Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2186-2195.DOI: 10.6023/cjoc201305023 Previous Articles     Next Articles

Articles

新型含咪唑啉2,4-二酮的磷酰胺类化合物的合成和生物活性

王进敏a, 徐志红a,b, 韩金涛a, 董宏波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:2013-05-14 修回日期:2013-06-11 出版日期:2013-10-25 发布日期:2013-06-21
  • 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 Phosphoramide with Hydantoin

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

  1. a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
    b College of Agricuture, Yangtze University, Jingzhou 434025
  • Received:2013-05-14 Revised:2013-06-11 Online:2013-10-25 Published:2013-06-21
  • 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 (No. 0902, 201003).

Based on the synthesis of phosphates and phosphorylamidates with hydantoin, thirty and eight new O,O-dialkyl-(aryl)-5-[4-aminophenyl(benzyl)]-2,4-imidazolidinedione thiophosphoramide derivatives with hydantoin were synthesized by the reaction of O,O-dialkyl(aryl) thiophosphoryl chloride with 5-(4-aminophenyl)-and 5-(4-aminobenzyl)-2,4-imidazolidine-dione intermediates, and their structures were confirmed by 1H NMR, 31P NMR, IR, elemental analysis and X-ray diffraction. 9b: C14H20N3O3PS2·1/3H2O, Mr=379.43, triclinic, space group P-1, a=0.82092(5) nm, b=1.79810(14) nm, c=2.0153(2) nm, α=72.289(8)°, β=79.355(7)°, γ=77.288(6)°, V=2.7421(4) nm3, Dc=1.379 g/cm3, Z=6, F(000)=1196, μ(Mo Kα)=0.397 mm-1, S=1.031, final R=0.0426, wR=0.0797. The preliminary bioassay showed that O,O-dimethyl-5-(4-amino-phenyl)-2,4-imidazolidinedione thiophosphoramide (7a), O-ethyl-O-phenyl-5-(4-aminobenzyl)-2,4-imidazolidine-dione thio-phosphoramide (9n) and O,O-dimethyl-5-(3-aminophenyl)-2-thio-2,4-imidazolidinedione thiophosphoramide (11a)have inhibitory rates 75.4%, 80.5% and 81.7% against Brasica campestris at the concentration of 100 μg/mL, while eleven compounds showed excellent insecticidal activities against Myzus Persicae with the LD50 data in the range of 182.41~368.52 μg/mL, respectively.

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