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Synthesis of andrographolide-related esters as insecticidal and acaricidal agents
Authors:Xiaobo Huang  Bingchuan Zhang  Hui Xu
Institution:1. Research Institute of Pesticidal Design & Synthesis, College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China;2. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjing 300071, China;3. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi Province, China
Abstract:In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of andrographolide-related esters, such as 3,19-dialkyl(aryl)carbonyloxy andrographolide (3ag), 3-alkyl(aryl)carbonyloxyandrographolide (4ag), and 19-alkyl(aryl)carbonyloxyandrographolide (5ag), were prepared. Their structures were well characterized by 1H NMR, IR, optical rotation, HRMS and mp. Especially three-dimensional structures of compounds 3a, 4g, and 5g were unambiguously confirmed by single-crystal X-ray diffraction. Compounds 3a and 5a exhibited good insecticidal and acaricidal activities against Mythimna separata and Tetranychus cinnabarinus. Their structure-activity relationships were also discussed.
Keywords:Ester  Andrographolide  Natural-product-based  Insecticidal activity  Acaricidal activity
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