Pesticidal N-phenylpyrazole derivatives

1. A compound of formula (I):

wherein:

R 1 is CN;

R 2 is halogen;

W is N or C-halogen;

R 3 is CF 3 , OCF 3 or SF 5 ;

R 4 is H, CO 2 —(C 1 -C 6 )-alkyl, CO 2 —(C 1 -C 6 )-haloalkyl, CO 2 —(C 3 -C 6 )-alkenyl, CO 2 —(C 2 -C 6 )-alkynyl, CO 2 —(CH 2 ) m R 8 , (CH 2 ) q R 8 , COR 9 , (CH 2 ) q R 10 or SO 2 R 11 ; or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or CO—(C 1 -C 6 )-alkyl, which last 4 mentioned groups are unsubstituted or substituted by one or more R 12 radicals; or (C 3 -C 6 )-cycloalkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;

R 5 and R 5a are each independently hydrogen; (C 1 -C 4 )-alkyl or (CH 2 ) q R 8 ;

R 6 and R 7 are each independently (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl or (CH 2 ) q R 8 ; or

R 6 and R 7 together with the connecting X—C—Y moiety form a ring of formula (A-1), (A-2), (A-3), (A-4) or (A-5):

R a , R b , R c , R d , R e and R f are each independently selected from the group consisting of H, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, R 8 and CH 2 OR 8 ; or CR e R f together formula C═O or C═CH 2 radical;

R g , R h , R i and R j are each independently selected from the group consisting of H, halogen and (C 1 -C 6 )-alkyl;

X and Y are each independently O or S(O) t ;

R 8 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 , OH, S(O) p R 13 and NR 14 R 15 ;

R 9 and R 9a are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, (CH 2 ) q R 8 or (CH 2 ) q R 10 ;

R 10 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, (C 1 -C 4 )-haloalkoxy, NO 2 , CN, CO 2 —(C 1 -C 6 )-alkyl, S(O) p R 13 OH and oxo;

R 11 is (C 3 -C 6 )-cycloalkyl (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (CH 2 ) q R 8 or (CH 2 ) q R 10 ; or is (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more R 12 radicals;

R 12 is 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 16 , CN, NO 2 , OH, COR 13 , NR 9 R 14 , NR 9 COR 14 , NR 9 SO 2 R 18 , CONR 9 R 14 , SO 2 NR 9 R 14 , OR 8 , OR 10 , ONR 9 R 9a or CO 2 R 13 ;

R 13 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;

R 14 and R 15 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl; or

R 14 and R 15 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, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy and oxo;

R 16 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or R 8 ;

V is H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (CH 2 ) q R 8 , COR 13 , CO 2 —(C 1 -C 6 )-alkyl, S(O) p R 13 or S(O) p R 8 ;

Q is (C 1 -C 6 )-alkyl or CH 2 R 8 ;

S is 1, 2 or 3;

m, q and u are each independently 0 or 1;

n, p, r and t are each independently 0, 1 or 2; 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 W is C—Cl.

3. A compound or a salt thereof as claimed in claim 1 wherein R 4 is (C 1 -C 3 )-alkyl.

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

R 1 is CN;

R 2 is Cl;

W is C—Cl;

R 3 is CF 3 ;

R 4 is H, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, CO 2 —(C 1 -C 3 )-alkyl, CO 2 —(C 3 -C 6 )-alkenyl, CO 2 —(C 3 -C 6 )-alkynyl, CO 2 (CH 2 )mR 8 , (CH 2 ) q R 8 , COR 9 , (CH 2 ) q R 10 or SO 2 R 11 ; or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-alkenyl or CO—(C 1 -C 6 )alkyl, which last 3 mentioned groups are unsubstituted or substituted by one or more R 12 radicals,

R 5 and R 5a are each independently H or (C 1 -C 3 )alkyl;

R 6 and R 7 are each independently (C 1 -C 3 )-alkyl; or

R 5 and R 7 together with the connecting X—C—Y moiety form a ring of formula (A-1), wherein u is 0 or 1 and R a , R b , R c , R d , R e and R f are each H; or

R 6 and R 7 together with the connecting X—C—Y moiety form a ring of formula (A-2) or (A-4), wherein R g , R h , R i and R j are each H;

R 8 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, NO 2 , OH, S(O) p —(C 1 -C 3 )-alkyl, S(O) p —(C 1 -C 3 )-haloalkyl and NR 14 R 15 , wherein R 14 and R 15 are each independently H or (C 1 -C 3 )-alkyl;

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

R 10 is heterocyclyl 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, NO 2 , CN, CO 2 (C 1 -C 3 )-alkyl, S(O) p —(C 1 -C 3 )-alkyl, OH and oxo;

R 11 is (C 3 -C 7 )-cycloalkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-haloalkenyl, (C 3 -C 4 )-alkynyl, (C 3 -C 4 )-haloalkynyl, (CH 2 )qR 8 or (CH 2 )qR 10 ; or is (C 1 -C 3 )-alkyl unsubstituted or substituted by one or more R 12 radicals;

R 12 is halogen, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O)pR 16 , CN, NO 2 , OH, COR 13 , NR 9 R 14 , OR 8 or CO 2 R 13 , wherein R 3 and R 16 are each independently (C 1 -C 3 )-alkyl, and R 9 and R 14 are each independently H or (C 1 -C 3 )alkyl; and

s is 1 or 2.

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) where: R 1 is CN, and the other values are as defined in claim 1 , reacting a compound of formula (II)

wherein R 1 is CN, L is a leaving group, and the other values are as defined above, with a compound of formula (III):

wherein the various values are as defined in claim 1 ; or

b) where R 1 is CN, and the other values are as defined in claim 1 , reacting a compound of formula (IV):

wherein R 1 is CN, and the other values are as defined in claim 1 , with a compound of formula (V):

wherein L 1 is a leaving group, and the other values are as defined in claim 1 ; or

c) where R 1 is CN, R 4 is (CH 2 ) q R 8 or (CH 2 ) q R 10 and q is 1; or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl, which last 3 mentioned groups are unsubstituted or substituted by one or more R 12 radicals; or (C 3 -C 6 )-cycloalkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl; and the other values are as defined in claim 1 , reacting the corresponding compound of formula (I) wherein R 4 is H, with a compound of formula (VI):

R 4 -L 2   (VI).

wherein R 4 is as defined in claim 1 and L 2 is a leaving group; or

d) where R 1 is CN, X and Y are each O, and the other values are as defined in claim 1 , reacting a compound of formula (VII):

wherein R 1 is CN, and the other values are as defined in claim 1 , with a compound of formula (VIII) or (IX):

R 6 O—H  (VIII)

R 7 O—H  (IX)

wherein R 6 and R 7 are as defined in claim 1 ; or

e) where R 1 is CN, X and Y are each S, and the other values are as defined in claim 1 , reacting a compound of formula (VII) as defined in claim 1 , with a compound of formula (X) or (XI):

R 6 S—H  (X)

R 7 S—H  (XI)

wherein R 6 and R 7 are as defined in claim 1 , in the presence of a halogenating agent; or

f) where R 1 is CN, X and Y are each S, and the other values are as defined in claim 1 , reacting a compound of formula (VII) as defined in claim 1 , with a compound of formula (XII) or (XIII):

R 6 S—SR 6   (XII)

R 7 S—SR 7   (XIII)

wherein R 6 and R 7 are as defined in claim 1 , in the presence of a trialkylphosphine; or

g) where R 1 is CN, X is O and Y is S, or X is S and Y is O, and the other values are as defined in claim 1 , reacting a compound of formula (VII) as defined in claim 1 , with equimolar amounts of compounds of formula (VIII) and (XI), or in the case of a cyclic hemithioacetal with the corresponding hydroxyalkanethiol compound, in the presence of a catalyst; or

Q-L 3   (XIV)

Q 3 O + BF4  (XV)

V-L 4   (XVI)

l) where R 1 is CN, n or t is 1 or 2 and the other values are as defined in claim 1 , oxidising the corresponding compound in which n or t is 0 or 1; and

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

6. 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 and/or surface active agent.

7. A method for the control of parasites on an animal comprising the step of administering an effective amount of a compound of formula (I) or a salt thereof according to claim 1 to the animal.

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