有机化学 ›› 2012, Vol. 32 ›› Issue (11): 2134-2140.DOI: 10.6023/cjoc201206002 上一篇    下一篇

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 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 (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).

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), B14O,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

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