摘要
[目的]合成5-氟-7-烯丙基-8-羟基喹啉并测其农用生物活性。[方法]以4-氟苯酚为原料,经过醚化、Claisen重排,用发烟硝酸与乙酸酐硝化,用锌粉还原硝基,然后与丙烯醛反应得到产物。[结果]产物的1H NMR及红外分析与目标化合物一致;产物总收率为7.33%;产物对苹果腐烂病菌、棉花枯萎病菌、柑橘炭疽病菌、小麦全蚀病菌的EC50值分别为36.78、68.36、34.51、94.73 mg/L;质量浓度为100 mg/L时,对稗草、反枝苋的胚根、胚轴的抑制率均达到85%以上。[结论]以4-氟苯酚为原料进行醚化、重排、硝化还原、与丙烯醛反应来制备5-氟-7-烯丙基-8-羟基喹啉是一条可行的路线;产物具有良好的抑菌和除草活性。
[Aims] The purpose of this paper is to prepare 5-fluoro-7-allyl-8-hydroxyquinoline and to obtain its agricultural bioactivity. [Methods] The target compound was synthesized fi＇om 4-fluorophenol, via etherification, Claisen rearrangement, nitrification by fuming nitric acid and acetic anhydride, reduction by zinc, and the last reaction of aminophenol with acrolein. [Results] The chemical structure of the target compound was confirmed by ＇H NMR and IR analysis. The overall yield of 5-fluoro-7-allyl-8-hydroxyquinoline was 7.33%. The ECs0 values of the target compound against V. mall, F. oxysporium, C. gloeosporioides and G. graminis were 36.78, 68.36, 34.51, 94.73 mg/L, respectively. The inhibitory rates against the radical and hypocotyl ofEchinochloa crusgalli and Amaranthus retroflexus were all higher than 85% at 100 mg/L. [Conclusions] The preparation route using 4-fluorophenol as the raw material, via etherification, Claisen rearrangement, nitrification, reduction and reaction with acrolein final is feasible. The target compound showed good antifungal and herbicidal activities.
出处
《农药》
CAS
CSCD
北大核心
2015年第1期16-18,共3页
Agrochemicals
基金
山东省高校科技计划项目(J11LC21)
山东省优秀中青年科学家科研奖励基金项目(BS2009NY006)
青岛农业大学高层次人才基金项目(630714)
