Pesticidal diaryl—heterocyclyl derivatives

Patent metadata

Field	Value
Publication number	US-9307764-B2
Application number	US-201214113778-A
Country	US
Kind code	B2
Filing date	Apr 24, 2012
Priority date	Apr 28, 2011
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

To provide pesticidal allylAryl heterocycle derivatives that are useful as a pesticidal compound.
Pesticidal allylAryl heterocycle derivatives that are expressed by the Formula (I),

and pesticides and an agent for controlling animal parasites which include the allylAryl heterocycle derivatives as an effective component.

First claim

The invention claimed is:

1. An Aryl heterocycle derivative that is represented by Formula (I)

wherein R′ represents C 1-12 alkyl or C 1-12 haloalkyl,
l represents 0 or 1,
U represents CH 2 , S═O or SO 2 ,
A 1 , A 2 , A 3 and A 4 each independently represent C—Y or N, with the proviso that two of A 1 , A 2 , A 3 and A 4 may simultaneously represent N, or two Ys may form, together with the carbon atom to which they are bound, a benzene ring or a 5- to 6-membered heteroaromatic ring when A 1 and A 2 represent C—Y,
B 1 , B 2 , B 3 and B 4 each independently represent C—X or N,
L represents (CR 1 R 2 ) n ,
n represents 1, 2 or 3,
R 1 and R 2 each independently represent hydrogen, cyano, C 1-12 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-C 1-12 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-12 alkoxy-carbonyl or C 1-12 thioalkoxy-carbonyl, and herein, each group from C 1-12 alkyl to C 1-12 thioalkoxy-carbonyl above may be optionally substituted with halogen,
or R 1 and R 2 may form, together with the carbon atom to which they are bound, a 3- to 6-membered hydrocarbon ring,
or R 1 may form, together with Y of A 2 , C 2-3 alkylene when n represents 1 and A 2 represents C—Y,
R 3 represents hydrogen, amino, hydroxy, cyano, C 1-12 alkyl, C 1-12 alkoxy, C 1-12 alkyl-carbonylamino, C 1-12 alkylamino, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 alkyl-carbonyl, —CH 2 —R 5 , —C(═O)R 5 or C(═S)R 5 , and herein, each group from C 1-12 alkyl to C 1-12 alkyl-carbonyl above may be optionally substituted,
R 4 represents hydrogen, cyano, formyl, thioformyl, C 1-12 alkyl-carbonyl, C 1-12 alkyl-thiocarbonyl, C 1-12 alkylamino-carbonyl, C 1-12 alkylamino-thiocarbonyl, C 2-24 (total carbon number) dialkylamino-carbonyl, C 2-24 (total carbon number) dialkylamino-thiocarbonyl, C 1-12 alkoxyamino-carbonyl, C 1-12 alkoxyamino-thiocarbonyl, C 1-12 alkoxy-carbonyl, C 1-12 alkoxy-C 1-12 alkyl-carbonyl, C 1-12 thioalkoxy-C 1-12 alkyl-carbonyl, C 1-12 alkylsulfenyl-C 1-12 alkyl-carbonyl, C 1-12 alkylsulfonyl-C 1-12 alkyl-carbonyl, C 1-12 alkoxy-thiocarbonyl, C 1-12 thioalkoxy-carbonyl, C 1-12 thioalkoxy-thiocarbonyl, C 1-12 alkylsulfonyl, C 3-8 cycloalkyl-carbonyl, C 3-8 cycloalkyl-C 1-12 alkyl-carbonyl, C 2-12 alkenyl-carbonyl, C 2-12 alkynyl-carbonyl, C 3-8 cycloalkylamino-carbonyl, C 2-12 alkenylamino-carbonyl, C 2-12 alkynylamino-carbonyl, —C(═O)R 5 or C(═S)R 5 , and herein, each group from C 1-12 alkyl-carbonyl to C 2-12 alkylamino-carbonyl above may be optionally substituted,
or R 3 and R 4 may form, together with the nitrogen atom to which they are bound, a 3- to 6-membered heterocycle, and herein, the heterocycle may be optionally substituted with X, keto, thioketo, or nitroimino,
X and Y, which may be the same or different from each other, represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, SF 5 , amino, C 1-12 alkyl, C 3-8 cycloalkyl, C 1-12 alkoxy, C 1-12 alkylthio, C 1-12 alkylsulfinyl, C 1-12 alkylsulfonyl, C 1-12 alkylsulfonyloxy, C 1-12 alkylaminosulfonyl, C 2-24 (total carbon number) dialkylaminosulfonyl, C 1-12 alkylcarbonylamino, benzoylamino, tri(C 1-12 alkyl)silyl, C 1-12 alkoxyimino, C 1-12 alkylsulfinylimino, C 1-12 alkylsulfonylimino, C 1-12 alkoxy-carbonyl, C 1-12 alkylcarbonyl, aminocarbonyl, C 1-12 alkylamino-carbonyl, amino-thiocarbonyl, C 1-12 alkylamino-thiocarbonyl, C 2-24 (total carbon number) dialkylamino-carbonyl or C 2-24 (total carbon number) dialkylamino-thiocarbonyl, and herein, each group from C 1-12 alkyl to C 2-24 (total carbon number) dialkylamino-thiocarbonyl above may be optionally substituted, and
R 5 represents a phenyl group which may be optionally substituted or a 5- to 6-membered heterocyclic group that contains at least one hetero atom optionally selected from the group consisting of N, O, and S, and may be optionally substituted.

2. The Aryl heterocycle derivative according to claim 1 , in which
R′ represents C 1-6 alkyl or C 1-6 haloalkyl,
A 1 , A 2 , A 3 and A 4 each independently represent C—Y or N,
B 1 , B 2 , B 3 and B 4 each independently represent C—X or N,
X and Y each independently represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, SF 5 , C 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyloxy, C 1-6 alkylaminosulfonyl, di(C 1-6 alkyl)amino-sulfonyl, C 1-6 alkyl-carbonylamino, benzoylamino, tri(C 1-6 alkyl)silyl, C 1-6 alkoxyimino, C 1-6 alkylsulfinylimino, C 1-6 alkylsulfonylimino, C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, aminocarbonyl, C 1-6 alkylamino-carbonyl, aminothiocarbonyl, C 1-6 alkylamino-thiocarbonyl, di(C 1-6 alkyl)amino-carbonyl or di(C 1-6 alkyl)amino-thiocarbonyl, and herein, each group from C 1-6 alkyl to di(C 1-6 alkyl)amino-thiocarbonyl above may be optionally substituted with halogen,
R 1 and R 2 each independently represent hydrogen, cyano, C 1-6 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl-C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy-carbonyl or C 1-6 thioalkoxy-carbonyl, and herein, each group from C 1-6 alkyl to C 1-6 thioalkoxy-carbonyl above may be optionally substituted with halogen,
or R 1 and R 2 may form, together with the carbon atom to which they are bound, a 3- to 6-membered hydrocarbon ring,
or R 1 may form, together with Y of A 2 , C 2-3 alkylene when n represents 1 and A 2 represents C—Y,
R 3 represents hydrogen, amino, hydroxy, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-carbonylamino, C 1-6 alkylamino, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkyl-carbonyl, —CH 2 —R 5 , —C(═O)R 5 or C(═S)R 5 , and herein, each group from C 1-6 alkyl to C 1-6 alkyl-carbonyl above may be optionally substituted with halogen,
R 4 represents hydrogen, cyano, formyl, thioformyl, C 1-6 alkyl-carbonyl, C 1-6 alkyl-thiocarbonyl, C 1-6 alkylamino-carbonyl, C 1-6 alkylamino-thiocarbonyl, di(C 1-6 alkyl) amino-carbonyl, di(C 1-6 alkyl)amino-thiocarbonyl, C 1-6 alkoxyamino-carbonyl, C 1-6 alkoxyamino-thiocarbonyl, C 1-6 alkoxy-carbonyl, C 1-6 alkoxy-C 1-6 alkyl-carbonyl, C 1-6 thioalkoxy-C 1-6 alkyl-carbonyl, C 1-6 alkylsulfenyl-C 1-6 alkyl-carbonyl, C 1-6 alkylsulfonyl-C 1-6 alkyl-carbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 thioalkoxy-carbonyl, C 1-6 thioalkoxy-thiocarbonyl, C 1-6 alkylsulfonyl, C 3-7 cycloalkyl-carbonyl, C 3-7 cycloalkyl-C 1-6 alkyl-carbonyl, C 2-6 alkenyl-carbonyl, C 2-6 alkynyl-carbonyl, C 3-7 cycloalkylamino-carbonyl, C 2-6 alkenylamino-carbonyl, C 2-6 alkynylamino-carbonyl, —C(═O)R 5 or C(═S)R 5 , and herein, each group from C 1-6 alkyl-carbonyl to C 2-6 alkynylamino-carbonyl above may be optionally substituted with halogen, and
R 5 represents a phenyl group which may be optionally substituted or a 5- to 6-membered heterocyclic group that contains at least one hetero atom optionally selected from the group consisting of N, O, and S, and may be optionally substituted.

3. The Aryl heterocycle derivative according to claim 1 , in which
R′ represents C 1-4 alkyl or C 1-4 haloalkyl,
A 1 , A 2 , A 3 and A 4 each independently represent C—Y or N,
B 1 , B 2 , B 3 and B 4 each independently represent C—X or N,
X and Y each independently represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, SF 5 , C 1-4 alkyl, C 3-6 cycloalkyl, C 1-4 alkoxy, C 1-4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, C 1-4 alkylsulfonyloxy, C 1-4 alkylaminosulfonyl, di(C 1-4 alkyl)amino-sulfonyl, C 1-4 alkyl-carbonylamino, benzoylamino, tri(C 1-4

Assignees

• Hatazawa Mamoru
• Murata Tetsuya
• Bruechner Peter
• Yamazaki Daiei
• Shimojo Eiichi
• Ichihara Teruyuki
• Shibuya Katsuhiko
• Ishikawa Tadashi
• Bayer Ip Gmbh

Inventors

• Hatazawa Mamoru
• Murata Tetsuya
• Bruechner Peter
• Yamazaki Daiei
• Shimojo Eiichi
• Ichihara Teruyuki
• Shibuya Katsuhiko
• Ishikawa Tadashi

Classifications

• C07C215/16

  the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C237/20

  the carbon skeleton containing six-membered aromatic rings · CPC title

• A01N33/08

  containing oxygen or sulfur · CPC title

• C07C323/60

  with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms · CPC title

• C07D291/04

  Five-membered rings · CPC title