新型肉桂醛衍生物的设计合成与抗虫活性研究

Design,synthesis and anti-insect activity of novel cinnamaldehyde derivatives

目的发现具有杀虫、驱虫活性的新型肉桂醛衍生物。方法以肉桂醛和蚜虫报警信息素(反)-β-法尼烯(EβF)的基本母核为基础,采用骨架迁跃原理设计、合成了一类2,5-二取代肉桂醛衍生物,并测定其对棉铃虫、大豆蚜虫和粉尘螨的毒杀活性,以及对蚜虫的驱避活性。结果通过1H-NMR、FTIR和ESI-HRMS表征了目标化合物的结构;杀虫活性实验表明目标化合物对棉铃虫、大豆蚜虫和粉尘螨都具有一定的毒杀作用,500 mg/L剂量下对害虫的致死率为53.4%~92.1%,其中杀虫活性最强的为2-氯-5-硝基肉桂醛(化合物4);蚜虫行为实验表明,在2 mg/L剂量时,2-甲基-5-异丙基肉桂醛(化合物5)及2-甲基-4-甲氧基-5-异丙基肉桂醛(化合物6)具有一定的蚜虫驱避活性。结论2-甲基-5-异丙基肉桂醛及其结构类似物同时具有较好的杀虫活性。2位和5位的取代基变为硝基或卤素后,杀虫活性提高,但蚜虫驱避活性下降。

Objective To discover the novel cinnamaldehyde derivatives with insecticidal and repellent activities.Methods Based on the frameworks of cinnamaldehyde and(E)-β-farnesene(EβF),a series of 2,5-disubstituted cinnamaldehyde derivatives were designed and synthesized by scaffold-hopping approach.The insecticidal activities of target compounds against Helicoverpa armigera,Aphis glycines and Dermatophagoides farinae were determined,and the repellent activities to Aphis glycines were tested.Results The structures of target compounds were characterized through 1H-NMR,FTIR and ESI-HRMS.The insecticidal activity test showed that all the cinnamaldehyde derivatives held some toxic effect on Helicoverpa armigera,Dermatophagoides farinae and Aphis glycines.The death rates of tested insects at 500 mg/L were between 53.4% and 92.1%,and 2-chloro-5-nitrocinnamaldehyde(compound 4)possessed the strongest insecticidal activity.Behavior experiment results indicated that 2-methyl-5-isopropylcinnamaldehyde(compound 5)and 2-methyl-4-methoxy-5-isopropylcinnamaldehyde(compound 6)at the dosage of 2 mg/L displayed some aphid repellent activities.Conclusion 2-methyl-5-isopropylcinnamaldehyde and its structural analogues owned favorable insecticidal activities.And when the 2-and 5-site substituents were converted to nitro or halogen,the insecticidal activity increased,but the aphid repellent activity decreased.