5-氟-7-烯丙基-8-羟基喹啉的合成及生物活性测定

Synthesis and Agricultural Bioactivity of 5-Fluoro-7-allyl-8-hydroxyquinoline

[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.