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Design, Synthesis and Evaluation of Novel Isoxazolines/Oxime Sulfonates of 2'(2',6')-(Di)Chloropodophyllotoxins as Insecticidal Agents.

ABSTRACT: A series of 2'(2',6')-(di)halogeno-isoxazolopodophyllic acids-based esters, and oxime sulfonates of 2'(2',6')-(di)halogenopodophyllones were prepared by structural modifications of podophyllotoxin as insecticidal agents against Mythimna separata Walker. It was found that when 2'(2',6')-(di)halogenopodophyllones or 2'(2',6')-(di)chloropicropodophyllones reacted with hydroxylamine hydrochloride, the desired products were related with the configuration of their lactones. Three key single-crystal structures of Ie, IIe and IIIb were determined by X-ray diffraction. Especially compounds IIc and Vc showed the highest insecticidal activity. Moreover, some interesting results of structure-insecticidal activity relationships of tested compounds were also observed.

SUBMITTER: Yu M

PROVIDER: S-EPMC5036094 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Design, Synthesis and Evaluation of Novel Isoxazolines/Oxime Sulfonates of 2'(2',6')-(Di)Chloropodophyllotoxins as Insecticidal Agents.

Yu Mingqiao M Liu Guangci G Zhang Yuanyuan Y Feng Tao T Xu Ming M Xu Hui H

Scientific reports 20160926

A series of 2'(2',6')-(di)halogeno-isoxazolopodophyllic acids-based esters, and oxime sulfonates of 2'(2',6')-(di)halogenopodophyllones were prepared by structural modifications of podophyllotoxin as insecticidal agents against Mythimna separata Walker. It was found that when 2'(2',6')-(di)halogenopodophyllones or 2'(2',6')-(di)chloropicropodophyllones reacted with hydroxylamine hydrochloride, the desired products were related with the configuration of their lactones. Three key single-crystal st ...[more]

PMID: 27667584

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