Abstract
AbstractA novel fungicide, (‐)(E)‐1‐(2,4‐dichlorophenyl)‐4, 4‐dimethyl‐2(1,2,4‐triazol‐1‐yl)‐1‐penten‐3‐ol (S‐3308 L) and its three optically active stereoisomers were labeled with carbon‐14 at the triazole ring for use in the metabolic and environmental fate studies. 1,2,4‐Triazole‐14C (4) prepared from formamide‐14C (3) was treated with bromopinacolone to give triazolylpinacolone‐14C (5), which was condensed with 2,4‐dichlorobenzaldehyde giving (Z)‐ketone‐14C (6). (Z)‐Ketone‐14C (6) was photoisomerized to (E)‐ketone‐ 14C (7), which was reduced to racemic (Z)‐S‐3308‐ 14C (1) in 20% yield from 3. Reduction of 6 gave racemic (Z))S‐3308‐14C (2) in 23% field from 3. Optical resolution of both racemates 1 and 2 by a HPLC method with a chiral column gave (‐)(E)‐, (+)(E)‐, (‐)(Z)‐ and (+)(Z)‐1‐(2,4‐dichlorophenyl)‐4,4‐dimethyl‐2‐(1,2,4‐triazol‐[14C]‐1‐yl)‐1‐penten‐3‐ols (1a, 1b, 2a and 2b) in essentially Quantitative yields.
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