School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou, People's Republic of China.
Department of Chemistry, University of Liverpool, Liverpool, UK.
Pest Manag Sci. 2020 Feb;76(2):636-644. doi: 10.1002/ps.5559. Epub 2019 Aug 27.
The use of safe and effective insecticides against mosquito-borne stocks is still one of the most effective ways to rapidly interrupt the spread of diseases such as malaria, dengue etc., but many insects are resistant to most insecticides and most of the traditional pyrethroids (like permethrin, deltamethrin etc.) contain phenoxy groups so it is easy to form dibenzofuran, a pollutant, after photodegradation. It is therefore necessary to synthesize novel pyrethroids which have better mosquito-killing activity, poor resistance to mosquitoes, and no dibenzofuran formation during photodegradation.
A series of novel dihaloacetylated heterocyclic pyrethroids were synthesized to enhance antimosquito activity. Bioassays based on the guidelines of the Chinese Center for Disease Control and Prevention (CDC) indicate that the synthesized compounds DCA-O (LC = 2.95 ± 0.05 μg L ), DCA-01 (LC = 5.83 ± 0.36 μg L ) and DCA-11 (LC = 5.79 ± 1.51 μg L ) exhibit high insecticidal activities and sensitivity against Aedes albopictus while deltamethrin and permethrin produced moderate levels of resistance. Moreover, the analysis of the photodegradation implies that the novel compounds synthesized by substituting a phenoxy group with a heterocyclic ring do not form dibenzofuran, a pollutant. Lastly, the cytotoxicity data of pyrethroids on human dopaminergic neuroblastoma SH-SY5Y cells confirm that the synthesized compounds have low toxicity for the cells.
Novel dihaloacetylated heterocyclic pyrethroids, made by simple synthesis steps, have better antimosquito activity, lower drug resistance, are less polluting to the environment and show low toxicity to human nerve cells. This also provides an effective idea for the synthesis of pyrethroids. Novel dihaloacetylated heterocyclic pyrethroids have better antimosquito activity, lower drug resistance, are less polluting to the environment, ahow low toxicity to human nerve cells and simple synthesis steps. © 2019 Society of Chemical Industry.
使用安全有效的杀虫剂来对抗蚊虫传播的疾病仍然是迅速阻断疟疾、登革热等疾病传播的最有效方法之一，但许多昆虫对大多数杀虫剂具有抗药性，而大多数传统拟除虫菊酯（如氯菊酯、溴氰菊酯等）都含有苯氧基团，因此在光降解后很容易形成二苯并呋喃这种污染物。因此，有必要合成新型的拟除虫菊酯，这些新型的拟除虫菊酯具有更好的杀虫活性、对蚊虫的抗药性差、光降解过程中不会形成二苯并呋喃。
为了提高抗蚊活性，我们合成了一系列新型的二卤乙酰基杂环拟除虫菊酯。基于中国疾病预防控制中心（CDC）指导方针进行的生物测定表明，所合成的化合物 DCA-O（LC 50 = 2.95 ± 0.05 μg/L）、DCA-01（LC 50 = 5.83 ± 0.36 μg/L）和 DCA-11（LC 50 = 5.79 ± 1.51 μg/L）对白纹伊蚊表现出高杀虫活性和敏感性，而氯菊酯和溴氰菊酯则产生了中度的抗药性。此外，光降解分析表明，用杂环取代苯氧基合成的新型化合物不会形成二苯并呋喃这种污染物。最后，对人多巴胺能神经母细胞瘤 SH-SY5Y 细胞的拟除虫菊酯细胞毒性数据证实，所合成的化合物对细胞的毒性较低。
通过简单的合成步骤合成的新型二卤乙酰基杂环拟除虫菊酯具有更好的抗蚊活性、更低的抗药性、对环境的污染更小、对人神经细胞的毒性更低。这也为拟除虫菊酯的合成提供了有效的思路。新型二卤乙酰基杂环拟除虫菊酯具有更好的抗蚊活性、更低的抗药性、对环境的污染更小、对人神经细胞的毒性更低，并且合成步骤简单。 © 2019 化学工业协会。
