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

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

研究论文

新型含咪唑啉2,4-二酮的(硫代)磷酸酯类化合物的合成和生物活性测定

  • 徐志红 ,
  • 王进敏 ,
  • 韩金涛 ,
  • 刘斌 ,
  • 王明安
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  • 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

  网络出版日期: 2012-07-04

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.

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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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摘要

以对羟基苯基和对羟基苄基咪唑啉2,4-二酮羧酸酯类化合物为二次先导结构, 根据Hydantocidin在植物体内的作用形式是Hydantocidin 5'-Phosphate的特点, 将3种对羟基苯(苄基)-2,4-咪唑啉二酮中间体与(硫代)磷酰氯反应合成得到了38个结构新颖的含有2,4-咪唑啉二酮的(硫代)磷酸酯类化合物, 其结构通过IR, 1H NMR, 31P NMR和元素分析表征. 初步生物测定结果表明O-乙基-O-苯基-5-(4-羟基苯基)-2,4-咪唑啉二酮硫代磷酸酯(B14)和O,O-二苯基-5-(4-羟基苄基)-2-硫代-4-咪唑啉二酮硫代磷酸酯(B25)在100 mg/mL浓度下对油菜的抑制率为53.1%和62.7%, 化合物O,O-二(邻甲氧基苯基)-5-(4-羟基苯基)-2,4-咪唑啉二酮硫代磷酸酯(B7), B14和O,O-二(对甲基苯基)-5-(4-羟基苄基)-2,4-咪唑啉二酮硫代磷酸酯(B17)对蚜虫表现了一定的杀虫活性, 在300 μg/mL浓度下24 h的校正死亡率分别为52%, 51%和69%.

关键词： 咪唑啉-2,4-二酮; (硫代)磷酸酯; 腺苷酸琥珀酸合成酶; 生物活性

本文引用格式

徐志红 , 王进敏 , 韩金涛 , 刘斌 , 王明安 . 新型含咪唑啉2,4-二酮的(硫代)磷酸酯类化合物的合成和生物活性测定[J]. 有机化学, 2012 , 32(11) : 2134 -2140 . DOI: 10.6023/cjoc201206002

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

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