Pesticidally active azetidine sulfones amide isoxazoline derivatives
Compounds of formula (I) wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.
1. A compound of formula (I),
wherein
A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl;
R 2 is C 1 -C 8 alkyl or C 1 -C 8 haloakyl;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl, aryl substituted by one to three R 7 , heteroaryl or heteroaryl substituted by one to three R 7 ;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH 2 —CH 2 —CH 2 — bridge, a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge; and
each R 7 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.
2. A compound of formula (I) according to claim 1 , wherein
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl- or C 1 -C 8 alkoxycarbonyl.
3. A compound of formula (I) according to claim 1 , wherein
R 2 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.
4. A compound of formula (I) according to claim 1 , wherein R 3 is C 1 -C 4 haloalkyl.
5. A compound of formula (I) according to claim 1 , wherein R 4 is phenyl, phenyl substituted by one to three R 7 .
6. A compound of formula (I) according to claim 1 , wherein each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, or C 1 -C 8 haloalkyl.
7. A compound of formula (I) according to claim 1 , wherein each R 7 is independently Cl, Br, F or CF 3 .
8. A compound of formula (I) according to claim 1 , wherein A 1 is C—R 5 , A 2 , A 3 and A 4 are C—H.
9. A compound of formula (Int-II)
wherein:
A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl;
R 2 is C 1 -C 8 alkyl or C 1 -C 8 haloakyl;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl, aryl substituted by one to three R 7 , heteroaryl or heteroaryl substituted by one to three R 7 ;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH 2 —CH 2 —CH 2 — bridge, a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
each R 7 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy;
R 6 is hydrogen or S(O) 2 R 2 ; and X C is CH 2 -halogen, wherein halogen is bromo or chloro, CH═C(R 3 )R 4 or CH 2 C(OH)(R 3 )R 4 ; and a salt or N-oxide thereof.
10. A compound of formula (Int-III)
wherein:
A 1 , A 2 , A 3 and A 4 , independently of one another, are C—H, C—R 5 or nitrogen;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxycarbonyl;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl, aryl substituted by one to three R 7 , heteroaryl or heteroaryl substituted by one to three R 7 ;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH 2 —CH 2 —CH 2 — bridge, a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
each R 7 is independently halogen, cyano, nitro C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy; and R 6 is hydrogen; and a salt or N-oxide thereof.
11. A pesticidal composition, which comprises at least one compound of formula (I) according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
12. A method for controlling pests, which comprises applying a composition according to claim 11 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
13. A method for the protection of seeds from the attack by pests, which comprises treating the seeds or the site, where the seeds are planted, with a composition according to claim 11 .
14. A pesticidal composition, which comprises at least one compound according to claim 9 , in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
15. A method for controlling pests, which comprises applying a composition according to claim 14 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
16. A method for the protection of seeds from the attack by pests, which comprises treating the seeds or the site, where the seeds are planted, with a composition according to claim 14 .
17. A pesticidal composition, which comprises at least one compound of according to claim 10 , in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
18. A method for controlling pests, which comprises applying a composition according to claim 17 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
19. A method for the protection of seeds from the attack by pests, which comprises treating the seeds or the site, where the seeds are planted, with a composition according to claim 17 .