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/amino- benzyl)-2-thiohydantoin Phenylsulfonate/Phenylsulfonamide

作　　者：刘斌[1] 董宏波[1] 韩金涛[1] 徐志红[1] 金淑惠[1] 王明安[1] 

机构地区：[1]中国农业大学应用化学系,北京100193

出　　处：《有机化学》2013年第12期2538-2544,共7页Chinese Journal of Organic Chemistry

基　　金："十二五"科技支撑计划(No.2011BAE06B03);国家自然科学基金(No.20772150);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~~

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100μg/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%.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.

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 

分 类 号：TQ450.1[化学工程—农药化工]