Mono- and diepoxide derivatives of 23-deoxy-ll-f28249 compounds

C - Chemistry – Metallurgy – 07 – D

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167/202, 260/233

C07D 493/22 (2006.01) A01N 43/90 (2006.01) C07H 19/01 (2006.01) C12P 17/18 (2006.01)

Patent

CA 1300617

30,549 MONO-AND DIEPOXIDE DERIVATIVES OF 23-DEOXY-LL-F28249 COMPOUNDS ABSTRACT The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23- hydroxyl group is replaced with hydrogen and the double bond at the C(26,27)-position is epoxidized concomitant with or without epoxidation of the double bond at the C(14,15)-position. The LL-F28249 compounds (collec- tively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanoaenus having deposit accession number NRRL 15773. The compounds of the present invention are derived by regioselective epoxidation of 5,23-0,0-bissilylated LL-F28249 compounds at low temperature, desilylation, re-silylation of the 5-hydroxyl group, thiocarbonyla- tion of the 23-hydroxyl group, disilyation followed by tributyltin hydride reduction. The novel deoxy compounds of the present invention have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these described derivatives as active ingredients thereof are described herein.

560553

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