Control of arthropods in animals

1. A method of controlling parasites in or on an animal in need of such control, said method comprising orally administering to said animal a parasiticidally effective, substantially non-emetic amount of a 1-arylpyrazole having the formula (XX):

wherein:

R 201 is cyano, C(O)alkyl, C(S)NH 2 , alkyl, C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 202 is S(O) h R 203 ;

R 203 is alkyl or haloalkyl;

R 204 is —N(R 205 )C(O)aryl wherein aryl is thienyl or furyl, each of which is unsubstituted or is substituted by alkoxy, haloalkyl or haloaen;

R 205 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, C 3 -C 5 alkenyl, C 3 -C 5 haloalkenyl, C 3 -C 5 alkynyl, or C 3 -C 5 haloalkynyl;

X 1 is C—R 212 ;

R 211 and R 212 are, independently, halogen, hydrogen, CN or NO 2 ;

R 213 is halogen, haloalkyl, haloalkoxy, —S(O) k CF 3 , or —SF 5 ; and

h and k are, independently, 0, 1, or 2;

or a veterinarily acceptable salt thereof.

2. The method according to claim 1 , wherein R 201 is cyano; R 202 is SCF 3 , S(O)CF 3 or S(O) 2 CF 3 ; R 211 is Cl; X, is C—Cl; R 213 is CF 3 or SF 5 ; and R 205 is CH 3 .

3. The method according to claim 2 , wherein each of thienyl and furyl is unsubstituted or substituted by methoxy, trifluoromethyl or chloro.

4. The method according to claim 3 , wherein aryl is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 5-chloro-2-furyl, 5-trifluoromethyl-2-furyl, 5-methoxy-2-thienyl, or 5-trifluoromethyl-2-thienyl.

5. The method according to claim 4 , wherein R 213 is CF 3 .

6. The method according to claim 5 , wherein:

R 202 is SCF 3 and aryl is 2-furyl.

7. The method according to claim 1 , wherein the animal is a domestic animal.

8. The method according to claim 7 , wherein the domestic animal is a cat or dog.

9. The method according to claim 1 , wherein the compound of formula (XX) is orally administered to the animal in a dosage of from 0.1 to 500 mg/kg.

10. The method according to claim 1 , wherein the compound of formula (XX) is administered at a frequency of from about once per week to about once per year.

11. The method according to claim 9 , wherein the compound of formula (XX) is administered at a frequency of from about once per week to about once per year.

12. A compound having the formula (XX):

wherein:

R 201 is cyano, C(O)alkyl, C(S)NH 2 , alkyl, C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 202 is S(O) h R 203 ;

R 203 is alkyl or haloalkyl;

R 204 is —N(R 205 )C(O)aryl wherein aryl is thienyl or furyl, each of which is unsubstituted or is substituted by alkoxy, haloalkyl or halogen;

R 205 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, C 3 -C 5 alkenyl, C 3 -C 5 haloalkenyl, C 3 -C 5 alkynyl, or C 3 -C 5 haloalkynyl;

X 1 C—R 212 ;

R 211 and R 212 are, independently, halogen, hydrogen, CN or NO 2 ;

R 213 is halogen, haloalkyl, haloalkoxy, —S(O) k CF 3 , or —SF 5 ; and

h and k are, independently, 0, 1 or 2;

or a veterinarily acceptable salt thereof.

13. A compound according to claim 12 , wherein R 201 is cyano; R 202 is SCF 3 , S(O)CF 3 or S(O) 2 CF 3 ; R 211 is Cl; X 1 is C—Cl; R 213 is CF 3 or SF 5 ; and R 205 is CH 3 .

14. A compound according to claim 13 , wherein each of thienyl and furyl is unsubstituted or substituted by methoxy, trifluoromethyl or chloro.

15. A compound according to claim 14 , wherein aryl is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 5-chloro-2-furyl, 5-trifluoromethyl-2-furyl, 5-methoxy-2-thienyl, or 5-trifluoromethyl-2-thienyl.

16. A compound according to claim 15 , wherein R 213 is CF 3 .

17. The compound according to claim 16 , wherein:

R 202 is SCF 3 and aryl is 2-furyl.

18. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound having the formula (XX):

wherein:

R 201 is cyano, C(O)alkyl, C(S)NH 2 , alkyl, C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 202 is S(O) h R 203 ;

R 203 is alkyl or haloalkyl;

R 204 is —N(R 205 )C(O)aryl wherein aryl is thienyl or furyl, each of which is unsubstituted or is substituted by alkoxy, haloalkyl or halogen;

R 205 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, C 3 -C 5 alkenyl, C 3 -C 5 haloalkenyl, C 3 -C 5 alkynyl, or C 3 -C 5 haloalkynyl;

X 1 is C—R 212 ;

R 211 and R 212 are, independently, halogen, hydrogen, CN or NO 2 ;

R 213 is halogen, haloalkyl, haloalkoxy, —S(O) k CF 3 , or —SF 5 ; and

h and k are, independently, 0, 1, or 2;

or a veterinarily acceptable salt thereof;

and a veterinarily acceptable carrier therefor.

19. A veterinary composition according to claim 18 comprising, in oral unit dosage form:

(a) a parasiticidally effective, substantially non-emetic amount of a compound having the formula (XX) as defined in claim 18 , or a veterinarily acceptable salt thereof; and

(b) a veterinarily acceptable carrier therefor.

20. A veterinary composition according to claim 19 , wherein the oral unit dosage amount of the compound of formula (XX) is from 0.1 to 500 mg per kg of animal body weight.

21. A compound having the formula (XX):

wherein:

R 201 is cyano;

R 202 is S(O) h R 203 ;

R 203 is alkyl or haloalkyl;

R 204 is —N(R 205 )C(O)aryl wherein aryl is thienyl or furyl each of which is unsubstituted or substituted by alkoxy, haloalkyl or halogen;

R 205 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, C 3 -C 5 alkenyl, C 3 -C 5 haloalkenyl, C 3 -C 5 alkynyl, or C 3 -C 5 haloalkynyl;

X 1 is C—R 212 ;

R 211 and R 212 are, independently, halogen, hydrogen, CN or NO 2 ;

R 213 is halogen, haloalkyl, haloalkoxy, —S(O) k CF 3 , or —SF 5 ; and

h and k are, independently, 0, 1 or 2;

or a veterinarily acceptable salt thereof.

22. A compound according to claim 21 , wherein R 203 is haloalkyl.

23. A compound according to claim 21 , wherein R 211 and R 212 are, independently, halogen.

24. A compound according to claim 21 , wherein R 213 is haloalkyl, haloalkoxy or —SF 5 .

25. A compound according to claim 21 , wherein R 205 is C 1 -C 4 alkyl.

26. A compound according to claim 21 , wherein h is 0 or 1.

27. A compound according to claim 21 , wherein aryl is thienyl, which is unsubstituted or substituted by alkoxy, haloalkyl or halogen.

28. A compound according to claim 14 , wherein aryl is thienyl, which is unsubstituted or substituted by methoxy, trifluoromethyl or chloro.

29. A compound according to claim 28 , wherein aryl is 2-thienyl, 3-thienyl, 5-methoxy-2-thienyl, or 5-trifluoromethyl-2-thienyl.

30. A compound according claim 29 , wherein R 213 is CF 3 .

31. The compound according to claim 15 , wherein:

(a) R 202 is S(O)CF 3 and aryl is 2-thienyl;

(b) R 202 is S(O)CF 3 and aryl is 3-thienyl;

(c) R 202 is S(O)CF 3 and aryl is 2-furyl;

(d) R 202 is S(O)CF 3 and aryl is 3-furyl;

(e) R 202 is S(O)CF 3 and aryl is 5-chloro-2-furyl;

(f) R 202 is S(O)CF 3 and aryl is 5-trifluoromethyl-2-furyl;

(g) R 202 is S(O)CF 3 and aryl is 5-methoxy-2-thienyl; or

(h) R 202 is S(O)CF 3 and aryl is 5-trifluoromethyl-2-thienyl.

32. The compound according to claim 31 , wherein:

R 202 is S(O)CF 3 and aryl is 2-thienyl.

33. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound according to claim 21 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

34. A veterinary composition according to claim 33 comprising, in oral unit dosage form:

(a) a parasiticidally effective, substantially non-emetic amount of a compound according to claim 33 , or a veterinarily acceptable salt thereof; and

(b) a veterinarily acceptable carrier therefor.

35. A veterinary composition according to claim 34 , wherein the oral unit dosage amount of the compound of formula (XX) is from 0.1 to 500 mg per kg of animal body weight.

36. A method of controlling parasites in or on an animal in need of such control, said method comprising orally administering to said animal a parasiticidally effective, substantially non-emetic amount of a compound according to claim 21 or a veterinarily acceptable salt thereof.

37. The method according to claim 36 , wherein the animal is a domestic animal.

38. The method according to claim 37 , wherein the domestic animal is a cat or dog.

39. The method according to claim 36 , wherein the compound is orally administered to the animal in a dosage of from 0.1 to 500 mg/kg.

40. The method according to claim 36 , wherein the compound is administered at a frequency of from about once per week to about once per year.

41. The method according to claim 39 , wherein the compound is administered at a frequency of from about once per week to about once per year.