4β-卤代-4-脱氧鬼臼毒素和4β-氨基-4-脱氧鬼臼 毒素的合成及其拒食活性

为研究鬼臼毒素类化合物结构与杀虫活性的关系,设计合成了3个4β-卤代- 4-脱氧鬼臼毒素和4个4β-氨基- 4-脱氧鬼臼毒素类化合物,通过IR、MS、1H NMR和元素分析对其结构进行了确证。采用小叶碟添加法测试了合成化合物对3龄粘虫Mythimna separate幼虫24 h和48 h的拒食活性,结果表明: 4β-卤代- 4-脱氧鬼臼毒素类化合物的活性相对高于氨基取代产物、母体化合物鬼 臼毒素和对照品脱氧鬼臼毒素, 其中4β-溴代- 4-脱氧鬼臼毒素活性最高,其对粘虫幼虫24 h和48 h 的 AFC50分别为280.8和392.9 mg/L,分别是母体化合物鬼臼毒素的3.43和 1.90 倍,是对照品脱氧鬼臼毒素的2.46和1.57倍; 4β位引入氨基活性降低, 4β-叠氮衍生物的活性最低。

Synthesis and Antifeedant Activity of 4β-Halogenated- 4-deoxypodophyllotoxin and 4β-Amino-4-deoxypodophyllotoxin

Three 4β-halogenated- 4-deoxypodophyllotoxin and four 4β-amino- 4-deoxypodophyllotoxin analogues were synthesized, and their structures were confirmed by IR, MS, 1H NMR and elemental analysis. The 24 h and 48 h antifeedant activities against the 3rd larvae of Mythimna separate were assayed with leaf-disk method. The bioassay results showed that the activity of 4β-halogenated- 4-deoxypodophyllotoxin analogues were higher than its amino ones, podophyllotoxin(PPT) and control compounds deoxypodophyllotoxin(DPPT). The 4β-Br- 4-deoxypodophyllotoxin exhibited the highest vatives activity among synthesized compounds,and its 24 h and 48 h AFC50(concentration for 50% antifeedant activity) were 280.8 mg/L and 392.9 mg/L,3.43 and 1.90 times of PPT, 2.46 and 1.57 times of DPPT, respectively. The activities of 4β-amino derivatives were decreased,and 4β-N3 - 4-deoxypodophyllotoxin was the lowest one among them.