Design and Synthesis of Scopoletin Sulfonate Derivatives as Potential Insecticidal Agents
-
Published:2023-01-05
Issue:2
Volume:28
Page:530
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Liu Congmin,Zheng Panyuan,Wang Hongmei,Wei Yan,Wang Chuanping,Hao Shuanghong
Abstract
(1) Background: Scopoletin and scoparone, two naturally occurring coumarins, have garnered considerable attention and have been introduced to the market in China due to their high insecticidal efficacy and low toxicity. To investigate the structure–activity relationship of these coumarins, a series of scopoletin derivatives with aryl sulfate at C7 and different substitutes at C3 were designed and synthesized, and their insecticidal activity was studied. (2) Methods: A total of 28 new scopoletin derivatives were designed and synthesized. Most target compounds exhibited moderate insecticidal activity against the phytophagous mite Tetranychus cinnabarinus and the brine shrimp Artemia salina. (3) Results: Among these compounds, compounds 5a and 5j possessed the best insecticidal activities against T. cinnabarinus, with LC50 values of 57.0 and 20.0 μg/mL, respectively, whereas that of the control drug was 15.0 μg/mL. Compound 4j exhibited selective insecticidal activities against A. salina, with an LC50 value of 9.36 μg/mL, whereas its LC50 value against T. cinnabarinus was 93.0 μg/mL. The enzymatic inhibitory activity on acetylcholinesterase (AChE) showed a consistent tendency with the insecticidal activity. Further molecular docking analyses predicted the binding conformations of these compounds, which showed a good correlation between the insecticidal activity and the binding scores. (4) Conclusions: In general, a decreased electron cloud density of the Δ3,4 olefinic bond is beneficial for improving the insecticidal activity against both T. cinnabarinus and A. salina. In addition, naphthyl or benzene groups with a sulfate ester at the C7 position could further improve the insecticidal activity against A. salina. AChE was implied to be a site of action for potential insecticidal activity. The results provide insight into the rational design of a new generation of effective coumarin insecticides.
Funder
National Natural Science Foundation of China
Natural Science Foundation of Shandong Province of China
Qingdao Agricultural University Doctoral Start-Up Fund
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference33 articles.
1. Jeppson, R., Keifer, H.H., and Baker, E.W. (1975). Mites Injurious to Economic Plants, University of California Press.
2. Zhang, Q. (2003). Mites of Greenhouses: Identification, Biology and Control, CABI Publishing.
3. On the causes of mite pest outbreaks in mono- and poly-cultured moso bamboo forests;Zhang;J. Appl. Ecol.,2004
4. Management of spider mite Tetranychus cinnabarinus (Boisduval) (Tetranychidae) infestation in cotton by releasing the predatory mite Neoseiulus pseudolongispinosus (Xin, Liang and Ke) (Phytoseiidae);Sarwar;Biol. Control,2013
5. Control of the carmine spider mite Tetranychus cinnabarinus boisduval by the predatory mite Phytoseinlus persimilis (Athias-Henriot) in protected strawberries in Aydin, Turkey;Cakmak;Turk. J. Agric. For.,2005
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献