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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2134 - 2140

DOI: https://doi.org/10.6023/cjoc201206002

Articles

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

  • Xu Zhihong ,
  • Wang Jinmin ,
  • Han Jintao ,
  • Liu Bing ,
  • Wang Mingan
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  • a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
    b College of Agricuture, Yangtze University, Jingzhou 434025

Received date: 2012-06-04

  Revised date: 2012-06-27

  Online 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).

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Abstract

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

Cite this article

Xu Zhihong , Wang Jinmin , Han Jintao , Liu Bing , Wang Mingan . Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2134 -2140 . DOI: 10.6023/cjoc201206002

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