4'-podophyllotoxin demethyl deoxidated aromatic ester, substituted benzene sulfonate, ether derivative and use in plant source pesticide preparation

Abstract

The invention relates to a series of novel 4'-nordeoxypodophyllotoxin aromatic acid esters, substituted benzene sulfonates, and ether derivatives and application thereof in preparing a botanical insecticide. The 4'-nordeoxypodophyllotoxin aromatic acid esters, the substituted benzene sulfonates, and the ether derivatives have a general chemical formula shown at the right. An experiment proves that the 4'-nordeoxypodophyllotoxin aromatic acid esters, the substituted benzene sulfonates, and the ether derivatives are partially higher than podophyllotoxin and deoxypodophyllotoxin, wherein insecticidal activities of certain compounds are all higher than that of a botanical insecticide-toosendanin which has come into the market, and the compounds can be used for preparing the botanical insecticides with high-efficiency and low-toxicity.

Description

technical field The present invention relates to a series of 4'-nordeoxypodophyllotoxin compounds with insecticidal activity, in particular to 4'-nordeoxypodophyllotoxin aromatic esters, substituted benzenesulfonate esters and ether derivatives and the 4' -Application of nordeoxypodophyllotoxin aromatic ester, substituted benzenesulfonate and ether derivatives in the preparation of botanical pesticides. Background technique Deoxypodophyllotoxin is a plant secondary substance isolated from Cypress sativa, which has attracted much attention because of its antitumor activity. In recent years, it has been found that it has antifeedant, poisonous and growth inhibitory effects on various agricultural and forestry pests. The antitumor and insecticidal activities of deoxypodophyllotoxin and its derivatives have been reported in literature, such as: [Young-Jae You, Yong Kim, Nguyen-Hai Nam, Byung-Zun Ahn.Antitumor activity of unsaturated fatty acid esters of 4′ -demethyldeoxypodop...

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Problems solved by technology

The antitumor and insecticidal activities of deoxypodophyllotoxin and its derivatives have been reported in literature, such as: [Young-Jae You, Yong Kim, Nguyen-Hai Nam, Byung-Zun Ahn.Antitumor activity of unsaturated fatty acid esters of 4′ -demethyldeoxypodophyllotoxin[J].Bioorganic & Medicinal Chemistry Letters.2003,13:2629-2632.] and [Young-Jae You, Yong Kim, Nguyen-HaiNam, Byung-Zun Ahn, et al.Alkyl and carboxylalkyl esters of 4′- demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumoractivity [J]. European Journal of Medicinal Chemistry.2004, 39: 189-193.] reported the reaction of 4'-deoxypodophyllotoxin with unsaturated and saturated fatty acids The prepared derivatives have good anti-tumor activity in vitro; literature [Zhang Shougang, Hou Huamin, Gao Rong. The toxicity of deoxypodophyllotoxin to Periplaneta americana and the influence of several enzyme systems [J]. Acta Entomology, 2007, 50 (3): 248-252.] reported that deoxypodophyllotoxin has a strong poisonous activity against newly hatched nymphs of Periplaneta americana; Preliminary study on biological activity [J]. Northwest Agricultural Journal, 2005, 14(1): 94-97.] reported that deoxypodophyllotoxin has strong antifeedant activity on armyworm, and also inhibits its growth and development, resulting in growth All stages of development are delayed, pupation rate, eclosion rate, egg production, etc. are all significantly reduced

However, the synthesis of 4'-nordeoxypodophyllotoxin aromatic esters, substituted benzenesulfonate esters and ether derivatives and their insecticidal activity have not been reported.

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