新型5-芳甲酰胺基-6-芳胺基-吡唑并[3,4-d]嘧啶-4-酮衍生物的合成及其除草活性

Synthesis and Herbicidal Activities of Novel 5-Aryl Formamido-6-arylamino-pyrazolo[3,4-d]pyrimidin-4-one Derivatives

以吡唑膦亚胺、芳基异氰酸酯和芳基甲酰肼为原料,通过串联氮杂Wittig反应关环合成了12种新型的5-芳甲酰胺基-6-芳胺基-吡唑并[3,4-d]嘧啶-4-酮衍生物(3a^3l),其结构经1H NMR,13C NMR,IR和HR-MS(ESI)表征。对单双子叶除草活性的初步测试结果发现:部分化合物具有优异的除草活性,特别是浓度为100 mg·L^-1时,5-(4-氟苯甲酰胺基)-6-(4-氯苯胺基)-3-甲硫基-1-苯基-1 H-吡唑[3,4-d]-嘧啶-4(5 H)-酮3i和5-(4-吡啶苯甲酰胺基)-6-(4-氯苯胺基)-3-甲硫基-1-苯基-1 H-吡唑[3,4-d]-嘧啶-4(5 H)-酮3k对油菜和稗草的茎和根的抑制率高达100%。

Twelve novel 5-aryl formamido-6-arylamino-pyrazolo[3,4-d]pyrimidin-4-one derivatives(3a^3l)were synthesized via tandem aza-Wittig and annulation reactions of the iminophosphoranes,aryl isocyanate,and aryl formyl hydrazine.The structures of the title compounds were characterized by 1 H NMR,13 C NMR,IR and HR-MS(ESI).The results of preliminary bioassay demonstrated that some target compounds such as 5-(4-fluoro benzamido)-6-(4-chloro phenylamino)-3-methylthio-1-phenyl-1 H-pyrazolo[3,4-d]-pyrimidin-4(5 H)-one(3i)and 5-(4-pyridyl formamido)-6-(4-chloro phenylamino)-3-methylthio-1-phenyl-1 H-pyrazolo[3,4-d]-pyrimidin-4(5 H)-one(3k)displayed remarkable inhibition activity against the stalk and root of rape and barnyard grass with 100%inhibition rate at the dosage of 100 mg·L^-1.