有机化学 ›› 2013, Vol. 33 ›› Issue (03): 596-601.DOI: 10.6023/cjoc201210046 上一篇    下一篇

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a, 王进敏a, 董宏波a, 徐志红a,b, 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:2012-10-29 修回日期:2012-11-28 发布日期:2012-12-03
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 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 Phosphoramidate with Hydantoin

Han Jintaoa, Wang Jinmina, Dong Hongboa, Xu Zhihonga,b, Liu Bina, Wang Mingana   

  1. a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
    b College of Agricuture, Yangtze University, Jingzhou 434025
  • Received:2012-10-29 Revised:2012-11-28 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).

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

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