含咪唑啉2，4-二酮的新型磷酰胺酯类化合物的合成和生物活性  

Synthesis and Biological Activity of Novel Phosphoramidate with Hydantoin

作　　者：韩金涛[1] 王进敏[1] 董宏波[1] 徐志红[1,2] 刘斌[1] 王明安[1] 

机构地区：[1]中国农业大学应用化学系,北京100193 [2]长江大学农学院,荆州434205

出　　处：《有机化学》2013年第3期596-601,共6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：在合成含咪唑啉2,4-二酮磷酸酯和磷酰胺类化合物的基础上,根据Hydantocidin在植物体内的作用形式是Hydantocidin 5'-phosphate的特点,将5-[4-羟基-3-硝基-苯(苄)基]-2,4-咪唑啉二酮中间体与O,N-二烷基硫代磷酰氯反应合成得到了18个结构新颖的O-烷基-N-烷基-5-[4-羟基-3-硝基-苯(苄)基]-2,4-咪唑啉二酮硫代磷酰胺酯类化合物,其结构通过IR,1H NMR,31P NMR和元素分析表征.初步生物测定结果表明,化合物O-乙基(丙基)-N-异丙基-5-(4-羟基-3-硝基苄基)-2,4-咪唑啉二酮硫代磷酰胺酯(B10,B16)在100μg/mL浓度下对油菜的抑制率为64.1%和69.6%,O-甲基-N-正丁基-5-(4-羟基-3-硝基苄基)-2,4-咪唑啉二酮硫代磷酰胺酯(B15)对蚜虫和小菜蛾均表现了良好的杀虫活性,在300μg/mL浓度下24 h的校正死亡率分别为100%和95%.Based on the synthesis of phosphates and phosphorylamides with hydantoin, the natural inhibitor of AdSS and its activated hydantocidin-5＇-phosphate in the plant, eighteen new O-alkyl-N-alkyl-5-[4-hydroxy-3-nitrophenyl（benzyl）]-2,4- imidazolidinedione thiophosphoramidate derivatives with hydantoin were synthesized by the reaction of O,N-dialkyl thio- phosphoryl chloride with 5-（4-hydroxy-3-nitrophenyl）- and 5-（4-hydroxy-3-nitrobenzyl）-2,4-imidazolidinedione intermediates, and their structures were confirmed by IR, 1H NMR, 31p NMR spectral data and elemental analysis. The preliminary bioassay showed that O-ethyl（propyl）-N-isopropyl-5-（4-hydroxy-3-nitrobenzyl）-2,4-imidazolidinedione thiophosphoramidates （B10 and B16） have inhibitory rates of 64.1% and 69.6% against Brasica campestris at the concentration of 100 μg/mL, while O-propyl-N-butyl-5-（4-hydroxy-3-nitrobenzyl）-2,4-imidazolidinedione thiophosphoramidate （B15） showed 100%, and 95% insecticidal activities against Myzus persicae and Plutella xylostella at the concentration of 300μg/mL.

关 键 词：咪唑啉-2 4-二酮 硫代磷酰胺酯 腺苷酸琥珀酸合成酶 生物活性 

分 类 号：TQ457.2[化学工程—农药化工]