1-[2-苄氧基-2-(2,4-二氟苯基)乙基]-1H-1,2,4-三唑衍生物的合成及杀菌活性  

Synthesis and fungicidal activities of 1-[2-benzyloxy-2-(2,4-difluorophenyl)ethyl]-1H-1,2,4-triazole derivatives

作　　者：张敏[1] 张立孔 孟振国 朱祥 高亚强 李俊凯[1,2] 徐志红[1,2] ZHANG Min;ZHANG Likong;MENG Zhenguo;ZHU Xiang;GAO Yaqiang;LI Junkai;XU Zhihong(School of Agriculture,Yangtze University,Jingzhou 434025,Hubei Province,China;Institute of Pesticides,Yangtze University,Jingzhou 434025,Hubei Province,China)

机构地区：[1]长江大学农学院,湖北荆州434025 [2]长江大学农药研究所,湖北荆州434025

出　　处：《农药学学报》2020年第3期413-422,共10页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31672069);新农药创制与开发国家重点实验室开放基金(2017NYRD02).

摘　　要：以抗真菌药物益康唑为先导化合物,设计合成了17个1-((2-取代苄基)氧基)-2-(2,4-二氟苯基)乙基)-1H-1,2,4-三唑类目标化合物,其中14个为首次报道,其结构均经1H NMR、13C NMR和HRMS确认。采用菌丝生长速率法测定了目标化合物对7种植物病原菌的抑制效果,并对毒力较高的化合物进行了其对水稻纹枯病和小麦条锈病的盆栽和田间药效试验,而且测定了其对水稻纹枯病菌麦角甾醇生物合成的抑制作用。结果表明:大多数目标化合物对测试病原菌菌丝生长有较强的抑制作用,尤其对水稻纹枯病菌和番茄早疫病菌的抑制作用最好,其中对水稻纹枯病菌的EC50值均低于3μmol/L,明显高于对照药剂苯醚甲环唑和益康唑;化合物4a、4b、4c、4g、4i和4l对番茄早疫病菌的EC50值均低于10μmol/L。在浓度为250μmol/L时,化合物4b和4i对小麦条锈病的盆栽防效均超过70%,在有效剂量为240 g/hm^2时,化合物4b对小麦条锈病的田间防效达到81.93%。而且,化合物4b和4i在100μmol/L时可有效抑制水稻纹枯病菌麦角甾醇的生物合成,抑制效果在80%左右。Using antifungal medication econazole as the lead compound,a series of 1-[2-benzyloxy-2-(2,4-difluorophenyl)ethyl]-1H-1,2,4-triazole derivatives were designed,synthesized,and characterized by 1H NMR,13C NMR and HRMS.The in vitro fungicidal activities of those compounds against 7 plant pathogenic fungi were evaluated to discover effective compounds preliminarily.The efficiencies of the most effective compounds were further tested against rice sheath blight and wheat stripe rust in greenhouse and field.Furthermore,the inhibitory effect on the ergosterol biosynthesis of R.solani also were determined.Most of the target compounds exhibited good fungicidal activities against the tested plant pathogenic fungi in vitro,especially against Rhizoctonia solani and Alternaria solani.By measuring their EC50 values,it was found that the EC50 values of the tested compounds against R.solani were less than 3μmol/L,which were significantly higher than those of difenoconazole and econazole.The EC50 values of 4a,4b,4c,4g,4i and 4l against A.solani were all lower than 10μmol/L.Compounds 4b and 4i showed higher than 70%control efficiencies against wheat stripe rust at 250μmol/L in greenhouse.And the control efficiency of compound 4b against wheat stripe rust was 81.93%at 240 g a.i./hm^2 in field.In addition,compounds 4b and 4i were found to be effective in inhibiting ergosterol biosynthesis of R.solani with the inhibition rate of around 80%at the concentration of 100μmol/L.

关 键 词：三唑衍生物 益康唑 合成 杀菌活性 麦角甾醇生物合成抑制剂 田间防效 

分 类 号：O626.417[理学—有机化学] S482.2[理学—化学]