Synthesis of deuterated herbicidal ZJ0273, ZJ0702, ZJ0777, and SIOC0163

ZJ0273 (propyl 4‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)benzylamino)benzoate), ZJ0702 (isopropyl 4‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)benzylamino)benzoate), ZJ0777 (2‐bromo‐N‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)benzyl)aniline), and SIOC0163 (5‐bromo‐N‐(2‐(4,6‐dimethoxypyrimidin‐2‐yloxy)benzyl)pyridin‐2‐amine) are active ingredients in oilseed rape herbicides. The middle aromatic ring‐deuterated form of ZJ0273 was synthesized from (²H₆)phenol and have been successfully used as tracer in its metabolism and degradation study. The methoxyl‐deuterated forms of four ingredients were synthesized from (²H₄)methanol, respectively, and they could be used as internal standards in quantitation of herbicide residue in rapeseed and its downstream foodstuff by using HPLC‐MS/MS. Copyright © 2010 John Wiley & Sons, Ltd.