Synthesis of carbon-14 labeled pyraoxystrobin, a novel fungicide

SYP-3343, (E)-2-(2-((3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-yloxy)methyl)) phenyl)-3-methoxyacrylate, is a novel fungicide with broad-spectrum and high activity against fungi. In this paper, radioactive pyraoxystrobin, labeled in the pyrazole ring system was achieved from 14C labeled 4-chlorobenzoic acid through substitution, cyclization, and condensation, in an overall chemical and radiochemical yield of 44%. The chemical and radiochemical purity of the title compound was 98.5% and 98.2%, respectively. This labeled SYP-3343 was used as a radiotracer for metabolism, toxicology, mode of action, and other environmental studies. Copyright (C) 2011 John Wiley & Sons, Ltd.