Pesticidal carboxamides
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.
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
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,
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
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;
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;
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 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.