JP2012062267A - Pesticidal pyrroline n-oxide derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pyrroline N-oxide derivative useful as a pesticidal compound.SOLUTION: The pyrroline N-oxide derivative is represented by formula (I), and a pesticide and an agent for controlling animal parasites contain the pyrroline N-oxide derivative as an active ingredient.

Description

  The present invention relates to a novel pyrroline N-oxide derivative, and an insecticide and an animal parasite control agent containing the same as an active ingredient.

  Patent Documents 1, 2, and 3 describe nitrogen-containing heterocyclic compounds having insecticidal activity.

International Publication No. 2009/072621 International Publication No. 2009/097992 International Publication No. 2009/112275

  The present inventors have found that pyrroline N-oxide derivatives represented by the following formula (I) have insecticidal activity, and have completed the present invention. That is, a pyrroline N-oxide derivative represented by the formula (I);

（式中、Ｔは下記の基：

Wherein T is the following group:

又は、

Or

を示し、
Ｇは、置換されていてもよい飽和又は不飽和の５〜６員のヘテロ環式基を示すか、若しくは、ハロゲン、Ｃ_１−１２アルキル、シアノ、Ｃ_１−１２アルコキシ−カルボニル又はカルボキシを示し、
Ｒは任意に置換されてもよいＣ_１−１２アルキル又はＣ_１−１２ハロアルキルを示し、
Ｒ^１は水素、アミノ、ヒドロキシ、シアノ、Ｃ_１−１２アルコキシ、Ｃ_１−１２アルキル−カルボニルアミノ、Ｃ_１−１２アルキルイミノ、Ｃ_１−１２アルキル、Ｃ_３−８シクロアルキル、Ｃ_２−６アルケニル、Ｃ_２−６アルキニル、Ｃ_１−１２アルキル−カルボニル、ＣＨ_２−Ｒ^６、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^１の定義中、Ｃ_１−１２アルコキシからＣ_１−１２アルキル−カルボニルまでの各基は、任意に置換されてもよく、
Ｒ^２は水素、シアノ、カルボニル、チオカルボニル、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、Ｃ_２−２４ジアルキルアミノ−カルボニル、Ｃ_２−２４ジアルキルアミノ−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アルキルチオ−カルボニル、Ｃ_１−１２アルキルチオ−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_２−６アルケニル−カルボニル、Ｃ_２−６アルキニル−カルボニル、Ｃ_３−８シクロアルキル−Ｃ_１−４アルキル−カルボニル、Ｃ_１−１２アルキルチオ−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_２−６アルケニルアミノ−カルボニル、Ｃ_２−６アルキニルアミノ−カルボニル、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^２の定義中、Ｃ_１−１２アルキル−カルボニルからＣ_２−６アルキニルアミノ−カルボニルまでの各基は、任意に置換されてもよく、
Ｒ^１とＲ^２は、それらが結合するＮ原子と一緒になって、３〜６員のヘテロ環を形成してもよく、該環は、後記のＸ、オキソ、チオキソ又はニトロイミノにより置換されてもよく、
Ｒ_３は、水素、シアノ、任意に置換されてもよいＣ_１−１２アルキル又は任意に置換されてもよいＣ_１−１２ハロアルキルを示し、
Ｒ^４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^５は、水素又はＣ_１−１２アルキルを示し、
Ｒ^６は、任意に置換されてもよいフェニル又は任意に置換されてもよい５〜６員のヘテロ環式基を示し、
Ｂは、Ｃ−Ｘ又はＮを示し、
ｋは、１又は２を示し、
ｍは、０〜４を示し、
ｎは、０〜２を示し、
Ｘは、ｍが２以上の場合、同一でも異なってもよく、ハロゲン、ニトロ、シアノ、Ｃ_１−１２アルキル、Ｃ_１−１２アルコキシ、Ｃ_１−１２ハロアルキル、Ｃ_１−１２ハロアルコキシ、Ｃ_１−１２アルキルチオ、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ハロアルキルチオ、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、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、五フッ化イオウ、ヒドロキシ、メルカプト又はアミノを示し、Ｘの定義中、Ｃ_１−１２アルキルからＣ_１−１２アルキルスルホニルアミノまでの各基は任意に置換されてもよく、
Ｙは、水素、ハロゲン、ニトロ、ヒドロキシ、メルカプト、シアノ、アミノ、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_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、Ｃ_１−１２アルキルチオ、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ハロアルキルチオ、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ハロ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、Ｃ_２−２４ジアルキルアミノスルホニル、Ｃ_２−２４ジ−ハロアルキル−アミノスルホニル、Ｃ_１−１２アルキルアミノ、Ｃ_２−２４ジアルキルアミノ、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、Ｃ_３−３６トリアルキルシリル、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、Ｃ_２−２４ジアルキルイミノカルボニル又はＣ_２−２４ジアルキルアミノ−チオカルボニルを示し、
Ｚ^１、Ｚ^２及びＺ^３は、夫々独立して、ＣＲ^７Ｒ^８、Ｃ＝Ｏ、Ｃ＝Ｎ−ＯＲ^９、Ｎ−Ｒ^９、Ｓ（Ｏ）_ｎ、Ｓ＝Ｎ−Ｒ^９、又はＳ（Ｏ）＝Ｎ−Ｒ^９を示し、ただしＺ^１、Ｚ^２及びＺ^３が同時にＣＲ^７Ｒ^８を示すことはなく、
Ｒ^７及びＲ^８は、夫々独立して、水素、ハロゲン、置換されてもよいＣ_１−１２アルキル又は置換されてもよいＣ_１−１２ハロアルキルを示し、
Ｒ^９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_１−６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、Ｃ_６−１０アリール−Ｃ_１−６アルキル又はヘテロアリール−Ｃ_１−６アルキルを示し、Ｒ^９の定義中、Ｃ_１−１２アルキルからＣ_１−１２ハロアルキルスルホニルまでの各基は任意に置換されてもよく、またＣ_６−１０アリール−Ｃ_１−６アルキルのアリール部分及びヘテロアリール−Ｃ_１−６アルキルのヘテロアリール部分は、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ハロアルコキシ及びＣ_１−１２アルコキシ−カルボニル（かかる定義中、Ｃ_１−１２アルキルからＣ_１−１２アルコキシ−カルボニルまでの各基は任意に置換されてもよい）からなる群より選ばれる１〜３個の任意の基で置換されてもよい。）

Indicate
G represents a saturated or unsaturated 5- or 6-membered heterocyclic group which may be substituted, or represents halogen, C _1-12 alkyl, cyano, C _1-12 alkoxy-carbonyl or carboxy. ,
R represents an optionally substituted C _1-12 alkyl or C _1-12 haloalkyl;
R ¹ is hydrogen, amino, hydroxy, cyano, C _1-12 alkoxy, C _1-12 alkyl-carbonylamino, C _1-12 alkylimino, C _1-12 alkyl, C _3-8 cycloalkyl, C _2-6 Alkenyl, C _2-6 alkynyl, C _1-12 alkyl-carbonyl, CH ₂ —R ⁶ , C (═O) R ⁶ or C (═S) R ⁶ are shown, and in the definition of R ¹ , C _1-12 Each group from alkoxy to C _1-12 alkyl-carbonyl may be optionally substituted,
R ² is hydrogen, cyano, carbonyl, thiocarbonyl, C _1-12 alkyl-carbonyl, C _1-12 alkyl-thiocarbonyl, C _1-12 haloalkyl-carbonyl, C _1-12 haloalkyl-thiocarbonyl, C _1-12 Alkyl-aminocarbonyl, C _1-12 alkylamino-thiocarbonyl, C _2-24 dialkylamino-carbonyl, C _2-24 dialkylamino-thiocarbonyl, C _1-12 alkoxyamino-carbonyl, C _1-12 alkoxyamino- Thiocarbonyl, C _1-12 alkoxy-carbonyl, C _1-12 alkoxy-thiocarbonyl, C _1-12 alkylthio-carbonyl, C _1-12 alkylthio-thiocarbonyl, C _1-12 alkylsulfonyl, C _1-12 haloalkylsulfonyl , C _-8 cycloalkyl - _{carbonyl, C 2-6} alkenyl - _{carbonyl, C 2-6} alkynyl - _{carbonyl, C 3-8} cycloalkyl _{-C 1-4} alkyl - _{carbonyl, C 1-12} alkylthio _{-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 2-6} alkenyl amino - _{carbonyl, C 2-6} alkynylamino - indicates carbonyl, C (= O) ^{R 6} or C (= S) ^{R 6,} in the definition of ^{R 2,} Each group from C _1-12 alkyl-carbonyl to C _2-6 alkynylamino-carbonyl is Optionally substituted,
R ¹ and R ² together with the N atom to which they are attached may form a 3-6 membered heterocycle, which ring is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R ₃ represents hydrogen, cyano, optionally substituted C _1-12 alkyl or optionally substituted C _1-12 haloalkyl,
R ⁴ represents hydrogen, C _1-12 alkyl, C _1-12 alkyl-carbonyl or C _1-12 alkoxy-carbonyl,
R ⁵ represents hydrogen or C _1-12 alkyl;
R ⁶ represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N;
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C _1-12 alkyl, C _1-12 alkoxy, C _1-12 haloalkyl, C _1-12 haloalkoxy, C _{1 -12 alkylthio, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylthio, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, _{acylamino, C 1-12} alkoxy - carbonyl amino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkoxyimino, C _1-12 haloalkoxyimino, C _1-12 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , _{C 1-12} Arukirusu from _{C 1-12} alkyl Each group of up Honiruamino may optionally be substituted,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl, C _3-8 cyclohaloalkyl, C _1-12 alkoxy, C _{1-12 haloalkoxy, C 1-12 alkylthio, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylthio, C 1-12 haloalkylsulfinyl, C 1-12 haloalkylsulfonyl, C 1- 12} alkylsulfonyloxy, C _1-12 haloalkylsulfonyloxy, C _1-12 alkylaminosulfonyl, C _1-12 haloalkylaminosulfonyl, C _2-24 dialkylaminosulfonyl, C _2-24 di-haloalkyl-aminosulfonyl, C _{1 -12} alkyla Mino, C _2-24 dialkylamino, acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkylsulfonylamino, C _1-12 haloalkylsulfonylamino, C _3-36 Trialkylsilyl, C _1-12 alkoxyimino, C _1-12 haloalkoxyimino, C _1-12 alkoxyimino-C _1-12 alkyl, C _1-12 haloalkoxyimino-C _1-12 alkyl, C _1-12 alkyl sulfinyl _{amino, C 1-12} alkyl sulfinyl amino _{-C 1-12 alkyl, C 1-12} alkyl sulfinyl amino _{-C 1-12} alkyl - _{carbonyl, C 1-12} alkylsulfonyl alkoximinoalkyl _{amino, C 1-12} alkylsulfoxide imino _{-C 1-12} alkyl , _{C 1-12} alkoxy - _{carbonyl, C 1-12} alkyl - carbonyl, _{aminocarbonyl, C 1-12} alkylaminocarbonyl - carbonyl, amino - _{thiocarbonyl, C 1-12} alkylaminocarbonyl - _{thiocarbonyl, C 2-24} dialkyl imino _Represents carbonyl or C _2-24 dialkylamino-thiocarbonyl,
Z ¹ , Z ² and Z ³ are each independently CR ⁷ R ⁸ , C═O, C═N—OR ⁹ , N—R ⁹ , S (O) _n , S = N—R ⁹ , or S (O) = N—R ⁹ except that Z ¹ , Z ² and Z ³ do not represent CR ⁷ R ⁸ at the same time,
R ⁷ and R ⁸ each independently represent hydrogen, halogen, _optionally substituted C _1-12 alkyl or _optionally substituted C _1-12 haloalkyl;
R ⁹ is hydrogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl-C _1-6 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, C _6-10 aryl-C _1-6 alkyl or heteroaryl-C _{1- In} the definition of R ⁹ , each group from C _1-12 alkyl to C _1-12 haloalkylsulfonyl may be optionally substituted, and C _6-10 aryl-C _1-6 alkyl aryl heteroaryl moiety of partial and heteroaryl _{-C 1-6} alkyl, halogen, cyano, _{nitro, C 1-1 Alkyl, C 1-12 haloalkyl, C 1-12 alkoxy, C 1-12} haloalkoxy, and _{C 1-12} alkoxy - each having up carbonyl - in carbonyl (such _definitions, the _{C 1-12} alkyl _{C 1-12} alkoxy May be optionally substituted) may be substituted with 1 to 3 arbitrary groups selected from the group consisting of: )

  In the following description, unless otherwise specified, each symbol in the formula has the same definition as described above.

  The compound of the formula (I) of the present invention can be produced by the following method.

  Production method (a): A method of reducing a compound represented by the following formula (II) with a metal hydride.

Production method (b): A method in which a compound represented by the following formula (III) and a compound represented by the following formula (IV) are reacted in an inert solvent in the presence of a base.
(In the formula (I), when T represents T-1, G represents the heterocyclic group in the above definition, and Y represents halogen, G represents Het and Y represents Hal.)

Ｈｅｔ−Ｈ （ＩＶ）

Het-H (IV)

Production method (c): A method in which a compound represented by the following formula (V) is reacted with a cyanating agent.
(In the formula (I), when T represents T-1, G represents the heterocyclic group in the above definition, and Y represents cyano, G represents Het and Y represents Hal.)

  The compound of the formula (I) of the present invention has an insecticidal action and can be used as an insecticide.

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- A linear or branched C _1-12 alkyl such as octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc. is shown, 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”.

  “Acylamino” represents, for example, alkylcarbonylamino, cyclopropylcarbonylamino and benzoylamino, and the alkyl moiety may be exemplified by the same meaning as described above for “alkyl”.

  “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.

“Alkenyl” refers to C _2-6 alkenyl, preferably C _2-4 alkenyl such as vinyl, allyl, 1-propenyl, 1- (or 2-, or 3-) butenyl, more preferably C _{2. -3} Alkenyl is shown.

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

  “Arylalkyl” refers to, for example, benzyl and phenethyl.

  “Heterocycle” refers to a saturated or unsaturated 5- or 6-membered heterocyclic group containing at least one of N, O, and S as a heteroatom, and the ring may be benzo-fused. A condensed heterocyclic group is shown.

  Specific examples of the heterocycle include furyl, thienyl, pyrrolyl, isoxazolyl, pyrazolyl, oxazolyl, oxathiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, benzoxazolyl, quinolyl Etc.

  “Heteroaryl” refers to a cyclic unsaturated 5- or 6-membered heterocyclic group having a heteroatom other than carbon in the ring structure. Specific examples include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, Examples include isoxazolyl, thiazolyl, triazolyl, pyridyl, pyrazyl, pyridazyl, pyrimidyl, triazinyl and the like.

Examples of the substituent that substitutes for each “optionally substituted” group include nitro, cyano, hydroxy, mercapto, isocyano, cyanato, isothiocyanato, carboxy, carbamoyl, aminosulfonyl, monoalkylamino, dialkylamino, and N-alkyl. carbonylamino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, SF _5, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkyl Alkylsulfurs including carbonyl, alkenylkillthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, isomers Nyl, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylphosphinyl, alkylphosphonyl, alkylphosphinyl including isomer, alkylphosphonyl including isomer, N-alkyl-aminocarbonyl, N, N -Dialkyl-aminocarbonyl, N-alkylcarbonyl-aminocarbonyl, N-alkylcarbonyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, trialkylsilyl, alkoxy Alkyl, alkylthioalkyl, alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl Selected from carbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkylcarbonyl or haloalkoxyalkyl, cycloalkylaminocarbonyl, alkylsulfinylimino, alkylsulfonylimino, alkoxyimino, heterocyclic groups, etc. It can be illustrated.

  In the compounds of formula (I) of the present invention, T is the following group:

又は

Or

を示し、
Ｇが、置換されていてもよい飽和又は不飽和の５〜６員のヘテロ環式基を示すか、若しくはハロゲン、Ｃ_１−６アルキル、シアノ、Ｃ_１−６アルコキシ−カルボニル又はカルボキシを示し、
Ｒが任意に置換されてもよいＣ_１−６アルキル又はＣ_１−６ハロアルキルを示し、
Ｒ^１が、水素、アミノ、ヒドロキシ、シアノ、Ｃ_１−６アルコキシ、Ｃ_１−６アルキル−カルボニルアミノ、Ｃ_１−６アルキルイミノ、Ｃ_１−６アルキル、Ｃ_３−７シクロアルキル、Ｃ_２−４アルケニル、Ｃ_２−４アルキニル、Ｃ_１−６アルキル−カルボニル、ＣＨ_２−Ｒ^６、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^１の定義中、Ｃ_１−６アルコキシからＣ_１−６アルキル−カルボニルまでの各基が、任意に置換されてもよく、
Ｒ^２が、水素、シアノ、カルボニル、チオカルボニル、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、Ｃ_２−１２ジアルキルアミノ−カルボニル、Ｃ_２−１２ジアルキルアミノ−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アルキルチオ−カルボニル、Ｃ_１−６アルキルチオ−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_２−４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_１−４アルキル−カルボニル、Ｃ_１−６アルキルチオ−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_２−４アルケニルアミノ−カルボニル、Ｃ_２−４アルキニルアミノ−カルボニル、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^２の定義中、Ｃ_１−６アルキル−カルボニルからＣ_２−４アルキニルアミノ−カルボニルまでの各基が、任意に置換されてもよく、
Ｒ^１とＲ^２が、それらの結合するＮ原子と一緒になって、３〜６員のヘテロ環を形成してもよく、該環が、後記のＸ、オキソ、チオキソ又はニトロイミノにより置換されてもよく、
Ｒ^３が、水素、シアノ、任意に置換されてもよいＣ_１−６アルキル又は任意に置換されてもよいＣ_１−６ハロアルキルを示し、
Ｒ^４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^５が、水素又はＣ_１−６アルキルを示し、
Ｒ^６が、任意に置換されてもよいフェニル又は任意に置換されてもよい５〜６員のヘテロ環式基を示し、
Ｂが、Ｃ−Ｘ又はＮを示し、
ｋは、１又は２を示し、
ｍは、０〜４を示し、
ｎは、０〜２を示し、
Ｘが、ｍが２以上の場合、同一でも異なってもよく、ハロゲン、ニトロ、シアノ、Ｃ_１−６アルキル、Ｃ_１−６アルコキシ、Ｃ_１−６ハロアルキル、Ｃ_１−６ハロアルコキシ、Ｃ_１−６アルキルチオ、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ハロアルキルチオ、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、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、五フッ化イオウ、ヒドロキシ、メルカプト又はアミノを示し、Ｘの定義中、Ｃ_１−６アルキルからＣ_１−６アルキルスルホニルアミノまでの各基が任意に置換されてもよく、
Ｙが、水素、ハロゲン、ニトロ、ヒドロキシ、メルカプト、シアノ、アミノ、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_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、Ｃ_１−６アルキルチオ、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ハロアルキルチオ、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ハロ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、Ｃ_２−１２ジアルキルアミノスルホニル、Ｃ_２−１２ジ−ハロアルキル−アミノスルホニル、Ｃ_１−６アルキルアミノ、Ｃ_２−１２ジアルキルアミノ、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、Ｃ_３−１８トリアルキルシリル、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、Ｃ_２−１２ジアルキルイミノカルボニル又はＣ_２−１２ジアルキルアミノ−チオカルボニルを示し、
Ｚ^１、Ｚ^２及びＺ^３が、夫々独立して、ＣＲ^７Ｒ^８、Ｃ＝Ｏ、Ｃ＝Ｎ−ＯＲ^９、Ｎ−Ｒ^９、Ｓ（Ｏ）_ｎ、Ｓ＝Ｎ−Ｒ^９又はＳ（Ｏ）＝Ｎ−Ｒ^９を示し、ただしＺ^１、Ｚ^２及びＺ^３が同時にＣＲ^７Ｒ^８を示すことはなく、
Ｒ^７及びＲ^８が、夫々独立して、水素、ハロゲン、置換されてもよいＣ_１−６アルキル又は置換されてもよいＣ_１−６ハロアルキルを示し、
Ｒ^９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_１−４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、Ｃ_６−１０アリール−Ｃ_１−４アルキル又はヘテロアリール−Ｃ_１−４アルキルを示し、Ｒ^９の定義中、Ｃ_１−６アルキルからＣ_１−６ハロアルキルスルホニルまでの各基が、任意に置換されてもよく、またＣ_６−１０アリール−Ｃ_１−４アルキルのアリール部分及びヘテロアリール−Ｃ_１−４アルキルのヘテロアリール部分が、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ハロアルコキシ及びＣ_１−６アルコキシ−カルボニル（かかる定義中、Ｃ_１−６アルキルからＣ_１−６アルコキシ−カルボニルまでの各基が任意に置換されてもよい）からなる群より選ばれる１〜３個の任意の基で置換されてもよい、化合物を好適なものとして挙げることができる。

Indicate
G represents an optionally substituted saturated or unsaturated 5- to 6-membered heterocyclic group, or represents halogen, C 1-6 alkyl, cyano, C 1-6 alkoxy-carbonyl or carboxy,
R represents optionally substituted C 1-6 alkyl or C 1-6 haloalkyl,
R 1 is hydrogen, amino, hydroxy, cyano, C 1-6 alkoxy, C 1-6 alkyl-carbonylamino, C 1-6 alkylimino, C 1-6 alkyl, C 3-7 cycloalkyl, C 2− 4 alkenyl, C 2-4 alkynyl, C 1-6 alkyl-carbonyl, CH 2 —R 6 , C (═O) R 6 or C (═S) R 6 are shown, and in the definition of R 1 , C 1- Each group from 6 alkoxy to C 1-6 alkyl-carbonyl may be optionally substituted,
R 2 is hydrogen, cyano, carbonyl, thiocarbonyl, C 1-6 alkyl-carbonyl, C 1-6 alkyl-thiocarbonyl, C 1-6 haloalkyl-carbonyl, C 1-6 haloalkyl-thiocarbonyl, C 1- 6 alkyl-aminocarbonyl, C 1-6 alkylamino-thiocarbonyl, C 2-12 dialkylamino-carbonyl, C 2-12 dialkylamino-thiocarbonyl, C 1-6 alkoxyamino-carbonyl, C 1-6 akoxyamino- Thiocarbonyl, C 1-6 alkoxy-carbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkylthio-carbonyl, C 1-6 alkylthio-thiocarbonyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl , C 3-7 cycloalkyl - carbonitrile Le, C 2-4 alkenyl - carbonyl, C 2-6 alkynyl - carbonyl, C 3-7 cycloalkyl -C 1-4 alkyl - carbonyl, C 1-6 alkylthio -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 2-4 alkenyl amino - carbonyl, C 2-4 alkynylamino - carbonyl, C (= O) shows the R 6 or C (= S) R 6, in the definition of R 2, C 1-6 alkyl Each group from -carbonyl to C2-4 alkynylamino-carbonyl may be optionally substituted;
R 1 and R 2 together with their attached N atoms may form a 3-6 membered heterocycle, which is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R 3 represents hydrogen, cyano, optionally substituted C 1-6 alkyl or optionally substituted C 1-6 haloalkyl,
R 4 represents hydrogen, C 1-6 alkyl, C 1-6 alkyl-carbonyl or C 1-6 alkoxy-carbonyl,
R 5 represents hydrogen or C 1-6 alkyl,
R 6 represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N,
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1 -6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, acylamino, C 1-6 alkoxy - carbonyl amino, C 1-6 haloalkoxy-carbonylamino, C 1-6 alkoxyimino, C 1-6 haloalkoxyimino, C 1-6 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , optionally location in each group from C 1-6 alkyl to C 1-6 alkylsulfonylamino It may be,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C 1-6 alkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl, C 3-7 cyclohaloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, C 1- 6 alkylsulfonyloxy, C 1-6 haloalkylsulfonyloxy, C 1-6 alkylaminosulfonyl, C 1-6 haloalkylaminosulfonyl, C 2-12 dialkylaminosulfonyl, C 2-12 di-haloalkyl-aminosulfonyl, C 1 -6 alkylamino, C 2-12 Jiarukirua Bruno, acylamino, C 1-6 alkoxy - carbonyl amino, C 1-6 haloalkoxy - carbonylamino, C 1-6 alkylsulfonylamino, C 1-6 haloalkylsulfonyl amino, C 3-18 trialkylsilyl, C 1- 6 alkoxyimino, C 1-6 haloalkoxyimino, C 1-6 alkoxyimino-C 1-6 alkyl, C 1-6 haloalkoxyimino-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 alkylsulfoxyimino, C 1-6 alkylsulfoxyimino-C 1-6 alkyl C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, Represents aminocarbonyl, C 1-6 alkylamino-carbonyl, amino-thiocarbonyl, C 1-6 alkylamino-thiocarbonyl, C 2-12 dialkyliminocarbonyl or C 2-12 dialkylamino-thiocarbonyl,
Z 1 , Z 2 and Z 3 are each independently CR 7 R 8 , C═O, C═N—OR 9 , N—R 9 , S (O) n , S = N—R 9 or S. (O) = N—R 9 except that Z 1 , Z 2 and Z 3 do not represent CR 7 R 8 at the same time,
R 7 and R 8 each independently represent hydrogen, halogen, optionally substituted C 1-6 alkyl or optionally substituted C 1-6 haloalkyl;
R 9 is hydrogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl-C 1-4 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, C 6-10 aryl-C 1-4 alkyl or heteroaryl-C 1- In the definition of R 9 , each group from C 1-6 alkyl to C 1-6 haloalkylsulfonyl may be optionally substituted, and C 6-10 aryl-C 1-4 alkyl The aryl moiety and the heteroaryl moiety of heteroaryl-C 1-4 alkyl are halogen, cyano, nitro, C 1-6 alkyl, C 1-6 Haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy and C 1-6 alkoxy - in carbonyl (such definitions, the C 1-6 alkyl C 1-6 alkoxy - each group until the carbonyl is optionally substituted Preferred examples include compounds that may be substituted with 1 to 3 arbitrary groups selected from the group consisting of:

  In the compounds of formula (I) of the present invention, T is the following group:

又は

Or

を示し、
Ｇが、置換されていてもよい飽和又は不飽和の５〜６員のヘテロ環式基を示すか、若しくはハロゲン、Ｃ_１−４アルキル、シアノ、Ｃ_１−４アルコキシ−カルボニル又はカルボキシを示し、
Ｒが任意に置換されてもよいＣ_１−４アルキル又はＣ_１−４ハロアルキルを示し、
Ｒ^１が、水素、アミノ、ヒドロキシ、シアノ、Ｃ_１−４アルコキシ、Ｃ_１−４アルキル−カルボニルアミノ、Ｃ_１−４アルキルイミノ、Ｃ_１−４アルキル、Ｃ_３−６シクロアルキル、Ｃ_２−３アルケニル、Ｃ_２−３アルキニル、Ｃ_１−４アルキル−カルボニル、ＣＨ_２−Ｒ^６、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^１の定義中、Ｃ_１−４アルコキシからＣ_１−４アルキル−カルボニルまでの各基が、任意に置換されてもよく、
Ｒ^２が、水素、シアノ、カルボニル、チオカルボニル、Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキル−チオカルボニル、Ｃ_１−４ハロアルキル−カルボニル、Ｃ_１−４ハロアルキル−チオカルボニル、Ｃ_１−４アルキル−アミノカルボニル、Ｃ_１−４アルキルアミノ−チオカルボニル、Ｃ_２−８ジアルキルアミノ−カルボニル、Ｃ_２−８ジアルキルアミノ−チオカルボニル、Ｃ_１−４アルコキシアミノ−カルボニル、Ｃ_１−４アコキシアミノ−チオカルボニル、Ｃ_１−４アルコキシ−カルボニル、Ｃ_１−４アルコキシ−チオカルボニル、Ｃ_１−４アルキルチオ−カルボニル、Ｃ_１−４アルキルチオ−チオカルボニル、Ｃ_１−４アルキルスルホニル、Ｃ_１−４ハロアルキルスルホニル、Ｃ_３−６シクロアルキル−カルボニル、Ｃ_２−３アルケニル−カルボニル、Ｃ_２−３アルキニル−カルボニル、Ｃ_３−６シクロアルキル−Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキルチオ−Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキルスルフィニル−Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキルスルホニル−Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキル−カルボニル−Ｃ_１−４アルキル−カルボニル、Ｃ_３−６シクロアルキルアミノ−カルボニル、Ｃ_２−３アルケニルアミノ−カルボニル、Ｃ_２−３アルキニルアミノ−カルボニル、Ｃ（＝Ｏ）Ｒ^６又はＣ（＝Ｓ）Ｒ^６を示し、Ｒ^２の定義中、Ｃ_１−４アルキル−カルボニルからＣ_２−３アルキニルアミノ−カルボニルまでの各基が、任意に置換されてもよく、
Ｒ^１とＲ^２が、それらが結合するＮ原子と一緒になって、３〜６員のヘテロ環を形成してもよく、該環が、後記のＸ、オキソ、チオキソ又はニトロイミノにより置換されてもよく、
Ｒ^３が、水素、シアノ、任意に置換されてもよいＣ_１−４アルキル又は任意に置換されてもよいＣ_１−４ハロアルキルを示し、
Ｒ^４が、水素、Ｃ_１−４アルキル、Ｃ_１−４アルキル−カルボニル又はＣ_１−４アルコキシ−カルボニルを示し、
Ｒ^５が、水素又はＣ_１−４アルキルを示し、
Ｒ^６が、任意に置換されてもよいフェニル又は任意に置換されてもよい５〜６員のヘテロ環式基を示し、
Ｂが、Ｃ−Ｘ又はＮを示し、
ｋは、１又は２を示し、
ｍは、０〜４を示し、
ｎは、０〜２を示し、
Ｘが、ｍが２以上の場合、同一でも異なってもよく、ハロゲン、ニトロ、シアノ、Ｃ_１−４アルキル、Ｃ_１−４アルコキシ、Ｃ_１−４ハロアルキル、Ｃ_１−４ハロアルコキシ、Ｃ_１−４アルキルチオ、Ｃ_１−４アルキルスルフィニル、Ｃ_１−４アルキルスルホニル、Ｃ_１−４ハロアルキルチオ、Ｃ_１−４ハロアルキルスルフィニル、Ｃ_１−４ハロアルキルスルホニル、アシルアミノ、Ｃ_１−４アルコキシ−カルボニルアミノ、Ｃ_１−４ハロアルコキシ−カルボニルアミノ、Ｃ_１−４アルコキシイミノ、Ｃ_１−４ハロアルコキシイミノ、Ｃ_１−４アルキルスルホニルアミノ、五フッ化イオウ、ヒドロキシ、メルカプト又はアミノを示し、Ｘの定義中、Ｃ_１−４アルキルからＣ_１−４アルキルスルホニルアミノまでの各基が任意に置換されてもよく、
Ｙが、水素、ハロゲン、ニトロ、ヒドロキシ、メルカプト、シアノ、アミノ、Ｃ_１−４アルキル、Ｃ_１−４ハロアルキル、Ｃ_３−６シクロアルキル、Ｃ_３−シクロハロアルキル、Ｃ_１−４アルコキシ、Ｃ_１−４ハロアルコキシ、Ｃ_１−４アルキルチオ、Ｃ_１−４アルキルスルフィニル、Ｃ_１−４アルキルスルホニル、Ｃ_１−４ハロアルキルチオ、Ｃ_１−４ハロアルキルスルフィニル、Ｃ_１−４ハロアルキルスルホニル、Ｃ_１−４アルキルスルホニルオキシ、Ｃ_１−４ハロアルキルスルホニルオキシ、Ｃ_１−４アルキルアミノスルホニル、Ｃ_１−４ハロアルキルアミノスルホニル、Ｃ_２−８ジアルキルアミノスルホニル、Ｃ_２−８ジ−ハロアルキル−アミノスルホニル、Ｃ_１−４アルキルアミノ、Ｃ_２−８ジアルキルアミノ、アシルアミノ、Ｃ_１−４アルコキシ−カルボニルアミノ、Ｃ_１−４ハロアルコキシ−カルボニルアミノ、Ｃ_１−４アルキルスルホニルアミノ、Ｃ_１−４ハロアルキルスルホニルアミノ、Ｃ_３−１２トリアルキルシリル、Ｃ_１−４アルコキシイミノ、Ｃ_１−４ハロアルコキシイミノ、Ｃ_１−４アルコキシイミノ−Ｃ_１−４アルキル、Ｃ_１−４ハロアルコキシイミノ−Ｃ_１−４アルキル、Ｃ_１−４アルキルスルフィニルイミノ、Ｃ_１−４アルキルスルフィニルイミノ−Ｃ_１−４アルキル、Ｃ_１−４アルキルスルフィニルイミノ−Ｃ_１−４アルキル−カルボニル、Ｃ_１−４アルキルスルホキシイミノ、Ｃ_１−４アルキルスルホキシイミノ−Ｃ_１−４アルキル、Ｃ_１−４アルコキシ−カルボニル、Ｃ_１−４アルキル−カルボニル、アミノカルボニル、Ｃ_１−４アルキルアミノ−カルボニル、アミノ−チオカルボニル、Ｃ_１−４アルキルアミノ−チオカルボニル、Ｃ_２−８ジアルキルイミノカルボニル又はＣ_２−８ジアルキルアミノ−チオカルボニルを示し、
Ｚ^１、Ｚ^２及びＺ^３が、夫々独立して、ＣＲ^７Ｒ^８、Ｃ＝Ｏ、Ｃ＝Ｎ−ＯＲ^９、Ｎ−Ｒ^９、Ｓ（Ｏ）_ｎ、Ｓ＝Ｎ−Ｒ^９又はＳ（Ｏ）＝Ｎ−Ｒ^９を示し、ただしＺ^１、Ｚ^２及びＺ^３が同時にＣＲ^７Ｒ^８を示すことはなく、
Ｒ^７及びＲ^８が、夫々独立して、水素、ハロゲン、置換されてもよいＣ_１−４アルキル又は置換されてもよいＣ_１−４ハロアルキルを示し、
Ｒ^９が、水素、シアノ、ニトロ、Ｃ_１−４アルキル、Ｃ_１−４ハロアルキル、Ｃ_３−６シクロアルキル−Ｃ_１−２アルキル、Ｃ_１−４アルキル−カルボニル、Ｃ_１−４ハロアルキル−カルボニル、Ｃ_１−４アルコキシ−カルボニル、Ｃ_１−４ハロアルコキシ−カルボニル、Ｃ_１−４アルキルスルホニル、Ｃ_１−４ハロアルキルスルホニル、Ｃ_６−１０アリール−Ｃ_１−２アルキル又はヘテロアリール−Ｃ_１−２アルキルを示し、Ｒ^９の定義中、Ｃ_１−４アルキルからＣ_１−４ハロアルキルスルホニルまでの各基が、任意に置換されてもよく、またＣ_６−１０アリール−Ｃ_１−２アルキルのアリール部分及びヘテロアリール−Ｃ_１−２アルキルのヘテロアリール部分が、ハロゲン、シアノ、ニトロ、Ｃ_１−４アルキル、Ｃ_１−４ハロアルキル、Ｃ_１−４アルコキシ、Ｃ_１−４ハロアルコキシ及びＣ_１−４アルコキシ−カルボニル（かかる定義中、Ｃ_１−４アルキルからＣ_１−４アルコキシ−カルボニルまでの各基は任意に置換されてもよい）からなる群より選ばれる１〜３個の任意の基で置換されてもよい、化合物を特に好適なものとして挙げることができる。

Indicate
G represents an optionally substituted saturated or unsaturated 5- to 6-membered heterocyclic group, or represents halogen, C _1-4 alkyl, cyano, C _1-4 alkoxy-carbonyl or carboxy,
R represents optionally substituted C _1-4 alkyl or C _1-4 haloalkyl,
R ¹ is hydrogen, amino, hydroxy, cyano, C _1-4 alkoxy, C _1-4 alkyl-carbonylamino, C _1-4 alkylimino, C _1-4 alkyl, C _3-6 cycloalkyl, C _{2- 3} alkenyl, C _2-3 alkynyl, C _1-4 alkyl-carbonyl, CH ₂ —R ⁶ , C (═O) R ⁶ or C (═S) R ⁶ are shown, and in the definition of R ¹ , C _1- Each group from ₄ alkoxy to C _1-4 alkyl-carbonyl may be optionally substituted,
R ² is hydrogen, cyano, carbonyl, thiocarbonyl, C _1-4 alkyl-carbonyl, C _1-4 alkyl-thiocarbonyl, C _1-4 haloalkyl-carbonyl, C _1-4 haloalkyl-thiocarbonyl, C _{1- 4} alkyl - _{aminocarbonyl, C 1-4} alkylaminocarbonyl - _{thiocarbonyl, C 2-8} dialkylamino - _{carbonyl, C 2-8} dialkylamino - _{thiocarbonyl, C 1-4} alkoxycarbonyl amino - _{carbonyl, C 1-4} Akokishiamino - Thiocarbonyl, C _1-4 alkoxy-carbonyl, C _1-4 alkoxy-thiocarbonyl, C _1-4 alkylthio-carbonyl, C _1-4 alkylthio-thiocarbonyl, C _1-4 alkylsulfonyl, C _1-4 haloalkylsulfonyl , _{C 3-6} cycloalkyl - carbonyl C _2-3 alkenyl - _{carbonyl, C 2-3} alkynyl - _{carbonyl, C 3-6} cycloalkyl _{-C 1-4} alkyl - _{carbonyl, C 1-4} alkylthio _{-C 1-4} alkyl - _{carbonyl, C 1-4} alkyl Sulfinyl-C _1-4 alkyl-carbonyl, C _1-4 alkylsulfonyl-C _1-4 alkyl-carbonyl, C _1-4 alkyl-carbonyl-C _1-4 alkyl-carbonyl, C _3-6 cycloalkylamino-carbonyl , C _2-3 alkenylamino-carbonyl, C _2-3 alkynylamino-carbonyl, C (═O) R ⁶ or C (═S) R ⁶ in the definition of R ² , C _1-4 alkyl-carbonyl To C _2-3 alkynylamino-carbonyl may be optionally substituted,
R ¹ and R ² together with the N atom to which they are attached may form a 3-6 membered heterocycle, which is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R ³ represents hydrogen, cyano, optionally substituted C _1-4 alkyl or optionally substituted C _1-4 haloalkyl;
R ⁴ represents hydrogen, C _1-4 alkyl, C _1-4 alkyl-carbonyl or C _1-4 alkoxy-carbonyl,
R ⁵ represents hydrogen or C _1-4 alkyl;
R ⁶ represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N,
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C _1-4 alkyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _{1 -4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4} haloalkylsulfonyl, _{acylamino, C 1-4} alkoxy - carbonyl amino, C _1-4 haloalkoxy-carbonylamino, C _1-4 alkoxyimino, C _1-4 haloalkoxyimino, C _1-4 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , optionally location in each group from _{C 1-4} alkyl to _{C 1-4} alkylsulfonylamino It may be,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C _1-4 alkyl, C _1-4 haloalkyl, C _3-6 cycloalkyl, C ₃ -cyclohaloalkyl, C _1-4 alkoxy, C _{1 -4 haloalkoxy, C 1-4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4 haloalkylsulfonyl, C 1-4 alkylsulfonyloxy, C 1-4 haloalkylsulfonyloxy, C 1-4 alkylaminosulfonyl, C 1-4} haloalkylsulfonyl _{aminosulfonyl, C 2-8} dialkylamino _{sulfonyl, C 2-8} di - haloalkyl - _{aminosulfonyl, C 1- 4 alkylamino, C 2-8} dialkylamino, A _{Arylamino, C 1-4} alkoxy - carbonyl _{amino, C 1-4} haloalkoxy - _{carbonylamino, C 1-4 alkylsulfonylamino, C 1-4} haloalkylsulfonyl _{amino, C 3-12 trialkylsilyl, C 1-4} alkoxy Imino, C _1-4 haloalkoxyimino, C _1-4 alkoxyimino-C _1-4 alkyl, C _1-4 haloalkoxyimino-C _1-4 alkyl, C _1-4 alkylsulfinylimino, C _1-4 alkyl Sulfinylimino-C _1-4 alkyl, C _1-4 alkylsulfinylimino-C _1-4 alkyl-carbonyl, C _1-4 alkylsulfoxyimino, C _1-4 alkylsulfoxyimino-C _1-4 alkyl, C _1-4 alkoxy-carbonyl, C _1-4 alkyl-carbonyl, aminoca Represents rubonyl, C _1-4 alkylamino-carbonyl, amino-thiocarbonyl, C _1-4 alkylamino-thiocarbonyl, C _2-8 dialkyliminocarbonyl or C _2-8 dialkylamino-thiocarbonyl;
Z ¹ , Z ² and Z ³ are each independently CR ⁷ R ⁸ , C═O, C═N—OR ⁹ , N—R ⁹ , S (O) _n , S = N—R ⁹ or S. (O) = N—R ⁹ except that Z ¹ , Z ² and Z ³ do not represent CR ⁷ R ⁸ at the same time,
R ⁷ and R ⁸ each independently represent hydrogen, halogen, optionally substituted C _1-4 alkyl or optionally substituted C _1-4 haloalkyl;
R ⁹ is hydrogen, cyano, nitro, C _1-4 alkyl, C _1-4 haloalkyl, C _3-6 cycloalkyl-C _1-2 alkyl, C _1-4 alkyl-carbonyl, C _1-4 haloalkyl-carbonyl C _1-4 alkoxy-carbonyl, C _1-4 haloalkoxy-carbonyl, C _1-4 alkylsulfonyl, C _1-4 haloalkylsulfonyl, C _6-10 aryl-C _1-2 alkyl or heteroaryl-C _{1- In} the definition of R ⁹ , each group from C _1-4 alkyl to C _1-4 haloalkylsulfonyl may be optionally substituted, and C _6-10 aryl-C _1-2 alkyl The aryl moiety and the heteroaryl moiety of heteroaryl-C _1-2 alkyl may be halogen, cyano, nitro, C _1-4 alkyl, C _{1-4 Haloalkyl, C 1-4 alkoxy, C 1-4} haloalkoxy and _{C 1-4} alkoxy - in carbonyl (such _definitions, the _{C 1-4} alkyl _{C 1-4} alkoxy - each group to carbonyl which is optionally substituted Particularly preferred are compounds that may be substituted with 1 to 3 arbitrary groups selected from the group consisting of:

  Since the compound of the formula (I) of the present invention has an asymmetric carbon atom, the compound of the present invention specified by the formula (I) includes optical isomers.

  The production method (a) is, for example, 1- (3-bromo-4-fluorophenyl) -4,4,4-trifluoro-3- (nitromethyl) -3- (3,4,5-trichlorophenyl) as a raw material. Reduction with sodium borohydride using butan-1-one is represented by the following reaction formula.

  The production method (b) is, for example, 5- (3-bromo-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro- When 2H-pyrrole-1-oxide and 1H-1,2,4-triazole are used, they are represented by the following reaction formula.

  The production method (c) is, for example, 1- {2-bromo-4- [1-oxide-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro When −2H-pyrrol-5-yl] phenyl} -1H-1,2,4-triazole and zinc cyanide are used, they are represented by the following reaction formula.

  The compound of the formula (II) in the production method (a) is a compound described in the invention filed in Japanese Patent No. 2010-92182 immediately before the present application.

  Examples of the metal hydride compound used in the production method (a) include sodium borohydride and lithium aluminum hydride.

  Process (a) can be carried out in a suitable diluent, and examples of diluents used here include aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated). For example, pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, etc .; ethers such as ethyl Ethers, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM) and the like; ketones such as acetone, methyl ethyl ketone (MEK), methyl-isopropyl ketone, Til isobutyl ketone (MIBK), etc .; nitriles such as acetonitrile, propionitrile, acrylonitrile, etc .; alcohols such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc .; esters such as ethyl acetate, amyl acetate, etc. Acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide (HMPA) and the like; sulfone, Examples include sulfoxides such as dimethyl sulfoxide (DMSO), sulfolane and the like; and bases such as pyridine and the like.

  The production method (a) is preferably carried out in the presence of nickel chloride for hydrogenation.

  The production method (a) can be carried out within a substantially wide temperature range. In general, it can be carried out at about -10 ° C to about 80 ° C, preferably about 0 ° C to about 50 ° C. The reaction is preferably carried out under normal pressure, but can be operated under pressure or reduced pressure.

  In carrying out the production method (a), as an example, 1 mol of the compound of the formula (II) and 0.5 mol of nickel (II) chloride hexahydrate in a mixed solution of methanol and dioxane 3 By reacting with mol, the target compound of formula (I) can be obtained.

  The compound of the formula (III) in the production method (b) can be synthesized by the production method (a).

  Similarly, the compound of the formula (IV) is well known as a heterocyclic compound.

  Examples of the compound of formula (IV) include 1H-1,2,4-triazole, 1H-1,2,3-triazole, pyrazole, 1H-1,2,3,4-tetrazole and the like. .

  The reaction of the preparation method (b) can be carried out in a suitable diluent, and examples of the diluent used in this case include aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorine). Such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, etc .; ethers, For example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM), etc .; ketones such as acetone, methyl ethyl ketone (MEK), methyl-isopropyl Nitriles such as acetonitrile, propionitrile, acrylonitrile, etc .; alcohols such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc .; esters such as ethyl acetate, acetic acid Amyl and the like; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide (HMPA) and the like; Examples include sulfone, sulfoxides such as dimethyl sulfoxide (DMSO), sulfolane and the like; and bases such as pyridine and the like.

  The production method (b) comprises sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium tert-butoxide and other alkali metal bases, lithium hydride , Triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, 4-tert-butyl-N, N-dimethylaniline, pyridine, picoline, lutidine, diazabicyclo It can be carried out using an organic base such as undecene, diazabicyclooctane and imidazole.

  The reaction of the production method (b) can be carried out within a substantially wide temperature range. In general, it can be carried out at about -80 ° C to about 200 ° C, preferably -10 ° C 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, and preferably 1 to 24 hours.

  In carrying out the production method (b), for example, 1 mol of a compound of the formula (III) is reacted with 1 mol or a slight excess of the compound of the formula (IV) in a diluent, for example, DMF. Can give the target compound of formula (I).

  The compound of the formula (V) in the production method (c) can be synthesized by the production method (b).

  Examples of the cyanating agent used in the production method (c) include zinc cyanide and copper cyanide.

  The reaction of the preparation method (c) can be carried out in a suitable diluent, and examples of the diluent used in this case include aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorine). Such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, etc .; ethers, For example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM), etc .; ketones such as acetone, methyl ethyl ketone (MEK), methyl-isopropyl Nitriles such as acetonitrile, propionitrile, acrylonitrile, etc .; alcohols such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc .; esters such as ethyl acetate, acetic acid Amyl and the like; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide (HMPA) and the like; Examples include sulfone, sulfoxides such as dimethyl sulfoxide (DMSO), sulfolane and the like; and bases such as pyridine and the like.

  The production method (c) is preferably carried out in the presence of a transition metal catalyst, and examples of the transition metal catalyst include a palladium complex. Typical examples include tetrakis (triphenylphosphine) palladium, tris (benzylidene). Acetone) dipalladium, bis (benzylideneacetone) palladium and the like.

  The reaction of the production method (c) can be carried out within a substantially wide temperature range. In general, it can be carried out at about -80 ° C to about 200 ° C, preferably -10 ° C 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, and preferably 1 to 24 hours.

  In carrying out the production method (c), for example, 1 mol to a slight excess of zinc cyanide is added to 1 mol of the compound of formula (V) in DMF as a diluent in a catalytic amount of tetrakis ( The target compound of formula (I) can be obtained by reacting in the presence of triphenylphosphine) palladium.

  The compounds of formula (I) 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, stubborn 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, such as Callosoburchus chinensis, Sitophilus zeamais, Tribolium castaum, and Eraclacina cintacumata genus fuscicollis, Anomala rufocuprea, Leptinotarsa dezemlineata, Diabrotica spp., Monochatus M. amus alternatus, Lissohoptrus oryzophilus, Lyctus bruneus, Auracophora femoraris, Alacophora femalaris; Lemanto sp Pieris rapae, Spodoptera litura, Mamestra brassicae, Chiropsuprasalis, Pirasta nuuraris nubilalis, Efestia cautella, Adoxophyes orana, Carpocapsa pomerella, Agrotisfucosella. ), Heliothis virescens, Phyllocnistis citrella; Hemiptera, eg, Nephotetics cinchetics, Nilaparbata 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.

  With respect to the order of the mites, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citris, and Acropus perecus 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, the following:

  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., Brevipali spp. 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 bivalva, 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, Agriotes sol, Agripotesol, Aphimallon solstitalis, Anobium punctatum, Anoplophora spp., Anthony spp., Anthonia 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. Sp. 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., Tania 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, Bunostumum spp. Abel, sp. Genus species (C onorchis spp.), Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria cirium, Diphyllobulum diarum Echinococcus granulosus, Echinococcus multioculiris, Enterobius vermicularis, Fachyola sp. Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostronglus spp., Loa loa, Nea to 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 (Campylommida libida), Caverelius spp., Cimex spp., Creontides dilutus, Casinus piperis, cyprus D・ Hewetti (Dicocoris hetet) ti), Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horchilus nos. Genus species (Leptocorisa spp.), Leptogrosus phyllopus, Lygus spp., Macropes excavatus, Miridae, Ne. Sp. Genus (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. (Aleurobus barodensis), Aleurothrixus spp., Amrasca spp., Anuraphis cardhii, Aonidiella pasp. ), Aphis spp., Arboride Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Auracorsum spp. (Aulacorthum spp.) Bemisia spp.), Brachycaudus helichrysi, Brachycorus sp., Brevicoryne brassiae, Bregicoryne brassiae. Ratobakuna-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 species pp. ), Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis sp. Doralis spp., Drosica spp., Disapis spp., Dysmicoccus spp., Empoaska spp., Eriozo 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-Fimubiriorata (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 (Nesovetix spp.), Nilaparvata lugens (Olacombata lugens), Oncometia sp. opia spp. ), Orthezia praelonga, Parabemisia myricae, Paratriosa spp., P. pismus, P. purimus 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 gigasu, Rastrococcus sp. Species (Rhopalosiphum spp.), Saise Species of the genus Tia (Saissetia spp.), Scahoides titanus, Schizophis graminum, Selena spidus ur sera, Sferta sp. ), Sugatodes spp., Stictocephala festina, Tenaraphala melenaensis, Tinocaris caryaefoliae, Tinocallis falina Species (Tomaspis spp. ), Toxoptera spp., Trialureodes vaporariorum, Torioza spp., Typlocyba spp., 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, Pyrusta nubilalis, Spodoptera sp. , Tinea pelionella, Tinola bisselliella, Toritrix viridana, Trichoplusia spp.

  From the order of the Orthoptera, for example, Acheta domesticus, Bratta orientalis, Bratella germanium, Grylotalpa de Miguel, , 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.

  Examples of plant parasitic nematodes include, for example, Anguina spp., Apelenchoides spp., Belonoaimus spp., Bursaphelenchus spp. Dityrenchus dipsasi, Globodera spp., Heliocotylencus spp., Heterodera spp., Longidor spr. Meloidogyne spp.), Pratylenchus spp., Radforus Genus species (Radhophorus similis), rotylenecus spp., Trichodorus spp., Tylenchorinchus spp., Tylencyllus spp. (Thlenchulus semipenetans), 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 by conventional treatment methods such as immersion, spraying, evaporation, atomization, scattering, application, injection, In the case of growth substances, in particular in the case of seeds, this is done by applying the compounds to their surroundings, habitat or storage location 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 “desire part” are as explained 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 early mushrooms or salt in water or soil, improved flowering ability, simplified harvesting, accelerated maturation, increased yield, improved quality of harvested products There may be an improvement and / or an increase in nutritional value, an improvement in the storage stability and / or processability of the harvested product.

  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 include improved plant growth, increased tolerance to high or low temperatures, increased precociousness or tolerance to water or salt in the soil, improved flowering ability, simplified harvesting, maturation Acceleration, increased yield, improved quality of collected products and / or increased nutritional value, improved storage stability and / or processability of collected products. 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 due to toxins formed in plants, in particular genetic material derived from Bacillus thuringiensis (eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2 , Cry9c, Cry2Ab, Cry3Bd and CryIF, and combinations thereof) increase in plant defense against insects, arachnids, nematodes, slugs and snails (hereinafter "Bt"). Referred to as "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® (eg corn, cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® ( Mention may be made of corn varieties, cotton varieties, soy varieties and cocoon varieties sold under the trade names of Cotton, Nucotn® (cotton) and NewLeaf® (芋). Examples of herbicide-tolerant plants include Roundup Ready® (resistance to glyphosate, eg corn, cotton, soybean), Liberty Link® (resistance to phosphinotricin, eg rapeseed), IMI (registered) Corn varieties, cotton varieties and soy varieties sold under the trade names Trademark) (resistance to imidazolinones) and STS® (resistance to sulfonylureas, eg corn). Plants that are resistant to herbicides (plants that have been bred in a conventional manner to confer herbicide tolerance) are sold under the trade name Clearfield® (eg, corn) Variants are 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 pests 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 Anoplida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtyrus 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-Fanusu-Kyapitisu (Pediculus humanus capitis), Pedikyurasu-Fanusu-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., Phlebotomas spp., Lutzomia spp., Curicoid 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 sp., 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 ), Gastrophilus haemoroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus gastrophilus Gastrophilus 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 and the Mesostigmatidae, for example, Argas spp., Ornithodras 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. Stoma genus (Sternostoma spp.), Genus Barroa spp., Genus Acarapis (Acarapis spp.), For example, Argas persicus, Argas reflexus, Arnuit reflexus (Ornithodorus moubata), Otobius megnini, Lipisephalas Rhipicephus (Boophilus) microplus, Ripicephalus (Bouphyrus) decoloratas (Rhipicephalus (Boophilus) decoloratus), Lipicephalus (Bhuphylus) anuratus (Rhipiculus) Boophilus calceratus), Hyaloma anatomicum, Hyaloma aegypticum, Hyaloma marginatum, Hyalon marginatum Hyalomma transiens, Rhipicephalus eversi, Ixodes sidus, Ixodes eus d (Ixodes rubicundus), Ixodes scapularis, Ixodes holocyclas, Haemaphysalis concinna, Haemaphysalis phae is punctata), Hemafisarisu-Shin'abarina (Haemaphysalis cinnabarina), Hemafisarisu-Otofira (Haemaphysalis otophila), Hemafisarisu-Reachi (Haemaphysalis leachi), Hemafisarisu-Rongikoruni (Haemaphysalis longicorni), Delmas Centaur-Maruginatasu (Dermacentor marginatus), Delmas Sen Toll Retikyura Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor Ande Sony (Dermacentor andersoni), Delmas Centaur variabilis (Dermacentor variabilis), Hiaronma-Mauritanikamu (Hyalomma mauritanicum), Ripisefarasu-sanguineus (Rhipicephalus sanguineus), Ripisefarasu - Bursa (Rhipicephalus bursa), Ripisefarasu-up pen di Cura task (Rhipicephalus appendiculatus) , Ripicephalus capensis, Rhipicephalus turnicus, Rhipicephalus zambeziensis (Rhipicephalus za) mbeziensis), Anburioma America Nam (Amblyomma americanum), Anburioma-Bariegatamu (Amblyomma variegatum), Anburioma-Makyuratamu (Amblyomma maculatum), Anburioma-Heburaeumu (Amblyomma hebraeum), Anburioma-Kajenensu (Amblyomma cajennense), Derumanisasu-Garinae (Dermanyssus gallinae ), Ornithonyssus bursa, Ornisonysus sylviaram, Barroa 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 yasuguri, Cheyretiella blackei, Demodex canis, Demodex bovis, Demodex bovis, Demodex visd Demodex caprae, Demodex equi, Demodex cavalli, Demodex suis, Neotrombicula neumbulumula Dezareri Neoschongastia xerothermobia, Trombicula akamushi, vis cos s, te te co , Sarcoptes ovis, Sarcoptes rupicaprae (= S. Caprae), Sarcoptes equui, Sarcoptes suis, Sarcoptes sou Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Psoroputes equi, Psoroptes bovis, Psoergates vis・ 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 tablets, capsules, beverages, liquid medicine, granules, pastes, boluses, feed or in the form of suppositories, 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, washing and powder spraying, and collars, With the aid of articles containing active compounds, such as ear tags, tail tags, foot rings, edge nets, marking tools, etc., active compounds are applied in known ways in the veterinary medicine sector and in livestock (= 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”], Can be applied as an emulsion, emulsion [“EC”], flowable, uniform 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 gaseous 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.), and albumin hydrolysates.

  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 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.

  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.

  Next, the present invention is illustrated by the following examples, but the present invention is not intended to be limited thereto.

Synthesis example 1 (raw material synthesis)

水素化リチウム（０．１ｇ）を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（４．０ｇ）及び１−（３−ブロモ−４−フルオロフェニル）エタノン（１．５ｇ）のテトラハイドロフラン（５０ｍｌ）溶液に加え、８時間加熱還流した。ｔ−ブチルメチルエーテルで希釈した後、飽和炭酸水素ナトリウム水溶液及び飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、反応液を濃縮し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、１−（３−ブロモ−４−フルオロフェニル）−４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）ブテ−２−エン−１−オン（２．６ｇ）を得た。

Lithium hydride (0.1 g) was replaced with 2,2,2-trifluoro-1- (3,4,5-trichlorophenyl) ethanone (4.0 g) and 1- (3-bromo-4-fluorophenyl) ethanone (1.5 g) in tetrahydrofuran (50 ml) was added and heated to reflux for 8 hours. After diluting with t-butyl methyl ether, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the reaction solution was concentrated under reduced pressure, and the residue was purified by calom chromatography (ethyl acetate / hexane) to give 1- (3-bromo-4-fluorophenyl) -4,4. , 4-trifluoro-3- (3,4,5-trichlorophenyl) but-2-en-1-one (2.6 g) was obtained.

¹ H-NMR (CDCl ₃ ) δ: 7.23-7.34 (4H, m), 7.79-7.82 (1H, m), 8.03-8.08 (1H, m)

Synthesis example 2 (raw material synthesis)

１−（３−ブロモ−４−フルオロフェニル）−４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）ブテ−２−エン−１−オン（２．０ｇ）とニトロメタン（０．４ｇ）のアセトニトリル（５０ｍｌ）溶液中に、ジアザビシクロウンデセン（０．７ｇ）を加え、室温にて１０時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈した後、飽和食塩水で３回洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、反応液を濃縮し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、１−（３−ブロモ−４−フルオロフェニル）−４，４，４−トリフルオロ−３−（ニトロメチル）−３−（３，４，５−トリクロロフェニル）ブタン−１−オン（１．６ｇ）を得た。

1- (3-bromo-4-fluorophenyl) -4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) but-2-en-1-one (2.0 g) and Diazabicycloundecene (0.7 g) was added to a solution of nitromethane (0.4 g) in acetonitrile (50 ml), and the mixture was stirred at room temperature for 10 hours. The reaction solution was diluted with t-butyl methyl ether and then washed 3 times with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the reaction solution was concentrated under reduced pressure, and the residue was purified by calom chromatography (ethyl acetate / hexane) to give 1- (3-bromo-4-fluorophenyl) -4,4. , 4-trifluoro-3- (nitromethyl) -3- (3,4,5-trichlorophenyl) butan-1-one (1.6 g) was obtained.

¹ H-NMR (CDCl ₃ ) δ: 4.02 (2H, dd), 5.49 (2H, dd), 7.25-7.32 (3H, m), 7.92-7.95 (1H , M), 8.18-8.20 (1H, m)

Synthesis Example 3 (Synthesis of the present compound)

アルゴン雰囲気下、１−（３−ブロモ−４−フルオロフェニル）−４，４，４−トリフルオロ−３−（ニトロメチル）−３−（３，４，５−トリクロロフェニル）ブタン−１−オン（０．２５ｇ）と塩化ニッケル（ＩＩ）六水和物（０．０６ｇ）をメタノール（２０ｍｌ）とジオキサン（４ｍｌ）の混合溶液に溶解した。氷冷下、水素化ホウ素ナトリウム（０．０６ｇ）を加え、反応液を１時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈し、水と飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、溶媒を留去し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、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−１−オキシド（０．２ｇ）を得た。

Under an argon atmosphere, 1- (3-bromo-4-fluorophenyl) -4,4,4-trifluoro-3- (nitromethyl) -3- (3,4,5-trichlorophenyl) butan-1-one ( 0.25 g) and nickel (II) chloride hexahydrate (0.06 g) were dissolved in a mixed solution of methanol (20 ml) and dioxane (4 ml). Under ice cooling, sodium borohydride (0.06 g) was added, and the reaction solution was stirred for 1 hour. The reaction mixture was diluted with t-butyl methyl ether and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and 5- (3-bromo-4-fluorophenyl) -3- ( 3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-1-oxide (0.2 g) was obtained.

¹ H-NMR (CDCl ₃ ) δ: 3.76 (2H, dd), 4.77 (2H, dd), 7.22 (2H, d), 7.39 (2H, s), 8.31- 8.34 (1H, m), 8.60-8.63 (1H, m)

Synthesis Example 4 (Synthesis of the present compound)

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１−オキシド（０．６５ｇ）、１Ｈ−１，２，４−トリアゾール（０．１ｇ）、炭酸カリウム（０．２ｇ）のＮ，Ｎ−ジメチルホルムアミド（２０ｍｌ）溶液を８０度にて３時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈し、飽和食塩水で３回洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、溶媒を留去し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、１−｛２−ブロモ−４−［１−オキシド−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］フェニル｝−１Ｈ−１，２，４−トリアゾール（０．５ｇ）を得た。

5- (3-Bromo-4-fluorophenyl) -3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole 1-oxide (0.65 g) ) A solution of 1H-1,2,4-triazole (0.1 g) and potassium carbonate (0.2 g) in N, N-dimethylformamide (20 ml) was stirred at 80 ° C. for 3 hours. The reaction solution was diluted with t-butyl methyl ether and washed 3 times with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and 1- {2-bromo-4- [1-oxide-3- (3,4,5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] phenyl} -1H-1,2,4-triazole (0.5 g) Got.

¹ H-NMR (CDCl ₃ ) δ: 3.82 (2H, dd), 4.82 (2H, dd), 7.41 (2H, s), 7.67 (1H, d), 8.16 ( 1H, s), 8.38 (1H, dd), 8.62 (1H, s), 8.83 (1H, d)

Synthesis Example 5 (Synthesis of the present compound)

アルゴン雰囲気下、１−｛２−ブロモ−４−［１−オキシド−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］フェニル｝−１Ｈ−１，２，４−トリアゾール（０．５ｇ）、シアン化亜鉛（０．１ｇ）、テトラキストリフェニルホスフィンパラジウム（０．０５ｇ）のＮ−ジメチルホルムアミド（２０ｍｌ）溶液を８０℃にて４時間攪拌した。ｔ−ブチルメチルエーテルで希釈した後、飽和食塩水で３回洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、反応液を濃縮し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、５−［１−オキシド−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（０．３ｇ）を得た。

1- {2-Bromo-4- [1-oxide-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrole-5 under argon atmosphere -Il] phenyl} -1H-1,2,4-triazole (0.5 g), zinc cyanide (0.1 g), tetrakistriphenylphosphine palladium (0.05 g) in N-dimethylformamide (20 ml). Stir at 80 ° C. for 4 hours. After diluting with t-butyl methyl ether, it was washed 3 times with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the reaction solution was concentrated under reduced pressure, and the residue was purified by calom chromatography (ethyl acetate / hexane) to give 5- [1-oxide-3- (3,4,5- Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2- (1H-1,2,4-triazol-1-yl) benzonitrile (0.3 g) )

¹ H-NMR (DMSO-d ₆ ) δ: 4.06 (2H, dd), 4.91 (2H, dd), 7.88 (2H, s), 8.07 (1H, d), 8. 40 (1H, s), 8.94 (2H, d) 9.28 (1H, s)

Synthesis example 6 (raw material synthesis)

水素化リチウム（０．０５ｇ）を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（１．０ｇ）及び（５−アセチル−２，３−ジヒドロ−１Ｈ−インデン−１−イル）カーバメート（０．５ｇ）のテトラハイドロフラン（２０ｍｌ）溶液に加え、８時間加熱還流した。ｔ−ブチルメチルエーテルで希釈した後、飽和炭酸水素ナトリウム水溶液及び飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、反応液を濃縮し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、ｔｅｒｔ−ブチル｛５−［４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）ブテ−２−エノイル］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイトを得た。

Lithium hydride (0.05 g) was added to 2,2,2-trifluoro-1- (3,4,5-trichlorophenyl) ethanone (1.0 g) and (5-acetyl-2,3-dihydro-1H— Inden-1-yl) carbamate (0.5 g) was added to a tetrahydrofuran solution (20 ml) and heated to reflux for 8 hours. After diluting with t-butyl methyl ether, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the reaction solution was concentrated under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and tert-butyl {5- [4,4,4-trifluoro- 3- (3,4,5-Trichlorophenyl) bute-2-enoyl] -2,3-dihydro-1H-inden-1-yl} carbamate was obtained.

¹ H-NMR (CDCl ₃ ) δ: ¹ H-NMR (CDCl ₃ ) δ: 1.49 (9H, s), 1.71-1.83 (1H, m), 2.55 to 2.59 (1H, m), 2.84-2.90 (2H, m), 4.77-5.08 (2H, m), 7.21-7.27 (2H, m), 7.72 (1H, s) , 8.05-8.05 (3H, m)

Synthesis example 7 (raw material synthesis)

ｔｅｒｔ−ブチル｛５−［４，４，４−トリフルオロ−３−（３，４，５−トリクロロフェニル）ブテ−２−エノイル］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイト（２．０ｇ）とニトロメタン（０．４５ｇ）のＮ，Ｎ−ジメチルホルムアミド（５０ｍｌ）溶液中へ、ジアザビシクロウンデセン（０．６ｇ）を加え、室温にて１０時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈した後、飽和食塩水で３回洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、反応液を濃縮し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、ｔｅｒｔ−ブチル｛５−［４，４，４−トリフルオロ−３−（ニトロメチル）−３−（３，４，５−トリクロロフェニル）ブタノイル］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイト（１．０ｇ）を得た。

tert-butyl {5- [4,4,4-trifluoro-3- (3,4,5-trichlorophenyl) bute-2-enoyl] -2,3-dihydro-1H-inden-1-yl} Diazabicycloundecene (0.6 g) was added to a solution of carbamate (2.0 g) and nitromethane (0.45 g) in N, N-dimethylformamide (50 ml), and the mixture was stirred at room temperature for 10 hours. The reaction solution was diluted with t-butyl methyl ether and then washed 3 times with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the reaction solution was concentrated under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and tert-butyl {5- [4,4,4-trifluoro- 3- (Nitromethyl) -3- (3,4,5-trichlorophenyl) butanoyl] -2,3-dihydro-1H-inden-1-yl} carbamate (1.0 g) was obtained.

¹ H-NMR (CDCl ₃ ) δ: ¹ H-NMR (CDCl ₃ ) δ: 1.50 (9H, s), 1.85-1.93 (1H, m), 2.64-2.67 (1H, m), 2.90-3.02 (2H, m), 4.06 (2H, dd), 4.77-4.81 (1H, m), 5.23-5.26 (1H, m) , 5.53 (2H, dd), 7.33 (2H, s), 7.46 (1H, d), 7.82-7.85 (2H, m)

Synthesis Example 8 (Synthesis of the present compound)

アルゴン雰囲気下、ｔｅｒｔ−ブチル｛５−［４，４，４−トリフルオロ−３−（ニトロメチル）−３−（３，４，５−トリクロロフェニル）ブタノイル］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイト（１．０ｇ）と塩化ニッケル（ＩＩ）六水和物（０．２ｇ）をメタノール（２０ｍｌ）とジオキサン（４ｍｌ）の混合溶液に溶解した。氷冷下、水素化ホウ素ナトリウム（０．２ｇ）を加え、反応液を１時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈し、水と飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、溶媒を留去し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、ｔｅｒｔ−ｂｕｔｙｌ｛５−［１−オキシド−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］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイト（０．６６ｇ）を得た。

Tert-Butyl {5- [4,4,4-trifluoro-3- (nitromethyl) -3- (3,4,5-trichlorophenyl) butanoyl] -2,3-dihydro-1H-indene under argon atmosphere -1-yl} carbamate (1.0 g) and nickel (II) chloride hexahydrate (0.2 g) were dissolved in a mixed solution of methanol (20 ml) and dioxane (4 ml). Under ice cooling, sodium borohydride (0.2 g) was added, and the reaction solution was stirred for 1 hour. The reaction mixture was diluted with t-butyl methyl ether and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and tert-butyl {5- [1-oxide-3- (3, 4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} carbamate (0.66 g )

¹ H-NMR (CDCl ₃ ) δ: 1.50 (9H, s), 1.80-1.83 (1H, m), 2.60-2.63 (1H, m), 2.83-3 0.00 (2H, m), 3.78 (2H, dd), 4.76 (3H, dd), 5.21 (1H, brs), 7.41-7.43 (3H, m), 8. 01-8.06 (1H, m), 8.36 (1H, d)

Synthesis Example 9 (Synthesis of the present compound)

ｔｅｒｔ−ｂｕｔｙｌ｛５−［１−オキシド−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］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝カーバメイト（０．５ｇ）を塩化メチレン（２０ｍｌ）に溶解し、トリフルオロ酢酸（１．５ｇ）を加えた。室温にて、３時間攪拌の後、減圧下、溶媒を留去し、残渣をｔ−ブチルメチルエーテルに溶解した。飽和炭酸水素ナトリウム水溶液及び飽和食塩水で洗浄後、有機層を無水硫酸マグネシウムで乾燥した。減圧下、溶媒を留去し、残渣をテトラハイドロフラン（１０ｍｌ）に溶解し、プロピオン酸無水物（０．１３ｇ）、ピリジン（０．７ｇ）を加え、室温にて３時間攪拌した。反応液をｔ−ブチルメチルエーテルで希釈し、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下、溶媒を留去し、残渣をカロムクロマトグラフィ（酢酸エチル／ヘキサン）にて精製し、Ｎ−｛５−［１−オキシド−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］−２，３−ジヒドロ−１Ｈ−インデン−１−イル｝プロパンアミド（０．２ｇ）を得た。

tert-butyl {5- [1-oxide-3- (3,4,5-trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3 -Dihydro-1H-inden-1-yl} carbamate (0.5 g) was dissolved in methylene chloride (20 ml) and trifluoroacetic acid (1.5 g) was added. After stirring at room temperature for 3 hours, the solvent was distilled off under reduced pressure, and the residue was dissolved in t-butyl methyl ether. After washing with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was dissolved in tetrahydrofuran (10 ml), propionic anhydride (0.13 g) and pyridine (0.7 g) were added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with t-butyl methyl ether and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the residue was purified by calom chromatography (ethyl acetate / hexane), and N- {5- [1-oxide-3- (3,4). , 5-Trichlorophenyl) -3- (trifluoromethyl) -3,4-dihydro-2H-pyrrol-5-yl] -2,3-dihydro-1H-inden-1-yl} propanamide (0.2 g )

¹ H-NMR (acetone-d6) δ: 1.80 (3H, t), 1.79-1.85 (1H, m), 2.21 (2H, q), 2.43-2.48 ( 1H, m), 2.83-2.90 (2H, m), 4.04 (2H, dd), 4.87 (2H, dd), 5.42-5.44 (1H, m), 7 .29-7.37 (2H, m), 7.80 (2H, s), 8.23-8.35 (2H, m)

  The compounds obtained by the same method as in the synthesis examples are exemplified in the following table. Among the compounds of the above synthesis examples, the compounds of the present invention are also shown in the table.

[Biological test]
The reagent supply solutions of Biological Test Examples 1 to 3 were prepared as follows.

Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether 1 part by weight of the compound of the present invention is mixed with the above amount of solvent containing the above amount of emulsifier in order to prepare a suitable active compound formulation. The mixture was diluted with water to a predetermined concentration.

[Biological Test Example 1]: Test for larvae of Spodoptera litura (test method)
Immerse the sweet potato leaves in a reagent solution diluted with water at a predetermined concentration, air-dry the chemical solution, put it in a petri dish with a diameter of 9 cm, and release 10 3 larvae of the pearl moth, and place them in a constant temperature room at 25 ° C for 2 days and 4 days. Sweet potato leaves were added after the day, 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.

(Test results)
In the above biological test example 1, as a representative example, the compound No. 1 was used. The compounds of 1-222, 1-372, and 3-72 exhibited a control effect with an insecticidal rate of 100% at an active ingredient concentration of 20 ppm.

[Biological Test Example 2]: Test against Tetanychus urticae (test method)
50 to 100 adult spider mites were inoculated on the leaves of two real leaves grown in a 6 cm diameter pot, and one day later, a diluted aqueous solution of the active compound prepared above was spray gun A sufficient amount was sprayed using 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.

(Test results)
As a representative example, the previous compound No. The compounds of 1-222, 1-372, and 3-72 showed a control effect with an acaricidal rate of 100% at an active ingredient concentration of 20 ppm.

[Biological Test Example 3]: Test for Auracophora femorialis (test method)
Cucumber leaves were soaked in a diluted aqueous solution of the active compound prepared above, air-dried, then placed in a plastic cup containing sterilized black soil, and 5 larvae of the leaf beetle were released. Seven days later, the number of dead insects was examined and the insecticidal rate was calculated. 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.

(Test results)
As a representative example, the compound No. 1 is used. The compounds of 1-222, 1-372, and 3-72 exhibited a control effect with an insecticidal rate of 100% at an active ingredient concentration of 20 ppm.

[Biological Test Example 4]: Test on Boophilus microplus (Preparation of reagent solution)
Solvent: Dimethylsulfoxide To make a suitable active compound formulation, 10 mg of active compound is dissolved in 0.5 ml of solvent and the concentrate is diluted with solvent to a predetermined concentration.

(Test method)
The compound solution prepared above is injected into the abdomen of five adult males with stagnation. The mite is transferred to a petri dish and kept in a cage for a certain period. After a certain period of time, the lethality of the tick tick was determined. 100% means that all eggs laid were not hatched, and 0% means that all eggs were hatched.

(Test results)
As a representative example, the compound No. 1 is used. Compounds 1-222 and 1-372 showed 100% insecticidal activity at an active ingredient concentration of 100 ppm.

[Biological test example 5]: Test on sheep flies (Lucillia cuprina) (Preparation of reagent)
Solvent: dimethyl sulfoxide 10 mg of the active compound is dissolved in 0.5 ml of dimethyl sulfoxide and diluted successively with water to obtain the desired concentration.

(Test method)
About 20 sheep wing fly first larvae are placed in a test tube containing 1 cubic centimeter of ground beef 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.

(Test results)
As a representative example, Compound No. Compounds 1-222 and 1-372 showed 100% insecticidal activity at an active ingredient concentration of 100 ppm.

[Biological Test Example 6]: Test on housefly (Musca domestica) (test method)
As a test preparation stage, a sponge of a certain size is impregnated with a mixture of sugar and a test compound solution prepared in the same manner as in Biological Test Example 5 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.

(Test results)
As a representative example, the compound No. 1 is used. Compounds 1-222 and 1-372 showed 100% insecticidal activity at an active ingredient concentration of 100 ppm.

[Biological Test Example 7]: Test for cat flea (CTECFE) (Preparation of reagent)
Solvent: dimethyl sulfoxide To make a suitable active compound formulation, 10 mg of active compound is dissolved in 0.5 ml of the above solvent and the concentrate is diluted with bovine blood to a predetermined concentration.

(Test method)
About 20 adult unsucked cat fleas (Ctenocepahrides felis) are prepared in a flea container. A blood container sealed 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 they are all alive.

(Test results)
As a representative example, Compound No. Compounds 1-222 and 1-372 showed 100% insecticidal activity at an active ingredient concentration of 100 ppm.

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

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

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

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

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

  The pyrroline N-oxide derivative of the present invention has extremely excellent insecticidal activity as an insecticide, as shown in the Examples.

Claims (5)

Pyrroline N-oxide derivatives represented by the formula (I);

Wherein T is the following group:

Or

Indicate
G represents a saturated or unsaturated 5- or 6-membered heterocyclic group which may be substituted, or represents halogen, C _1-12 alkyl, cyano, C _1-12 alkoxy-carbonyl or carboxy. ,
R represents an optionally substituted C _1-12 alkyl or C _1-12 haloalkyl;
R ¹ is hydrogen, amino, hydroxy, cyano, C _1-12 alkoxy, C _1-12 alkyl-carbonylamino, C _1-12 alkylimino, C _1-12 alkyl, C _3-8 cycloalkyl, C _2-6 Alkenyl, C _2-6 alkynyl, C _1-12 alkyl-carbonyl, CH ₂ —R ⁶ , C (═O) R ⁶ or C (═S) R ⁶ are shown, and in the definition of R ¹ , C _1-12 Each group from alkoxy to C _1-12 alkyl-carbonyl may be optionally substituted,
R ² is hydrogen, cyano, carbonyl, thiocarbonyl, C _1-12 alkyl-carbonyl, C _1-12 alkyl-thiocarbonyl, C _1-12 haloalkyl-carbonyl, C _1-12 haloalkyl-thiocarbonyl, C _1-12 Alkyl-aminocarbonyl, C _1-12 alkylamino-thiocarbonyl, C _2-24 dialkylamino-carbonyl, C _2-24 dialkylamino-thiocarbonyl, C _1-12 alkoxyamino-carbonyl, C _1-12 alkoxyamino- Thiocarbonyl, C _1-12 alkoxy-carbonyl, C _1-12 alkoxy-thiocarbonyl, C _1-12 alkylthio-carbonyl, C _1-12 alkylthio-thiocarbonyl, C _1-12 alkylsulfonyl, C _1-12 haloalkylsulfonyl , C _-8 cycloalkyl - _{carbonyl, C 2-6} alkenyl - _{carbonyl, C 2-6} alkynyl - _{carbonyl, C 3-8} cycloalkyl _{-C 1-4} alkyl - _{carbonyl, C 1-12} alkylthio _{-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 2-6} alkenyl amino - _{carbonyl, C 2-6} alkynylamino - indicates carbonyl, C (= O) ^{R 6} or C (= S) ^{R 6,} in the definition of ^{R 2,} Each group from C _1-12 alkyl-carbonyl to C _2-6 alkynylamino-carbonyl is Optionally substituted,
R ¹ and R ² together with the N atom to which they are attached may form a 3-6 membered heterocycle, which ring is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R ₃ represents hydrogen, cyano, optionally substituted C _1-12 alkyl or optionally substituted C _1-12 haloalkyl,
R ⁴ represents hydrogen, C _1-12 alkyl, C _1-12 alkyl-carbonyl or C _1-12 alkoxy-carbonyl,
R ⁵ represents hydrogen or C _1-12 alkyl;
R ⁶ represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N;
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C _1-12 alkyl, C _1-12 alkoxy, C _1-12 haloalkyl, C _1-12 haloalkoxy, C _{1 -12 alkylthio, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylthio, C 1-12 haloalkylsulfinyl, C 1-12} haloalkylsulfonyl, _{acylamino, C 1-12} alkoxy - carbonyl amino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkoxyimino, C _1-12 haloalkoxyimino, C _1-12 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , _{C 1-12} Arukirusu from _{C 1-12} alkyl Each group of up Honiruamino may optionally be substituted,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl, C _3-8 cyclohaloalkyl, C _1-12 alkoxy, C _{1-12 haloalkoxy, C 1-12 alkylthio, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 haloalkylthio, C 1-12 haloalkylsulfinyl, C 1-12 haloalkylsulfonyl, C 1- 12} alkylsulfonyloxy, C _1-12 haloalkylsulfonyloxy, C _1-12 alkylaminosulfonyl, C _1-12 haloalkylaminosulfonyl, C _2-24 dialkylaminosulfonyl, C _2-24 di-haloalkyl-aminosulfonyl, C _{1 -12} alkyla Mino, C _2-24 dialkylamino, acylamino, C _1-12 alkoxy-carbonylamino, C _1-12 haloalkoxy-carbonylamino, C _1-12 alkylsulfonylamino, C _1-12 haloalkylsulfonylamino, C _3-36 Trialkylsilyl, C _1-12 alkoxyimino, C _1-12 haloalkoxyimino, C _1-12 alkoxyimino-C _1-12 alkyl, C _1-12 haloalkoxyimino-C _1-12 alkyl, C _1-12 alkyl sulfinyl _{amino, C 1-12} alkyl sulfinyl amino _{-C 1-12 alkyl, C 1-12} alkyl sulfinyl amino _{-C 1-12} alkyl - _{carbonyl, C 1-12} alkylsulfonyl alkoximinoalkyl _{amino, C 1-12} alkylsulfoxide imino _{-C 1-12} alkyl , _{C 1-12} alkoxy - _{carbonyl, C 1-12} alkyl - carbonyl, _{aminocarbonyl, C 1-12} alkylaminocarbonyl - carbonyl, amino - _{thiocarbonyl, C 1-12} alkylaminocarbonyl - _{thiocarbonyl, C 2-24} dialkyl imino _Represents carbonyl or C _2-24 dialkylamino-thiocarbonyl,
Z ¹ , Z ² and Z ³ are each independently CR ⁷ R ⁸ , C═O, C═N—OR ⁹ , N—R ⁹ , S (O) _n , S = N—R ⁹ , or S (O) = N—R ⁹ except that Z ¹ , Z ² and Z ³ do not represent CR ⁷ R ⁸ at the same time,
R ⁷ and R ⁸ each independently represent hydrogen, halogen, _optionally substituted C _1-12 alkyl or _optionally substituted C _1-12 haloalkyl;
R ⁹ is hydrogen, cyano, nitro, C _1-12 alkyl, C _1-12 haloalkyl, C _3-8 cycloalkyl-C _1-6 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, C _6-10 aryl-C _1-6 alkyl or heteroaryl-C _{1- In} the definition of R ⁹ , each group from C _1-12 alkyl to C _1-12 haloalkylsulfonyl may be optionally substituted, and C _6-10 aryl-C _1-6 alkyl aryl heteroaryl moiety of partial and heteroaryl _{-C 1-6} alkyl, halogen, cyano, _{nitro, C 1-1 Alkyl, C 1-12 haloalkyl, C 1-12 alkoxy, C 1-12} haloalkoxy, and _{C 1-12} alkoxy - each having up carbonyl - in carbonyl (such _definitions, the _{C 1-12} alkyl _{C 1-12} alkoxy May be optionally substituted) may be substituted with 1 to 3 arbitrary groups selected from the group consisting of: ) T is the following group:

Or

Indicate
G represents an optionally substituted saturated or unsaturated 5- to 6-membered heterocyclic group, or represents halogen, C 1-6 alkyl, cyano, C 1-6 alkoxy-carbonyl or carboxy,
R represents optionally substituted C 1-6 alkyl or C 1-6 haloalkyl,
R 1 is hydrogen, amino, hydroxy, cyano, C 1-6 alkoxy, C 1-6 alkyl-carbonylamino, C 1-6 alkylimino, C 1-6 alkyl, C 3-7 cycloalkyl, C 2− 4 alkenyl, C 2-4 alkynyl, C 1-6 alkyl-carbonyl, CH 2 —R 6 , C (═O) R 6 or C (═S) R 6 are shown, and in the definition of R 1 , C 1- Each group from 6 alkoxy to C 1-6 alkyl-carbonyl may be optionally substituted,
R 2 is hydrogen, cyano, carbonyl, thiocarbonyl, C 1-6 alkyl-carbonyl, C 1-6 alkyl-thiocarbonyl, C 1-6 haloalkyl-carbonyl, C 1-6 haloalkyl-thiocarbonyl, C 1- 6 alkyl-aminocarbonyl, C 1-6 alkylamino-thiocarbonyl, C 2-12 dialkylamino-carbonyl, C 2-12 dialkylamino-thiocarbonyl, C 1-6 alkoxyamino-carbonyl, C 1-6 akoxyamino- Thiocarbonyl, C 1-6 alkoxy-carbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkylthio-carbonyl, C 1-6 alkylthio-thiocarbonyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl , C 3-7 cycloalkyl - carbonitrile Le, C 2-4 alkenyl - carbonyl, C 2-6 alkynyl - carbonyl, C 3-7 cycloalkyl -C 1-4 alkyl - carbonyl, C 1-6 alkylthio -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 2-4 alkenyl amino - carbonyl, C 2-4 alkynylamino - carbonyl, C (= O) shows the R 6 or C (= S) R 6, in the definition of R 2, C 1-6 alkyl Each group from -carbonyl to C2-4 alkynylamino-carbonyl may be optionally substituted;
R 1 and R 2 together with their attached N atoms may form a 3-6 membered heterocycle, which is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R 3 represents hydrogen, cyano, optionally substituted C 1-6 alkyl or optionally substituted C 1-6 haloalkyl,
R 4 represents hydrogen, C 1-6 alkyl, C 1-6 alkyl-carbonyl or C 1-6 alkoxy-carbonyl,
R 5 represents hydrogen or C 1-6 alkyl,
R 6 represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N,
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1 -6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, acylamino, C 1-6 alkoxy - carbonyl amino, C 1-6 haloalkoxy-carbonylamino, C 1-6 alkoxyimino, C 1-6 haloalkoxyimino, C 1-6 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , optionally location in each group from C 1-6 alkyl to C 1-6 alkylsulfonylamino It may be,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C 1-6 alkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl, C 3-7 cyclohaloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, C 1- 6 alkylsulfonyloxy, C 1-6 haloalkylsulfonyloxy, C 1-6 alkylaminosulfonyl, C 1-6 haloalkylaminosulfonyl, C 2-12 dialkylaminosulfonyl, C 2-12 di-haloalkyl-aminosulfonyl, C 1 -6 alkylamino, C 2-12 Jiarukirua Bruno, acylamino, C 1-6 alkoxy - carbonyl amino, C 1-6 haloalkoxy - carbonylamino, C 1-6 alkylsulfonylamino, C 1-6 haloalkylsulfonyl amino, C 3-18 trialkylsilyl, C 1- 6 alkoxyimino, C 1-6 haloalkoxyimino, C 1-6 alkoxyimino-C 1-6 alkyl, C 1-6 haloalkoxyimino-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 alkylsulfoxyimino, C 1-6 alkylsulfoxyimino-C 1-6 alkyl C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, Represents aminocarbonyl, C 1-6 alkylamino-carbonyl, amino-thiocarbonyl, C 1-6 alkylamino-thiocarbonyl, C 2-12 dialkyliminocarbonyl or C 2-12 dialkylamino-thiocarbonyl,
Z 1 , Z 2 and Z 3 are each independently CR 7 R 8 , C═O, C═N—OR 9 , N—R 9 , S (O) n , S = N—R 9 or S. (O) = N—R 9 except that Z 1 , Z 2 and Z 3 do not represent CR 7 R 8 at the same time,
R 7 and R 8 each independently represent hydrogen, halogen, optionally substituted C 1-6 alkyl or optionally substituted C 1-6 haloalkyl;
R 9 is hydrogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl-C 1-4 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, C 6-10 aryl-C 1-4 alkyl or heteroaryl-C 1- In the definition of R 9 , each group from C 1-6 alkyl to C 1-6 haloalkylsulfonyl may be optionally substituted, and C 6-10 aryl-C 1-4 alkyl The aryl moiety and the heteroaryl moiety of heteroaryl-C 1-4 alkyl are halogen, cyano, nitro, C 1-6 alkyl, C 1-6 Haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy and C 1-6 alkoxy - in carbonyl (such definitions, the C 1-6 alkyl C 1-6 alkoxy - each group until the carbonyl is optionally substituted The pyrroline N-oxide derivative according to claim 1, which may be substituted with 1 to 3 arbitrary groups selected from the group consisting of: T is the following group:

Or

Indicate
G represents an optionally substituted saturated or unsaturated 5- to 6-membered heterocyclic group, or represents halogen, C _1-4 alkyl, cyano, C _1-4 alkoxy-carbonyl or carboxy,
R represents optionally substituted C _1-4 alkyl or C _1-4 haloalkyl,
R ¹ is hydrogen, amino, hydroxy, cyano, C _1-4 alkoxy, C _1-4 alkyl-carbonylamino, C _1-4 alkylimino, C _1-4 alkyl, C _3-6 cycloalkyl, C _{2- 3} alkenyl, C _2-3 alkynyl, C _1-4 alkyl-carbonyl, CH ₂ —R ⁶ , C (═O) R ⁶ or C (═S) R ⁶ are shown, and in the definition of R ¹ , C _1- Each group from ₄ alkoxy to C _1-4 alkyl-carbonyl may be optionally substituted,
R ² is hydrogen, cyano, carbonyl, thiocarbonyl, C _1-4 alkyl-carbonyl, C _1-4 alkyl-thiocarbonyl, C _1-4 haloalkyl-carbonyl, C _1-4 haloalkyl-thiocarbonyl, C _{1- 4} alkyl - _{aminocarbonyl, C 1-4} alkylaminocarbonyl - _{thiocarbonyl, C 2-8} dialkylamino - _{carbonyl, C 2-8} dialkylamino - _{thiocarbonyl, C 1-4} alkoxycarbonyl amino - _{carbonyl, C 1-4} Akokishiamino - Thiocarbonyl, C _1-4 alkoxy-carbonyl, C _1-4 alkoxy-thiocarbonyl, C _1-4 alkylthio-carbonyl, C _1-4 alkylthio-thiocarbonyl, C _1-4 alkylsulfonyl, C _1-4 haloalkylsulfonyl , _{C 3-6} cycloalkyl - carbonyl C _2-3 alkenyl - _{carbonyl, C 2-3} alkynyl - _{carbonyl, C 3-6} cycloalkyl _{-C 1-4} alkyl - _{carbonyl, C 1-4} alkylthio _{-C 1-4} alkyl - _{carbonyl, C 1-4} alkyl Sulfinyl-C _1-4 alkyl-carbonyl, C _1-4 alkylsulfonyl-C _1-4 alkyl-carbonyl, C _1-4 alkyl-carbonyl-C _1-4 alkyl-carbonyl, C _3-6 cycloalkylamino-carbonyl , C _2-3 alkenylamino-carbonyl, C _2-3 alkynylamino-carbonyl, C (═O) R ⁶ or C (═S) R ⁶ in the definition of R ² , C _1-4 alkyl-carbonyl To C _2-3 alkynylamino-carbonyl may be optionally substituted,
R ¹ and R ² together with the N atom to which they are attached may form a 3-6 membered heterocycle, which is substituted by X, oxo, thioxo or nitroimino as described below. Well,
R ³ represents hydrogen, cyano, optionally substituted C _1-4 alkyl or optionally substituted C _1-4 haloalkyl;
R ⁴ represents hydrogen, C _1-4 alkyl, C _1-4 alkyl-carbonyl or C _1-4 alkoxy-carbonyl,
R ⁵ represents hydrogen or C _1-4 alkyl;
R ⁶ represents an optionally substituted phenyl or an optionally substituted 5-6 membered heterocyclic group;
B represents C—X or N,
k represents 1 or 2,
m represents 0 to 4,
n represents 0-2,
X may be the same or different when m is 2 or more, and is halogen, nitro, cyano, C _1-4 alkyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _{1 -4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4} haloalkylsulfonyl, _{acylamino, C 1-4} alkoxy - carbonyl amino, C _1-4 haloalkoxy-carbonylamino, C _1-4 alkoxyimino, C _1-4 haloalkoxyimino, C _1-4 alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, in the definition of X , optionally location in each group from _{C 1-4} alkyl to _{C 1-4} alkylsulfonylamino It may be,
Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C _1-4 alkyl, C _1-4 haloalkyl, C _3-6 cycloalkyl, C ₃ -cyclohaloalkyl, C _1-4 alkoxy, C _{1 -4 haloalkoxy, C 1-4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4 haloalkylsulfonyl, C 1-4 alkylsulfonyloxy, C 1-4 haloalkylsulfonyloxy, C 1-4 alkylaminosulfonyl, C 1-4} haloalkylsulfonyl _{aminosulfonyl, C 2-8} dialkylamino _{sulfonyl, C 2-8} di - haloalkyl - _{aminosulfonyl, C 1- 4 alkylamino, C 2-8} dialkylamino, A _{Arylamino, C 1-4} alkoxy - carbonyl _{amino, C 1-4} haloalkoxy - _{carbonylamino, C 1-4 alkylsulfonylamino, C 1-4} haloalkylsulfonyl _{amino, C 3-12 trialkylsilyl, C 1-4} alkoxy Imino, C _1-4 haloalkoxyimino, C _1-4 alkoxyimino-C _1-4 alkyl, C _1-4 haloalkoxyimino-C _1-4 alkyl, C _1-4 alkylsulfinylimino, C _1-4 alkyl Sulfinylimino-C _1-4 alkyl, C _1-4 alkylsulfinylimino-C _1-4 alkyl-carbonyl, C _1-4 alkylsulfoxyimino, C _1-4 alkylsulfoxyimino-C _1-4 alkyl, C _1-4 alkoxy-carbonyl, C _1-4 alkyl-carbonyl, aminoca Represents rubonyl, C _1-4 alkylamino-carbonyl, amino-thiocarbonyl, C _1-4 alkylamino-thiocarbonyl, C _2-8 dialkyliminocarbonyl or C _2-8 dialkylamino-thiocarbonyl;
Z ¹ , Z ² and Z ³ are each independently CR ⁷ R ⁸ , C═O, C═N—OR ⁹ , N—R ⁹ , S (O) _n , S = N—R ⁹ or S. (O) = N—R ⁹ except that Z ¹ , Z ² and Z ³ do not represent CR ⁷ R ⁸ at the same time,
R ⁷ and R ⁸ each independently represent hydrogen, halogen, optionally substituted C _1-4 alkyl or optionally substituted C _1-4 haloalkyl;
R ⁹ is hydrogen, cyano, nitro, C _1-4 alkyl, C _1-4 haloalkyl, C _3-6 cycloalkyl-C _1-2 alkyl, C _1-4 alkyl-carbonyl, C _1-4 haloalkyl-carbonyl C _1-4 alkoxy-carbonyl, C _1-4 haloalkoxy-carbonyl, C _1-4 alkylsulfonyl, C _1-4 haloalkylsulfonyl, C _6-10 aryl-C _1-2 alkyl or heteroaryl-C _{1- In} the definition of R ⁹ , each group from C _1-4 alkyl to C _1-4 haloalkylsulfonyl may be optionally substituted, and C _6-10 aryl-C _1-2 alkyl The aryl moiety and the heteroaryl moiety of heteroaryl-C _1-2 alkyl may be halogen, cyano, nitro, C _1-4 alkyl, C _{1-4 Haloalkyl, C 1-4 alkoxy, C 1-4} haloalkoxy and _{C 1-4} alkoxy - in carbonyl (such _definitions, the _{C 1-4} alkyl _{C 1-4} alkoxy - each group to carbonyl which is optionally substituted The pyrroline N-oxide derivative according to claim 1, which may be substituted with 1 to 3 arbitrary groups selected from the group consisting of:   An insecticide containing the pyrroline N-oxide derivative according to any one of claims 1 to 3 as an active ingredient.   The animal parasite control agent which contains the pyrroline N-oxide derivative in any one of Claims 1-3 as an active ingredient.