辣椒碱类似物的合成及杀虫活性

Synthesis and insecticidal activity of capsaicin analogues

基于辣椒碱结构,以取代苄胺为原料,经N-酰化反应合成了6个系列204个辣椒碱类似物,其中8个为新化合物。通过核磁共振氢谱(1H NMR)对化合物的结构进行了确证。采用叶碟法测定了目标化合物的杀虫活性。结果表明:大部分化合物在10μg/片下对供试的3龄东方黏虫Mythimna separata有较强的毒杀活性,其中化合物A30、D20、D30、D35、E30和F3048 h的致死率达100%,化合物D19、D21、D22、D23、D31和E3148 h的致死率在90%以上。初步构效关系表明,苄胺苯环上氟原子单取代衍生物的杀虫活性优于氟原子双取代衍生物,其中以2-氟苄胺衍生物(D系列)杀虫活性较好;此外,酰基为2-噻吩甲酰时的杀虫活性明显优于其他取代基,表明酰基对该类化合物的杀虫活性也有显著影响。

Using capsaicin as the lead compound,six series of 204 analogues,including 8 new compounds,were synthesized via N-acylation reactions using substituted benzylamines as precusors.The title compounds were characterized by 1 H NMR.Insecticidal activities of those compounds were determined by the leaf dish method.The results showed that most of the benzylamine derivatives had strong toxicities against the 3 rd Mythimna separata.The mortality rates of compounds A30,D20,D30,D35,E30 and F30 were 100%and compounds D19,D21,D22,D23,D31 and E31 were more than 90%against the 3 rd larvae at 10μg/disc after 48 h.The preliminary study of structure-activity relationship indicated that the insecticidal activity of the mono-fluorine substitution on the benzene ring of benzylamine was better than that of the correspounding difluorine substituend compound.The2-fluorobenzylamine derivatives showed better insecticidal activities than others.Additionally,2-thiopheneformyl derivative exhibited significant insecticidal activity,which indicated that the acyl group was also an active fragment.