【作者】 邓平；

【导师】 马柏林；

【作者基本信息】 西北农林科技大学 ， 植物学， 2009， 硕士

【摘要】 苯并咪唑类物质和Schiff碱化合物都具有很好的生物活性及许多其他性能,为寻找具有高活性和广谱的新杀菌剂化合物,并研究其结构与生物活性之间的关系,本论文根据药物拼合原理,设计合成既含有亚胺结构,又含有苯并咪唑母体的新型化合物同时改变醛上不同的取代基和取代基的位置,将2个具有生物活性的基团键合,有可能表现更典型的生物活性及其他性能,以期筛选出新的苯并咪唑类活性化合物。本论文主要由以下几方面组成:1、综述了近年来苯并咪唑及其衍生物、Schiff碱的合成研究和应用进展。2、以邻苯二胺及相应的羧酸为原料,微波辐射下,合成了2种2-取代苯并咪唑衍生物,研究并优化了反应条件探讨了物料比、微波输出功率和微波辐射时间对反应产率的影响。结果表明,较佳反应条件为:n(邻苯二胺)﹕n(甘氨酸)=1﹕2,微波输出功率为259 W,间歇辐射50 min。以上合成方法具有条件温和、操作简便、产率高、选择性良好、反应时间短、易纯化等优点,具有一定的实际应用价值。3、以上述中间体进一步合成了17个新苯并咪唑Schiff碱化合物,经IR、1HNMR、MS等波谱学方法确定了它们的化学结构,并测定了熔点。4、为了研究该类化合物的抑菌活性与结构的关系,用菌丝生成速率法测定了它们对植物病菌的抑菌活性。测定了上述化合物对马铃薯干腐病菌(Fusarium oxysporium),番茄早疫病菌(Alternaria solani),小麦赤霉病菌(Fusarium graminearum),玉米弯苞叶斑病菌(Cercospora sorghi),棉花枯萎病菌(Fusaurium oxysporiumf. sp.vasinfectum)的抑制活性,得出相关性系数EC50。以市售苯并咪唑类杀菌剂50%多菌灵可湿性粉剂为对照,对化合物的构效关系进行了初探。主要结果如下:化合物对这5种植物病原菌的有较好的抑菌活性,部分化合物的抑菌活性高于对照药剂。对照组药剂对植物病原真菌的抑制具有广谱性,而合成的苯并咪唑Schiff碱除个别外大多数对植物病原菌的抑制不具有广谱性,化合物c、i、o、q对小麦赤霉病菌、化合物a、b、c、d、g、i、j、q对番茄早疫病菌、化合物c、g、i对棉花枯萎病菌、化合物a、c、i、n、q对马铃薯干腐病菌、化合物a、b、c、d、f、g、h、i、j、q对玉米弯苞叶斑病菌的杀菌活性都明显高于对照药剂多菌灵。整体来看,化合物c、i、q对所试菌种的抑菌效果都明显优于对照药剂,而化合物m、n、o、p对所试几种病原菌均的抑制作用相对较弱。更多还原

【Abstract】 Benzimidazole derivatives and Schiff base compounds have good biological activities and possess a variety of other characters. To find new hyperactivity broad-spectrum fungicide compounds and study the relationship between structure and biological activities of these compounds, This paper designs and synthesises of a new type of mother-benzimidazole compounds containing imine structures according to principles of drug together,at the same time, changes substituent group and the substituent group position of aldehyde or ketone, bonds the two biological activity groups together, it maybe show more typical biological activity and other properties, Desire to select out new active benzimidazole compounds. This paper is mainly consisted of several parts as followed:1、the recent advances in the synthesis and application of benzimidazoles derivatives and Schiff bases are reviewed. and prospect of application for them were also discussed.2、Two 2-substituted benzimidazoles derivatives were synthesized by the reaction of o-phenylenediamine with corresponding carboxylic acid in hydrochloric acid under microwave irradiation.The effects of the mole ratio of materials,output power of microwave,reaction time on yield were discussed. We could receive the best reaction condition:o-phenylendiamine: glycine is 1:2(mole ratio),output power is 259 W,the reaction time is 50min,the total yield is 77%.The salient features of the above mentioned methods include a simple procedure,mild condiitons,shorter reaction time,and easy purification3、In the best condition,a series of new compounds were prepared. All the compound synthesized were confirmed by elemental analyses, 1H NMR, IR, and mass spectral data.4、To study the relationship between structure and effect of these compounds, the antimicrobial activity to pathogens were considered. All compounds synthesized were tested in vitro against five fungicide:Fusarium oxysporium , Alternaria solani , Fusarium graminearum,Cercospora sorghi Fusaurium oxysporiumf. sp.vasinfectum incomparison with 50% carbendazim wet powder. The relationship between the structures and the fungicidal activities of the compounds was discussed.The main results are as follows: All compounds showed their fungicidal activities, some showed better activities than the contrast. The contrast on the inhibition of plant pathogenic fungi has a broad-spectrum character, but most synthesis benzimidazole Schiff base compounds on the inhibition of plant pathogenic fungi don’t have broad-spectrum characters. The inhibitory activity of compounds c,i,o,q to Fusarium graminearum, compounds a,b,c,d,g,i,j,q to Alternaria solani, compounds c,g,i to Fusaurium oxysporiumf. sp.vasinfectum , compounds a,c,i,n,q to Fusarium oxysporium, compounds a,b,c,d,f,g,h,i,j,q to Cercospora sorghi are significantly higher than the contrast.On the whole, The inhibitory activity of compounds c,i,q to plant pathogenic fungi are significantly higher than the contrast,and The inhibitory activity of compounds m,n,o,p to plant pathogenic fungi are relatively weak.更多还原