The preparative-scale syntheses of cysteine and glutathione (GSH) conjugates (2,3) of the chloroacetanilide herbicide acetochlor (1a) and its plant degradation products (1b,c) were accomplished in high yield and in excellent purity by the reaction of chloroacetamides with stoichiometric GSH or cysteine in liquid ammonia in the presence of sodium amide. Cysteine conjugates of metabolites 1b,c without an N-alkoxyalkyl side chain could easily be prepared in alcoholic solutions of cysteine hydrochloride and sodium ethoxide by reactions with chloroacetamides. The physicochemical properties and NMR data of conjugates are also described.
ASJC Scopus subject areas
- Agricultural and Biological Sciences(all)