3-二氟甲基-1-甲基吡唑-4-羧酸肟酯衍生物的合成及抑菌活性  

Synthesis and antifungal activity of 3-(difluoromethyl)-1-methyl pyrazole-4-carboxylic oxime esters

作　　者：张兴甲 魏志敏 王宇佳 杨龙港 袁含笑 冯俊涛[1,2] 高艳清 雷鹏[1,2] 马志卿 ZHANG Xingjia;WEI Zhimin;WANG Yujia;YANG Longgang;YUAN Hanxiao;FENG Juntao;GAO Yanqing;LEI Peng;MA Zhiqing(College of Plant Protection,Northwest A&F University,Yangling 712100,Shaanxi Province,China;Shaanxi Research Center of Biopesticide Engineering&Technology,Yangling 712100,Shaanxi Province,China)

机构地区：[1]西北农林科技大学植物保护学院,陕西杨凌712100 [2]陕西省生物农药工程技术研究中心,陕西杨凌712100

出　　处：《农药学学报》2022年第1期59-65,共7页Chinese Journal of Pesticide Science

基　　金：陕西省自然科学基础研究计划(2020JQ-238,2021JQ-147);中央高校基本科研业务费专项资金(2452018093);省级大学生创新创业训练计划项目(S202110712352).

摘　　要：为发现具有高抑菌活性的先导化合物,结合本课题组前期研究,设计并合成了18个新型3-二氟甲基-1-甲基吡唑-4-羧酸肟酯衍生物,其结构均经核磁共振氢谱、碳谱及高分辨质谱分析确证,化合物9g的单晶衍射结果证明肟酯的构型为E式。离体生物活性测定结果表明,目标化合物在50μg/mL下对番茄灰霉病菌Botrytis cinerea、苹果树腐烂病菌Valsa mali和小麦全蚀病菌Gaeumannomyces graminis均表现出一定的抑制活性,其中化合物9d对苹果树腐烂病菌、9r对小麦全蚀病菌的EC50值分别为0.89μg/mL和3.34μg/mL,表现出比先导化合物L1(E-2-氯-6-氟苯甲醛-O-(1-甲基-3-苯基-1H-吡唑-5-羰基)肟)和肟菌酯更优或相似的抑菌活性。To discover lead compound with high antifungal activity,based on our previous studies,18 novel 3-(difluoromethyl)-1-methyl pyrazole-4-carboxylic oxime esters were designed and synthesized based on the previous studies.Their structures were confirmed by 1H NMR,13C NMR and HRMS.The configuration of oxime ester was confirmed to be E by the X-ray single crystal diffraction of the compound 9g.The in vitro bioassay results showed that the target compounds displayed antifungal activities against Botrytis cinerea,Valsa mali and Gaeumannomyces graminis.Especially,the compound 9d showed excellent activity against V.mali(EC50=0.89μg/mL)and 9r exhibited satisfied activity against G.graminis(EC50=3.34μg/mL),which are better than or smilar to the lead compound L1(E-2-chloro-6-fluorobenzaldehyde O-(1-methyl-3-phenyl-1H-pyrazole-5-carbonyl)oxime)and trifloxystrobin.

关 键 词：吡唑 肟酯 抑菌活性 苹果树腐烂病菌 小麦全蚀病菌 

分 类 号：O626.21[理学—有机化学] TQ450.11[理学—化学]