4,5-二氟-2-羟基苯丁酮的合成及生物活性测定  

Synthesis and Agricultural Bioactivity of 4,5-Difluoro-2-hydroxy Butyrophenone

作　　者：辛风丽[1] 杜春华[1] 成光辉[1] 

机构地区：[1]青岛农业大学化学与药学院,山东青岛266109

出　　处：《农药》2013年第6期405-407,共3页Agrochemicals

基　　金：山东省优秀中青年科学家科研奖励基金项目(KCCX1-SW-22);山东高校科技计划资助项目(J11LC21)

摘　　要：[目的]合成4,5-二氟-2-羟基苯丁酮并测其农用生物活性。[方法]以3,4-二氟苯酚为原料,与乙酰氯反应成酯以保护酚羟基、以丁酰氯为酰化剂进行傅-克酰基化反应、脱保护得目标产物;以菌丝生长速率法测抑菌活性;以琼脂混药法测除草活性。[结果]产物的1H NMR及质谱分析与目标化合物一致;以无水三氯化铝为催化剂,实施丁酰化过程中可直接得到目标化合物,反应的总收率为67.07%;对苹果腐烂病菌、白菜灰霉病菌、柑橘炭疽病菌的EC50值分别为74.37、100.18、102.77 mg/L;质量浓度为200 mg/L时,对生菜、稗草、反枝苋的根与茎的抑制率均达到60%以上。[结论]以3,4-二氟苯酚为原料进行酚羟基酯化保护,然后以无水三氯化铝为催化剂与正丁酰氯反应不需另外的脱保护过程来制备4,5-二氟-2-羟基苯丁酮是一条高效路线;目标化合物具有较好的抑菌和除草活性。[Aims] The chief aim is to prepare 4,5-difluoro-2-hydroxy butyrophenone and obtain the agricultural bioactivity of the target compound. [Methods] Using 3,4-difluorophenol as the raw material, the processes of forming ester with acetyl chloride to protect phenol hydroxyl, Friedel-Crafts acylation with n-butyryl chloride, and de-esterification, provide the target compound. The mycelium growth rate test was used to investigate the inhibition effects of the compound on plant pathogenic fungi. The method of agar（PPA） mixed with test pesticide was employed to evaluate the herbicidal activity. [Results] The ＇H NMR analysis and MS analysis of the product are consistent with the target compound. Using anhydrous aluminium trichloride as a catalyst, the step of Friedel-Crafts acylation can also fulfill de-esterification. The overall yield of 4,5-difluoro-2-hydroxy butyrophenone was 67.07%. The EC^0 values of the target compound against Valsa marl, Botrytis cinerea and Citzusanthrax bacteria were 74.37, 100.18 and 102.77 mg/L respectively. The inhibitory rates of compound against the root and stem of Lactuca sadva, Amazanthus retroflexus and CoIletotrichum gloeosporioides were all higher than 60% at 200 mg/L. [Conclusions] Using 3,4-difluorophenol as raw material, the processes of forming ester with acetyl chloride to protect phenol hydroxyl, acylation with n-butyryl chloride catalyzed by anhydrous aluminium trichloride, can efficiently provide 4,5-difluoro-2-hydroxy butyrophenone without additional de-esterification step. The target compound shows potent antifungal and herbicidal activities.

关 键 词：4 5-二氟-2-羟基苯丁酮 合成 抑菌活性 除草活性 脱保护 

分 类 号：TQ450.7[化学工程—农药化工]