Pesticidal carboxamides

Patent metadata

Field	Value
Publication number	US-9227923-B2
Application number	US-201013390302-A
Country	US
Kind code	B2
Filing date	Aug 3, 2010
Priority date	Aug 14, 2009
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

The object of the present invention is to provide novel carboxamides which exhibit an excellent pesticidal activity as pesticides. Disclosed are the carboxamides represented by the following Formula (I):

wherein each substituent is as defined in the specification, and use thereof as pesticides and animal parasite controlling agents.

First claim

The invention claimed is:

1. A carboxamide compound of Formula (I-V):

wherein
G represents oxygen or sulfur;
Q represents hydrogen, C 1-12 haloalkyl, (C 1-12 alkyl)carbonyl, (C 1-12 haloalkyl)carbonyl, (C 1-12 alkoxy)carbonyl or (C 1-12 hloalkxy)carbonyl;
J represents C 1-12 haloalkyl, C 1-12 haloalkyl-O—, C 1-12 haloalkyl-S—, C 1-12 haloalkyl-S(═O), C 1-12 haloalkyl-S(═O) 2 —, C 3-8 halocycloalkyl, —C(J 1 ) (J 2 ) (J 3 ) or —C(J 1 ) (J 2 ) (OJ 4 ),
wherein
J 1 and J 2 each independently represents C 1-12 haloalkyl,
J 3 represents a heterocyclic group, and
J 4 represents hydrogen, C 1-12 alkyl, C 1-12 haloalkyl, alkylsulfonyl, C 1-12 haloalkylsulfonyl, arylsulfonyl, an aryl group or a heterocyclic group;

R1, R2, R4, R5, R7, R8, R9 and R10 each independently represents hydrogen, cyano, halogen, nitro, hydroxy, mercapto, amino, formyl, oxide, C 1-12 alkyl, C 1-12 haloalkyl, aryl-(C 1-12 )alkyl, heterocyclyl-(C 1-12 )alkyl, C 1-12 alkyl-O—, C 1-12 alkyl-NH—, C 1-12 alkyl-S—, C 1-12 alkyl-S(O)—, C 1-12 alkyl-S(O) 2 —, C 1-12 alkyl-S(O) 2 O—, C 1-12 haloalkyl-O—, C 1-12 haloalkyl-NH—, C 1-12 haloalkyl-S—, C 1-12 haloalkyl-S(O)—, C 1-12 haloalkyl-S(O) 2 —, C 1-12 haloalkyl-S(═O) 2 O—, aryl-O—, aryl-NH—, aryl-S—, aryl-S(O)—, aryl-S(O) 2 —, aryl-S(O) 2 O—, heterocyclyl-O—, heterocyclyl-NH—, heterocyclyl-S—, heterocyclyl-S(O)—, heterocyclyl-S(O) 2 —, heterocyclyl-S(O) 2 O—, C 1-12 alkyl-O—(C 1-12 )alkyl, C 1-12 alkyl-NH—(C 1-12 )alkyl, C 1-12 alkyl-S—(C 1-12 )alkyl, C 1-12 alkyl-S(O)—(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 —(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 O—(C 1-12 )alkyl, C 1-12 haloalkyl-O—(C 1-12 )alkyl, C 1-12 haloalkyl-NH—(C 1-12 )alkyl, C 1-12 haloalkyl-S—(C 1-12 )alkyl, C 1-12 haloalkyl-S(O)—(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 —(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 O—(C 1-12 )alkyl, aryl-O—(C 1-12 )alkyl, aryl-NH—(C 1-12 )alkyl, aryl-S—(C 1-12 )alkyl, aryl-S (O)—(C 1-12 )alkyl, aryl-S(O) 2 —(C 1-12 )alkyl, aryl-S(O) 2 O—(C 1-12 )alkyl, heterocyclyl-O—(C 1-12 )alkyl, heterocyclyl-NH—(C 1-12 )alkyl, heterocyclyl-S—(C 1-12 )alkyl, heterocyclyl-S(O)—(C 1-12 )alkyl, heterocyclyl-S(O) 2 —(C 1-12 )alkyl, heterocyclyl-S(O) 2 O—(C 1-12 )alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-(C 1-12 )alkyl-, C 3-8 halocycloalkyl, C 3-8 halocycloalkyl-(C 1-12 )alkyl-, C 2-12 alkenyl, C 2-12 haloalkenyl, C 2-12 alkynyl, C 2-12 haloalkynyl, di(C 1-12 alkyl)amino, di(C 1-12 haloalkyl)amino, C 3-36 trialkylsilyl, hydroxyimino(C 1-12 )alkyl, C 1-12 alkyl-O—N═(C 1-12 )alkyl, C 1-12 alkyl-NH—N═(C 1-12 )alkyl, C 1-12 alkyl-S—N═(C 1-12 )alkyl, C 1-12 alkyl-S(O)—N═(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 —N═(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 O—N═(C 1-12 )alkyl, C 1-12 haloalkyl-O—N═(C 1-12 )alkyl, C 1-12 haloalkyl-NH—N═(C 1-12 )alkyl, C 1-12 haloalkyl-S—N═(C 1-12 )alkyl, C 1-12 haloalkyl-S(O)—N═(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 —N═(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 O—N═(C 1-12 )alkyl, (C 1-12 alkoxy)carbonyl, (C 1-12 haloalkoxy)carbonyl, (C 3-8 cycloalkoxy)carbonyl, (C 3-8 halocycloalkoxy)carbonyl, C 3-8 cycloalkyl-(C 1-12 alkoxy)carbonyl, C 3-8 halocycloalkyl-(C 1-12 alkoxy)carbonyl, (C 1-12 alkyl)carbonyl, (C 1-12 haloalkyl)carbonyl, (C 3-8 cycloalkyl)carbonyl, (C 3-8 halocycloalkyl)carbonyl, C 3-8 cycloalkyl-(C 1-12 )alkyl-carbonyl, (C 3-8 halocycloalkyl)-(C 1-12 )alkyl-carbonyl, an aryl group, a heterocyclic group, sulfur pentafluoride, or one of the groups of Formulae (X1-1) to (X1-5):

wherein
G is as defined above;
X 3 , X 4 and X 5 each independently represents hydrogen, cyano, halogen, nitro, hydroxy, mercapto, amino, formyl, C 1-12 alkyl, C 1-12 haloalkyl, aryl-(C 1-12 )alkyl, heterocyclyl-(C 1-12 )alkyl, C 1-12 alkyl-NH—C 1-12 alkyl-S—, C 1-12 alkyl-S(O)—, C 1-12 alkyl-S(O) 2 —, C 1-12 alkyl-S(O) 2 O—, C 1-12 haloalkyl-O—, C 1-12 haloalkyl-NH—, C 1-12 haloalkyl-S—, C 1-12 haloalkyl-S(O)—, C 1-12 haloalkyl-S(O) 2 —, C 1-12 haloalkyl-S(O) 2 O—, aryl-O—, aryl-NH—,aryl-S—, aryl-S(O)—, aryl-S(O) 2 —, aryl-S(O) 2 O—, heterocyclyl-O—, heterocyclyl-NH—, heterocyclyl-S—, heterocyciyl-S(O)—, heterocyclyl-S(O) 2 —, heterocyclyl-S(O) 2 O—, C 1-12 alkyl-O—(C 1-12 )alkyl-NH—(C 1-12 )alkyl, C 1-12 alkyl-S—(C 1-12 )alkyl, C 1-12 alkyl-S(O)—(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 —C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 O—(C 1-12 )alkyl, C 1-12 haloalkyl-O—(C 1-12 )alkyl, C 1-12 haloalkyl-NH—(C 1-12 )alkyl, C 1-12 haloalkyl-S—(C 1-12 )alkyl, C 1-12 haloalkyl-S(O)—(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 —(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 O—(C 1-12 )alkyl, aryl-O—(C 1-12 )alkyl, aryl-NH—(C 1-12 )alkyl, aryl-S—(C 1-12 )alkyl, aryl-S(O) —(C 1-12 )alkyl, aryl-S(O) 2 —(C 1-12 )alkyl, aryl-S(O) 2 O—(C 1-12 )alkyl, heterocyclyl-O—(C 1-12 )alkyl, heterocyclyl-NH—(C 1-12 )alkyl, heterocyclyl-S—(C 1-12 )alkyl, heterocyclyl-S(O)—(C 1-12 )alkyl, heterocyclyl-S(O) 2 —(C 1-12 )alkyl, heterocyclyl-S(O) 2 O—(C 1-12 )alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-(C 1-12 )alkyl-, C 3-8 halocycloalkyl, C 3-8 halocycloalkyl-(C 1-12 )alkyl-, C 2-12 alkenyl, C 2-12 haloalkenyl, C 2-12 alkynyl, C 2-12 haloalkynyl, di(C 1-12 alkyl)amino, di(C 1-12 haloalkyl)amino, C 3-36 trialkylsilyl, hydroxyimino(C 1-12 )alkyl, C 1-12 alkyl-O—N═(C 1-12 )alkyl, C 1-12 alkyl-NH—N═(C 1-12 )alkyl, C 1-12 alkyl-S—N═(C 1-12 )alkyl, C 1-12 alkyl-S(O)—N═(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 —N═(C 1-12 )alkyl, C 1-12 alkyl-S(O) 2 O—N═(C 1-12 )alkyl, C 1-12 haloalkyl-O—N═(C 1-12 )alkyl, C 1-12 haloalkyl-NH—N═(C 1-12 )alkyl, C 1-12 haloalkyl-S—N—(C 1-12 )alkyl, C 1-12 haloalkyl-S(O)—N═(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 —N═(C 1-12 )alkyl, C 1-12 haloalkyl-S(O) 2 O—N═(C 1-12 )alkyl, (C 1-12 haloalkoxy)carbonyl, (C 3-8 cycloalkoxy)carbonyl, (C 3-8 halocycloalkoxy)carbonyl, C 3-8 cycloalkyl-(C 1-12 alkoxy)carbonyl, C 3-8 halocycloalkyl-(C 1-12 alkoxy)carbonyl, (C 1-12 alkyl)carbonyl, (C 1-12 haloalkyl)carbonyl, (C 3-8 cycloalkyl)carbonyl, (C 3-8 halocycloalkyl)carbonyl, C 3-8 cycloalkyl-(C 1-12 )alkyl-carbonyl, C 3-8 halocycloalkyl-(C 1-12 )alkyl-carbonyl, aryl-carbonyl, heterocyclyl-carbonyl, aryl-(C 1-12 )alkyl-carbonyl, heterocyclyl-(C 1-12 )alkyl-carbonyl, sulfur pentafluoride, or an aryl group, or
X 3 and X 4 optionally forms a heterocycle together with the nitrogen atom, carbon atom, oxygen atom or sulfur atom to which they are bonded, or
X 3 and X 5 optionally forms a heterocycle together with the nitrogen atom, carbon atom, oxygen atom or sulfur atom to which they are bonded,
X 6 represents hydrogen, C 1-12 alkyl, C 1-12 haloalkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 haloalkenyl, an aryl group, a heterocyclic group, aryl-(C 1-12 )alkyl or heterocyclyl-(C 1- 12 )alkyl,
X 7 represents hydrogen, nitro, cyano, formyl, X 8 -carbonyl or X 8 -oxycarbonyl, and wherein X 8 independently has the same meaning as X 6 defined above;

R12 has the same meaning as X 3 defined above;
R13 has the same meaning as X 4 defined above;
m represents an integer of 1 to 4;
R14 has the same meaning as X 3 defined above; and
R15 represents hydrogen or has the same meaning as —C(=G)-X 5 , and wherein G and X 5 are as defined above.

2. The carboxamide compound according to claim 1 ,
wherein
the heterocyclic group represents any one of groups W1 to W9:

wherein
Z each independently represents hydrogen, halogen, nitro

Assignees

• Mihara Jun
• Araki Koichi
• Mori Takuma
• Murata Tetsuya
• Yoneta Yasushi
• Watanabe Yukiyoshi
• Shimojo Eiichi
• Ichihara Teruyuki
• Ataka Masashi
• Shibuya Katsuhiko
• Gorgens Ulrich
• Bayer Ip Gmbh

Inventors

• Mihara Jun
• Araki Koichi
• Mori Takuma
• Murata Tetsuya
• Yoneta Yasushi
• Watanabe Yukiyoshi
• Shimojo Eiichi
• Ichihara Teruyuki
• Ataka Masashi
• Shibuya Katsuhiko
• Gorgens Ulrich

Classifications

• C07C255/19

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton · CPC title

• C07C255/57

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton · CPC title

• C07D249/20

  with aryl radicals directly attached in position 2 · CPC title

• C07D213/61

  Halogen atoms or nitro radicals · CPC title

• C07D213/84

  Nitriles · CPC title