Synthesis, antifungal activities, and potential detoxification of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiocarbamates

A series of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiocarbamates were synthesized by the reaction of glucosyl isothiocyanates with monohydric and dihydric alcohols, and acetone oxime, using methods of both normal reaction and microwave-assisted synthesis. Antifungal activities of the title compounds were determined with three kinds of plant pathogenic fungi, Fusarium graminearum, Rhizoctoria cerealis, and Colletotrichum orbiculare. The synthesized glucosyl thiocarbamates easily reacted with HgCl2 to give novel metal–organic compounds, bis[O-alkyl N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiocarbamato]mercury, in yields of 80%. This strong affinity of thiocarbamates for mercury showed their potential utility in medical or marine environmental detoxification.

Figure optionsDownload as PowerPoint slide