Chinese Journal of Organic Chemistry >
Design, Synthesis and Bioactivity Study on Novel Furan α-Butenolactone Compounds
Received date: 2022-06-08
Revised date: 2022-08-01
Online published: 2022-09-09
Supported by
National Natural Science Foundation of China(31972289)
In recent years, the widespread use of neonicotinoid insecticides caused the resistance of pests to gradually become stronger, especially more and more attention on the toxic effect on bees. Therefore, it is urgent to design and synthesize novel eco-friendly alternatives to neonicotinoid insecticides. In our previous study, a novel furan α-butenolactone skeleton was found to have aphicidal activity based on the structrue similariy searching strategy to the butenolide pharmacophore from the low-bee toxicity commercial insecticide flupyradifurone. In this work, a series of novel furan α-butenolactone compounds were designed and synthesized combined the characteristics of nicotinic acetylcholine receptor protein and empirical design method. The bioassay results at the concentration of 500 μg/mL showed that all target compounds exhibited some aphicidal activity against soybean aphid and peach aphid. Especially, (E)-3-((5-(3-chlorophenyl)furan-2-yl)methylene)-5-methylfuran-2(3H)- one (7bh) and (E)-3-((5-ethylfuran-2-yl)methylene)-5-(p-tolyl)furan-2(3H)-one (7ch) were found to be more than 70% with a mortality rate against not only soybean aphid but also peach aphid. Furthermore, the insecticidal activities of 7bh were the same order of magnitude with pymetrozine against soybean aphid (LC50=70.83 μg/mL) and green peach aphid (LC50=71.96 μg/mL). To our surprised, these target compounds also showed certain antifungal activity in vitro against Rhizoctonia solani at the concentration of 50 μg/mL. Molecular docking studies indicated that the furan α-butenolactone compounds displayed moderate aphicidal activity due to their similar interaction with flupyradifurone toward nicotinic acetylcholine receptor. The study on new furan α-butenolactone compounds will lay a foundation for the development of new aphicidal candidates with high efficiency and low bee-toxicity in the future.
Xiang Li , Kai Zhu , Qing Han , Xingxing Lu , Mingjun Li , Yun Ling , Hongxia Duan . Design, Synthesis and Bioactivity Study on Novel Furan α-Butenolactone Compounds[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 202 -213 . DOI: 10.6023/cjoc202206010
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