1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof

A topical veterinary formulation for treating or preventing a parasitic infestation or infection in an animal comprising:

• (a) a 1-aryl-5-alkyl or 5-haloalkylpyrazole of formula (I):
• wherein:
• R1 is hydrogen, cyano, halogen, R8, formyl, —C(O)R8, —C(O)OR8, —C(O)NR9R10, or —C(S)NH2;
• R2 is R8 or —S(O)mR11;
• R3 is methyl, ethyl or C1-C4 haloalkyl;
• R4, R5 and R7 are independently hydrogen, halogen, alkyl, haloalkyl, cyano or nitro;
• R6 is halogen, alkyl, haloalkyl, alkoxy, haloalkyloxy, cyano, nitro, —C(O)R12, —S(O)nR12 or SF5;
• Z is a nitrogen atom or C—R13;
• R8 is alkyl, haloalkyl, cycloalkyl or halocycloalkyl;
• R9 is hydrogen, alkyl, haloalkyl or alkoxy;
• R10 is hydrogen, alkyl, haloalkyl or alkoxy;
• R11 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl or cycloalkyl;
• R12 is alkyl or haloalkyl;
• R13 is hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;
• m is 0, 1 or 2;
• and
• n is 0, 1 or 2;
• or
• a salt thereof;
• (b) a veterinarily acceptable carrier;
• and
• (c) optionally a crystallization inhibitor.