Pesticidal bis-organosulfur compounds

1. A bis-organo sulfur compound of formula (I):

or a veterinarily or agriculturally acceptable salt thereof, wherein:

m=0, 1, 2;

n=0, 1, 2;

p=1, 2 or 3;

q=0, 1, 2, 3 or 4;

R 1 is C 1 -C 12 -haloalkyl, haloalkenyl, haloalkynyl; or

R 1 is aryl, aralkyl, heteroaryl, or heterocyclyl each of which is substituted by one or more R 10 ;

R 2 is cyano, or —C=(G)-R 9

R 3 is hydrogen, halogen, alkyl, or haloalkyl

R 4 is haloalkyl, haloalkenyl, haloalkynyl, or aralkyl, which is substituted by one or more halogen atoms; all of which may be further substituted by one or more R 10 , or

R 4 is aryl or a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur,

wherein aryl, the heterocyclic ring, or the heteroaromatic ring may be fused to another aryl ring or a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur;

and wherein the aryl, heteroaryl or heterocyclic rings or the respective fused ring systems may be unsubstituted or substituted by any combination of 1 to 6 R 10 groups;

R 5 , R 6 , R 7 and R 8 are independently from each other hydrogen, halogen, alkyl, or haloalkyl;

R 9 is alkyl, hydroxy, amino, alkoxy, aryloxy, alkylamino, or dialkylamino, the latter four optionally substituted with halogen;

G is Oxygen or Sulfur; and

R 10 =halogen, cyano, nitro, hydroxy, mercapto, amino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, halocycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, cycloalkenyloxy, halocycloalkoxy, halocycloalkenyloxy, alkylthio, haloalkylthio, cycloalkylthio, halocycloalkylthio, alkylsulfinyl, alkenylsulfinyl, alkynyl-sulfinyl, haloalkylsulfinyl, haloalkenylsulfinyl, haloalkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, haloalkyl-sulfonyl, halo alkenylsulfonyl, haloalkynylsulfonyl, alkylamino, alkenylamino, alkynylamino, di(alkyl)amino, di(alkenyl)-amino, di(alkynyl)amino, or trialkylsilyl;

with the proviso that at least one group from R 2 , R 3 , R 4 , R 5 and R 6 is not hydrogen, alkyl or haloalkyl.

2. The compound of claim 1 , wherein n is 0, m is 2, and q is 1.

3. The compound of claim 1 , wherein:

R 1 is haloalkyl, haloalkenyl or haloalkynyl;

R 4 haloalkyl, haloalkenyl or haloalkynyl; and

p and q are independently 1 or 2.

4. The compound of claim 1 , wherein:

R 1 is haloalkyl, haloalkenyl or haloalkynyl;

R 4 is selected from

wherein r is 0, 1, 2 or 3,

R 11 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, or C 3 -C 6 halocycloalkenyl and

R 12 halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 halocycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy, C 3 -C 6 halocycloalkoxy, C 3 -C 6 halocycloalkenyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 6 cycloalkylthio, C 3 -C 6 halocycloalkylthio or trialkylsilyl which may be substituted with one or more substituents selected from halogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl or C 3 -C 6 halocycloalkyl and

p and q are independently 1 or 2.

5. The compound of claim 1 , wherein:

R 1 is C 1 -C 6 -haloalkyl;

R 4 haloalkyl;

R 2 is cyano or —C=(G)-R 9 ;

m is 1 or 2;

n is 0;

G is oxygen or sulfur; and

R 9′ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, amino, C 1 -C 6 alkylamino, or C 1 -C 6 dialkylamino and p and q are independently 1 or 2.

6. The compound of claim 1 , wherein the compound has the formula (II):

wherein:

m=0, 1 or 2;

n=0, 1 or 2;

p=1 or 2;

R 1′ is C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl; or aryl, aralkyl, heteroaryl, each of which is substituted by one or more halogen atoms; all of which may be further substituted by one or more substituents;

R 2′ is cyano, or —C=(G)-R 7′

R 3′ is hydrogen, halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl

R 4′ is C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkenyl, or C 1 -C 6 -haloalkynyl, each of which is partially or fully halogenated, and which may be further substituted by one or more other substituents; or

R 4′ is aryl or a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur,

wherein aryl, the heterocyclic ring, or the heteroaromatic ring may be fused to another aryl ring or a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulphur;

aryl, heteroaryl or the respective fused ring systems may be unsubstituted or substituted by any combination of 1 to 6 groups

R 5′ and R 6′ are independently from each other hydrogen, halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;

R 7′ is C 1 -C 6 alkyl, hydroxy, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, or C 1 -C 6 -dialkylamino, the latter three optionally substituted with halogen;

G is Oxygen or Sulfur; and

R 8′ =halogen, cyano, nitro, hydroxy, mercapto, amino, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 — alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 — haloalkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -halocycloalkenyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, C 3 -C 6 -halocycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 2 -C 6 -alkenylsulfinyl, C 2 -C 6 -alkynyl-sulfinyl, C 1 -C 6 — haloalkylsulfinyl, C 2 -C 6 -haloalkenylsulfinyl, C 2 -C 6 -haloalkynylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 2 -C 6 -alkenylsulfonyl, C 2 -C 6 -alkynylsulfonyl, C 1 -C 6 -haloalkyl-sulfonyl, C 2 -C 6 -haloalkenylsulfonyl, C 2 -C 6 -haloalkynylsulfonyl, C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -di(alkyl)amino, di(C 2 -C 6 -alkenyl)-amino, di(C 2 -C 6 -alkynyl)amino, or tri(C 1 -C 10 )alkylsilyl.

7. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano or —C=(G)-R 7′ ;

R 3′ is hydrogen, halogen, C 1 -C 6 -alkyl;

R 4′ is C 1 -C 6 -haloalkyl;

G is oxygen or sulfur; and

R 7′ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, amino, C 1 -C 6 alkylamino, or C 1 -C 6 dialkylamino.

8. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano or —C=(G)-R 7′ ;

R 3′ is hydrogen, halogen, C 1 -C 6 -alkyl;

R 4′ is phenyl, which may be substituted with one or more halogen atoms, alkyl groups or haloalkyl groups;

G is oxygen or sulfur; and

R 7′ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, amino, C 1 -C 6 alkylamino, or C 1 -C 6 dialkylamino.

9. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano or —C=(G)-R 7′ ;

R 3′ is hydrogen, halogen, C 1 -C 6 -alkyl;

R 4′ is selected from

wherein r is 0, 1 or 2 or 3

R 9′ is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, or C 3 -C 6 halocycloalkenyl and

R 10′ is halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 halocycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy, C 3 -C 6 halocycloalkoxy, C 3 -C 6 halocycloalkenyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 6 cycloalkylthio, C 3 -C 6 halocycloalkylthio or trialkylsilyl which may be substituted with one or more substituents selected from halogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl or C 3 -C 6 halocycloalkyl;

G is oxygen or sulfur; and

R 7′ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, amino, C 1 -C 6 alkylamino, or C 1 -C 6 dialkylamino.

10. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano;

R 3′ is hydrogen or C 1 -C 6 -alkyl;

R 4′ is C 1 -C 6 -haloalkyl; and

R 5′ and R 6′ are hydrogen.

11. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano;

R 3′ is hydrogen or C 1 -C 6 -alkyl;

R 4′ is phenyl, which may be substituted with one or more halogen atoms, alkyl or haloalkyl groups; and

R 5′ and R 6′ are hydrogen.

12. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 haloalkyl;

R 2′ is cyano;

R 3′ is hydrogen or C 1 -C 6 -alkyl;

R 4′ is selected from

wherein r is 1 or 2

R 9′ is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, or C 3 -C 6 halocycloalkenyl; and

R 10′ halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 halocycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy, C 3 -C 6 halocycloalkoxy, C 3 -C 6 halocycloalkenyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 6 cycloalkylthio, C 3 -C 6 halocycloalkylthio or trialkylsilyl which may be substituted with one or more substituents selected from halogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl or C 3 -C 6 halocycloalkyl

R 5′ and R 6′ are hydrogen.

13. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 fluoroalkyl;

R 2′ is cyano;

R 3′ is hydrogen, methyl or trifluoromethyl;

R 4′ is C 1 -C 6 -haloalkyl; and

R 5′ and R 6′ are hydrogen.

14. The compound of claim 6 , wherein:

R 1′ is C 1 -C 6 fluoroalkyl;

R 2′ is —C=(G)-R 7′ ;

R 3′ is hydrogen, methyl or trifluoromethyl;

R 4′ is C 1 -C 6 -haloalkyl;

G is oxygen or sulfur; and

R 7′ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, amino, C 1 -C 6 alkylamino, or C 1 -C 6 dialkylamino.

15. An agricultural or veterinary composition comprising a pesticidally effective amount or a parasiticidally effective amount of the compound of claim 1 , or a veterinarily or agriculturally acceptable salt thereof, in combination with a veterinarily or agriculturally acceptable carrier or diluent.

16. The veterinary composition of claim 15 , wherein the composition is suitable for oral, injectable or topical administration.

17. The veterinary composition of claim 16 , wherein the composition is a spot-on or pour-on composition.

18. A method for controlling a parasitic infestation in or on an animal, comprising administering a parasiticidally effective amount of a compound of claim 1 to the animal.

19. The method of claim 18 , wherein the parasite is an endoparasite.

20. The method of claim 18 , wherein the parasite is an ectoparasite.

21. A method for controlling infestation of animal pests at a locus, comprising administering a pesticidally effective amount or a parasiticidally effective amount of a compound of claim 1 to the locus.

22. A method for combating or controlling animal pests, comprising contacting the animal pests with a pesticidally effective amount of a compound of claim 1 .

23. A method for protecting crops and growing plants from attack or infestation by animal pests, comprising contacting a plant, or soil or water in which the plant is growing, with a compound of claim 1 .

24. A method for protecting plant propagation material from attack or infestation by animal pests, comprising contacting a plant, or soil or water in which the plant is growing, with a compound of claim 1 .

25. A seed comprising a compound of claim 1 or 6 or an agriculturally useful salt thereof.

26. The seed of claim 25 , wherein the compound of claim 1 or 6 or the agriculturally useful salt thereof is present in an amount of from 0.1 g to 10 kg per 100 kg of seed.