Malononitrile compounds

1. A method of protecting growing plants from attack or infestation by pests by applying to the plants, or to the soil or water in which they are growing, a pesticidally effective amount of a compound of formula (I),

wherein

A is D-X—R 1 or Q;

X is, independently, oxygen or S(═O) n ;

n is 0, 1 or 2;

R 1 is, independently, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl or C 3 -C 10 -halocycloalkenyl,

phenyl or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which heteroaromatic ring is bonded to the X atom via a carbon atom of the ring, and which phenyl or which heteroaromatic ring may be bonded via a C 1 -C 10 -alkyl group thus forming an aryl-C 1 -C 10 -alkyl or hetaryl-C 1 -C 10 -alkyl moiety,

wherein phenyl or the heteroaromatic ring may be fused to a ring selected from phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur,

wherein the hydrogen atoms in the above groups R 1 may be partially or in total be replaced by any combination of groups R 2 ;

D is, independently, a saturated or partially unsaturated hydrocarbon chain with one to 5 carbon chain atoms or C 3 -C 6 -cycloalkyl, wherein the hydrogen atoms of this chain or of this cycloalkyl may all or in part be replaced with any combination of groups selected from R 3 ;

R 2 is halogen, cyano, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl or which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom, or

two groups R 2 together with the carbon atom of the hydrocarbon chain may form a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen,

wherein the above groups R 2 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a ;

R 3 is halogen, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkenyloxycarbonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl and which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom,

wherein the above groups R 3 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a , or

the moiety R 3 -D-X—R 1 together may form a saturated or unsaturated ring of formula α

 which may have 5 to 7 ring members and besides X, 1 to 2 further heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which ring may be substituted with 1 to 5 groups selected from R a ,

R a is each independently halogen, cyano, nitro, 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 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, phenoxy, OR i , SR i , S(═O)R i , S(═O) 2 R i , NR i R j , —S(═O) 2 NR i R, C(═O)R i , C(═O)OR i , C(═O)NR i R j , C(═NOR i )R j , —NR i C(=G)R j , —N[C(=G)R i ]2, —NR i C(=G)OR j , —C(=G)NR i —NR j 2 , —NR i SO 2 R j , SiR i y R j 3-y (y is 0 to 3), or

phenyl or a 5- to 6-membered heteroaromatic ring which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the carbon atoms in phenyl or in the heteroaromatic ring may be substituted with 1 to 5 halogens;

with the proviso that if X is oxygen, then R 3 is selected from the group consisting of halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl and tri(C 1 -C 10 )alkylsilyl;

G is oxygen or sulfur;

R i , R j are each independently hydrogen, 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 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, or C 3 -C 6 -halocycloalkenyl; and

Q is C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 2 -C 7 -alkynyl, C 2 -C 7 -haloalkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 5 -alkyl, or C 3 -C 7 -halocycloalkyl-C 1 -C 5 -alkyl,

wherein each group is unsubstituted or substituted with one or more, groups C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl or tri(C 1 -C 10 )alkylsilyl;

and the enantiomers, diastereomers, salts, and N-oxides thereof.

2. The method of claim 1 wherein A in formula (I) is Q.

3. The method of claim 1 wherein A in formula (I) is D-X—R 1 .

4. The method of claim 1 ,

wherein in formula (I)

A is Q;

X is S(═O) n ;

n is 0, 1 or 2;

R 1 is C 1 -C 10 -alkyl or C 1 -C 10 -haloalkyl;

D is a saturated hydrocarbon chain with one to 5 carbon chain atoms; and

Q is C 1 -C 12 -alkyl or C 1 -C 12 -haloalkyl.

5. The method of claim 1 ,

wherein in formula (I)

A is Q;

X is S(═O) n ;

n is 0, 1 or 2;

R 1 is C 1 -C 6 -haloalkyl;

D is a saturated hydrocarbon chain with one to 3 carbon chain atoms; and

Q is C 1 -C 12 -fluoroalkyl.

6. A process for the preparation of a compound of formula (I)

wherein

A is D-X—R 1 or Q;

X is, independently, oxygen or S(═O) n ;

n is 0, 1 or 2;

R 1 is, independently, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl or C 3 -C 10 -halocycloalkenyl,

phenyl or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which heteroaromatic ring is bonded to the X atom via a carbon atom of the ring, and which phenyl or which heteroaromatic ring may be bonded via a C 1 -C 10 -alkyl group thus forming an aryl-C 1 -C 10 -alkyl or hetaryl-C 1 -C 10 -alkyl moiety,

wherein phenyl or the heteroaromatic ring may be fused to a ring selected from phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur,

wherein the hydrogen atoms in the above groups R 1 may be partially or in total be replaced by any combination of groups R 2 ;

D is, independently, a saturated or partially unsaturated hydrocarbon chain with one to 5 carbon chain atoms or C 3 -C 6 -cycloalkyl, wherein the hydrogen atoms of this chain or of this cycloalkyl may all or in part be replaced with any combination of groups selected from R 3 ;

R 2 is halogen, cyano, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl or which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom, or

two groups R 2 together with the carbon atom of the hydrocarbon chain may form a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen,

wherein the above groups R 2 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a ;

R 3 is halogen, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkenyloxycarbonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl and which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom,

wherein the above groups R 3 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a , or

the moiety R 3 -D-X—R 1 together may form a saturated or unsaturated ring of formula α

which may have 5 to 7 ring members and besides X, 1 to 2 further heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which ring may be substituted with 1 to 5 groups selected from R a ,

R a is each independently halogen, cyano, nitro, 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 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, phenoxy, OR i , SR i , S(═O)R i , S(═O) 2 R i , NR i R j , —S(═O) 2 NR, C(═O)R i , C(═O)OR i , C(═O)NR i R j , C(═NOR i )R j , —NR i C(=G)R j , —N[C(=G)R i ]2, —NR i C(=G)OR j , —C(=G)NR i —NR j 2 , —NR i SO 2 R j , SiR i y R j 3-y (y is 0 to 3), or

phenyl or a 5- to 6-membered heteroaromatic ring which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the carbon atoms in phenyl or in the heteroaromatic ring may be substituted with 1 to 5 halogens;

with the proviso that if X is oxygen, then R 3 is selected from the group consisting of halogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl and tri(C 1 -C 10 )alkylsilyl;

G is oxygen or sulfur;

R i , R j are each independently hydrogen, 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 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, or C 3 -C 6 -halocycloalkenyl; and

Q is C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 2 -C 7 -alkynyl, C 2 -C 7 -haloalkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 5 -alkyl, or C 3 -C 7 -halocycloalkyl-C 1 -C 8 -alkyl,

wherein each group is unsubstituted or substituted with one or more, groups C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl or tri(C 1 -C 10 )alkylsilyl;

which comprises reacting a compound (II) with a compound (III) in the presence of a base to give compound (I),

wherein Z 1 represents a suitable leaving group.

7. The process of claim 6 , wherein two equivalents of a compound (III) are reacted with malononitrile in the presence of a base:

wherein D, X, R 1 are defined as in claim 5 and Z 1 is a suitable leaving group.

8. A compound of formula (I),

wherein

A is D-X—R 1 or Q;

n is 0, 1 or 2;

R 1 is, independently, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -halocycloalkyl, C 3 -C 10 -cycloalkenyl or C 3 -C 10 -halocycloalkenyl,

phenyl or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which heteroaromatic ring is bonded to the X atom via a carbon atom of the ring, and which phenyl or which heteroaromatic ring may be bonded via a C 1 -C 10 -alkyl group thus forming an aryl-C 1 -C 10 -alkyl or hetaryl-C 1 -C 10 -alkyl moiety,

wherein phenyl or the heteroaromatic ring may be fused to a ring selected from phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur,

wherein the hydrogen atoms in the above groups R 1 may be partially or in total be replaced by any combination of groups R 2 ;

D is, independently, a saturated or partially unsaturated hydrocarbon chain with one to 5 carbon chain atoms or C 3 -C 6 -cycloalkyl, wherein the hydrogen atoms of this chain or of this cycloalkyl may all or in part be replaced with any combination of groups selected from R 3 ;

R 2 is halogen, cyano, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl or which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom, or

two groups R 2 together with the carbon atom of the hydrocarbon chain may form a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen,

wherein the above groups R 2 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a ;

R 3 is halogen, amino, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkenyloxycarbonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, tri(C 1 -C 10 )alkylsilyl, or

phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which contains 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring system which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl and which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom,

wherein the above groups R 3 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from R a , or

the moiety R 3 -D-X—R 1 together may form a saturated or unsaturated ring of formula α

which may have 5 to 7 ring members and besides X, 1 to 2 further heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which ring may be substituted with 1 to 5 groups selected from R a ,

R a is each independently halogen, cyano, nitro, 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 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, phenoxy, OR i , SR i , S(═O)R i , S(═O) 2 R i , NR i R j , —S(═O) 2 NR i R, C(═O)R i , C(═O)OR i , C(═O)NR i R j , C(═NOR i )R j , —NR i C(=G)R j , —N[C(=G)R i ]2, —NR i C(=G)OR j , —C(=G)NR i —NR j 2 , —NR i SO 2 R j , SiR i y R j 3-y (y is 0 to 3), or

phenyl or a 5- to 6-membered heteroaromatic ring which contains 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the carbon atoms in phenyl or in the heteroaromatic ring may be substituted with 1 to 5 halogens;

with the proviso that if X is oxygen, then R 3 is selected from the group consisting of halogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl and tri(C 1 -C 10 )alkylsilyl;

G is oxygen or sulfur;

R i , R j are each independently hydrogen, 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 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, or C 3 -C 6 -halocycloalkenyl; and

Q is C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 2 -C 7 -alkynyl, C 2 -C 7 -haloalkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 5 -alkyl, or C 3 -C 7 -halocycloalkyl-C 1 -C 5 -alkyl,

wherein each group is unsubstituted or substituted with one or more, groups C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl or tri(C 1 -C 10 )alkylsilyl;

X is S(═O) n ,

with the proviso that the following compounds are excluded:

(CN) 2 C(CH 2 —CH 2 —SO 2 —CF 3 ) 2 and CF 3 —CH(CF 3 )—C(CN) 2 —CH(C 6 H 5 )—S—CH 3 .

9. A method of protecting growing plants from attack or infestation by pests by applying to the plants, or to the soil or water in which they are growing, a pesticidally effective amount of a compound of claim 8 .

10. A method for treating or protecting animals against infestation or infection by parasitical pests which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) as defined in claim 8 or their or veterinarily acceptable salts.

11. A process for the preparation of a composition for treating or protecting animals against infestation or infection by parasitical pests which comprises mixing a parasiticidally effective amount of a compound of formula (I) as defined in claim 8 or a veterinarily acceptable salt thereof, with a veterinarity acceptable carrier.

12. A composition comprising a pesticidally active amount of a compound of claim 8 and an agronomically or veterinarily acceptable carrier.

13. A mixture comprising a compound of claim 8 and a pesticide selected from the organo(thio)phosphates, carbamates, pyrethroids, growth regulators, neonicotinoids, nicotinic receptor agonists/antagonists compounds, GABA antagonist compounds, macrocyclic lactone insecticides, METI I acaricides, METI II and III compounds, oxidative phosphorylation inhibitor compounds, moulting disruptor compounds, mixed function oxidase inhibitor compound, sodium channel blocker compounds, benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-ααα-tri-fluoro-p-tolyl)hydrazone or N—R′-2,2-di(R″′)propionamide-2-(2,6-dichloro-ααα-trifluoro-p-tolyl)-hydrazone, wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is hydrogen or methyl and R″′ is methyl or ethyl, and anthranilamide compounds of formula Γ 3

wherein B 1 is hydrogen, chlorine or cyano, B 2 is a bromine atom or CF 3 , and R B is H, CH 3 or CH(CH 3 ) 2 .

14. A veterinary medicament comprising a compound of claim 8 or a veterinarily acceptable salt thereof.