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有机化学.pdfVIP

DOI: 10.6023/cjoc201307019 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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) 摘要 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 Synthesis and Biological Activity of Novel 5-(4-Hydroxy/amino- benzyl)-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) Abstract 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