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烷基氢化诺卜基酰胺类衍生物的合成、表征及抑菌活性研究

Studies on the Synthesis,Characterization and Antibacterial Activity of Alkyl Hydronopyl Amide Derivatives

【作者】 陈金珠

【导师】 王宗德; 王玉;

【作者基本信息】 江西农业大学 , 农业推广林业(专业学位), 2016, 硕士

【摘要】 植物病害主要是由植物致病菌引起的,分布范围广,对农作物造成的危害大,目前常用的杀菌剂对环境存在毒性大、难降解,对病菌易产生抗药性等不足,新型绿色抗菌剂的研发是当前迫切需要解决的问题。许多研究表明,植物源萜类化合物诺卜醇的衍生物具有不同程度的杀菌和驱虫效果,可以较好地缓解此类问题。本文以氢化诺卜醇为起始原料,经过卤代、氨化及酰基化等反应合成了15个新化合物,其中烷基氢化诺卜基胺5个,N-烷基-N-氢化诺卜基乙酰胺类化合物5个,N-烷基-N-氢化诺卜基丙酰胺类化合物5个,所得化合物经纯化后GC纯度均为95%以上,利用红外光谱、质谱和核磁共振等手段进行了结构表征。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)及绿色木霉(Trichoderma viride)为供试菌株,采用生长速率法测定10个新化合物对上述5种植物致病菌的抑制率,实验数据依靠SPSS等软件进行分析,并得出各化合物的抑制中浓度(EC50)和毒立回归方程。初步抑菌活性结果表明,各化合物对5种植物致病菌均表现出不同程度的抑菌活性,随着浓度的增加,抑菌作用也随之增强。在500 mg/L浓度下,化合物具有很高的抑制率,大多可达80%。当浓度降至31.25 mg/L时,N-乙基-N-氢化诺卜基丙酰胺对莴苣菌核病菌的抑制率为83.87%、N-异丙基-N-氢化诺卜基乙酰胺和N-正丁基-N-氢化诺卜基乙酰胺对绵腐卧孔菌的抑制率分别为91.35%、84.76%,抑制效果比较好;其余化合物对5种供试植物致病菌的抑制率均低于80%,效果不明显。EC50的计算分析结果表明,N-正丁基-N-氢化诺卜基乙酰胺对西瓜枯萎病菌和莴苣菌核病菌的抑制效果较好,其EC50值分别为25.72 mg/L和19.77 mg/L,N-异丙基-N-氢化诺卜基乙酰胺对绵腐卧孔菌和绿色木霉的抑制效果较好,其EC50值分别为2.13 mg/L和26.69 mg/L。N-甲基-N-氢化诺卜基丙酰胺对彩绒革盖菌的EC50值67.63 mg/L,抑菌效果不佳。

【Abstract】 Plant disease is mainly caused by plant pathogenic bacteria,distribution range is wide,the damage to crops,the current commonly used bactericides has many disadvantages,such as high toxicity,degradation-resistant,Therefore,the development of green antibacterial agent is of significance and necessary.Many studies have shown that Terpenoids botanical fungicides have good antifungal activity,and can alleviate such problems.In this paper,fifteen new derivatives were synthesized by the reaction of halogenated,ammonolysis and acylation from hydronopol,while hydronopol was the starting material.The feifteen derivatives included 5 alkyl hydronopyl amines,five N-alkyl-N-hydronopyl acetamides and five N-alkyl-N-hydronopyl propionamides.All the compounds were separated and purified,The GC content of the products were over 95%and their structures were characterized and analyzed by IR,NMR and MS.Among this article,The antifungal activity against Fusarium oxysporum,Sclerotinia sclerotiorum,Poria vaporaria,Coriolus versicolor and Trichoderma viride were tested to these amides derivatives.The inhibition ratios of 10 compounds to five plant pathogens were determined by the growth rate method.The experimental data was analyzed by SPSS software in order to obtain the inhibition concentration and independent regression equation of the compounds.The preliminary antifungal activity results showed that the compounds had different inhibition ratio to five plant pathogens.With the increasing concentration of the compounds,the inhibitory effect also increased.Most compounds exhibited 80%good inhibition ratio at concentration of 500 mg/L.When the concentration was reduced to 31.25 mg/L,the inhibition ratios of N-ethyl-N-hydronopyl propionamide to Sclerotinia sclerotiorum was 83.87%,the inhibition ratios of N-i-propyl-N-hydronopyl acetamide and N-n-buthyl-N-hydronopyl acetamide to Poria vaporaria were91.35%and 84.76%.The rest compounds had lower inhibition ratios to five plant pathogens and didn’t show good antifungal activities.EC500 results showed as fowllows,the EC500 of N-n-buthyl-N-hydronopyl acetamide to Fusarium oxysporum and Sclerotinia sclerotiorum were 25.72 mg/L and 19.77mg/L,the EC500 of N-i-propyl-N-hydronopyl acetamide to Poria vaporaria and Trichoderma viride were 2.13 mg/L and 26.69 mg/L,These four compounds had better antibacterial activity.The EC500 of N-methyl-N-hydronopyl propionamide was67.63 mg/L and had poor antibacterial effect.

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