4"-脱氧阿维菌素脲类及硫脲类衍生物的合成与杀虫活性

张娜; 成丕乐; 南祥; 吴小兵; 刘映前; 余海涛; 张健; 杨程杰; 胡冠芳

doi:10.16801/j.issn.1008-7303.2016.0080

4"-脱氧阿维菌素脲类及硫脲类衍生物的合成与杀虫活性

Synthesis and insecticidal activity of 4"-deoxy-abamectin urea and thioure analogues

摘要

摘要: 以构效关系为线索，根据类同合成法和活性官能团拼接策略，以阿维菌素为先导分子，在其4"-位引入硫脲或脲活性结构单元，合成了一系列酰基硫脲（9a~9o）和芳基脲（10a~10i）阿维菌素衍生物，所有目标化合物均经1H NMR、MS和元素分析确证。室内杀虫活性测定结果表明：所有衍生物对朱砂叶螨Tetranychus cinnabarinus和甘蓝蚜Brevicoryne brassicae均表现出不同程度的毒杀活性，大部分化合物对甘蓝蚜的杀虫活性优于阿维菌素B1a，其中化合物9h对朱砂叶螨和甘蓝蚜的LC50值分别为0.100和1.71 μmol/L，表现出很高的毒杀活性，化合物9o对甘蓝蚜的毒性最高，LC50值为1.13 μmol/L。

Abstract: Based on SAR investigation, two series of abamectin analogues containing urea and acyl thiourea groups were designed according to analog synthesis and sub-structure. Their structures were confirmed by 1H NMR, MS and elemental analysis. Their insecticidal activity was tested against Tetranychus cinnabarinus and Brevicoryne brassicae. All the tested compounds showed significant inhibitory activity against the above two insect species. Notably, the majority of those compounds exhibited high selectivity against B. brassicae, some of which were much better in comparison to abamectin. Especially, compound 9h displayed more potent activity than abamectin against the above two insect species, namely, T. cinnabarinus (LC50=0.100 μmol/L) and B. brassicae (LC50=1.71 μmol/L).Moreover, compound 9o showed superior activity against B. brassicae, with LC50 value of 1.13 μmol/L.

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