二烷基氢化诺卜基苄基卤化铵的合成及抑菌活性
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摘要
以氢化诺卜基溴为原料,分别与二甲胺、二乙胺、二正丙胺反应得到3种二烷基氢化诺卜基胺,后者再分别与溴化苄、氯化苄、碘化苄反应制得了7种二烷基氢化诺卜基苄基卤化铵,其结构经红外光谱、质谱、核磁共振确认,这7种化合物均为新化合物.以葡萄座腔菌(Botryosphaeria parva)、柑橘茎点霉菌(Phoma citricarpa)、柑橘炭疽菌(Colletotrichum glecosporioides)、猕猴桃拟盘多毛孢菌(Pestalotiopsis actinidia)、枣拟茎点霉菌(Phomopsis mauritiana)为供试菌种,采用菌丝生长速率法测定7种化合物对供试菌种的抑菌效果.结果表明:在500 mg·L-1的浓度下,7种化合物对葡萄座腔菌的抑制率均达80%以上,对柑橘黑斑病菌的抑制率均比多菌灵的抑制率更高,且N,N-二乙基-N-氢化诺卜基苄基碘化铵对柑橘黑斑病菌的抑制率高达100%.化合物N,N-二甲基-N-氢化诺卜基苄基碘化铵和N,N-二乙基-N-氢化诺卜基苄基碘化铵对猕猴桃拟盘多毛孢菌的抑制率均在80%以上,具有良好的抑制效果.
The dialkyl-hydronopylamine is synthesized from hydronopyl bromide with dimethylamine,diethylamine and dipropylamine,respectively. Seven dialkyl hydronopylbenzyl ammonium halides are prepared from dialkylhydronopylamine with benzyl bromide,benzyl chloride and benzyl iodide,the structures of all compounds are confirmed by IR,MS,1 H NMR and13 C NMR. Using mycelial growth rate method,studies on the antifungal activity of all the compounds against with Botryosphaeria parva,Phoma citricarpa,Colletotrichum glecosporioides,Pestalotiopsis actinidia and Phomopsis mauritiana. The antifungal activity results showed that at the concentration of 500 mg ·L-1,the inhibition rates of all compounds against Botryosphaeria parva are above 80%,and the inhibition rates aganist Phoma citricarpa are all higher than carbendazim. Moreover,N,N-diethyl-N-hydronopylbenzyl ammonium iodide is the best compound against Phoma citricarpa,the inhibition rates are 100%,and compounds except N,Ndimethyl-N-hydronopylbenyl ammonium chloride have equal even higher antifungal activity than carbendazim against Colletotrichum glecosporioides. The inhibition rate of N,N-dimethyl-N-hydronopylbenyl ammonium iodide and N,N-diethyl-N-hydronopylbenzyl ammonium iodide against Pestalotiopsis actinidia are all above 80%,have a good inhibitory effect.
The dialkyl-hydronopylamine is synthesized from hydronopyl bromide with dimethylamine,diethylamine and dipropylamine,respectively. Seven dialkyl hydronopylbenzyl ammonium halides are prepared from dialkylhydronopylamine with benzyl bromide,benzyl chloride and benzyl iodide,the structures of all compounds are confirmed by IR,MS,1 H NMR and13 C NMR. Using mycelial growth rate method,studies on the antifungal activity of all the compounds against with Botryosphaeria parva,Phoma citricarpa,Colletotrichum glecosporioides,Pestalotiopsis actinidia and Phomopsis mauritiana. The antifungal activity results showed that at the concentration of 500 mg ·L-1,the inhibition rates of all compounds against Botryosphaeria parva are above 80%,and the inhibition rates aganist Phoma citricarpa are all higher than carbendazim. Moreover,N,N-diethyl-N-hydronopylbenzyl ammonium iodide is the best compound against Phoma citricarpa,the inhibition rates are 100%,and compounds except N,Ndimethyl-N-hydronopylbenyl ammonium chloride have equal even higher antifungal activity than carbendazim against Colletotrichum glecosporioides. The inhibition rate of N,N-dimethyl-N-hydronopylbenyl ammonium iodide and N,N-diethyl-N-hydronopylbenzyl ammonium iodide against Pestalotiopsis actinidia are all above 80%,have a good inhibitory effect.
引文
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[4]古研,毕良武,赵振东,等.松节油标准样品的制备及特征组分研究[J].生物质化学工程,2006,40(6):1-5.
[5]商士斌,宋湛谦.我国林产化学品“十一五”发展思路[J].精细与专用化学品,2006,14(8):1-5.
[6]廖圣良,陈金珠,陈尚钘,等.氢化诺卜醇苄基醚的合成研究[J].应用化工,2012,41(4):578-579.
[7]赵玲华,肖转泉,陈金珠,等.氢化诺卜醇及其烷基醚的合成与表征[J].化学研究与应用,2012,24(1):123-126.
[8]赵玲华,肖转泉,陈金珠,等.氢化诺卜酸及其酰胺的合成[J].化学研究与应用,2013,25(2):245-248.
[9]刘艳,肖转泉,卢平英,等.氢化诺卜基甲酸及其酯的合成与结构分析[J].林产化学与工业,2013,33(4):57-61.
[10]金霖霖,肖转泉,陈金珠,等.氢化诺卜基3同烷基卤化铵的合成与结构分析[J].江西师范大学学报:自然科学版,2015,39(5):484-487.
[11]徐丽锋,肖转泉,王鹏,等.氢化诺卜醛环状缩醛类化合物的合成及其抑菌活性[J].江西师范大学学报:自然科学版,2014,38(5):472-475.
[12]Wang Zongde,Song Jie,Han Zhaojiu,et al.Quantitative structure:activity relationship of terpenoid aphid antifeedants[J].J Agric Food Chem,2008,56(23):11361-11366.
[13]廖圣良,宋杰,范国荣,等.定量计算萜类蚊虫驱避化合物与羧酸缔合作用对其驱避活性的影响[J].昆虫学报,2014,57(5):547-556.
[14]陈金珠,肖转泉,徐丽锋,等.含氢化诺卜基的叔胺类化合物的合成与结构分析[J].江西师范大学学报:自然科学版,2016,40(2):179-182.
[15]吴文君.植物化学保护实验技术导论[M].西安:陕西科学技术出版社,1988.
[16]邢其毅,裴伟伟,徐瑞秋,等.基础有机化学:上册[M].3版.北京:高等教育出版社,2005.