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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%.
With p-hydroxyphenyl and p-hydroxybenzylimidazoline 2,4-diketonate compounds as the second leading structure, according to the role of Hydantocidin in plants in the form of Hydantocidin 5’-Phosphate, the three pairs The synthesis of 38 novel (thio) phosphate esters containing 2,4-imidazolidinediones by the reaction of hydroxybenzene (benzyl) -2,4-imidazolidinedione with (thio) phosphoryl chloride The structure of the compound was characterized by IR, 1H NMR, 31P NMR and elemental analysis. The preliminary bioassay results showed that O-ethyl-O-phenyl-5- (4-hydroxyphenyl) -2,4-imidazolidinedione Phosphorothioate (B14) and O, O-diphenyl-5- (4-hydroxybenzyl) -2-thioxo-4- imidazolidinone thiophosphate (B25) at a concentration of 100 μg / mL The inhibitory rates to rapeseed were 53.1% and 62.7% respectively. Compounds O, O-bis (o-methoxyphenyl) -5- (4- hydroxyphenyl) -2,4-imidazolidinone thiophosphate B7, B14 and O, O-bis (p-methylphenyl) -5- (4-hydroxybenzyl) -2,4-imidazolidinone thiophosphate (B17) The corrected mortality at 24 h at 300 μg / mL was 52%, 51% and 69%, respectively.