有机化学 ›› 2013, Vol. 33 ›› Issue (12): 2538-2544.DOI: 10.6023/cjoc201307019 上一篇    下一篇

研究论文

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   

  1. 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 出版日期:2013-12-25 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   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2013-07-13 Revised:2013-08-15 Online:2013-12-25 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).

以5-(4-羟基/氨基苄基)-2-硫代-2,4-咪唑啉二酮为原料,在三乙胺作傅酸剂的条件下与取代磺酰氯反应,得到28个新的5-(4-羟基/氨基苄基)-2-硫代-2,4-咪唑啉二酮苯磺酸酯/酰胺类化合物,它们的化学结构经1H NMR,MS和元素分析确证. 初步生测结果表明:在100 μg/mL浓度下,部分目标化合物均对供试植物病原菌和油菜显现出一定的抑制活性,如5-(4-氨基苄基)-2-硫代-2,4-咪唑啉二酮对碘苯磺酰胺(4d)对黄瓜灰霉病菌抑制率为80.7%,5-(4-羟基苄基)-2-硫代-2,4-咪唑啉二酮邻甲基苯磺酸酯(3n)和5-(4-氨基苄基)-2-硫代-2,4-咪唑啉二酮-2,4-二氯苯磺酰胺(4m)对油菜的生长抑制率分别为87.4%和81.5%.

关键词: 5-(4-羟基/氨基苄基)-2-硫代-2,4-咪唑啉二酮, 苯磺酸酯/酰胺, 除草活性, 杀菌活性

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