Pesticidal compositions

1. A compound of formula (I):

wherein:

R 1 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, CN, C(S)NH 2 , or halogen;

W is, C—CH 3 or C-halogen;

R 2 is H, CH 3 or halogen;

R 3 is halo, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, S(O) p —(C 1 -C 6 )-haloalkyl or SF 5 ;

R 4 is (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 6 )-alkyl, —CO 2 —(C 3 -C 7 )-cycloalkyl, —CO 2 -(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 3 -C 6 )-alkenyl, —CO 2 —(C 3 -C 6 )-alkynyl, —CO 2 —(CH 2 ) q R 7 CONR 8 R 9 , —CO 2 —(CH 2 ) q R 1 , —(CH 2 ) q R 7 , (CH 2 ) q R 1 , COR 9 , COCH 2 NR 8 R 9 , —CO—(CH 2 ) q R 7 or (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 11 , CO 2 —(C 1 -C 6 )-alkyl, —O(C═O)—(C 1 -C 6 )-alkyl, NR 8 R 9 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, CN, NO 2 , OR 7 , NR 8 COR 12 and NR 8 SO 2 R 11 ;

R 5 is (C 3 -C 7 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, R 13 or —CH═CH—R 15 ; or is (C 1 -C 15 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-haloalkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 6 )-haloalkynyloxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 7 , S(O) p R 11 , CN, NO 2 , OH, COR 8 , NR 8 COR 12 , NR 8 SO 2 R 11 , CONR 8 R 9 , NR 8 R 9 , OR 7 , R 13 and CO 2 R 8 , or a methylene group in the unsubstituted or substituted (C 1 -C 6 )-alkyl is replaced by a group selected from —CO—, —O—, —S(O) p —, —NR 8 —, —COO—, —OCO—, —CONR 8 —, —NR 8 CO—, —C(═NOR 8 )—, —C(═N—NR 8 R 9 )— and —C(═NR 8 )— provided that the replacing group is not directly bonded to the SO 2 group in formula (I);

R 6 and R 11 are each independently (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl or (C 3 -C 7 )-cycloalkyl;

R 7 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, CN, NO 2 , S(O) p R 11 and NR 9 R 12 ;

R 8 is H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl, or —(CH 2 ) q R 7 ;

R 9 and R 12 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl;

R 13 is aryl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, CN, NO 2 , S(O) p R 11 , SF 5 , NR 8 R 9 , COR 11 , COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, OR 7 , R 15 , SO 3 H, (C 1 -C 6 )-alkylideneimino, CH═NOR 14 , S(O) p R 18 , and CO 2 R 19 ;

R 14 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;

R 15 is phenyl or naphthyl which groups are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl and (C 1 -C 6 )-alkoxy;

R 18 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl and (C 1 -C 6 )-alkoxy;

R 19 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, R 13 or —(C 1 -C 6 )-alkyl-(C 1 -C 3 )-alkoxy;

n, p and q are each independently zero, one or two;

or a pesticidally acceptable salt thereof.

2. A compound or a salt thereof as claimed in claim 1 wherein:

R 1 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, CN, C(S)NH 2 , or halogen;

W is, C—CH 3 or C-halogen;

R 2 is H, CH 3 or halogen;

R 3 is halo, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, S(O) p —(C 1 -C 6 )-haloalkyl or SF 5 ;

R 4 is (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 6 )-alkyl, —CO 2 —(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 3 -C 6 )-alkenyl, —CO 2 —(C 3 -C 6 )-alkynyl, —CO 2 —(CH 2 ) q R 7 , CONR 8 R 9 , CO 2 —(CH 2 ) q R 10 , —(CH 2 ) q R 7 , —(CH 2 ) q R 10 , COR 9 , COCH 2 NR 8 R 9 , —CO—(CH 2 ) q R 7 ; or (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 11 , CO 2 —(C 1 -C 6 )-alkyl, —O(C═O)—(C 1 -C 6 )-alkyl, NR 8 R 9 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, CN, NO 2 , OR 7 , NR 8 COR 12 and NR 8 SO 2 R 11 ;

R 5 is (C 3 -C 7 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, R 13 or —CH═CH—R 15 ; or is (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-haloalkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 6 )-haloalkynyloxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 7 , S(O) p R 11 , S(O) p R 11 , CN, NO 2 , OH, COR 8 , NR 8 COR 12 , NR 8 SO 2 R 11 , CONR 8 R 9 , NR 8 R 9 , OR 7 , R 13 and CO 2 R 8 , or a methylene group in the unsubstituted or substituted (C 1 -C 6 )-alkyl is replaced by a group selected from —CO—, —O—, —S(O) p —, —NR 8 —, —COO—, —OCO—, —CONR 8 —, —NR 8 CO—, —C(═NOR 8 )—, —C(═N—NR 8 R 9 )— and —C(═NR 8 )— provided that the replacing group is not directly bonded to the SO 2 group in formula (I);

R 6 and R 11 are each independently (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl or (C 3 -C 7 )-cycloalkyl;

R 7 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, CN, NO 2 , S(O) p R 11 and NR 9 R 12 ;

R 8 is H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl, or —(CH 2 ) q R 7 ;

R 9 and R 12 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl;

R 13 is aryl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, CN, NO 2 , S(O) p R 11 , SF 5 , NR 8 R 9 , COR 11 , COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, OR 7 , R 15 , SO 3 H and (C 1 -C 6 )-alkylideneimino;

R 14 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;

R 15 is phenyl or naphthyl which groups are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl and (C 1 -C 6 )-alkoxy.

3. A compound or a salt thereof as claimed in claim 1 wherein R 1 is CN.

4. A compound or a salt thereof as claimed in claim 1 , wherein W is C—Cl.

5. A compound or a salt thereof as claimed in claim 1 wherein R 2 is chlorine.

6. A compound or a salt thereof as claimed in claim 1 wherein R 3 is CF 3 .

7. A compound or a salt thereof as claimed in claim 1 wherein R 4 is (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 6 )-alkyl, —(CH 2 ) q R 7 or COCH 2 NR 8 R 9 ; or (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 3 -C 7 )-cycloalkyl and S(O) p R 11 .

8. A compound or a salt thereof as claimed in claim 1 wherein R 5 is R 13 ; or (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and R 13 .

9. A compound or a salt thereof as claimed in claim 1 wherein R 6 is CF 3 .

10. A compound or a salt thereof as claimed in claim 1 wherein

R 1 is CN;

W is C—Cl;

R 2 is chlorine;

R 3 is CF 3 ;

R 4 is (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl, —CO 2 —(C 1 -C 3 )-alkyl, —(CH 2 ) q R 7 or COCH 2 NR 8 R 9 ; or (C 1 -C 4 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 3 -C 6 )-cycloalkyl and S(O) p R 11 ;

R 5 is R 13 ; or (C 1 -C 4 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, R 13 ;

R 6 is CF 3 ;

R 7 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 2 )-alkyl, (C 1 -C 2 )-haloalkyl and (C 1 -C 2 )-alkoxy;

R 8 is H or (C 1 -C 3 )-alkyl;

R 9 is H or (C 1 -C 3 )-alkyl;

R 11 and R 14 are each independently (C 1 -C 2 )-alkyl or (C 1 -C 2 )-haloalkyl;

R 13 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 2 )-alkyl, (C 1 -C 2 )-haloalkyl, (C 1 -C 2 )-alkoxy, (C 1 -C 2 )-haloalkoxy, CN, NO 2 , S(O) p R 11 and NR 8 R 9 ;

n and p are each independently 0, 1 or 2;

q is 0 or 1.

11. A process for the preparation of a compound of formula (I) or a salt thereof as defined in claim 1 , which process comprises:

a) where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W and n are as defined in claim 1 , reacting a compound of formula (II):

wherein R 1 , R 2 , R 3 , R 4 , R 6 , W and n are as defined in claim 1 , with a compound of formula (III):

(A) R 5 —SO 2 L 1   (III)

wherein R 5 is as defined in claim 1 and L 1 is halogen; and

b) if desired, converting a resulting compound of formula (I) into a pesticidally acceptable salt thereof.

12. A pesticidal composition for the control of arthropods and helminths comprising a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in claim 1 for the control of arthropods and helminths, in association with a pesticidally acceptable diluent or carrier and/or surface active agent for the control of arthropods and helminths.

13. A method for the control of arthropods and helminths at a locus which comprises applying to said locus a pesticidally effective amount of a compound of formula (I) or a salt thereof according to claim 1 .

14. A method for the control of arthropods and helminths at a locus which comprises applying to said locus a pesticidally effective amount of a composition as claimed in claim 12 .

15. A method for the control of arthropods and helminths in or on an animal which comprises administering to said animal a pesticidally effective amount of a compound of formula (I) or a salt thereof as claimed in claim 1 .

16. A method for the control of arthropods and helminths in or on an animal which comprises administering to said animal a pesticidally effective amount of a veterinary medicament as claimed in claim 12 .

17. A compound as claimed in claim 1 , which is selected from the group consisting of:

(a) the compound of formula

(b) the compound of the formula

(c) the compound of the formula

and

(d) the pesticidally acceptable salts thereof.

18. The pesticidal composition of claim 12 , wherein the arthropods and helminths are selected from the group consisting of insects, arachnids, nematodes and combinations thereof.

19. The method of claim 15 , wherein the arthropods and helminths are selected from the group consisting of insects, arachnids, nematodes and combinations thereof.