刚性氢化诺卜基双子季铵盐的合成与抗菌作用

Synthesis and Antifungal Activity of Rigid Hydronopyl Gemini Quaternary Ammonium Salts

由含氢化诺卜基的叔胺化合物与1,4-二溴(氯)化苄反应合成了6种新型含刚性碳氢链联结基的氢化诺卜基双子季铵盐,分别为二苄基-1,4-双(氢化诺卜基二甲基溴化铵)(3a)、二苄基-1,4-双(氢化诺卜基二乙基溴化铵)(3b)、二苄基-1,4-双(氢化诺卜基二正丙基溴化铵)(3c)、二苄基-1,4-双(氢化诺卜基二甲基氯化铵)(3d)、二苄基-1,4-双(氢化诺卜基二乙基氯化铵)(3e)和二苄基-1,4-双(氢化诺卜基二正丙基氯化铵)(3f),通过红外光谱、质谱和核磁共振确证了合成的化合物为目标产物。采用菌丝生长速率法测定了新化合物对8种植物病原真菌的抑菌活性,结果表明:6种含刚性碳氢链联结基的氢化诺卜基双子季铵盐对所试的8种植物病原真菌的生长有很好的抑制作用,其中对七叶树壳梭孢菌抑菌的半数有效质量浓度(EC50)值都低于10 mg/L,并且对彩绒革盖菌和西瓜枯萎病菌的EC50值都低于百菌清对其的EC50值;化合物3a、3b和3c对水稻纹枯病菌、油茶炭疽病菌、松枯梢病菌和七叶树壳梭孢菌的抑制效果随着连接基团的相对分子质量的增加而增强。化合物3f对油茶炭疽病菌有良好的抑菌活性,EC50值为3.4478 mg/L。

Six novel hydronopyl gemini quaternary ammonium salts containing rigid alkyl chain groups,namely dibenzyl-1,4-bis(hydronopyl dimethyl ammonium bromide)(3a),dibenzyl-1,4-bis(hydronopyl diethyl ammonium bromide)(3b),dibenzyl-1,4-bis(hydronopyl di-n-propyl ammonium bromide)(3c),dibenzyl-1,4-bis(hydronopyl dimethyl ammonium chloride)(3d),dibenzyl-1,4-bis(hydronopyl diethyl ammonium chloride)(3e),and dibenzyl-1,4-bis(hydronopyl di-n-propyl ammonium chloride)(3f)were synthesized from hydronopyl tertiary amine compounds and 1,4-dibenzyl bromide(chloride),respectively.Their structures were confirmed by FT-IR,MS and NMR.The antifungal activities of the novel compounds against eight plant pathogens were evaluated by mycelium growth rate method.The results showed that six hydronopyl gemini quaternary ammonium salts containing rigid alkyl chain groups had obvious antifungal activities against 8 plant pathogenic fungi.Among them,the EC50 values of all the compounds against Fusicoccum aesculi were lower than 10 mg/L,and the EC50 values against Coriolus versicolor and Fusarium oxysporum were lower than that of chlorothalonil.The antifungal activities of compounds 3a,3b and 3c against Rhizocyonia solani,Colletotrichum gloeosporioides,Sphaeropsis sapinea and Fusicoccum aesculi showed a rise as the molecular weight of linkers.Compound 3f had good antifungal activity against Colletotrichum gloeosporioides,and the EC50 value was 3.4478 mg/L.