期刊
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 63, 期 30, 页码 6668-6674出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.5b02036
关键词
podophyllotoxin; oxime sulfonate; insecticidal activity; natural-product-based insecticide; structural modification; Mythimna separata Walker
资金
- Special Funds of Central Colleges Basic Scientific Research Operating Expenses [2452015096]
- National Natural Science Foundation of China [31071737]
To discover novel natural-product-based pesticidal agents, we prepared a series of oxime sulfonate derivatives of 2'(2',6')-(Di)chloropicropodophyllotoxins by structural modification of podophyllotoxin. Their structures were well-characterized by proton nuclear magnetic resonance (H-1 NMR), high-resolution mass spectrometry (HRMS), optical rotation, and melting point. Moreover, the key steric structure of compound 5f was unambiguously determined by single-crystal X-ray diffraction. Additionally, their insecticidal activity was evaluated at 1 mg/mL against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran pest. Among all derivatives, compounds 4c, 5c, and 5d exhibited more promising insecticidal activity, with the final mortality rates greater than 60%, when compared to their precursor podophyllotoxin and the positive control, toosendanin. It demonstrated that introduction of the chlorine atom at the C-2' or C-2',6' position on the E ring of picropodophyllotoxin or oxime sulfonate derivatives of picropodophyllotoxin was important for the insecticidal activity and introduction of a halogen (e.g., fluorine, chlorine, or bromine) atom-substituted phenylsulfonyl group on the oxime fragment of 2'(2',6')-(di)chloropicropodophyllones could lead to more promising compounds.
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