Substituted arylpyrazoles

1. A veterinary or agricultural composition comprising a compound of Formula (1),

wherein:

X is CR 8 ;

R 1 is CF 3 , OCF 2 H, OCF 3 , —SCF 3 , —SOCF 3 , —SO 2 CF 3 , or SF 5 ;

R 2 is H, fluoro, or C 1-4 alkyl optionally substituted by 1 to 5 halogen atoms independently selected from chloro and fluoro;

R 3 , R 4 , R 5 , and R 6 are independently selected from hydrogen, chloro, fluoro, and C 1-4 alkyl optionally substituted by 1 to 5 halogen groups independently selected from chloro and fluoro;

R 7 is Cl or fluoro;

R 8 is Cl or fluoro; and

R 9 is NR a R b ;

R a is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 3-8 cycloalkyl, C(O)OC 1-6 alkyl and C 1-6 alkanoyl, wherein each of the above groups may include one or more optional substituents where chemically possible independently selected from halo, phenyl, hydroxy, —C(O)OH, —C(O)O C 1-6 alkyl, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, amino, C 1-6 alkyl amino and di C 1-6 alkyl amino;

R b is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkanoyl and C(O)OC 1-6 alkyl, wherein each of the above groups may include one or more optional substituents where chemically possible independently selected from, halo, phenyl, hydroxy, —COOH, —C(O)O C 1-6 alkyl, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, amino, C 1-6 alkyl amino and di C 1-6 alkyl amino; or a veterinarily, or agriculturally acceptable salt thereof; with the proviso that at least one of R 2 , R 3 , R 4 , R 5 , or R 6 is fluoro, and optionally, a veterinarily or agriculturally acceptable excipient.

2. The composition of claim 1 , wherein R 1 is CF 3 or SF 5 .

3. The composition of claim 2 , wherein R 2 is F, CF 3 or CHF 2 .

4. The composition of claim 3 , wherein R 3 and R 4 are each fluoro and R 5 and R 6 are each hydrogen.

5. The composition of claim 4 , wherein R 2 is CF 3 , R 3 and R 4 both represent fluoro and R 5 and R 6 represent hydrogen.

6. The composition of claim 5 , wherein R 7 and R 8 are both chloro.

7. The composition of claim 6 , wherein R 9 is NH 2 .

8. The composition of claim 1 , further comprising a veterinarily or agriculturally acceptable excipient.

9. The composition of claim 1 , wherein the Formula (1) compound is selected from:

5-amino-1-[2,6-dichloro-4-pentafluorothiophenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,2,2-trifluorocyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(pentafluorocyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-4-(2,2-dichloro-1-fluorocyclopropyl)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-pentafluorothiophenyl]-4-(pentafluorocyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-pentafluorothiophenyl]-4-(1,2,2-trifluorocyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[1-(difluoromethyl)-2,2-difluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(2,2-difluorocyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-pentafluorothiophenyl]-4-[1-(difluoromethyl)-2,2-difluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-4-{1-[chloro(fluoro)methyl]-2,2-difluorocyclopropyl}-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[1-(difluoromethyl)-2,2,3,3-tetrafluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2,3,3-tetrafluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-5-(methylamino)-1H-pyrazole-3-carbonitrile

5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-[1-(difluoromethyl)-2,2,3,3-tetrafluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-[1-(difluoromethyl)-2,2-difluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(fluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrazole-3-carbonitrile;

5-amino-1-{2,6-dichloro-4-[(trifluoromethyl)thio]phenyl}-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

ethyl 3-cyano-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazol-5-ylcarbamate;

2-(dimethylamino)ethyl 3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazol-5-ylcarbamate;

2,2,2-trifluoroethyl 3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazol-5-ylcarbamate;

5-amino-1-{2,6-dichloro-4-[(trifluoromethyl)sulfonyl]phenyl}-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-(difluoromethoxy)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile;

5-amino-1-[2,6-dichloro-4-pentafluorothiophenyl]-4-[1-(difluoromethyl)-2,2,3,3-tetrafluorocyclopropyl]-1H-pyrazole-3-carbonitrile;

Isopropyl 3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazol-5-ylcarbamate; and

5-amino-4-{1-[chloro(difluoro)methyl]-2,2-difluorocyclopropyl}-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile, or a veterinarily, or agriculturally acceptable salt thereof.

10. A method of using a compound of Formula (1),

wherein:

X is CR 8 ;

R 1 is CF 3 , OCF 2 H, OCF 3 , —SCF 3 , —SOCF 3 , —SO 2 CF 3 , or SF 5 ;

R 2 is H, fluoro, or C 1-4 alkyl optionally substituted by 1 to 5 halogen atoms independently selected from chloro and fluoro;

R 3 , R 4 , R 5 , and R 6 are independently selected from hydrogen, chloro, fluoro, and C 1-4 alkyl optionally substituted by 1 to 5 halogen groups independently selected from chloro and fluoro;

R 7 is Cl or fluoro;

R 8 is Cl or fluoro; and

R 9 is NR a R b ;

R a is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 3-8 cycloalkyl, C(O)OC 1-6 alkyl and C 1-6 alkanoyl, wherein each of the above groups may include one or more optional substituents where chemically possible independently selected from halo, phenyl, hydroxy, —C(O)OH, —C(O)OC 1-6 alkyl, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, amino, C 1-6 alkyl amino and di C 1-6 alkyl amino;

R b is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkanoyl and C(O)OC 1-6 alkyl, wherein each of the above groups may include one or more optional substituents where chemically possible independently selected from, halo, phenyl, hydroxy, —COOH, —C(O)O C 1-6 alkyl, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, alkoxy, C 1-6 haloalkoxy, amino, C 1-6 alkyl amino and di C 1-6 alkyl amino; or a veterinarily, or agriculturally acceptable salt thereof; with the proviso that at least one of R 2 , R 3 , R 4 , R 5 , or R 6 is fluoro; for the control of a parasitic infestation in an animal or plant.

11. The method of claim 10 , wherein the control of a parasitic infestation is in an animal.

12. The method of claim 10 , wherein the control of a parasitic infestation is in a plant.

13. The composition of claim 9 wherein the Formula (1) compound is 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile; or a veterinarily, or agriculturally acceptable salt thereof.

14. The method of claim 10 wherein the Formula (1) compound is 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[2,2-difluoro-1-(trifluoromethyl)cyclopropyl]-1H-pyrazole-3-carbonitrile; or a veterinarily, or agriculturally acceptable salt thereof.

15. The method of claim 14 , wherein the control of a parasitic infestation is in an animal.