Naphthalene isoxazoline compounds for control of invertebrate pests
Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.
1. A compound selected from Formula 1, an N-oxide or salt thereof,
wherein
R 1 is halogen, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy;
R 2 is H, halogen, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 3 is H, halogen, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy;
R 4 is H, halogen, cyano, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 5 is H, CH 3 , C 2 -C 7 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 7 alkoxycarbonyl or CH 2 O(C 1 -C 3 alkyl);
R 6 is C 1 -C 6 alkyl group optionally substituted with halogen, OR 11 , S(O) n R 12 or NR 13 C(O)R 14 ; or
R 6 is C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl, each optionally substituted with 1 to 4 substituents selected from the group consisting of halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl and up to 1 cyclopropyl; or
R 6 is (CH 2 ) m Q; or
R 6 is OR 8 or NR 9a R 9b ;
Q is a 4- to 6-membered saturated ring containing carbon atoms and one O or S(O) n as ring members and optionally substituted with 1 or 2 R 10 ;
R 8 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 9a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl;
R 9b is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl;
each R 10 is independently halogen, cyano or C 1 -C 2 alkyl;
R 11 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 12 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 13 is H or C 1 -C 4 alkyl;
R 14 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl;
m is 0 or 1; and
each n is independently 0, 1 or 2.
2. A compound of claim 1 wherein:
R 1 is halogen or CF 3 ;
R 2 is H or halogen; and
R 3 is H, halogen or CF 3 .
3. A compound of claim 2 wherein:
R 4 is H, cyano or CH 3 ; and
R 5 is H.
4. A compound of claim 3 wherein:
R 6 is cyclopropyl, isopropyl, CH 2 CH 2 SCH 3 , CF 2 CF 3 or CH 2 NC(O)CF 3 .
5. A compound of claim 1 wherein
R 1 is C 1 or CF 3 ;
R 2 is H;
R 3 is Cl or CF 3 ;
R 4 is H, cyano or CH 3 ;
R 5 is H;
R 6 is cyclopropyl, isopropyl, CH 2 CF 3 , CH(CF 3 ) 2 or CF 2 CF 3 .
6. A compound of claim 5 wherein
R 1 is Cl; and
R 3 is Cl.
7. A compound of claim 6 wherein
R 4 is H.
8. A compound of claim 7 wherein
R 6 is cyclopropyl or isopropyl.
9. A compound of claim 8 wherein
R 6 is cyclopropyl.
10. A composition for protecting an animal from an invertebrate parasitic pest comprising a parasiticidally effective amount of a compound of claim 1 and at least one carrier.
11. A method for protecting an animal from an invertebrate parasitic pest comprising administering to the animal a parasiticidally effective amount of a compound of claim 1 .