Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin

doi:10.6023/cjoc201206002

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2134-2140.DOI: 10.6023/cjoc201206002 Previous Articles Next Articles

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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

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 Zhihong^a,b, Wang Jinmin^a, Han Jintao^a, Liu Bing^a, Wang Mingan^a

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).

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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Xu Zhihong, Wang Jinmin, Han Jintao, Liu Bing, Wang Mingan. Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin[J]. Chin. J. Org. Chem., 2012, 32(11): 2134-2140.

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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

Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin

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