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Piperine hydrazone or acylhydrazone or sulfonyl hydrazone derivative substances and application for preparing a botanical insecticide

A technology of piperine hydrazone and sulfonyl hydrazone, which is applied in the direction of pesticides, plant growth regulators, applications, etc., and can solve the problems that the activity of piperine and its derivatives has not been reported.

Inactive Publication Date: 2013-06-05
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In view of this, piperine and its derivatives, in addition to the research on enzyme activity inhibition, anti-oxidation, anti-tumor, etc., are also used in protozoa Trypanosoma cruzi and Lehmania donovani, insect Culex larvae and Spodoptera frugiperda. There are certain studies on the poisonous activity of piperine and its derivatives, but the activity of piperine and its derivatives in antifeedant and poisonous killing of armyworms has not been reported, so the piperine hydrazones / acylhydrazones / sulfonyl hydrazone derivatives The synthesis and its research on antifeedant and poisonous activity of armyworm have strong novelty

Method used

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  • Piperine hydrazone or acylhydrazone or sulfonyl hydrazone derivative substances and application for preparing a botanical insecticide
  • Piperine hydrazone or acylhydrazone or sulfonyl hydrazone derivative substances and application for preparing a botanical insecticide
  • Piperine hydrazone or acylhydrazone or sulfonyl hydrazone derivative substances and application for preparing a botanical insecticide

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Experimental program
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Embodiment 1

[0032] 1. Products: piperine acid, piperine ester, piperine alcohol, piperine aldehyde and compound 1-33 (see the following content for details on the physical and chemical properties of each compound)

[0033] 2. Preparation method:

[0034] The following is the synthetic route of piperine acid:

[0035] Dissolve a certain amount of potassium hydroxide in 95% ethanol, then add piperine to the above reaction solution, reflux in an oil bath for a certain period of time, cool and filter at room temperature to obtain a solid, dissolve it in a certain amount of water, and adjust the pH with hydrochloric acid The value is acidic, suction filtered, the filter cake is washed with a small amount of water and dried to obtain the desired pure product.

[0036]

[0037] Physical and chemical properties of piperine acid:

[0038] 1), yellow solid, melting point 218°C.

[0039] 2) Mass spectrometry (ESI-MS) characteristics of piperine acid:

[0040] Using electrospray ionization: m / ...

Embodiment 2

[0231] Embodiment 2: bioassay experiment

[0232] 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.

[0233] 2. Samples and reagents:

[0234] The samples are: toosendanin, piperine acid, piperine ester, piperine alcohol, piperine aldehyde and compound 1-33 prepared in the examples. The solvent was acetone, analytically pure, from Chengdu Kelong Chemical Reagent Factory.

[0235] 3. Bioassay method:

[0236] 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, piperine acid, piperine ester, piperine alcohol, piperine aldehyde and compound 1-33 prepared in the examples and add 5 ml of acetone to prepare a drug solut...

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Abstract

The invention relates to piperine hydrazone, acylhydrazone or sulfonyl hydrazone derivative substances and application for preparing a botanical insecticide. The piperine hydrazone, acylhydrazone or sulfonyl hydrazone derivative substance takes the piperine hydrazone as raw materials, piperine aldehyde is obtained by means of hydrolysis, esterification, reduction and oxidation, and the piperine aldehyde is respectively reacted with replaced phenylhydrazine, the acylhydrazone and sulfonyl hydrazide. The structural formula is shown as follows. The experiment shows that the piperine hydrazone, or the acylhydrazone or the sulfonyl hydrazone derivative substances has the advantages of having good antifeedant and insecticidal activity, partly exceeds the parent piperine, wherein the insecticidal activity of some components is higher than the commercialized botanical pesticide toosendanin, and therefore the piperine hydrazone, or the acylhydrazone or the sulfonyl hydrazone derivative substances is expected to be used for preparing high-efficient, environment-friendly and low-toxic botanical insecticides.

Description

technical field [0001] The invention relates to a series of piperine hydrazone / acylhydrazone / sulfonyl hydrazone compounds with insecticidal activity, in particular to piperine hydrazone / acylhydrazone / sulfonyl hydrazone derivatives and their application for preparing plant-derived insecticides. Background technique [0002] Piperine is an amide derivative alkaloid in the piperaceae (Piperaceae) plant of the genus Piper. focus of research. [0003] In the existing literature, some studies have been done on the inhibition of enzyme activity, anti-oxidation, anti-tumor, and insecticide of piperine and its derivatives: for example: [0004] Document [Li-Hua Mu, Bo Wang, Hao-Yang Ren, et al.Synthesis and inhibitory effect of piperine derives on monoamine oxidase. Bioorganic & Medicinal Chemistry Letters.2012, 22, 3343-3348.] reported piperine and its synthetic amide, Ester derivatives have the effect of selectively inhibiting monoamine oxidase (MAO) A and B in vitro and [Surrind...

Claims

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Application Information

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IPC IPC(8): C07D317/58C07D405/12C07D409/12A01N43/30A01N43/40A01N51/00A01P7/04
Inventor 徐晖屈欢
Owner NORTHWEST A & F UNIV
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