Patent EA-000973-B1 (EA)
Title: Novel 5-amino-3-cyano-4-ethylsulfinyl-1-phenylpyrazole compounds and their use as pesticides
Inventor: HAAS CHARLES LEE
IPC: C07D/
Filed: 1996-12-19
Abstract: 1. A compound of formula (I):   wherein X is chlorine or bromine; Y is trifluoromethyl or trifluoromethoxy and R1 is hydrogen, methyl or ethyl 2. A compound according to claim 1 in which X is chlorine and Y is trifluoromethyl. 3. A compound according to claim 1 or 2 in which R1 is hydrogen or methyl. 4. The compound according to claim 1, 2 or 3 which is: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole; 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-ethylsulfinylpyrazole 5-amino-3 cyano-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole; 5-amino-3-cyano-1-(2-bromo-6-chloro-4-trifluoromethoxyphenyl)-4-ethylsulfinylpyrazole; 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinyl-5-methylaminopyrazole; 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinyl-5-ethylaminopyrazole; or  1-(2-bromo-6-chloro-4-trifluoromethoxyphenyl)-4-ethylsulfinyl-5-ethylaminopyrazole. 5. 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole. 6. 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinyl-5-methylaminopyrazole. 7. A pesticidal composition comprising as active ingredient an effective amount of a compound according to any one of claims 1 to 6 in association with at least one member of the group consisting of a pesticidally acceptable carrier and a pesticidally acceptable surface-active agent. 8. A method for the control of pests at a locus which comprises applying to said locus an effective amount of a compound according to any one of claims 1 to 6. 9. A method according to claim 8 in which the dose rate of the compound of formula (I) is from about 5 to about 1000g per hectare. 10. A method according to claim 8 or 9 in which the locus is an area used, or to be used, for the growing of crops. 11. A method according to claim 8 in which the locus is other than an agricultural area. 12. A synergistic pesticidal composition comprising: (a) a compound of formula (I) as defined in claim 1; and (b) piperonyl butoxide. 13. A process for preparing a compound of formula (I) according to claim 1, where R1 is hydrogen, wherein comprising the reaction of a hydrazine of formula II   or an acid addition salt thereof, wherein X and Y are as defined in claim 1 with a compound of formula III:   R2(R3)C=C(SOEt)(CN) (III)   wherein R2 is cyano and R3 is chlorine or fluorine; 14. A process for preparing a compound of formula (I) according to claim 1, wherein oxidizing a compound of formula (IV):   wherein R1, X and Y are as defined in claim 1, using an oxidizing agent; 15. A process for preparing a compound of formula (I) according to claim 1, where R1 is hydrogen, the reaction of a compound of formula V:   wherein X and Y are as defined in claim 1, with a compound of formula VI: EtS(=O)CH2CN (VI)   16. A process for preparing a compound of formula (I) according to claim 1, wherein the reaction of a compound of formula (VII):   wherein X, Y and R1 are as defined above, with a compound of formula EtS(O)Z1, wherein Z1 is a leaving group. 17. A process for preparing a compound of formula (I) according to claim 1, where R1 is methyl or ethyl, wherein reacting the corresponding compound of formula (I) in which R1 is hydrogen with a methylating or ethylating agent in the presence of a base. 18. A process for preparing a compound of formula (I) according to claim 1, where R1 is methyl or ethyl, wherein reacting the corresponding compound of formula (I) in which R1 is hydrogen with an orthoformate of formula CH(OR12)3 or MeC(OR12)3, wherein R12 is alkyl, to give a compound of formula (VIII):   wherein R12 is as defined above, X and Y are as defined in claim 1 and R11 is hydrogen or methyl, which is subsequently treated with a reducing agent. 19. A process for preparing a compound of formula (I) according to claim 1, wherein reacting a compound of formula (IX):   wherein X and Y are as defined in claim 1 and X1 is halogen, with a compound of formula (X):   wherein R1 is as defined in claim 1. 20. A compound of formula (VIII):   wherein R11 is hydrogen or methyl; R12 is alkyl; X is chlorine or bromine; and Y is trifluoromethyl or trifluoromethoxy.