N-(1-arylpyrazol-4L)sulfonamides and their use as parasiticides

1. A method of treating a parasitic infestation or infection in a non-human animal or plant comprising administration of a therapeutically effective amount of a compound of Formula 1

or a pharmaceutically, veterinarily, or agriculturally acceptable salt thereof, wherein

R 1 is phenyl optionally substituted by one or more groups independently selected from the group consisting of halo, cyano, hydroxy, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 , alkoxy, C 1-6 haloalkoxy, C 1-6 alkanoyl, C 1-6 haloalkanoyl, —S(O) n C 1-6 alkyl, —S(O) n C 1-6 haloalkyl and pentafluorothio;

R 2 is cyano;

R 3 is C 1-6 alkyl, C 1-6 haloalkyl, or —(C 0-3 alkylene)-phenyl;

R 4 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, —(C 0-3 alkylene)-R 7 or —(C 1-3 alkylene)-R 8 ;

or R 3 and R 4 taken together with the nitrogen and sulphur atoms to which they are attached form a 4 to 7-membered ring;

R 5 is hydrogen;

R 6 is C 1-6 alkyl or haloalkyl;

R 7 is C 3-8 cycloalkyl, —S(O) n R 9 , phenyl, het, —CO 2 R 6 or C(O)N(R a )R b ;

R 8 is hydroxy, C 1-6 alkoxy, C 1-6 haloalkoxy, cyano, —N(R a )R b or —O—C(O)R 6 ;

R 9 is C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, —N(R a )R b , phenyl or het;

R a and R b independently represent hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl or C 2-6 haloalkenyl, or R a additionally is —(C 0-3 alkylene)-C 3-8 cycloalkyl, —(C 0-3 alkylene)-phenyl or —(C 0-3 alkylene)-het, or together R a and R b form a 4- to 7-membered ring, optionally substituted by one or more groups independently selected from the group consisting of halo, hydroxy, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy and C 1-6 haloalkoxy;

n is the integer 0, 1 or 2;

where het represents a four- to seven-membered heterocyclic group, which is aromatic or non-aromatic and which contains one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and mixtures thereof;

where both phenyl and het may be optionally substituted, where the valence allows, by one or more substituents independently selected from the group consisting of halo, hydroxy, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkenyl, C 1-6 haloalkenyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 3-8 cycloalkyl, C 1-6 alkanoyl, C 1-6 haloalkanoyl, C 1-6 alkylcarbonyloxy, C 1-6 alkoxycarbonyl and NR a R b ;

where C 3-8 cycloalkyl may be optionally substituted by one or more groups independently selected from the group consisting of halo, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkenyl, C 1-6 haloalkenyl, hydroxy, C 1-6 alkoxy and C 1-6 haloalkoxy; and

where any alkylene or alkenylene group may be optionally substituted by one or more halo.

2. The method of claim 1 wherein R 1 of the Formula (1) compound is a phenyl group which bears chloro substituents at the 2- and 6-positions, and a substitutent at the 4-position selected from the group consisting of trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio and pentafluorothio.

3. The method of claim 2 wherein R 3 is C 1-6 alkyl or C 1-6 haloalkyl.

4. The method of claim 3 wherein R 3 is methyl.

5. The method of claim 4 wherein R 4 is hydrogen, methyl, ethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methylsulfonyl, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, aminosulfonyl, N,N-dimethylaminosulfonyl, methylsulfonymethyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, 1-(trifluoromethyl)cyclopropylmethyl, cyanomethyl, methoxycarbonyl, triazolylethyl, pyrimidin-4-ylmethyl, 1,2,4-oxadiazol-3-ylmethyl, pyrazol-3-ylmethyl, 1-methyl-1H-imidazol-2-yl, 5-methyl-isoaxazol-3-ylmethyl, 2-pyridin-4-ylethyl, aminocarbonylmethyl, benzyl or 4-fluorobenzyl.

6. The method of claim 1 wherein the Formula (1) compound is selected from the group consisting of

N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-1,1,1-trifluoro-N-methylmethanesulfonamide;

N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-N-(methylsulfonyl)methanesulfonamide;

N-{3-cyano-1-[2,6-dichloro-4-pentafluorothiophenyl]-1H-pyrazol-4-yl}-N-(methylsulfonyl)methanesulfonamide;

N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}methanesulfonamide; and

N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-N-(2,2,2-trifluoroethyl)methanesulfonamide;

or a pharmaceutically, veterinarily, or agriculturally acceptable salt thereof.

7. The method of claim 1 , wherein the non-human animal is livestock or companion animals.

8. The method of claim 7 wherein livestock is sheep, pigs, or cattle.

9. The method of claim 7 wherein the companion animal is a cat, dog, or horse.

10. The method of claim 1 , wherein the parasitic infestation or infection in a non-human animal or plant is caused from arthropods, arachnids, nematodes, or helminthes.

11. The method of claim 1 , wherein the compound of Formula (1) is administered orally, topically, or parenterally to the non-human animal.

12. The method of claim 1 , wherein the parasitic infestation or infection is in a plant.

13. The method of claim 1 , further comprising one or more biologically active compounds selected from the group consisting of insecticides, acaricides, anthelmintics, fungicides, nematocides, antiprotozoals, bactericides, growth regulators, entopathogenic bacteria, viruses, and fungi.