Iodine-catalyzed oxidative cyclisation for the synthesis of sarisan analogues containing 1,3,4-oxadiazole as insecticidal agents
Iodine-catalyzed oxidative cyclisation for the synthesis of sarisan analogues containing 1,3,4-oxadiazole as insecticidal agents
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碘催化氧化环化合成含 1,3,4-恶二唑杀虫剂的 sarisan 类似物
DOI：
10.1039/c6ra22343e
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发表时间：
2016-01-01
期刊：
影响因子：
3.9
通讯作者：
Zhang, Yanbing
中科院分区：
文献类型：
--
作者：
Guo, Yong;Qu, Lailiang;Zhang, Yanbing
为了继续我们的研究，旨在发现和开发基于天然产物的杀虫剂，通过碘催化的氧化环化反应制备了一系列含有1，3，4-恶二唑的新型纱丽散类似物，作为1 mg mL−1体内抗前三代粘虫步行者的杀虫剂。化合物8 r、8 t、8 k和8 q表现出较好的杀虫活性，与商品杀虫剂沙林和川楝素相比，最终死亡率> 60%。以碘为催化剂，碳酸钾为碱，合成了含1，3，4-恶二唑的沙里散类似物。结果表明，在1，3，4-恶二唑环的C-3位上引入氟苯基或4-氰基苯基单元可以得到更有效的化合物。此外，在1，3，4-恶二唑环的C-3位上引入杂芳基片段对杀虫活性非常关键。
In continuation of our research aimed at the discovery and development of natural products-based insecticidal agents, a series of novel sarisan analogues containing 1,3,4-oxadiazole through iodine-catalyzed oxidative cyclisation were prepared as insecticidal agents against the pre-third Mythimna separata Walker at 1 mg mL−1 in vivo. Compound 8r, 8t, 8k and 8q exhibited more promising insecticidal activities with final mortality rates of >60%, when compared with sarisan and toosendanin (a commercial insecticide). An efficient way using iodine as the catalyst and K2CO3 as base for the synthesis sarisan analogues containing 1,3,4-oxadiazole was developed. The results revealed that introduction of fluorophenyl or 4-cyanophenyl units on the 1,3,4-oxadiazole ring at the C-3 position of sarisan could afford more potent compounds. Moreover, introduction of heteroaromatic fragments on the 1,3,4-oxadiazole ring at the C-3 position of sarisan was very crucial for the insecticidal activity.