Synthesis of herbicidal ZJ0273 labeled with tritium and carbon‐14

Abstract ZJ0273, propyl 4‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)benzylamino)benzoate, is a broad‐spectrum herbicidal ingredient used for weed control in oilseed rape in China. Two mono‐labeled ZJ0273, propyl 4‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)[phenyl‐3,4,5,6‐3H4]benzylamino)benzoate (7) and propyl 4‐(2‐(4,6‐dimethoxy[4,6‐14C2]pyrimidin‐2‐yloxy)benzylamino)benzoate (12), were synthesized separately from [2,3,4,5,6‐3H5]phenol in a four‐step yield of 27% and from 4,6‐dichloro‐2‐(methylthio)[4,6‐14C2]pyrimidine in a three‐step yield of 54%. In addition, two dual‐labeled analogues of ZJ0273 were prepared by homogeneously mixing tritium‐labeled ZJ0273 (7) in the benzyl ring separately with two carbon‐14‐labeled ZJ0273 (2, 12) in the benzoate ring and the pyrimidine ring. These labeled ZJ0273 could be used as radiotracers in the studies on the metabolism, mode of action, environmental behavior, and fate of ZJ0273. Copyright © 2008 John Wiley & Sons, Ltd.