新型含咪唑啉2,4-二酮的(硫代)磷酸酯类化合物的合成和生物活性测定  

Synthesis and Biological Activity of Novel (Thio)phosphates with Hydantoin

作　　者：徐志红[1,2] 王进敏[1] 韩金涛[1] 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》2012年第11期2134-2140,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：以对羟基苯基和对羟基苄基咪唑啉2,4-二酮羧酸酯类化合物为二次先导结构,根据Hydantocidin在植物体内的作用形式是Hydantocidin 5'-Phosphate的特点,将3种对羟基苯(苄基)-2,4-咪唑啉二酮中间体与(硫代)磷酰氯反应合成得到了38个结构新颖的含有2,4-咪唑啉二酮的(硫代)磷酸酯类化合物,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O-乙基-O-苯基-5-(4-羟基苯基)-2,4-咪唑啉二酮硫代磷酸酯(B14)和O,O-二苯基-5-(4-羟基苄基)-2-硫代-4-咪唑啉二酮硫代磷酸酯(B25)在100μg/mL浓度下对油菜的抑制率为53.1%和62.7%,化合物O,O-二(邻甲氧基苯基)-5-(4-羟基苯基)-2,4-咪唑啉二酮硫代磷酸酯(B7),B14和O,O-二(对甲基苯基)-5-(4-羟基苄基)-2,4-咪唑啉二酮硫代磷酸酯(B17)对蚜虫表现了一定的杀虫活性,在300μg/mL浓度下24 h的校正死亡率分别为52%,51%和69%.Based on the structure of hydantocidin as a leading compound, the natural inhibitor of AdSS, its activated hydantocidin 5＇-phosphate in the plant and 5-substituted 2,4-imidazo-lidinedione esters as the second leading compound, thirty eight new （thio）phosphate derivatives with hydantoin were synthesized by the reaction of （thio）phosphoryl chloride with 5-（4-hydroxyphenyl）- and 5-（4-hydroxybenzyl）-2,4-imidazolidinedione intermediates, and their structures were confirmed by IR, 1H NMR, 31p NMR spectra and elemental analysis. The preliminary bioassay showed that O-ethyl-O-phenyl-5-（4-hy- droxyphenyl）-2,4-imidazolidineone thiophosphate （B14） and O,O-diphenyl-5-（4-hydroxybenzyl）-2-thio-4-imidazolidineone thiophosphate （B25） have an inhibitory ratio 53.1% and 62.7% against Brasica campestris at the concentration of 100μg/mL, while O,O-di（o-methoxyphenyl）-5-（4-hydroxyphenyl）-2,4-imidazolidineone thiophosphate （B7）, B14 and O,O-di（p-methylphenyl）-5-（4-hydroxybenzyl）-2,4-imidazolidineone thiophosphate （B17） showed 52%, 51% and 69% insecticidal activities against Myzus Persicae at the concentration of 300 μg/mL.

关 键 词：咪唑啉-2 4-二酮 (硫代)磷酸酯 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]