N-phenylpyrazole derivatives as pesticides

1. A compound of formula (I):

wherein:

R 1 is CN or CF 3 ;

R 2 and R 2a are each independently halogen or CH 3 ;

R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or SF 8 ;

R 4 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 or (C 1 -C 6 )-alkyl which last mentioned group is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 3 -C 7 )-cycloalkyl, CN, NO 2 , R 7 , COR 8 , R 9 and CO 2 R 8 ;

R 5 is (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 or (C 2 -C 6 )-haloalkynyl;

R 6 is (C 2 -C 8 )-alkyl, (C 4 -C 8 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl or aryl-(C 1 -C 6 )-alkyl, which last four mentioned groups are substituted in the alkyl or alkenyl portions, by one or more X-Z radicals; or a saturated heterocyclyl or a saturated heterocyclyl-(C 1 -C 6 )-alkyl radical, which last two mentioned groups are unsubstituted or substituted in the heterocyclyl ring by one or more Z 1 radicals;

Z is H, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkyl-((C 1 -C 6 )-alkoxy-(CH 2 O) r -(aryl-[(C 1 -C 6 )-alkyl] s , R 9 —[(C 1 -C 6 )-alkyl] t , CHO or R 10 —CO;

X is O, NR 11 or S(O) m ; or NR 11 —Z together form a five or six membered saturated ring which optionally contains an additional N, O or S atom and is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and oxo;

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 12 and NR 13 R 14 ;

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

Z 1 is (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxy, R 7 , O(CH 2 ) q R 7 , O-tetrahydropyranyl, OCO(C 1 -C 6 )-alkyl, OCO(CH 2 ) q R 7 , OCO 2 (C 1 -C 6 )-alkyl, OCO 2 CH 2 R 7 , hydroxy, oxo, thioxo, OCO(C 1 -C 6 )-alkyl-OCO(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkyl which last mentioned group is substituted by one or more OCO(C 1 -C 6 )-alkyl or dioxolanyl radicals which dioxolanyl ring is substituted by one or more (C 1 -C 6 )-alkyl radicals; or two adjacent ring C atoms of the heterocyclyl ring portion of R 6 form a benzene or 1,3-dioxolanyl ring unsubstituted or substituted by one or more (C 1 -C 6 )-alkyl radicals; or one ring carbon forms a spiro compound having a cyclopentyl or cyclohexyl ring;

R 9 is a saturated, unsaturated or heteroaromatic heterocyclyl radical 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 , OH and oxo;

R 10 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, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, O(CH 2 ) q R 7 , O(CH 2 ) g (C 3 -C 7 )-cycloalkyl, R 7 or R 9 ; 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 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 12 , CN, NO 2 , OH, R 7 , R 9 , COR 8 , NR 13 R 14 , OR 8 , CO 2 H and CO 2 R 8 ;

R 11 is H or R 10 ; or R 10 , R 11 and the attached N atom form a 5 to 7 membered ring which optionally contains an additional N, O or S atom and is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and oxo;

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

R 13 and R 14 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl or (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl;

m, n, p, q, s and t are each independently 0, 1 or 2;

r is 0, 1, 2 or 3;

each saturated, unsaturated or heteroaromatic 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; each saturated heterocyclyl in the above-mentioned radicals is independently a saturated 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, S and P; and each aryl in the above-mentioned radicals is independently a mono-, bi- or polycyclic aromatic radical; or a pesticidally acceptable salt thereof.

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

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

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

R 1 is CN;

R 2 and R 2a are each Cl;

R 3 is CF 3 ;

R 4 is H or (C 1 -C 6 )-alkyl which last mentioned group is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 3 -C 7 )-cycloalkyl, CN, NO 2 , R 7 , COR 8 , R 9 and CO 2 R 8 ;

R 5 is (C 1 -C 3 )-haloalkyl; and

R 6 is (C 2 -C 8 )-alkyl, (C 4 -C 8 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, which last four mentioned groups are substituted in the alkyl or alkenyl portions by one or two X-Z radicals; or a saturated heterocyclyl or a saturated heterocyclyl-(C 1 -C 6 )-alkyl radical, which last two mentioned groups are unsubstituted or substituted in the heterocyclyl ring by one or two Z 1 radicals.

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

R 1 is CN;

R 2 and R 2a are each Cl;

R 3 and R 5 are each CF 3 :

R 4 is H or (C 1 -C 6 )-alkyl;

R 6 is (C 2 -C 8 )-alkyl, (C 4 -C 8 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, which last four mentioned groups are substituted in the alkyl or alkenyl portions by one or two X-Z radicals; or a saturated heterocyclyl or a saturated heterocyclyl-(CH 2 ) radical, which last two mentioned groups are unsubstituted or substituted in the heterocyclyl ring by one or two Z 1 radicals; and

Z is H, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy-(CH 2 O) r —(C 1 -C 6 )-alkyl, phenyl-[(C 1 -C 6 )-alkyl] s , R 9 —[(C 1 -C 6 )-alkyl] t , CHO or R 10 —CO.

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

wherein the various values are as defined in claim 1 , with an acylating agent of formula (III) or (IV):

R 6 —O—CO-L  (III)

(R 6 —O—CO) 2 —O  (IV)

wherein R 6 is as defined in claim 1 and L is a leaving group, and a base; or

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

R 6 —OH  (V)

wherein R 6 is as defined in claim 1 , in the presence of a base; or

c) where R 6 is (C 2 -C 8 )-alkyl, (C 4 -C 8 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl or aryl-(C 1 -C 6 )-alkyl, which last four mentioned groups are substituted in the alkyl or alkenyl portions by one or more X-Z radicals; or a saturated heterocyclyl or a saturated heterocyclyl-(C 1 -C 6 )-alkyl radical, which last two mentioned groups are unsubstituted or substituted in the heterocyclyl ring by one or more Z 1 radicals;

X is O; Z is R 10 —CO and Z 1 is OCO(C 1 -C 6 )-alkyl, OCO(CH 2 ) q R 7 , OCO 2 (C 1 -C 6 )-alkyl, OCO 2 CH 2 R 7 or OCO(C 1 -C 6 )-alkyl-OCO(C 1 -C 6 )-alkyl, acylating a corresponding compound of formula (II) wherein Z is OH or Z 1 is OH, with a compound of formula (VI), (VII), (VIII), (IX), (X) or (XI):

L 1 -OCO(C 1 -C 6 )-alkyl  (VI)

L 1 -OCO(CH 2 ) q R 7   (VII)

L 1 -OCO 2 (C 1 -C 6 )-alkyl  (VIII)

L 1 -OCO 2 CH 2 R 7   (IX)

L 1 -OCO(C 1 -C 6 )-alkyl-OCO(C 1 -C 6 )-alkyl  (X)

R 10 —CO-L 1   (XI)

wherein R 7 and R 10 are as defined in claim 1 and L 1 is a leaving group, and a base; or

d) where R 6 is (C 2 -C 8 )-alkyl, (C 4 -C 8 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 6 )-alkyl or aryl-(C 1 -C 6 )-alkyl, which last four mentioned groups are substituted in the alkyl or alkenyl portions by two adjacent OH groups; or a saturated heterocyclyl or a saturated heterocyclyl-(C 1 -C 6 )-alkyl radical which groups are unsubstituted or substituted in the heterocyclyl ring by two adjacent OH groups, hydrolyzing a corresponding acetal derivative using a strong acid; or

e) where n is 1 or 2, and R 1 , R 2 , R 2a , R 3 , R 4 , R 5 and R 6 are as defined in claim 1 , oxidizing the corresponding compound in which n is 0 or 1; and

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

7. A pesticidal composition comprising 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.

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

9. The pesticidal composition of claim 7 , wherein the composition further comprises a surface active agent.