Semisynthesis of Esters of Fraxinellone C4/10-Oxime and Their Pesticidal Activities

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• 作者：Qin Li ; Xiaobo Huang ; Shaochen Li ; Jingchun Ma ; Min Lv ; Hui Xu
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2016
• 出版时间：July 13, 2016
• 年：2016
• 卷：64
• 期：27
• 页码：5472-5478
• 全文大小：453K
• 年卷期：0
• ISSN：1520-5118

文摘

A total of 20 esters of fraxinellone C4/10-oxime were synthesized and determined by melting points, optical rotation, infrared spectra, proton nuclear magnetic resonance spectra, and high-resolution mass spectrometry spectra. Two steric configurations of compounds 7i and 8i were unambiguously confirmed by X-ray crystallography. Additionally, their pesticidal activities were assessed on two typical lepidopteran pests, Mythimna separata Walker and Plutella xylostella Linnaeus. Generally, all compounds exhibited less potent oral toxicity than toosendanin against third-instar larvae of P. xylostella. However, all compounds showed the growth inhibitory property against early third-instar larvae of M. separata. Notably, compounds 7m, 8b, 8k, 9, and 11 displayed more potent pesticidal activity than toosendanin. This demonstrated that introducing the C-4 carbonyl or oxime group on fraxinellone resulted in more promising derivatives than those bearing a C-10 carbonyl or oxime substituent.