Synthesis and Biological Activity of Novel 5-(4-Hydroxy/aminobenzyl)-2-thiohydantoin Phenylsulfonate/Phenylsulfonamide

doi:10.6023/cjoc201307019

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (12): 2538-2544.DOI: 10.6023/cjoc201307019 Previous Articles Next Articles

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5-[4-羟(氨)基苄基]-2-硫代-2,4-咪唑啉二酮磺酸酯(酰胺)的合成及其生物活性

刘斌, 董宏波, 韩金涛, 徐志红, 金淑惠, 王明安

中国农业大学应用化学系北京 100193

收稿日期:2013-07-13 修回日期:2013-08-15 发布日期:2013-08-21
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 5-(4-Hydroxy/aminobenzyl)-2-thiohydantoin Phenylsulfonate/Phenylsulfonamide

Li Bin, Dong Hongbo, Han Jintao, Xu Zhihong, Jin Shuhui, Wang Mingan

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2013-07-13 Revised:2013-08-15 Published:2013-08-21
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 (Nos. 0902, 201003).

Novel 5-(4-hydroxy/aminobenzyl)-thiohydantoin phenylsulfonates/phenylsulfonamides were prepared using 5-(4-hydroxy/aminobenzyl)-thiohydantoin and substituted phenylsulfonyl chlorides as raw materials. Their structures were confirmed by ¹H NMR, MS spectra and elementary analysis. The preliminary bioassay results showed that some of them have certain fungicidal and herbicidal activities. For example, 5-(4-aminobenzyl)-thiohydantoin 4-iodophenylsulfonamide (4d) had 80.7% inhibition rate against Botrytis cinerea, 5-(4-hydroxybenzyl)-thiohydantoin 2-methylphenylsulfonate (3n) and 5-(4-aminobenzyl)-thiohydantoin 2,4-dichlorophenylsulfonamide (4m) had 87.4% and 81.5% inhibition rates against Brasica campestris at the concentration of 100 μg/mL, respectively.

Key words: 5-(4-hydroxy/aminobenzyl)-2-thiohydantoin, phenylsulfonate, phenylsulfonamide, herbicidal activity, fungicidal activity

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Li Bin, Dong Hongbo, Han Jintao, Xu Zhihong, Jin Shuhui, Wang Mingan. Synthesis and Biological Activity of Novel 5-(4-Hydroxy/aminobenzyl)-2-thiohydantoin Phenylsulfonate/Phenylsulfonamide[J]. Chin. J. Org. Chem., 2013, 33(12): 2538-2544.

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5-[4-羟(氨)基苄基]-2-硫代-2,4-咪唑啉二酮磺酸酯(酰胺)的合成及其生物活性

Synthesis and Biological Activity of Novel 5-(4-Hydroxy/aminobenzyl)-2-thiohydantoin Phenylsulfonate/Phenylsulfonamide

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