摘要：
Based on the structure of hydantocidin as a leading compound, the natural inhibitor of AdSS, its activated hydan-tocidin 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 100 μg/mL, while O,O-di(o-methoxyphenyl)-5-(4-hydroxyphenyl)-2,4-imidazolidineone thiophosphate (B7), B14 and O,O-di(p-methyl-phenyl)-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.%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100 μg/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300 μg/mL浓度下24 h的校正死亡率分别为52％,51％和69％.
