Pesticidal 5-substituted-oxyalkylamino-1-arylpyrazole derivatives

1. A compound of formula (I):

wherein:

R 1 is CN or CSNH 2 ;

W is C-halogen;

R 2 is hydrogen or halogen;

R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or SF 5 ;

R 4 is hydrogen, CO 2 —(C 1 -C 6 )-alkyl, CO 2 —(C 3 -C 6 )-alkenyl, CO 2 —(C 3 -C 6 )-alkynyl, CO 2 —(CH 2 ) m R 7 or SO 2 R 8 ; 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, OH, NR 9 R 10 , and OR 7 ;

A is (C 1 -C 6 )-alkylene;

X is C(═O), C(═S) or SO 2 ;

Y is O, NR 11 or a covalent bond;

R 5 is (C 3 -C 6 )-alkenyl, —(CH 2 ) q R 7 or —(CH 2 ) q R 12 ; 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, And NR 9 R 10 ;

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

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 , NR 9 R 10 and OH;

R 8 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;

R 9 and R 10 are each independently H or (C 1 -C 6 )-alkyl

R 11 is H or (C 1 -C 6 )-alkyl;

R 12 is heterocyclyl;

n is zero, one or two;

m and q are each independently is zero or one; 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 6 is CF 3 .

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

W is C—Cl;

R 2 is Cl;

R 3 is CF 3 ;

R 4 is hydrogen, CO 2 —(C 1 -C 4 )-alkyl, CO 2 —(C 3 -C 4 )-alkenyl, CO 2 —(C 3 -C 4 )-alkynyl, CO 2 —(CH 2 ) m R 7 or SO 2 R 8 ; or (C 1 -C 3 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C 1 -C 3 )-alkoxy;

A is —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —;

X is C(═O) or SO 2 ;

Y is O, NH or a covalent bond;

R 5 is (C 3 -C 4 )-alkenyl, —(CH 2 ) q R 7 , (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloakyl;

R 6 is CF 3 ;

each R 7 is independently phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, CN, NO 2 ; and

each R 8 is independently (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl.

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

W is C—Cl;

R 2 is Cl;

R 3 is CF 3 ;

R 4 is (C 1 -C 3 )-alkyl;

A is —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —;

X is C(═O);

Y is O, NH or a covalent bond;

R 5 is (C 3 -C 4 )-alkenyl, —(CH 2 ) q R 7 , (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl;

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 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, CN, and NO 2 ; and

R 8 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl.

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

a) when R 2 , R 3 , R 4 , R 5 , R 6 , W, A and n are as defined in claim 1 , R 1 is CN, and Y and X are as defined in claim 1 with the exclusion of compounds in which —Y—X— is —NH—CO— or —NH—CS—, acylating or sulfonylating a compound of formula (II):

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

R 5 —Y—X-L  (III)

wherein Y and X are as defined in formula (I) with the exclusion of compounds in which —Y—X— is —NH—CO— or —NH—CS—, and L is a leaving group; or

b) when R 1 is CN, and R 2 , R 3 , R 4 , R 5 , R 6 , W, A and n are as defined in claim 1 , reacting a compound of formula (II) wherein R 1 , R 2 , R 3 , R 6 , W, A and n are as defined in claim 1 and —Y—X— is —NH—CO— or —NH—CS—, with an isocyanate or isothiocyanate compound of formula (IV) or (V):

R 5 —N═C═O  (IV)

R 5 —N═C═S  (V)

wherein R 5 is as defined in formula(I); or

c) when R 1 is CN, n is 1 or 2, and R 2 , R 3 , R 4 , R 5 , R 6 , W, A, X and Y are as defined in claim 1 , oxidizing a corresponding compound in which n is 0 or 1; or

d) when R 1 is CSNH 2 , and R 2 , R 3 , R 4 , R 5 , R 6 , W, A, X, Y and n are as defined in claim 1 , reacting the corresponding compound of formula (I) wherein R 1 is CN, with an alkali or alkaline earth metal hydrosulfide, or with the reagent Ph 2 PS 2 ; or

(e) when R 1 is CSNH 2 , and R 2 , R 3 , R 4 , R 5 , R 6 , W, A, X, Y and n are as defined in claim 1 , reacting the corresponding compound of formula (I) wherein R 1 is CN, with a bis(trialkylsilyl)sulfide, in the presence of a base; and

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

6. 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.

7. A method for controlling pests at a locus which comprises applying to said locus a pesticidally effective amount of a compound of formula (I) or a salt thereof as claimed in claim 1 .

8. A method for controlling pests at a locus which comprises applying to said locus a pesticidally effective amount of a composition as claimed in claim 6 .

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

10. 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 .

11. 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 9 .

12. A compound or a salt thereof as claimed in claim 1 , wherein R 1 is CN, R 4 is CH 3 , R 6 is CF 3 , A is —CH 2 CH 2 —, W is C—Cl, R 2 is Cl and R 3 is CF 3 .

13. The compound or salt thereof

wherein:

R 1 is CN, R 4 is CH 3 , R 6 is CF 3 , A is —CH 2 CH 2 —, W is C—Cl, R 2 is Cl and R 3 is CF 3 ; and

(a) X is C(═O), Y is O, R 5 is CH 3 and n is 1;

(b) X is C(═O), Y is O, R 5 is 4-nitrophenyl and n is 2;

(c) X is C(═O), Y is a covalent bond, R 5 is CH 3 and n is 2;

(d) X is C(═O), Y is a covalent bond, R 5 is CH 2 OCH 3 and n is 2;

(e) X is C(═O), Y is a covalent bond, R 5 is 4-trifluoromethylphenyl and n is 2;

(f) X is C(═O), Y is a covalent bond, R 5 is 2,6-difluorophenyl and n is 2;

(g) X is C(═O), Y is a covalent bond, R 5 is 2-fluorophenyl and n is 2;

(h) X is C(═O), Y is NH, R 5 is 4-ethoxyphenyl and n is 2;

(i) X is C(═O), Y is NH, R 5 is 4-trifluoromethoxyphenyl and n is 2;

(j) X is SO 2 , Y is a covalent bond, R 5 is propyl and n is 2;

(k) X is SO 2 , Y is a covalent bond, R 5 is 4-chlorophenyl and n is 2; or

(l) X is SO 2 , Y is a covalent bond, R 5 is 4-methylphenyl and n is 2.