Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2134-2140.DOI: 10.6023/cjoc201206002 Previous Articles     Next Articles



徐志红a,b, 王进敏a, 韩金涛a, 刘斌a, 王明安a   

  1. a 中国农业大学应用化学系 北京 100193;
    b 长江大学农学院 荆州 434205
  • 收稿日期:2012-06-04 修回日期:2012-06-27 发布日期:2012-07-04
  • 通讯作者: 王明安
  • 基金资助:

    “十二五”科技支撑计划(No. 2011BAE06B03)、国家自然科学基金(No. 20772150)和南开大学元素有机化学国家重点实验室开放基金(Nos. 0902, 201003)资助项目.

Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin

Xu Zhihonga,b, Wang Jinmina, Han Jintaoa, Liu Binga, Wang Mingana   

  1. a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
    b College of Agricuture, Yangtze University, Jingzhou 434025
  • Received:2012-06-04 Revised:2012-06-27 Published:2012-07-04
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03), the National Natural Science Foundation of China (No. 20772150) and the National Key Laboratory of Elemento-Organic Chemistry in Nankai University (Nos. 0902, 201003).

Based on the structure of hydantocidin as a leading compound, the natural inhibitor of AdSS, its activated hydantocidin 5'-phosphate in the plant and 5-substituted 2,4-imidazo-lidinedione esters as the second leading compound, thirty eight new (thio)phosphate derivatives with hydantoin were synthesized by the reaction of (thio)phosphoryl chloride with 5-(4-hydroxyphenyl)- and 5-(4-hydroxybenzyl)-2,4-imidazolidinedione intermediates, and their structures were confirmed by IR, 1H NMR, 31P NMR spectra and elemental analysis. The preliminary bioassay showed that O-ethyl-O-phenyl-5-(4-hy- droxyphenyl)-2,4-imidazolidineone thiophosphate (B14) and O,O-diphenyl-5-(4-hydroxybenzyl)-2-thio-4-imidazolidineone thiophosphate (B25) have an inhibitory ratio 53.1% and 62.7% against Brasica campestris at the concentration of 100 μg/mL, while O,O-di(o-methoxyphenyl)-5-(4-hydroxyphenyl)-2,4-imidazolidineone thiophosphate (B7), B14 and O,O-di(p-methyl- phenyl)-5-(4-hydroxybenzyl)-2,4-imidazolidineone thiophosphate (B17) showed 52%, 51% and 69% insecticidal activities against Myzus Persicae at the concentration of 300 μg/mL.

Key words: hydantoin, (thio)phosphates, AdSS, biological activity