Pesticidal 5-(acylamino) pyrazole derivatives

1. A compound of formula (I):

wherein:

R 1 is (C 1 -C 6 )-haloalkyl, CN, NO 2 or halogen;

R 2 is H, halogen or CH 3 ;

R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or S(O) p —(C 1 -C 3 )-haloalkyl;

W is N or C—R 4 ;

R 4 is halogen or CH 3 ;

A is (C 2 -C 6 )-alkylene or (C 2 -C 6 )-haloalkylene;

or is (C 3 -C 6 )-alkylene in which a carbon in the chain is replaced by O, S, SO, SO 2 or NR 8 with the proviso that the replacing group is not bonded to the adjacent R 5 or carbonyl group; or is

(C 2 -C 6 )-alkenylene or (C 2 -C 6 )-haloalkenylene; or

is —[(C 1 -C 3 )-alkyl] r -aryl-[(C 1 -C 3 )-alkyl] s -,

or —[(C 1 -C 3 )-alkyl] r -heterocyclyl-[(C 1 -C 3 )-alkyl] s -,

or —[(C 1 -C 3 )-alkyl] r -(C 3 -C 6 )-cycloalkyl-[(C 1 -C 3 )-alkyl] s - or —[(C 1 -C 3 )-alkyl] r -(C 5 -C 6 )-cycloalkenyl-[(C 1 -C 3 )-alkyl] s -, in which last four mentioned groups the aryl,

heterocyclyl, cycloalkyl and cycloalkenyl 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, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, OR 11 , CN, NO 2 , S(O) p R 10 , COR 10 , COOR 10 , CONR 9 R 10 , SO 2 NR 9 R 10 , NR 9 R 10 , OH, SO 3 H and (C 1 -C 6 )-alkylideneimino;

R 5 is CONR 9 R 10 or CO 2 R 10 when m is 0 or 1; or R 5 is NR 9 R 17 when m is 1;

R 6 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl;

R 7 is H, (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, COR 11 , COR 12 , COR 13 , —CO 2 —(C 1 -C 6 )-alkyl, —CO 2 —(CH 2 ) q R 11 , —CO 2 —(CH 2 ) q R 13 , —CO 2 —(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 6 )-alkyl-(C 3 -C 7 )-cycloalkyl, CO—(C 2 -C 6 )-alkenyl, —CH 2 R 11 or CH 2 R 13 ; 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 14 , CO 2 —(C 1 -C 6 )-alkyl, —O(C═O)—(C 1 -C 6 )-alkyl, NR 9 R 10 , CONR 9 R 10 , SO 2 NR 9 R 10 , OH, CN, NO 2 , OR 11 , OR 13 ,

NR 10 COR 9 , NR 10 SO 2 R 14 and COR 12 ;

R 8 is R 9 , CO—R 9 , CO—R 11 , CO 2 R 12 or CO—(C 1 -C 6 )-alkyl substituted by amino;

R 9 is H, (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, (C 3 -C 7 )-cycloalkyl

or —(C 1 -C 6 )-alkyl-(C 3 -C 7 )-cycloalkyl;

R 10 is R 9 , —[(C 1 -C 6 )-alkyl] q -R 11 , (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl-,

(C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl- or (C 1 -C 3 )-alkyl-S(O) p —(C 1 -C 3 )-alkyl-; or

R 9 and R 10 or R 9 and R 17 each together with the respective attached N atom form a four- to seven-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being 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 CO 2 —(C 1 -C 6 )-alkyl;

R 11 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, OR 16 , CN, NO 2 , S(O) p R 12 , COR 9 , COOH, COOR 12 , CONR 9 R 15 ,

SO 2 NR 9 R 15 , NR 9 R 15 , OH, SO 3 H and (C 1 -C 6 )-alkylideneimino;

R 12 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;

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

S(O) p R 12 , OH and oxo;

R 14 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or —(C 1 -C 6 )-alkyl-(C 3 -C 7 )-cycloalkyl;

R 15 is H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or —(C 1 -C 6 )-alkyl-(C 3 -C 7 -cycloalkyl;

R 16 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 12 , COR 15 , COOH, COOR 12 , CONR 9 R 15 , SO 2 NR 9 R 15 , NR 9 R 15 and OH;

R 17 is R 10 , CO 2 (C 1 -C 6 )-alkyl, —CH 2 CO 2 (C 1 -C 6 )-alkyl, CO 2 CH 2 R 18 or CO(C 1 -C 6 )-alkyl;

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;

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

m and q are each independently 0 or 1;

r and s are each independently 0 or 1; and

each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S;

or a pesticidally acceptable salt thereof.

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

R 10 is R 9 , —[(C 1 -C 6 )-alkyl] q -R 11 , (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl- or

(C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl-;

R 17 is R 10 , CO 2 (C 1 -C 6 )-alkyl, CO 2 CH 2 R 18 or CO(C 1 -C 6 )-alkyl; and the other values are as defined in claim 1 .

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 R 2 is Cl.

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

6. A compound or a salt thereof as claimed in claim 1 wherein A is (C 1 -C 6 )-alkylene; or is (C 1 -C 6 )-alkylene in which a carbon in the chain is replaced by O, S, SO, SO 2 or NR 8 with the proviso that the replacing group is not bonded to the adjacent R 5 or carbonyl group; or is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, CN and NO 2 ; or is pyridyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl and (C 1 -C 4 )-alkoxy.

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

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

R 2 is Cl;

R 3 is CF 3 ;

W is CR 4 and R 4 is Cl;

A is (C 1 -C 6 )-alkylene; or is (C 1 -C 6 )-alkylene in which a carbon in the chain is replaced by O, S, SO, SO 2 or NR 8 with the proviso that the replacing group is not bonded to the adjacent R 5 or carbonyl group; or 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, CN and NO 2 ; or is pyridyl 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 5 is CONR 9 R 10 or CO 2 R 10 when m is 0 or 1; or R 5 is NR 9 R 17 when m is 1;

R 6 is (C 1 -C 2 )-alkyl or (C 1 -C 2 )-haloalkyl;

R 7 is hydrogen or (C 1 -C 2 )-alkyl;

R 8 is R 9 , CO—R 9 or CO—R 11 ;

R 9 is H or (C 1 -C 6 )-alkyl;

R 10 is H, (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, (C 3 -C 7 )-cycloalkyl, —(C 1 -C 6 )-alkyl-(C 3 -C 7 )-cycloalkyl or —(CH 2 ) q R 11 ; or

R 9 and R 10 together with the attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C 1 -C 2 )-alkyl;

R 11 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, CN, NO 2 , S(O) p R 12 and NR 9 R 15 ;

R 12 is (C 1 -C 2 )-alkyl or (C 1 -C 2 )-haloalkyl;

R 15 is H, (C 1 -C 2 )-alkyl or (C 1 -C 2 )-haloalkyl;

R 17 is R 10 , CO 2 (C 1 -C 2 )-alkyl, CO 2 CH 2 R 18 or CO(C 1 -C 2 )-alkyl; and

R 18 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.

9. 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 5 , R 6 , R 7 , W, A, m and n are as defined in claim 1 , reacting a compound of formula (II):

wherein R 1 , R 2 , R 3 , R 6 , R 7 , W and n are as defined in claim 1 , with a compound of formula (III):

R 5 -(A) m -CO-L   (III)

wherein R 5 , A and m are as defined in claim 1 and L is a leaving group; or

b) where R 1 , R 2 , R 3 , R 5 , R 6 , W, A, m and n are as defined in claim 1 , and R 7 is as defined in claim 1 with the exclusion of hydrogen, alkylating or acylating the corresponding compound of formula (I) in which R 7 is hydrogen, with a compound of formula (IV):

R 7 -L 1   (IV)

wherein R 7 is as defined in claim 1 with the exclusion of hydrogen and L 1 is a leaving group; or

c) where R 1 , R 2 , R 3 , R 6 , R 7 , W, A and n are as defined in claim 1 , R 5 is NR 9 R 10 and m is 1, effecting nucleophilic substitution of a corresponding compound of formula (V):

wherein R 1 , R 2 , R 3 , R 6 , R 7 , A, W and n are as defined in claim 1 , m is 1 and L 2 is a leaving group, with a compound of formula (VI):

H—NR 9 R 10   (VI)

wherein R 9 and R 10 are as defined in claim 1 ; or

d) where R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , W, A, L 2 , m and n are as defined in claim 1 , acylating a compound of formula (II) with a compound of formula (VII):

L 2 -(A) m -COCl   (VII)

wherein L 2 , A and m are as defined in claim 1 ; or

e) where R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , W, A and m are as defined in claim 1 , and n is 1 or 2, oxidizing a corresponding compound in which n is 0 or 1; and

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

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

11. A method for the control of pests 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 .

12. A method for the control of pests at a locus which comprises applying to said locus a pesticidally effective amount of a composition as claimed in claim 10 .

13. A veterinary medicament comprising a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in claim 1 , in association with a veterinarily acceptable diluent or carrier and/or surface active agent.

14. A method for the control of pests 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 .

15. A method for the control of pests in or on an animal which comprises administering to said animal a pesticidally effective amount of a veterinary medicament as claimed in claim 13 .