4"-and 4'-alkylthio-avermectin derivatives

Details 4"-and 4'-alkylthio-avermectin derivatives 4"-and 4'-alkylthio-avermectin derivatives

C - Chemistry, Metallurgy

07

D

C07D 493/22 (2006.01) A01N 43/90 (2006.01) C07F 7/18 (2006.01) C07H 19/01 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2064117

Avermectin derivatives are disclosed wherein the 4"-hydroxy group is replaced by a substituted alkylthio or acylthio group or an iodo group. These avermectin derivatives can be further derivatized at the 5- and 23-positions as ketoximes or 0-substituted ketoximes. The 4"-substituted avermectin derivatives are prepared from the 4"- and 4'-trifluoromethane- sulfonyl avermectin derivatives with halo- or sulfur-containing nucleophiles. The 4"- and 4'-.alpha.- and .beta.-trifluoromethane sulfonates are prepared selectively and converted into 4"- or 4'-alkyl- or acylsulfides, or iodides using the appropriate sulfur-containing or iodine nucleophile. Substituted sulfoxy and sulfonyl substituents at the 4"- and 4'-positions are prepared from oxidation of the corresponding substituted sulfides. The new compounds are potent anti-parasitic agents; in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.

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