Synthesis and chiral purification of 14C-labeled novel neonicotinoids, paichongding

Paichongding, a novel neonicotinoids pesticide with excellent insecticidal activity against imidacloprid-resistant brown planthopper, has been sold in the Chinese market as new pesticide. [14C]Paichongding was proposed as a tracer to support the further study to elucidate the metabolism of the commercialized pesticide. This paper describes an efficient synthesis of [14C]paichongding in five radiochemical steps from [14C]nitromethane (1). Then the four diastereoisomers (a, b, c, and d) were separated by preparative chiral HPLC and characterized by HPLC and HPLC-LSC. This methodology could be utilized in the syntheses of other 14C-labeled nitromethylene neonicotinoids derivatives. Copyright (C) 2011 John Wiley & Sons, Ltd.