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手性新烟碱类杀虫剂类似物的合成与杀虫活性评价: Laurel 萎蔫病案例。

Synthesis and Insecticidal Evaluation of Chiral Neonicotinoids Analogs: The Laurel Wilt Case.

机构信息

Instituto de Ecología, A.C., Red de Estudios Moleculares Avanzados, Clúster Científico y Tecnológico BioMimic®, Campus III, Carretera Antigua a Coatepec No. 351, Xalapa 91073, Mexico.

Cátedra CONACyT en el Instituto de Ecología, A.C. Carretera Antigua a Coatepec No. 351, Xalapa 91073, Mexico.

出版信息

Molecules. 2021 Jul 12;26(14):4225. doi: 10.3390/molecules26144225.

DOI:10.3390/molecules26144225
PMID:34299501
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8307524/
Abstract

sp beetles are types of ambrosia beetles invasive to the United States and recently also to Mexico. The beetle can carry a fungus responsible for the Laurel Wilt, a vascular lethal disease that can host over 300 tree species, including redbay and avocado. This problem has a great economic and environmental impact. Indeed, synthetic chemists have recently attempted to develop new neonicotinoids. This is also due to severe drug resistance to "classic" insecticides. In this research, a series of neonicotinoids analogs were synthesized, characterized, and evaluated against sp. Most of the target compounds showed good to excellent insecticidal activity. Generally, the cyclic compounds also showed better activity in comparison with open-chain compounds. Compounds -, , -, and showed a mortality percent of up to 73% after 12 h of exposure. These results highlight the enantioenriched compounds with absolute configuration. The docking results correlated with experimental data which showed both cation-π interactions in relation to the aromatic ring and hydrogen bonds between the search cavity 3C79 and the novel molecules. The results suggest that these sorts of interactions are responsible for high insecticidal activity.

摘要

sp 甲虫是入侵美国、最近也入侵墨西哥的天牛的一种。这种甲虫可以携带一种真菌,这种真菌是造成 Laurel 枯萎病的原因, Laurel 枯萎病是一种血管性致命疾病,可以寄生在包括红 bay 和鳄梨在内的 300 多种树种上。这个问题对经济和环境都有很大的影响。事实上,合成化学家最近试图开发新的烟碱类杀虫剂。这也是由于对“经典”杀虫剂的严重抗药性。在这项研究中,合成、表征了一系列新烟碱类杀虫剂类似物,并对 sp 进行了评价。大多数目标化合物表现出良好到优异的杀虫活性。一般来说,与开链化合物相比,环状化合物的活性更好。化合物 - 、 - 、 - 和 - 在暴露 12 小时后表现出高达 73%的死亡率。这些结果突出了具有绝对构型的对映体富集化合物。对接结果与实验数据相关,实验数据表明,芳香环与阳离子-π 相互作用以及搜索腔 3C79 与新分子之间的氢键都与实验数据相关。结果表明,这些相互作用是高杀虫活性的原因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/8940577e08b9/molecules-26-04225-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/45151057ccce/molecules-26-04225-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/3e4aeb7c7253/molecules-26-04225-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/2b9872e4ea5d/molecules-26-04225-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/6c7abe354a87/molecules-26-04225-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/15ba56f84fc4/molecules-26-04225-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/5f8fc42f0061/molecules-26-04225-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/fd7c8991f32c/molecules-26-04225-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/e968e63e6842/molecules-26-04225-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/8611b7f28c26/molecules-26-04225-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/87a3a692abf2/molecules-26-04225-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/3a8aefab1613/molecules-26-04225-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/316ae02ead13/molecules-26-04225-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/6bc8e0deb562/molecules-26-04225-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/8940577e08b9/molecules-26-04225-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/45151057ccce/molecules-26-04225-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/3e4aeb7c7253/molecules-26-04225-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/2b9872e4ea5d/molecules-26-04225-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/6c7abe354a87/molecules-26-04225-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/15ba56f84fc4/molecules-26-04225-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/5f8fc42f0061/molecules-26-04225-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/fd7c8991f32c/molecules-26-04225-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/e968e63e6842/molecules-26-04225-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/8611b7f28c26/molecules-26-04225-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/87a3a692abf2/molecules-26-04225-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/3a8aefab1613/molecules-26-04225-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/316ae02ead13/molecules-26-04225-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/6bc8e0deb562/molecules-26-04225-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f7d/8307524/8940577e08b9/molecules-26-04225-g007.jpg

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