多杀菌素C-9不同糖基衍生物的合成及杀虫活性分析

Synthesis and insecticidal activity of different aglycones derivatives of spinosad C-9

【目的】寻找具有更高杀虫活性的新型多杀菌素衍生物。【方法】以盐酸水解获得的多杀菌素C-9假糖苷配基为受体，以3种单糖（D-葡萄糖、D-半乳糖、L-鼠李糖）为供体，采用三氯乙酰亚胺法进行糖苷化反应得到C-9位不同糖基大环内酯类衍生物；用核磁共振谱（1HNMR、13C-NMR），MS和IR对所合成衍生物进行表征，并分别测定所合成衍生物的杀虫活性。【结1H-NMR、13C-NMR、MS和IR谱图分析表明，新合成的3种多杀菌素衍生物分别为9-0-（β-D-吡喃葡萄糖）多杀菌素衍生物、9-0-（β-D-吡喃半乳糖）多杀菌素衍生物、9-0（β-L-吡喃鼠李糖）多杀菌素衍生物；杀虫活性测定表明，3种新型多杀菌素衍生物在20mg／L剂量下对锯谷盗、赤拟谷盗、米蛾等均表现出一定的杀虫活性，致死率为31％-9％。【结论】新合成的多杀菌素衍生物均具有一定的杀虫活性，其构效关系还具有进一步研究的价值。

[Objective] The purpose of this study was to synthesize spinosad with better insecticidal ac- tivity. [Method] Using C-9 aglycone as receptor and three monosaccharaides （D-gluclse, D-galactose, and L-rhamnose） as donor, different aglycones derivatives of spinosad C-9 were synthesized using trichloro- acetimidate method. All compounds were confirmed by 1 H-NMR,13 C-NMR, MS and IR and their insecticid- al activities were determined. [Result] Spectra analysis with 1H NMR,13 C-NMR, MS and IR confirmed that the new synthesized three derivatives were 9-0 （β-D-pyran glucose）,9-0-（β-D-pyran galactose）,and 9- 0-（O-L-pyran rat lee sugar）. The new compounds exhibited intertidal activities against Oryzaephilus suri- namensis, TriboZium castaneum （Herbst）, Corcyra celhalonica at concentration of 20 mg/L, and the lethal- ity was 31%--59%. [Conclusion] The compounds synthesized in this study had good insecticidal activity and the structure activity relationship should be further studied.