N-烷基氢化诺卜基胺及其丙酰化衍生物的合成与活性研究

由氢化诺卜醇与亚硫酰氯反应制得氢化诺卜基氯,再分别与甲胺、乙胺、正丙胺、异丙胺、正丁胺在水热合成反应釜中加热下反应,合成了5种N-烷基氢化诺卜基胺(3a～3e).用共沸脱酸法使它们分别与丙酸酐反应,合成了5种N-烷基-N-氢化诺卜基丙酰胺(4a～4e),产物得率85%以上,GC纯度98%以上,对10个化合物均进行了IR、¹H NMR、¹³C NMR与MS分析,表征了它们的结构.以西瓜枯萎病菌(Fusarium oxysporum)、莴苣菌核病菌(Sclerotinia sclerotiorum)、绵腐卧孔菌(Poria vaporaria)、彩绒革盖菌(Coriolus versicolor)、绿色木霉(Triochoderma viride)为供试菌株,开展抑菌活性测定,结果表明,所合成的丙酰胺类化合物均有一定的活性,其中N-甲基-N-氢化诺卜基丙酰胺(4a)对西瓜枯萎病菌的抑制效果较好; N-乙基-N-氢化诺卜基丙酰胺(4b)对莴苣菌核病菌和绵腐卧孔菌的抑制活性较好.

The Synthesis and Antifungal of N-Alkyl Hydronopylamine and Its Propionylation Derivative

Hydronopyl chloride was prepared from the hydronopol and thionyl chloride.And five kinds of N-alkyl-N-hydronopylamines were synthesized from hydronopyl chloride and methylamine,ethylamine,propylamine,isopropylamine,butylamine in hydrothermal synthesis reactor under heating.Then five kinds of N-alkyl-N-hydronopylpropionamides were obtained from the reaction of alkyl hydronopylamine and propionic anhydride by azeotropic acid method.The yields of the products(GC contents were over 98%)were more than 85%.The structures of ten compounds synthesized were indentified by IR,¹H NMR,¹³C NMR and MS analysis.The antibacterial actlvity against Fusarium oxysporum,Sclerotinia sclerotiorum,Poria vaporia,Coriolus versicolor and Trichoderma viride were tested.The results showed that the five derivatives of propionamide had different inhibnion ratio to five plant pathogens,the inhibition ratios of N-methyl-N-hydronopyl(4a)to Fusarium oxysporum and of N-methyl-N-hydronpyl propionamide(4b)to Sclerotinia sclerotiorum and Porla vaporaria ande good.