５．６４（１Ｈ，ｓ），７．５１（１Ｈ，ｄ），７．８１（２Ｈ，ｓ），７．８８（１Ｈ，ｄｄ），７．９６（１Ｈ，ｓ），８．１９（１Ｈ，ｄ）．

tert- butyl (4- {3- [3,5-bis (tri-off Ruoromechiru) phenyl] -3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl} -2-bromobenzyl ) Carbamate (470 mg, 0.74 mmol) was dissolved in carbon tetrachloride (100 mL), N-chlorosuccinimide (99.1 mg, 0.74 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tert-butyl methyl ether and washed with water and saturated brine. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography to obtain the desired product (360 mg).
¹ H-NMR (CDCl ₃ ) δ: 1.46 (9H, s), 4.44 (2H, d), 4.64 (1H, d), 5.09-4.98 (2H, m), 5.64 (1H, s), 7.51 (1H, d), 7.81 (2H, s), 7.88 (1H, dd), 7.96 (1H, s), 8.19 (1H , D).

Step 3-2: 1- (4- {3- [3,5-bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrole- -Yl} -2-bromophenyl) methanamine

ｔｅｒｔ‐ブチル（４‐｛３‐［３，５‐ビス（トリフルオロメチル）フェニル］‐４‐クロロ‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモベンジル）カルバメート（３００ｍｇ，０．４４ｍｍｏｌ）を１，２‐ジクロロメタン（３０ｍＬ）に溶解し、トリフルオロ酢酸（２５６ｍｇ，２２．４ｍｍｏｌ）を加え、室温にて１時間撹拌した。反応混合物を減圧濃縮した後、残渣をｔｅｒｔ‐ブチルメチルエーテルに溶解し、飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮した（２１２ｍｇ）。なお、目的物は精製することなく次の反応に用いた。

tert- butyl (4- {3- [3,5-bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl} - 2-Bromobenzyl) carbamate (300 mg, 0.44 mmol) was dissolved in 1,2-dichloromethane (30 mL), trifluoroacetic acid (256 mg, 22.4 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in tert-butyl methyl ether, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure (212 mg). . The target product was used in the next reaction without purification.

Step 3-3: N- (4- {3- [ 3,5- bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrole- Synthesis of -yl} -2-bromobenzyl) cyclopropanecarboxamide

１‐（４‐｛３‐［３，５‐ビス（トリフルオロメチル）フェニル］‐４‐クロロ‐３‐（トリフルオロメチル）‐３，４‐ジヒドロ‐２Ｈ‐ピロール‐５‐イル｝‐２‐ブロモフェニル）メタンアミン（１００ｍｇ，０．１７ｍｍｏｌ）をテトラヒドロフラン（５ｍＬ）に溶解し、ピリジン（１３９ｍｇ，１．７６ｍｍｏｌ）、シクロプロパンカルボニルクロリド（２２ｍｇ，０．２１ｍｍｏｌ）を加え、終夜撹拌した。反応混合物をｔｅｒｔ‐ブチルメチルエーテルで希釈した後、２Ｎ塩酸、水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥、ろ過した後、減圧濃縮した。得られた残渣をカラムクロマトグラフィーで精製し、目的物を得た（１００ｍｇ）。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：０．７５‐０．８１（２Ｈ，ｍ），０．９８‐１．０４（２Ｈ，ｍ），１．３７‐１．４３（１Ｈ，ｍ），４．５７‐４．６７（３Ｈ，ｍ）， ５．０１（１Ｈ，ｄ），５．６４（１Ｈ，ｓ），６．２１（１Ｈ，ｂｒ ｓ），７．５３（１Ｈ，ｄ），７．８１（２Ｈ，ｓ），７．８６（１Ｈ，ｄｄ），７．９６（１Ｈ，ｓ），８．２０（１Ｈ，ｄ）．

1- (4- {3- [3,5-bis (tri-off Ruoromechiru) phenyl] -4-chloro-3- (trifluoromethyl) -3,4-dihydro -2H- pyrrol-5-yl} -2 -Bromophenyl) methanamine (100 mg, 0.17 mmol) was dissolved in tetrahydrofuran (5 mL), pyridine (139 mg, 1.76 mmol) and cyclopropanecarbonyl chloride (22 mg, 0.21 mmol) were added, and the mixture was stirred overnight. The reaction mixture was diluted with tert-butyl methyl ether, washed with 2N hydrochloric acid, water and saturated brine, and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography to obtain the desired product (100 mg).
¹ H-NMR (CDCl ₃ ) δ: 0.75-0.81 (2H, m), 0.98-1.04 (2H, m), 1.37-1.43 (1H, m), 4 .57-4.67 (3H, m), 5.01 (1H, d), 5.64 (1H, s), 6.21 (1H, br s), 7.53 (1H, d), 7 .81 (2H, s), 7.86 (1H, dd), 7.96 (1H, s), 8.20 (1H, d).

Step 4-1: 4- {3- [3,5-Bis (trifluoromethyl) phenyl] -4-bromo-3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl} synthesis of 2-bromo-benzoic acid

メチル ２−（３−シアノ−４−フルオロフェニル）−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−３−カルボキシレート（１８０ｍｇ，０．３７ｍｍｏｌ）、１Ｈ−１，２，４−トリアゾール（３３ｍｇ，０．４７ｍｍｏｌ）、及び炭酸カリウム（７６ｍｇ，０．５５ｍｍｏｌ）をＤＭＦ（１０ｍｌ）と共に１００℃で２時間反応させた。反応混合物を水に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した後、減圧下溶媒を溜去し、残渣をシリカゲルカラムクロマトグラフィーを用いて精製した。（溶媒 ヘキサン／酢酸エチル６０／４０から０／１００まで酢酸エチルの比率を増していった）。メチル ５−［３−シアノ−４−（１Ｈ−１，２，４−トリアゾロ−１−イル）フェニル］−３−（３，４，５−トリクロロフェニル）−３−（トリフルオロメチル）−３，４−ジヒドロ−２Ｈ−ピロール−４−カルボキシレート ^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．５２（３Ｈ，ｓ），４．７２−４．９９（３Ｈ，ｍ），７．４１−８．９３（７Ｈ，ｍ）、及びメチル ２−［３−シアノ−４−（１Ｈ−１，２，４−トリアゾロ−１−イル）フェニル］−４−（３，４，５−トリクロロフェニル）−４−（トリフルオロメチル）−４，５−ジヒドロ−１Ｈ−ピロール−３−カルボキシレート ^１Ｈ−ＮＭＲ（ＣＤＣｌ_３） δ：３．４６（３Ｈ，ｓ），３．８０（１Ｈ，ｄｄ），４．３４（１Ｈ，ｄｄ），４．４８（１Ｈ，ｓ），７．２５−８．８９（８Ｈ，ｍ）の混合物１１０ｍｇ、収率５５％、を得た。

Methyl 2- (3-cyano-4-fluorophenyl) -4- (3,4,5-trichlorophenyl) -4- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-3-carboxylate ( 180 mg, 0.37 mmol), 1H-1,2,4-triazole (33 mg, 0.47 mmol), and potassium carbonate (76 mg, 0.55 mmol) were reacted with DMF (10 ml) at 100 ° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography. (Solvent increased the ratio of ethyl acetate from hexane / ethyl acetate 60/40 to 0/100). Methyl 5- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3 , 4-dihydro-2H-pyrrole-4-carboxylate ¹ H-NMR (CDCl ₃ ) δ: 3.52 (3H, s), 4.72-4.99 (3H, m), 7.41-8 .93 (7H, m), and methyl 2- [3-cyano-4- (1H-1,2,4-triazolo-1-yl) phenyl] -4- (3,4,5-trichlorophenyl)- 4- (trifluoromethyl) -4,5-dihydro-1H-pyrrole-3-carboxylate ¹ H-NMR (CDCl ₃ ) δ: 3.46 (3H, s), 3.80 (1H, dd), 4.34 (1H, dd), 4.48 (1H, s), 7.25- .89 (8H, m) mixture 110 mg, 55% yield, was obtained.

別の方法を言及しない限り、供試薬剤は以下のとおり調製した。
溶剤：ジメチルホルムアミド ３重量部
乳化剤：ポリオキシエチレンアルキルフェニルエーテル １重量部

Unless stated otherwise, the reagents were prepared as follows.
Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether

Biological test example 8: Injection test on Boophilus microplus Solvent: Dimethyl sulfoxide To make a formulation of the appropriate active compound, 10 mg of the active compound is dissolved in 0.5 ml of solvent and the concentrate is dissolved in the solvent. To dilute to the desired concentration.

Claims (4)

Formula (I):

Where
Next formula

The part represented by the following formula:

Or
Or when R ² is hydroxy-carbonyl, C _1-12 alkoxy-carbonyl or cyano,
Next formula

The part represented by the following formula:

(In the formula, R ¹ represents hydrogen.)
Or

(Wherein R ¹ is absent)
Or a mixture of these positional isomers,
T represents one of the following formulas (T-1), (T-2), (T-3), (T-4) or (T-5),

B represents N or C—X ³ ;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _1-12 alkoxy, C _1-12 haloalkoxy , _{cyano, C 1-12} alkyl _{sulphenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, hydroxy, mercapto , Amino, C _1-12 acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkoxy-imino, C _1-12 haloalkoxy-imino, C _1-12 alkyl Represents sulfonylamino or sulfur pentafluoride,
Y ¹ , Y ² , Y ³ , Y ⁴ and Y ⁵ are each independently hydrogen, halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _3-8 cycloalkyl, C _3-8 cyclo _{haloalkyl, C 1-12 alkoxy, C 1-12} haloalkoxy, _{cyano, C 1-12} alkyl _{sulphenyl, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1- 12} haloalkylsulfinyl, C _1-12 haloalkylsulfonyl, C _1-12 alkylsulfonyloxy, C _1-12 alkylaminosulfonyl, C _1-12 haloalkylaminosulfonyl, di (C _1-12 alkyl) aminosulfonyl, di (C _{1 -12} haloalkyl) aminosulfonyl, hydroxy, mercapto, Amino, C _1-12 alkylamino, di (C _1-12 alkyl) amino, C _1-12 acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkylsulfonyl Amino, C _1-12 haloalkylsulfonylamino, tri (C _1-12 alkyl) silyl, C _1-12 alkoxy-imino, C _1-12 haloalkoxy-imino, C _1-12 alkoxy-imino-C _1-12 alkyl C _1-12 haloalkoxy-imino-C _1-12 alkyl, C _1-12 alkylsulfinylimino, C _1-12 alkylsulfinylimino-C _1-12 alkyl, C _1-12 alkylsulfinylimino-C _1-12 alkyl - _{carbonyl, C 1-12} alkylsulfonyl alkoximinoalkyl Mino C _1-12 alkylsulfonyl alkoximinoalkyl amino _{-C 1-12 alkyl, C 1-12} alkoxy - _{carbonyl, C 1-12} alkyl - carbonyl, _{aminocarbonyl, C 1-12} alkyl - amino, aminocarbonyl, - thiocarbonyl, _{C 1 -12 represents} alkylamino-thiocarbonyl, di ( _C1-12alkyl ) amino-carbonyl, di ( _C1-12alkyl ) amino-thiocarbonyl or hydroxycarbonyl;
G represents any of the following formulas G1 to G9,

Z is _{hydrogen, C 1-12} haloalkyl, _{nitro, C 1-12} alkoxy, _{cyano, C 1-12 haloalkoxy, C 1-12 alkylsulfenyl, C 1-12 alkylsulfinyl, C 1-12} alkylsulfonyl, C _1-12 haloalkylsulfenyl, C _1-12 haloalkylsulfinyl, C _1-12 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-12 alkyl or C _1-12 haloalkyl;
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkoxy-carbonyl , C _1-12 alkoxy, C _1-12 alkyl, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkylthio, C _1-12 alkylsulfinyl or C _1-12 alkylsulfonyl, provided that R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy, C _2-12 alkenyl, C _2-12 alkynyl, C _1-12 alkyl-carbonyl or C _1-12 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-12 alkyl-carbonyl, C _1-12 alkyl-thiocarbonyl, C _1-12 haloalkyl-carbonyl, C _1-12 haloalkyl-thiocarbonyl, C _1-12 alkylamino-carbonyl, C _1-12 alkylamino-thiocarbonyl, di (C _1-12 alkyl) amino-carbonyl, di (C _1-12 alkyl) amino- Thiocarbonyl, C _1-12 alkoxyamino-carbonyl, C _1-12 alkoxyamino-thiocarbonyl, C _1-12 alkoxy-carbonyl, C _1-12 alkoxy-thiocarbonyl, C _1-12 thioalkoxy-carbonyl, C _{1 -12} thioalkoxy - _{thiocarbonyl, C 1-12} alkylsulfamoyl _{Alkylsulfonyl, C 1-12 haloalkylsulfonyl, C 3-8} cycloalkyl - _{carbonyl, C 2-12} alkenyl - _{carbonyl, C 2-12} alkynyl - _{carbonyl, C 3-8} cycloalkyl _{-C 1-12} alkyl - carbonyl, C _1-12 alkylsulfenyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfinyl-C _1-12 alkyl-carbonyl, C _1-12 alkylsulfonyl-C _1-12 alkyl-carbonyl, C _1-12 alkyl - carbonyl _{-C 1-12} alkyl - _{carbonyl, C 3-8} cycloalkylamino - _{carbonyl, C 2-12} alkenylamino - carbonyl or _{C 2-12} Arukiniamino - indicates a carbonyl,
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, the heterocycle being oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-12 alkyl or C _1-12 haloalkyl,
R ⁶ represents hydrogen, C _1-12 alkyl, C _1-12 alkylcarbonyl or C _1-12 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-12 alkyl R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently -C (R ⁹ ) (R ¹⁰ )-, -C (= O)-, -C (= N-OR ¹¹ )-, -N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-12 alkyl or C _1-12 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl-C _1-12 alkyl, C _1-12 alkyl-carbonyl, C _1-12 haloalkyl-carbonyl , C _1-12 alkoxy-carbonyl, C _1-12 haloalkoxy-carbonyl, C _1-12 alkylsulfonyl, C _1-12 haloalkylsulfonyl, aryl wherein aryl may be substituted with 1, 2 or 3 R ¹² C _1-12 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-12} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _1-12 alkoxy, C _1-12 haloalkoxy or C _1-12 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-12 alkyl, C _1-12 haloalkyl, nitro, C _1-12 alkoxy, cyano, C _1-12 haloalkoxy, C _1-12 alkylsulfenyl, C _{1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12} haloalkyl _{sulfenyl, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, it may be substituted with any substituent consisting of hydroxy or mercapto,
A pyrroline derivative represented by: Next formula

The part represented by the following formula:

Or
Or when R ² is hydroxy-carbonyl, C _1-6 alkoxy-carbonyl or cyano,
Next formula

The part represented by the following formula:

(In the formula, R ¹ represents hydrogen.)
Or

(Wherein R ¹ is absent)
Or a mixture of these positional isomers,
T represents any one of the following formulas (T-1), (T-2), (T-3), (T-4) or (T-5),

B represents N or C—X ³ ;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _1-6 alkoxy, C _1-6 haloalkoxy , _{cyano, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6} haloalkylsulfonyl, hydroxy, mercapto , Amino, C _1-6 acylamino, C _1-6 alkoxy-carbonylamino, C _1-6 haloalkoxy-carbonylamino, C _1-6 alkoxy-imino, C _1-6 haloalkoxy-imino, C _1-6 alkyl Represents sulfonylamino or sulfur pentafluoride,
Y ¹ , Y ² , Y ³ , Y ⁴ and Y ⁵ are each independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _3-7 cycloalkyl, C _3-7 cyclo _{haloalkyl, C 1-6 alkoxy, C 1-6} haloalkoxy, _{cyano, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1- 6} haloalkylsulfinyl, C _1-6 haloalkylsulfonyl, C _1-6 alkylsulfonyloxy, C _1-6 alkylaminosulfonyl, C _1-6 haloalkylaminosulfonyl, di (C _1-6 alkyl) aminosulfonyl, di (C _{1 -6} haloalkyl) aminosulfonyl, hydroxy, mercapto, _{amino, C 1-6} alkylamino , Di _{(C 1-6} alkyl) _{amino, C 1-6 acylamino, C 1-6} alkoxy - carbonyl _{amino, C 1-6} haloalkoxy - _{carbonylamino, C 1-6 alkylsulfonylamino, C 1-6} haloalkylsulfonyl Amino, tri (C _1-6 alkyl) silyl, C _1-6 alkoxy-imino, C _1-6 haloalkoxy-imino, C _1-6 alkoxy-imino-C _1-6 alkyl, C _1-6 haloalkoxy- Imino-C _1-6 alkyl, C _1-6 alkylsulfinylimino, C _1-6 alkylsulfinylimino-C _1-6 alkyl, C _1-6 alkylsulfinylimino-C _1-6 alkyl-carbonyl, C _1-6 alkylsulfonyl alkoximinoalkyl _{amino, C 1-6} alkylsulfonyl alkoximinoalkyl Mino _{-C 1-6 alkyl, C 1-6} alkoxy Sheet - _{carbonyl, C 1-6} alkyl -, _{aminocarbonyl, C 1-6} alkyl - amino, aminocarbonyl, - _{thiocarbonyl, C 1-6} alkylaminocarbonyl - thiocarbonyl, di _{(C 1-6} alkyl) amino - carbonyl Di (C _1-6 alkyl) amino-thiocarbonyl or hydroxycarbonyl,
G represents any of the following formulas G1 to G9,

Z is _{hydrogen, C 1-6} haloalkyl, _{nitro, C 1-6} alkoxy, _{cyano, C 1-6 haloalkoxy, C 1-6 alkylsulfenyl, C 1-6 alkylsulfinyl, C 1-6} alkylsulfonyl, C _1-6 haloalkylsulfenyl, C _1-6 haloalkylsulfinyl, C _1-6 haloalkylsulfonyl, hydroxy or thiol
k represents 0, 1, 2, 3 or 4;
R represents C _1-6 alkyl or C _1-6 haloalkyl,
R ¹ and R ² are absent or independently hydrogen, halogen, cyano, amino, azide, hydroxy, mercapto, hydroxy-carbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkoxy-carbonyl , C _1-6 alkoxy, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkylthio, C _1-6 alkylsulfinyl or C _1-6 alkylsulfonyl, wherein R ¹ And R ² are not simultaneously absent, R ¹ and R ² are not simultaneously hydrogen,
R ³ is hydrogen, amino, hydroxy, cyano, R ⁸ —CH ₂ —, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkyl-carbonyl or C _1-6 alkyl-carbonylamino,
R ⁴ is hydrogen, cyano, carbonyl, thiocarbonyl, R ⁸ —CO—, R ⁸ —CS—, C _1-6 alkyl-carbonyl, C _1-6 alkyl-thiocarbonyl, C _1-6 haloalkyl-carbonyl, C _1-6 haloalkyl-thiocarbonyl, C _1-6 alkylamino-carbonyl, C _1-6 alkylamino-thiocarbonyl, di (C _1-6 alkyl) amino-carbonyl, di (C _1-6 alkyl) amino- Thiocarbonyl, C _1-6 alkoxyamino-carbonyl, C _1-6 alkoxyamino-thiocarbonyl, C _1-6 alkoxy-carbonyl, C _1-6 alkoxy-thiocarbonyl, C _1-6 thioalkoxy-carbonyl, C _{1 -6} thioalkoxy - _{thiocarbonyl, C 1-6 alkylsulfonyl, C 1-6} Haroarukirusu _{Honiru, C 3-7} cycloalkyl - _{carbonyl, C 2-6} alkenyl - _{carbonyl, C 2-6} alkynyl - _{carbonyl, C 3-7} cycloalkyl _{-C 1-6} alkyl - _{carbonyl, C 1-6} alkylsulfenyl - C _1-6 alkyl-carbonyl, C _1-6 alkylsulfinyl-C _1-6 alkyl-carbonyl, C _1-6 alkylsulfonyl-C _1-6 alkyl-carbonyl, C _1-6 alkyl-carbonyl-C _1-6 Represents alkyl-carbonyl, C _3-7 cycloalkylamino-carbonyl, C _2-6 alkenylamino-carbonyl or C _2-6 alkynamino-carbonyl,
R ³ and R ⁴ together with the nitrogen atom to which it is attached may form a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle, which is oxo, May be substituted with thioxo or nitro,
R ⁵ represents hydrogen, cyano, C _1-6 alkyl or C _1-6 haloalkyl,
R ⁶ represents hydrogen, C _1-6 alkyl, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl,
R ⁷ represents hydrogen or C _1-6 alkyl and R ⁸ represents phenyl or a 3, 4, 5 or 6 membered saturated or unsaturated heterocycle,
Z ¹ , Z ² and Z ³ are each independently —C (R ⁹ ) (R ¹⁰ ) —, —C (═O) —, —C (= N—OR ¹¹ ) —, —N (R ¹¹ )-, -S-, -S (= O)-, -S (= O) ₂ -or -S (O) (= N-R ¹¹ )-
R ⁹ and R ¹⁰ each independently represent hydrogen, halogen, C _1-6 alkyl or C _1-6 haloalkyl,
R ¹¹ is hydrogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _3-7 cycloalkyl-C _1-6 alkyl, C _1-6 alkyl-carbonyl, C _1-6 haloalkyl-carbonyl , _{C 1-6} alkoxy - _{carbonyl, C 1-6} haloalkoxy - _{carbonyl, C 1-6 alkylsulfonyl, C 1-6} haloalkylsulfonyl, aryl aryl portion may be substituted with ^{R 12} in 1, 2 or 3 - C _1-6 alkyl, or heterocyclic portion represents has been or heterocyclic _{-C 1-6} alkyl substituted with ^{R 12} in 1, 2 or 3,
R ¹² represents hydrogen, halogen, cyano, nitro, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy or C _1-6 alkoxy-carbonyl,
m represents 1 or 2,
The groups defined above are further halogen, C _1-6 alkyl, C _1-6 haloalkyl, nitro, C _1-6 alkoxy, cyano, C _1-6 haloalkoxy, C _1-6 alkylsulfenyl, C _{1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfenyl, C 1-6 haloalkylsulfinyl, C 1-6} haloalkylsulfonyl, may be substituted with any substituent consisting of hydroxy or mercapto,
The pyrroline derivative according to claim 1.   An insecticide containing the compound according to claim 1 or 2 as an active ingredient.   An animal parasite control agent comprising the compound according to claim 1 or 2 as an active ingredient.