Chemoenzymatic synthesis and biological activity of both enantiomeric forms of tetraconazole, a new antifungal triazole
1991
Bianchi, D. | Cesti, P. | Spezia, S. | Garavaglia, C. | Mirenna, L.
Both enantiomers of (R,S)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether (tetraconazole, 1), a new, broad spectrum, triazole fungicide, were prepared by stereoselective lipase-catalyzed hydrolysis of the racemic precursor (R,S)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-prop-1-yl acetate or by lipase-catalyzed transesterification of the prochiral precursor 2-(2,4-dichlorophenyl)-1,3-propanediol. The biological activity of both enantiomers has been investigated in vitro against a number of fungi and in vivo against Sphaerotheca fuliginea on cucumber and Erysiphe graminis on wheat. The R-(+) form has been found to be the more fungitoxic.
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