Synthesis and biological activity of novel phosphoramidate with hydantoin

Abstract

Based on the synthesis of phosphates and phosphorylamides with hydantoin, the natural inhibitor of AdSS and its activated hydantocidin-5'-phosphate in the plant, eighteen new O-alkyl-N-alkyl-5- [4-hydroxy-3-nitrophenyl(benzyl)]-2, 4- imidazolidinedione thiophosphoramidate derivatives with hydantoin were synthesized by the reaction of O,N-dialkyl thiophosphoryl chloride with 5-(4-hydroxy-3-nitrophenyl)- and 5-(4-hydroxy-3-nitrobenzyl)-2, 4-imidazolidinedione intermediates, and their structures were confirmed by IR, 1H NMR, 31P NMR spectral data and elemental analysis. The preliminary bioassay showed that O-ethyl(propyl)-N-isopropyl-5-(4-hydroxy-3-nitrobenzyl)-2, 4-imidazolidinedione thiophosphoramidates (B10 and B16) have inhibitory rates of 64.1% and 69.6% against Brasica campestris at the concentration of 100 μg/mL, while O-propyl-N-butyl-5-(4-hydroxy-3-nitrobenzyl)-2, 4-imidazolidinedione thiophosphoramidate (B15) showed 100%, and 95% insecticidal activities against Myzus persicae and Plutella xylostella at the concentration of 300 μg/mL. © 2013 Chinese Chemical Society and SIOC, CAS.