Synthesis and insecticidal activity of new deoxypodophyllotoxin derivatives modified in the D-ring |
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Institution: | 1. Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, 1 Weigang, Nanjing 210095, China;2. Institute of Plant Protection, Jiangsu Academy of Agricultural Sciences, 50 St. Zhongling, Nanjing 210014, China |
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Abstract: | In continuation of our program aimed at the discovery of new natural-product-based insecticidal agents, twenty-six deoxypodophyllotoxin derivatives modified in the D-ring were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The configuration of three compounds 3, 4, and IIIi was unambiguously determined by single-crystal X-ray diffraction. It demonstrated that aminolysis of deoxypodophyllotoxin in the presence of pyrrolidine and piperidine could result in complete inversion of the configuration of the carbonyl group at its C-2 position. Five compounds IIa, IIi–k, and IIIh showed the equal or higher insecticidal activity than toosendanin. Especially IIj displayed the most potent insecticidal activity with the final mortality rate of 65.5%. |
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Keywords: | Deoxypodophyllotoxin Insecticidal activity Natural-product-based insecticide Structural modification |
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