# US 8,785,372 B2 · 1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,372 B2 - Document ID: US8785372B2 - Status: Granted - Kind: B2 - Application number: 13/894,601 - Filed: 2013-05-15 - Published: 2013-12-05 - Granted: 2014-07-22 - Earliest claimed: 2007-07-03 - Assignees: Aventis Agriculture - Applicants: Aventis Agriculture - Inventors: Hyoung Ik Lee; Loic Patrick Le Hir de Fallois; Philip Reid Timmons; William Glenn Cawthorne; Adalberto Perez de Leon - Web page: https://patentgrep.com/patent/US8785372B2 ## CPC - A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles - A01N 25/02: containing liquids as carriers, diluents or solvents - A01N 47/02: the carbon atom having no bond to a nitrogen atom - A61K 31/415: 1,2-Diazoles - A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61P 33/00: Antiparasitic agents - A61P 33/10: Anthelmintics - A61P 33/14: Ectoparasiticides, e.g. scabicides - C07D 231/18: One oxygen or sulfur atom - C07D 401/04: directly linked by a ring-member-to-ring-member bond - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Provided are 1-aryl-5-alkyl pyrazole compounds, 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, the method of making compounds of formula (I) and the use of these compounds against ectoparasites, endoparasites and pests. ## Claims ### Claim 1 A compound of formula (I), wherein R5 and R7 are each hydrogen; and R1, R2, R3, R4, R6 and Z are as defined below for Compound 1 to Compound 48: (I) Compound # R1 R2 R3 R4 R6 Z 1 CN SCF3 CH3 Cl CF3 C—Cl 2 CN SCF3 CH2CH3 Cl CF3 C—Cl 3 CN SCF3 CH2F Cl CF3 C—Cl 4 CN S(O)2CF3 CH3 Cl CF3 C—Cl 5 CN S(O)CF3 CH3 Cl CF3 C—Cl 6 CN SCF3 CH3 F CF3 C—F 7 CN SCF3 CH3 Cl CF3 C—F 8 CN SCF3 CH2F Cl CF3 C—F 9 CN S(O)CF3 CH3 Cl CF3 C—F 10 CN S(O)CF3 CH2F Cl CF3 C—Cl 11 CN S(O)CF3 CH2F Cl CF3 C—F 12 CN S(O)CF3 CH3 F CF3 C—F 13 CN SCF3 CH3 H CF3 C—F 14 CN S(O)CF3 CH3 H CF3 C—F 15 CN SCCl2F CH3 Cl CF3 C—Cl 16 CN SCF3 CH2F Cl OCF3 C—Cl 17 CN SCF3 CH3 Cl OCF3 C—Cl 18 CN S(O)CF3 CH2F Cl OCF3 C—Cl 19 CN S(O)CF3 CH3 Cl OCF3 C—Cl 20 CN S(O)CCl2F CH3 Cl CF3 C—Cl 21 CN SCCl2F CH2F Cl OCF3 C—Cl 22 CN S(O)CCl2F CH2F Cl OCF3 C—Cl 23 CN SCCl2F CH3 Cl OCF3 C—Cl 24 CN S(O)CCl2F CH3 Cl OCF3 C—Cl 25 CN SCCl2F CH2F Cl CF3 C—F 26 CN SCCl2F CH3 Cl CF3 C—F 27 CN SCCl2F CH3 H CF3 C—Cl 28 CN S(O)CCl2F CH2F Cl CF3 C—F 29 CN S(O)CCl2F CH3 Cl CF3 C—F 30 CN S(O)CCl2F CH3 H CF3 C—Cl 31 CN S(O)2CCl2F CH3 Cl CF3 C—F 32 CN S(O)2CCl2F CH2F Cl CF3 C—F 33 CN SCF3 CH2F Cl SF5 C—Cl 34 CN SCF3 CH3 Cl SF5 C—Cl 35 CN SCClF2 CH2F Cl CF3 C—F 36 CN SCClF2 CH3 Cl CF3 C—F 37 CN S(O)CClF2 CH3 Cl CF3 C—F 38 CN S(O)CClF2 CH2F Cl CF3 C—F 39 CN S(O)2CClF2 CH3 Cl CF3 C—F 40 CN S(O)2CClF2 CH2F Cl CF3 C—F 41 CN S(O)2CCl2F CH3 Cl CF3 C—Cl 42 CN SCCl2F CH3 Cl SF5 C—Cl 43 CN SCF3 CH3 Cl CF3 C—CH3 44 CN S(O)CF3 CH3 Cl CF3 C—CH3 45 CN SCCl2F CHF2 Cl CF3 C—F 46 CN S(O)CCl2F CHF2 Cl CF3 C—F 47 CN SCCl2F CH3 Cl CF3 N 48 CN S(O)CCl2F CH3 Cl CF3 N. ### Claim 2 (depends on 1) The compound of claim 1, wherein the compound is Compound 5, Compound 9 or Compound 29. ### Claim 3 (depends on 2) The compound of claim 2, wherein the compound is Compound 5. ### Claim 4 (depends on 2) The compound of claim 2, wherein the compound is Compound 9. ### Claim 5 (depends on 2) The compound of claim 2, wherein the compound is Compound 29. ### Claim 6 (depends on 1) A veterinary composition comprising a compound of formula (I) in claim 1 together with a veterinarily acceptable carrier. ### Claim 7 (depends on 6) The veterinary composition of claim 6, wherein the composition is a topical composition. ### Claim 8 (depends on 7) The topical veterinary formulation of claim 7, wherein the composition is a spot-on or pour-on composition. ### Claim 9 (depends on 6) The composition of claim 6, wherein the compound of formula (I) is Compound 5. ### Claim 10 (depends on 6) The composition of claim 6, wherein the compound of formula (I) is Compound 9. ### Claim 11 (depends on 6) The composition of claim 6, wherein the compound of formula (I) is Compound 29. ### Claim 12 (depends on 6) The composition of claim 6, wherein the composition further comprises an additional veterinarily-active ingredient. ### Claim 13 (depends on 12) The composition of claim 12, wherein the additional veterinarily-active ingredient is selected from the group consisting of arylpyrazoles, nodulisporic acid or derivatives thereof, macrocyclic lactones, formamidines, pyrethroids, insect growth regulators, benzenedisulfonamide compounds, anti-cestodal agents, neonicotinoid active agents, a spinosyn, depsipeptides and metaflumizone, or mixtures thereof. ### Claim 14 (depends on 13) The composition of claim 13, wherein the macrocyclic lactone is abamectin, dimadectin, doramectin, emamectin, eprinomectin, ivermectin, latidectin, lepimectin, selamectin, milbemectin, milbemycin D, moxidectin, nemadectin or milbemycin oxime. ### Claim 15 (depends on 13) The composition of claim 13, wherein the formamidine is amitraz. ### Claim 16 (depends on 13) The composition of claim 13, wherein the anti-cestodal active agent is praziquantel, pyrantel or morantel. ### Claim 17 (depends on 1) A method for the therapeutic and/or prophylactic treatment of an animal against an ectoparasitic infestation or an endoparasitic infection comprising administering an effective amount of the compound of claim 1 to the animal in need thereof. ### Claim 18 (depends on 17) The method of claim 17, wherein the animal is treated against an ectoparasitic infestation. ### Claim 19 (depends on 18) The method of claim 18, wherein the ectoparasite is a parasitic fly selected from Haematobia sp., Stomoxys sp., Dermatobia sp. and Cochliomyia sp. ### Claim 20 (depends on 19) The method of claim 19, wherein the ectoparasite is Haematobia irritans.