Natural Products-Based Insecticidal Agents 1. Semisynthesis and Insecticidal Activity of 4β-Benzenesulfonamide Derivatives of Podophyllotoxin against Mythimna separata Walker
Hui Xu, Lei Zhang, Baofeng Su, Xing Zhang, Xuan Tian
Abstract
Hui Xu, Lei Zhang, Baofeng Su, Xing Zhang, Xuan Tian
Abstract
Eleven 4 beta-benzenesulfonamide derivatives of podophyllotoxin were synthesized and evaluated for insecticidal activity against the third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. All derivatives showed delayed insecticidal activity, which was different from the traditional neurotoxic insecticides. Compounds 4a-4f and 4i-4k were found to be more potent than podopyllotoxin in the mortality rate after 20 d against M separata. Especially compounds 4i, the corresponding final mortality rate of which was 88.9%, exhibited more potent insecticidal activity than toosendandin (81.4%), a commercial insecticide derived from Melia azedarach. Furthermore, some preliminary qualitative structure-activity relationships were also observed.
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Eleven 4 beta-benzenesulfonamide derivatives of podophyllotoxin were synthesized and evaluated for insecticidal activity against the third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. All derivatives showed delayed insecticidal activity, which was different from the traditional neurotoxic insecticides. Compounds 4a-4f and 4i-4k were found to be more potent than podopyllotoxin in the mortality rate after 20 d against M separata. Especially compounds 4i, the corresponding final mortality rate of which was 88.9%, exhibited more potent insecticidal activity than toosendandin (81.4%), a commercial insecticide derived from Melia azedarach. Furthermore, some preliminary qualitative structure-activity relationships were also observed.
Key concepts: Mythimna separata, Semisynthesis, Podophyllotoxin, Chemistry, Natural product, Stereochemistry, Organic chemistry, Botany