含苯基吡唑的苯氧基苯甲酰胺类化合物的合成及杀菌活性研究  

Synthesis and fungicidal activity of phenoxybenzamides containing phenylpyrazole

作　　者：邓化娟 曹佳帅 孙博运 马小龙 韩新宁[1] 王伟[2] DENG Huajuan;CAO Jiashuai;SUN Boyun;MA Xiaolong;HAN Xinning;WANG Wei(College of Chemistry and Chemical Engineering,Ningxia Normal University,Guyuan 756000,Ningxia,China;School of Agriculture,Ningxia University,Yinchuan 750021,China)

机构地区：[1]宁夏师范学院化学化工学院,宁夏固原756000 [2]宁夏大学农学院,银川750021

出　　处：《农药》2024年第8期558-567,共10页Agrochemicals

基　　金：豆科植物功能型的固沙模式对凋落物-土壤连续体氮循环关键过程的影响及机制(32360327);宁夏师范学院大学生科技创新基金(z202323);宁夏师范学院区级大学生创新创业计划项目基金(S202310753025)。

摘　　要：[目的]设计、合成了含苯基吡唑的苯氧基苯甲酰胺类化合物,以期获得具有优良杀菌活性的先导化合物。[方法]通过酰胺键将二苯醚片段与苯基吡唑片断连接合成目标化合物,其结构均经过1H NMR和13C NMR确证。采用菌丝生长速率法对目标化合物进行抗真菌活性测定,通过盆栽试验测试化合物8f的活体保护活性,并通过扫描电镜和分子对接初步探究了化合物8f的抑菌机制。[结果]质量浓度为50 mg/L时,目标化合物表现出较好的杀菌活性,其中化合物8f对核盘菌、苹果黑腐皮壳和小麦全蚀病菌的抑制率分别为87.03%、70.53%及82.28%;此外,化合物8f对核盘菌的EC_(50)值为0.76 mg/L,低于氟唑菌酰胺(EC_(50)=0.23 mg/L)。在质量浓度为100 mg/L下,化合物8f对黄瓜上核盘菌引起的病害的保护活性为77.8%,与氟唑菌酰胺(93.3%)仍有一定差距。扫描电镜显示,经化合物8f处理后,核盘菌菌丝出现收缩、凸起和破裂,从而抑制菌丝的正常生长。分子对接分析表明,化合物8f通过氢键、p-π和π-π共轭与琥珀酸脱氢酶(SDH)相互作用,其作用靶点可能为SDH。[结论]含苯基吡唑的苯氧基苯甲酰胺类化合物具有较好的杀菌活性,化合物8f可作为杀菌剂先导化合物进一步研究。[Aims]Phenoxybenzamides containing phenylpyrazole were designed and synthesized in order to obtain lead compounds with good fungicidal activities.[Methods]The target compounds were synthesized by connecting diphenyl ether and phenylpyrazole fragments through amide bond.The structures of all target compounds were confirmed by~1H NMR and~(13)C NMR.The fungistatic activities were determined using the mycelial growth rate method,the in vivo protective activity of compound 8f was tested through pot test,and the molecular docking study and scanning electron microscopy preliminary clarified the possible fungistatic mechanism of compound 8f.[Results]At a concentration of 50 mg/L,the target compounds exhibited good fungistatic activities,with compound8f exhibiting inhibition rates of 87.03%,70.53%and 82.28%against Sclerotinia sclerotiorum,Valsa mali and Gaeumannomyces graminis,respectively.Additionally,the EC_(50)value of compound 8f against S.sclerotiorum was 0.76 mg/L,lower than fluxapyroxad(EC_(50)=0.23 mg/L).In pot test,compound 8f possessed effective protective activities against S.sclerotiorum at a concentration of 100 mg/L,with inhibition rates of 77.8%,albeit lower than fluxapyroxad(93.3%).Scanning electron microscope showed that after treated with compound 8f,the mycelium of S.sclerotiorum contracted,protruded and ruptured,thereby inhibiting the normal growth of the mycelium.Molecular docking analysis showed that compound 8f interacted with succinate dehydrogenase(SDH)through hydrogen bonding,p-πandπ-πconjugation,and its target may be SDH.[Conclusions]The phenoxybenzamides containing phenylpyrazole exhibit good fungicidal activities,while compound 8f could be a promising fungicide candidate for further investigation.

关 键 词：苯基吡唑 二苯醚 杀菌活性 构效关系 分子对接 

分 类 号：TQ455.4[化学工程—农药化工]