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2013 , Vol. 33 >Issue 03: 596 - 601

DOI: https://doi.org/10.6023/cjoc201210046

研究论文

含咪唑啉2,4-二酮的新型磷酰胺酯类化合物的合成和生物活性

  • 韩金涛 ,
  • 王进敏 ,
  • 董宏波 ,
  • 徐志红 ,
  • 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: 2012-10-29

  修回日期: 2012-11-28

  网络出版日期: 2012-12-03

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 Phosphoramidate with Hydantoin

  • Han Jintao ,
  • Wang Jinmin ,
  • Dong Hongbo ,
  • Xu Zhihong ,
  • Liu Bin ,
  • 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: 2012-10-29

  Revised date: 2012-11-28

  Online published: 2012-12-03

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

在合成含咪唑啉2,4-二酮磷酸酯和磷酰胺类化合物的基础上, 根据Hydantocidin在植物体内的作用形式是Hydantocidin 5'-phosphate的特点, 将5-[4-羟基-3-硝基-苯(苄)基]-2,4-咪唑啉二酮中间体与O,N-二烷基硫代磷酰氯反应合成得到了18个结构新颖的O-烷基-N-烷基-5-[4-羟基-3-硝基-苯(苄)基]-2,4-咪唑啉二酮硫代磷酰胺酯类化合物, 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, 化合物O-乙基(丙基)-N-异丙基-5-(4-羟基-3-硝基苄基)-2,4-咪唑啉二酮硫代磷酰胺酯(B10, B16)在100 mg/mL浓度下对油菜的抑制率为64.1%和69.6%, O-甲基-N-正丁基-5-(4-羟基-3-硝基苄基)-2,4-咪唑啉二酮硫代磷酰胺酯(B15)对蚜虫和小菜蛾均表现了良好的杀虫活性, 在300 mg/mL浓度下24 h的校正死亡率分别为100%和95%.

关键词： 咪唑啉-2,4-二酮; 硫代磷酰胺酯; 腺苷酸琥珀酸合成酶; 生物活性

本文引用格式

韩金涛 , 王进敏 , 董宏波 , 徐志红 , 刘斌 , 王明安 . 含咪唑啉2,4-二酮的新型磷酰胺酯类化合物的合成和生物活性[J]. 有机化学, 2013 , 33(03) : 596 -601 . DOI: 10.6023/cjoc201210046

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.

Key words： 2,4-imidazolidinedione; thiophosphoramidate; adenylosuccinate synthetase; biological activity

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