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Fraxinellone acylhydrazone/hydrazone/ester derivatives and application in preparation of plant source insecticides

A technology of alkone acylhydrazone and derivatives, which is applied in the preparation of alkone acylhydrazone/hydrazone/ester derivatives and the application field in the preparation of botanical insecticides, which can solve the problems that have not been reported and achieve good antifeedant and poisonous activity

Inactive Publication Date: 2012-07-25
NORTHWEST A & F UNIV
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AI Technical Summary

Problems solved by technology

[0003] The anti-inflammatory, antibacterial, and insecticidal activities of alkalone have been reported in the literature, such as: [Yang Sun, Yu Qin, Qiang Xu, et al. Selective triggering of apoptosis of concanavalin A-activated T cells by fraxinellone for the treatment of T-cell-dependent hepatitis in mice. Biochemical Pharmacology 2009, 77, 1717-1724] reported that it can significantly improve cellular immune liver injury, and is expected to be applied in the treatment of various acute and chronic viral hepatitis; literature [Zhao Weimin, Wolfender J L, Hostettmann K, et al.Antifun-gal alkaloids and limonoid derivatives from Dictamnus dasycarpus[J].Phtochemistry, 1998,47(1):7-11.] and [Wang Mailing, Zhang Jiwen, Qian Yong, Li Junhao, Ji Zhiqin. Research on the bactericidal active components of Cortex Dictica. Pesticides. 2006, 45 (11), 739-741] reported that the active ingredient alkone in Cortex Dictica has certain bactericidal activity; literature [Liu Zhilong, Xu Yuanjian, Wu Jien, et al.Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects[J].Journary of Agriculture and Food Chemistry 2002,50:1447-1450.] and [Yuan Chunlan, Li Zongxiao. A new botanical insecticide Insecticidal activity of alkone. Plant Protection. 2005, 31 (5), 86-87.] reported that alkone has good biological activity against storage pests and third-instar armyworms, but the synthesis of alkone derivatives and Its research on insecticidal activity has not been reported yet

Method used

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  • Fraxinellone acylhydrazone/hydrazone/ester derivatives and application in preparation of plant source insecticides
  • Fraxinellone acylhydrazone/hydrazone/ester derivatives and application in preparation of plant source insecticides
  • Fraxinellone acylhydrazone/hydrazone/ester derivatives and application in preparation of plant source insecticides

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preparation example Construction

[0037] The following is the preparation method of alkone acylhydrazone / hydrazone / ester derivatives. The method uses alkone as a raw material through allylic oxidation and ketone aldehyde reduction to obtain alkone ketone, aldehyde and alcohol, and then respectively reacts with hydrazide and benzene Hydrazine and acid react to obtain a series of alkone acylhydrazone / hydrazone / ester derivatives.

[0038] Preparation of alkone acylhydrazone / hydrazone / ester derivatives 1-31:

[0039] After dissolving a certain amount of alkone ketone / aldehyde and corresponding hydrazide or phenylhydrazine with absolute ethanol, add two drops of glacial acetic acid dropwise, heat to reflux, TLC tracking detection, after the reaction is completed, concentrate and distill off the solvent before use Preparation of silica gel sheet to separate the desired pure product;

[0040] Or add N,N'-diisopropylcarbodiimide to a certain amount of alkone alcohol, carboxylic acid and an appropriate amount of 4-dim...

Embodiment 1

[0053] 1. Product: Ashenone Acylhydrazone / Hydrazone / Ester Derivatives 1-31 (See the following for details on the physical and chemical properties of each compound)

[0054] 2. Preparation method:

[0055] The following is the synthetic route of alkone ketone:

[0056] After dissolving a certain amount of chromium oxide, pyridine and tert-butyl hydroperoxide with dichloromethane, add equimolar alkone into the above reaction solution, and after reacting for about 8 hours, add a certain amount of dichloromethane to the reaction solution methane, followed by saturated NaHSO 3 and brine washing, anhydrous Na 2 SO 4 After drying and concentrating, the pure product of alkone ketone was obtained by separating on a preparative silica gel sheet.

[0057] The physical and chemical properties of alkone ketone are as follows:

[0058] 1), white solid, melting point 141-143°C.

[0059] 2), the infrared spectrogram (IR) characteristic of alkone ketone:

[0060] Using potassium bromide...

Embodiment 2

[0254] Embodiment 2: bioassay experiment:

[0255] 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.

[0256] 2. Samples and reagents:

[0257] The samples are: toosendanin, arketone, arketone aldehyde, arketone ketone and compounds 1-23 prepared in the examples.

[0258] The solvent was acetone, analytically pure, from Chengdu Kelong Chemical Reagent Factory.

[0259] 3. Bioassay method:

[0260] 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 of toosendanin, alkone, alkone aldehyde, alkone ketone, and compounds 1 to 23 prepared in Example 1 and add 5 ml of acetone to prepare a drug solution with a concentration of 1 mg / ml. ...

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Abstract

The invention relates to a series of novel fraxinellone acylhydrazone / hydrazone / ester derivatives. The fraxinellone acylhydrazone / hydrazone / ester derivatives have the chemical structures of a general formula as shown in the specification. The preparation method comprises the following steps of: carrying out allylic oxidation and ketoaldehyde reduction based on fraxinellone as a raw material to obtain fraxinellone ketone, aldehyde and alcohol; then respectively reacting with hydrazine, phenylhydrazine and acid to obtain the series of novel fraxinellone acylhydrazone / hydrazone / ester derivatives. Experiments show that the fraxinellone acylhydrazone / hydrazone / ester derivatives have good food refusal and poisoning activities on three-age armyworms, part of the activities are higher than those of fraxinellone, part of the insecticidal activity is higher than that of commercial plant source pesticide toosendanin, and the fraxinellone acylhydrazone / hydrazone / ester derivatives are expected to be used for preparing efficient, environment-friendly and low-toxic plant source insecticides.

Description

technical field [0001] The present invention relates to a series of alkone acylhydrazone / hydrazone / ester compounds with insecticidal activity, in particular to a preparation method of arketone acylhydrazone / hydrazone / ester derivatives, and the use of the series of derivatives in the preparation of botanical insecticides Applications. Background technique [0002] Dictamnus is a plant secondary metabolite extracted from the dry root bark of the Rutaceae plant Dictamnus dasycsrpus Turcz. It is favored for its anti-inflammatory, antibacterial, and insecticidal activities. Especially in terms of insecticidal activity, in recent years, many researchers have found that it has good antifeedant, poisonous and growth inhibitory effects on various pests. [0003] The anti-inflammatory, antibacterial and insecticidal activities of alkalone have been reported in the literature, such as: [Yang Sun, Yu Qin, Qiang Xu, et al. Selective triggering of apoptosis of concanavalin A-activated T ...

Claims

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Application Information

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IPC IPC(8): C07D307/88C07D405/14A01N43/12A01N43/40A01P7/04
Inventor 徐晖郭勇
Owner NORTHWEST A & F UNIV
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