8种4-甲基香豆素衍生物的合成及其农药活性.pdfVIP

中国农学通报 2013,29(15):199-203 Chinese Agricultural Science Bulletin 8 种4- 甲基香豆素衍生物的合成及其农药活性 王 栋，张方贺，孙 健，郝双红 （青岛农业大学化学与药学院/ 山东省农业仿生应用工程技术研究中心，山东青岛266109） 摘 要：香豆素类化合物的生物活性与苯并吡喃环上取代基的种类及其位置密切相关，研究不同取代香 豆素的农药生物活性，以期发现有价值的农药先导化合物。以间苯二酚为起始原料，合成了8 种4-甲基 香豆素衍生物。采用菌丝生长速率法和种子萌发法测定了合成化合物的抑菌及除草活性。结果表明：6 种4-甲基香豆素衍生物对4 种供试植物病原真菌具有一定抑制作用，其中4-甲基-7-羟基-8-苯甲酰基香 豆素的抑菌活性最强，对苹果腐烂病菌的EC50 为62.40 mg/L，对葡萄白腐病菌的EC50 为69.22 mg/L；4-甲 基-7-羟基-8-邻氟苯甲酰基香豆素次之，对葡萄白腐病菌EC50 接近100 mg/L。4-甲基-7-丙酰氧基香豆素 除草活性较强，1000 mg/L 下对反枝苋及生菜种子幼根生长的抑制率均大于43% 。由此可见，4-甲基-7- 羟基香豆素7 位酯化使抑菌作用降低，7 位苯甲酰基及邻氟苯甲酰基重排至8 位后抑菌活性明显增强； 合成化合物的除草活性均较弱。 关键词：4-甲基香豆素衍生物；合成；抑菌活性；除草活性 中图分类号：S482.2 文献标志码：A 论文编号：2012-3010 Synthesis and Pesticidal Activity of 8 Derivatives of 4-Methyl-Coumarin Wang Dong, Zhang Fanghe, Sun Jian, Hao Shuanghong (CollegeofChemistryPharm,QingdaoAgriculturalUniversity, ResearchCenterofAgro-bionicEngineeringTech.of ShandongProvince,Qingdao Shandong 266109) Abstract: The biological activity of coumarins was closely related to the kinds and positions of substituents on the benzopyran ring. The pesticidal activity of different substituted coumarins was studied in order to find the valuable lead compound. 8 kinds of derivatives of 4-methyl-coumarin were synthesized from resorcinol in this paper. The antifungal and herbicidal activities were determined by methods of mycelium growth rate and seed germination respectively. The results indicated that six derivatives of 4-methyl-coumarin had certain antifungal activity against all the 4 kinds of plant pathogens tested. The antifungal activity of 4-methyl-7-hydroxy-8-benzoyl-coumarin was the best of the six chemicals, with EC50 of 62.40 mg/L and 69.22 mg