IP Library › Granted Patent US 9,227,923

Granted Patent B2

US 9,227,923 · App. 13/390,302 · Granted Jan 5, 2016

Pesticidal carboxamides

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 9,227,923
App. No.: 13/390,302
Granted: Jan 5, 2016
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

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.

Claims (89)

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, cyano, hydroxy, thio, 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 or C 1-6 haloalkylsulfonyl; and

k represents an integer from 1 to 4.

3. The carboxamide compound according to claim 1 ,

wherein

G represents oxygen or sulfur;

Q represents hydrogen, C 1-4 haloalkyl, (C 1-4 alkyl)carbonyl, (C 1-4 haloalkyl)carbonyl, (C 1-4 alkoxy)carbonyl or (C 1-4 haloalkoxy)carbonyl;

J represents C 1-4 haloalkyl, C 1-4 haloalkyl-O—, C 1-4 haloalkyl-S—, C 1-4 haloalkyl-S(═O)—, C 1-4 haloalkyl-S(═O) 2 —, C 3-6 halocycloalkyl, —C(J 1 ) (J 2 ) (J 3 ) or —C(J 1 ) (J 2 ) (OJ 4 ),

wherein

J 1 and J 2 each independently represent C 1-4 haloalkyl,

J 3 represents any one of groups W1 to W9:

wherein

k represents an integer from 1 to 4,

J 4 represents hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkylsulfonyl, C 1-4 haloalkylsulfonyl, aryl sulfonyl, 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 1-4 alkyl, C 1-4 haloalkyl, aryl-(C 1-4 )alkyl, heterocyclyl-(C 1-4 )alkyl, C 1-4 alkyl-O—, C 1-4 alkyl-NH—, C 1-4 alkyl-S—, C 1-4 alkyl-S(O)—, C 1-4 alkyl-S(O) 2 —, C 1-4 alkyl-S(O) 2 O —, C 1-4 haloalkyl-O—, C 1-4 haloalkyl-NH—, C 1-4 haloalkyl-S—, C 1-4 haloalkyl-S(O)—, C 1-4 haloalkyl-S(O) 2 —, C 1-4 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 1-4 alkyl-O—(C 1-4 )alkyl, C 1-4 alkyl-NH—(C 1-4 )alkyl, C 1-4 alkyl-S—(C 1-4 )alkyl, C 1-4 alkyl-S(O)—(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 —(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 O—(C 1-4 )alkyl, C 1-4 haloalkyl-O—(C 1-4 )alkyl, C 1-4 haloalkyl-NH—(C 1-4 alkyl, C 1-4 haloalkyl-S—(C 1-4 )alkyl, C 1-4 haloalkyl-S(O)—(C 1-4 alkyl, C 1-4 haloalkyl-S(O) 2 —(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 O—(C 1-4 )alkyl, aryl-O—(C 1-4 )alkyl, aryl-NH—(C 1-4 )alkyl, aryl-S—(C 1-4 )alkyl, aryl-S(O)—(C 1-4 )alkyl, aryl-S(O) 2 —(C 1-4 )alkyl, aryl-S(O) 2 O—(C 1-4 )alkyl, heterocyclyl-O—(C 1-4 )alkyl, heterocyclyl-NH—(C 1-4 )alkyl, heterocyclyl-S—(C 1-4 )alkyl, heterocyclyl-S(O)—(C 1-4 )alkyl, heterocyclyl-S(O) 2 —(C 1-4 )alkyl, heterocyclyl-S(O) 2 O—(C 1-4 )alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-(C 1-4 )alkyl-, C 3-6 halocycloalkyl, C 3-6 halocycloalkyl-(C 1-4 )alkyl-, C 2-4 alkenyl, C 2-4 haloalkenyl, C 2-4 alkynyl, C 2-4 haloalkynyl, di(C 1-4 alkyl)amino, di(C 1-4 haloalkyl)amino, C 3-12 trialkylsilyl, hydroxyimino(C 1-4 alkyl, C 1-4 alkyl-O—N═(C 1-4 )alkyl, C 1-4 alkyl-NH—N═(C 1-4 )alkyl, C 1-4 alkyl-S—N═(C 1-4 )alkyl, C 1-4 alkyl-S(O)—N═(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 —N═(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 O—N═(C 1-4 )alkyl, C 1-4 haloalkyl-O—N═(C 1-4 )alkyl, C 1-4 haloalkyl-NH—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O)—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 —N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 O—N═(C 1-4 )alkyl, (C 1-4 alkoxy)carbonyl, (C 1-4 haloalkoxy)carbonyl, (C 3-6 cycloalkoxy)carbonyl, (C 3-6 halocycloalkoxy)carbonyl, C 3-6 cycloalkyl-(C 1-4 alkoxy)carbonyl, C 3-6 halocycloalkyl-(C 1-4 alkoxy)carbonyl, (C 1-4 alkyl)carbonyl, (C 1-4 haloalkyl)carbonyl, (C 3-6 cycloalkyl)carbonyl, (C 3-6 halocycloalkyl)carbonyl, C 3-6 cycloalkyl-(C 1-4 )alkyl-carbonyl, (C 3-6 halocycloalkyl)-(C 1-4 )alkyl-carbonyl, an aryl 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 represent hydrogen, cyano, halogen, nitro, hydroxy, mercapto, amino, formyl, C 1-4 alkyl, C 1-4 haloalkyl, aryl-(C 1-4 )alkyl, heterocyclyl-(C 1-4 )alkyl, C 1-4 alkyl-NH—, C 1-4 alkyl-S—, C 1-4 alkyl-S(O)—, C 1-4 alkyl-S(O) 2 —, C 1-4 alkyl-S(O) 2 O—, C 1-4 haloalkyl-O—, C 1-4 haloalkyl-NH—, C 1-4 haloalkyl-S—, C 1-4 haloalkyl-S(O)—, C 1-4 haloalkyl-S(O) 2 —, C 1-4 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 1-4 alkyl-O—(C 1-4 )alkyl, C 1-4 alkyl-NH—(C 1-4 )alkyl, C 1-4 alkyl-S—(C 1-4 )alkyl, C 1-4 alkyl-S(O)—(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 —(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 O—(C 1-4 )alkyl, C 1-4 haloalkyl-O—(C 1-4 )alkyl, C 1-4 haloalkyl-NH—(C 1-4 )alkyl, C 1-4 haloalkyl-S—(C 1-4 )alkyl, C 1-4 haloalkyl-S(O)—(C 1-4 )alkyl, C 1-4 haloalkyl-S(O ) 2 —(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 O—(C 1-4 )alkyl, aryl-O—(C 1-4 )alkyl, aryl-NH—(C 1-4 )alkyl, aryl-S—(C 1-4 )alkyl, aryl-S(O)—(C 1-4 )alkyl, aryl-S(O ) 2 —(C 1-4 )alkyl, aryl-S(O ) 2 O—(C 1-4 )alkyl, heterocyclyl-O—(C 1-4 )alkyl, heterocyclyl-NH—(C 1-4 )alkyl, heterocyclyl-S—(C 1-4 )alkyl, heterocyclyl-S(O)—(C 1-4 )alkyl, heterocyclyl-S(O) 2 —(C 1-4 )alkyl, heterocyclyl-S(O) 2 O—(C 1-4 )alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-(C 1-4 )alkyl-, C 3-6 halocycloalkyl, C 3-6 halocycloalkyl-(C 1-4 )alkyl-, C 2-4 alkenyl, C 2-4 haloalkenyl, C 2-4 alkynyl, C 2-4 haloalkynyl, di(C 1-4 alkyl)amino, di(C 1-4 haloalkyl)amino, C 3-12 trialkylsilyl, hydroxyimino(C 1-4 )alkyl, C 1-4 alkyl-O—N═(C 1-4 )alkyl, C 1-4 alkyl-NH—N═(C 1-4 )alkyl, C 1-4 alkyl-S—N═(C 1-4 )alkyl, C 1-4 alkyl-S(O)—N═(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 —N═(C 1-4 )alkyl, C 1-4 alkyl-S(O) 2 O—N═(C 1-4 )alkyl, C 1-4 haloalkyl-O—N═(C 1-4 )alkyl, C 1-4 haloalkyl-NH—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O)—N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 —N═(C 1-4 )alkyl, C 1-4 haloalkyl-S(O) 2 O—N═(C 1-4 ) alkyl, (C 1-4 haloalkoxy)carbonyl, (C 3-6 cycloalkoxy)carbonyl, (C 3-6 halocycloalkoxy)carbonyl, C 3-6 cycloalkyl-(C 1-4 alkoxy)carbonyl, C 3-6 halocycloalkyl-(C 1-4 alkoxy)carbonyl, (C 1-4 alkyl)carbonyl, (C 1-4 haloalkyl)carbonyl, (C 3-6 cycloalkyl)carbonyl, (C 3-6 halocycloalkyl)carbonyl, C 3-6 cycloalkyl-(C 1-4 )alkyl-carbonyl, C 3-6 halocycloalkyl-(C 1-4 )alkyl-carbonyl, aryl-carbonyl, heterocyclyl-carbonyl, aryl-(C 1-4 alkyl-carbonyl, heterocyclyl-(C 1-4 )alkyl-carbonyl, sulfur pentafluoride, or an aryl group, or

X 3 and X 4 optionally form 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 form a heterocycle together with the nitrogen atom, carbon atom, oxygen atom or sulfur atom to which they are bonded,

X 6 represents hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 3-6 cycloalkyl, C 2-4 alkenyl, C 2-4 haloalkenyl, an aryl group, a heterocyclic group, aryl-(C 1-4 )alkyl or heteroeyelyl-(C 1-4 )alkyl, and

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.

4. The carboxamide compound according to claim 1 , wherein

J represents C 1-4 perfluoroalkyl, C 1-4 monobromoperfluoroalkyl,

C 3-6 perfluorocycloalkyl, —C (J 1 ) (J 2 ) (J 3 ) or —C(J 1 ) (J 2 ) (OJ 4 ),

J 1 and J 2 each independently represent C 1-4 perfluoroalkyl,

J 3 represents any one of groups W1 to W9:

wherein

K represents an integer from 1 to 4;

and

J 4 represents C 1-4 alkyl, C 1-4 haloalkyl or a phenyl group.

5. The carboxamide compound according to claim 1 ,

wherein

G represents oxygen;

m represents an integer of 1; and

R9, R12 and R13 each represents hydrogen.

6. A composition comprising at least one compound according to any one of claims 1 to 5 , and an extender and/or a surfactant.

7. An animal parasite-controlling agent comprising at least one compound according to any one of claims 1 to 5 .

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

wherein

G represents oxygen or sulfur;

Q represents C 1-12 alkyl;

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 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-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 O—, C 1-12 haloalkyl-S(O) 2 O—, aryl-O—, aryl-NH—,aryl-S—, aryl-S—, aryl-S(O)—, aryl-S(O) 2 O—, 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 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 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, aryl-(C 1-12 )alkyl-carbonyl, heterocyclyl-(C 1-12 )alkyl-carbonyl, or sulfur pentafluoride, or a heterocyclic group,

X 4 independently represents hydrogen, cyano, halogen, nitro, hydroxy, mercapto, amino, formyl, C 1-12 alkyl, C 1-12 haloalkyl, 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)—(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, aryl-carbonyl, heterocyclyl-carbonyl, aryl-(C 1-12 )alkyl-carbonyl, heterocyclyl-(C 1-12 )alkyl-carbonyl, or sulfur pentafluoride, an aryl group or a heterocyclic group,

X 5 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—, 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, aryl-carbonyl, aryl-(C 1-12 )alkyl-carbonyl, heterocyclyl-(C 1-12 )alkyl-carbonyl, or sulfur pentafluoride, 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 —C(═G)—X 5 , and wherein G and X 5 are as defined above.

Assignments (4)

CHANGE OF NAME Recorded Feb 8, 2024

From: BAYER ANIMAL HEALTH GMBH

To: ELANCO ANIMAL HEALTH GMBH

Reel/Frame 066525/0898 →

NUNC PRO TUNC ASSIGNMENT Recorded Feb 7, 2024

From: BAYER INTELLECTUAL PROPERTY GMBH

To: BAYER ANIMAL HEALTH GMBH

Reel/Frame 066401/0955 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 18, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035037/0128 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2012

From: MIHARA, JUN; ARAKI, KOICHI; MORI, TAKUMA; MURATA, TETSUYA; YONETA, YASUSHI; WATANABE, YUKIYOSHI; SHIMOJO, EIICHI; ICHIHARA, TERUYUKI; ATAKA, MASASHI; SHIBUYA, KATSUHIKO; GORGENS, ULRICH

To: BAYER CROPSCIENCE AG

Reel/Frame 028477/0213 →