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2beta-chloropodophyllotoxin aromatic acid ester compounds, preparation and application in preparing botanical pesticide

A technology of chloropodophyllotoxins and aromatic acid esters, applied in the directions of plant growth regulators, applications, biocides, etc.

Inactive Publication Date: 2009-11-11
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of 2β-chloropodophyllotoxin derivatives and the research on their insecticidal activity have not been reported yet.

Method used

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  • 2beta-chloropodophyllotoxin aromatic acid ester compounds, preparation and application in preparing botanical pesticide
  • 2beta-chloropodophyllotoxin aromatic acid ester compounds, preparation and application in preparing botanical pesticide
  • 2beta-chloropodophyllotoxin aromatic acid ester compounds, preparation and application in preparing botanical pesticide

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Embodiment 1

[0026] 1. Products: 2β-chloropodophyllotoxin and compounds 1-8 The physical and chemical properties of each compound are introduced in detail in the following content.

[0027] 2. Preparation method:

[0028] The following is the synthetic route of 4-O-tetrahydropyranopodophyllotoxin:

[0029] Weigh 1 mmol of podophyllotoxin and dissolve it in 10 mL of dihydropyran, add dropwise 1 drop of phosphorus oxychloride, dissolve in a water bath at 60-63°C, stir the reaction at room temperature, and track and detect it by TLC. When the reaction is almost complete, the unreacted dihydropyran is evaporated to dryness under reduced pressure, and the pure product is obtained by silica gel column chromatography.

[0030]

[0031] Podophyllotoxin 4-O-tetrahydropyranopodophyllotoxin

[0032] The physical and chemical properties of 4-O-tetrahydropyranopodophyllotoxin are as follows:

[0033] 1), white solid, melting point 93-94°C.

[0034] 2), 4-O-tetrahydropyranopodophyllotoxin infrare...

Embodiment 2

[0147] Bioassay experiment of the present invention:

[0148] 1. Insects to be tested: armyworm larvae in the early 3rd instar, provided by the insect breeding room of the Pollution-free Pesticide Research Center of Northwest A&F University.

[0149] 2. Samples and reagents:

[0150] The samples are: toosendanin, podophyllotoxin, 4-O-tetrahydropyranopodophyllotoxin, 4-O-tetrahydropyrano-2β-chloropodophyllotoxin, 2β-chloropodophyllotoxin and examples 1 Compounds 1-8 prepared. The solvent was acetone, analytically pure, from Chengdu Kelong Chemical Reagent Factory.

[0151] 3. Bioassay method:

[0152] Using the method of adding small leaf butterfly: spread a layer of filter paper on the bottom of a petri dish with a diameter of 9 cm, and add water to moisturize it. Pick 10 3rd instar prophase armyworm larvae with the same size and robustness from each dish. Weigh 5 mg toosendanin, podophyllotoxin, 4-O-tetrahydropyranopodophyllotoxin, 4-O-tetrahydropyrano-2β-chloropodophyll...

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Abstract

The invention discloses a series of new 2beta-chloropodophyllotoxin aromatic acid ester compounds, a preparation method and application in preparing botanical pesticide by using the compounds. Chemical general formulas of the 2beta-chloropodophyllotoxin aromatic acid ester compounds are as figures. The series of compounds are prepared by using podophyllotoxin as a raw material, the material is prepared into 2beta-chloropodophyllotoxin through C-4 site hydroxy group protection, C-2 site beta-chloro substitution and C-4 site protection removal, and then the 2beta-chloropodophyllotoxin reacts with eight aromatic acids to form the 2beta-chloropodophyllotoxin aromatic acid ester compounds. Proved by experiments, the 2beta-chloropodophyllotoxin aromatic acid ester compounds of the invention have good insecticidal activities which are partially higher than that of podophyllotoxin, and the insecticidal activities of some compounds are higher than those of the prior commercial botanical pesticide toosendanin; and proved by the experiments, the compounds can be used for preparing the botanical pesticide with high efficiency and low toxicity.

Description

technical field [0001] The present invention relates to a series of 2β-chloropodophyllotoxin aromatic ester compounds with insecticidal activity, in particular to 2β-chloropodophyllotoxin aromatic ester compounds and their preparation methods, and their use in the preparation of botanical insecticides Applications. Background technique [0002] Podophyllotoxin is a plant secondary substance extracted and isolated from Cypress sativa. It has attracted much attention because of its anti-tumor, anti-virus, and anti-fungal activities, but it has serious side effects. In recent years, it has been found that it has antifeedant, poisonous and growth inhibitory effects on various agricultural and forestry pests. [0003] The antitumor and insecticidal activities of podophyllotoxin and its derivatives have been reported in literature, such as: [Margaret B.Glinski, James C.Freed, and Tony Durst.Preparation of 2-Substituted Podophyllotoxin Derivatives.The Journal of Organic Chemistry....

Claims

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Application Information

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IPC IPC(8): C07D493/04A01N43/90A01P7/00
Inventor 徐晖肖晓
Owner NORTHWEST A & F UNIV
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