Volution lactone compound and synthesis method and application thereof

A technology of ester compounds and compounds, which is applied in the field of pesticides and achieves the effects of long lasting effect, good acaricidal effect and low toxicity

Inactive Publication Date: 2017-02-22
山东东方农药科技实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nowadays, the market development has higher and higher requirements for the comprehensive quality of pesticides. It is a rare product in the modern pesticide market that can simultaneously have three effects: good insecticidal effect, long-lasting effect, and low toxicity.

Method used

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  • Volution lactone compound and synthesis method and application thereof
  • Volution lactone compound and synthesis method and application thereof
  • Volution lactone compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment one: a kind of spirolide compound provided by the present invention, its chemical structural formula is:

[0031]

[0032] The method for preparing the above-mentioned compound comprises the following steps, (1) using cyclopentanone as a raw material, after carrying out cyanohydrinization reaction, hydrolyzing and esterifying the cyano group to obtain ethyl hydroxycyclopentyl carboxylate;

[0033] (2) sulfonation reaction: synthesis of phenylacetyl chloride;

[0034] (3) Docking and cyclization reaction: the ethyl hydroxycyclopentyl carboxylate obtained in step (1), the phenylacetyl chloride and ethanol obtained in step (2) are mixed, after heating up and stirring, slowly add ethanol with a mass concentration of 20% Sodium ethanol solution, the ethanol is distilled off under reduced pressure after the reaction, and then hydrochloric acid with a mass concentration of 20% is added dropwise to obtain 4-hydroxy-3-phenyl-1-oxaspiro[4.4]non-3-ene after filtratio...

Embodiment 2

[0040] Embodiment two: a kind of spirolide compound provided by the present invention, its chemical structural formula is:

[0041]

[0042] The method for preparing the above-mentioned compound comprises the following steps, (1) using cyclopentanone as a raw material, after carrying out cyanohydrinization reaction, hydrolyzing and esterifying the cyano group to obtain ethyl hydroxycyclopentyl carboxylate;

[0043] When selecting the above-mentioned synthetic route, the applicant of the present invention weighs according to the recovery rate and the cost, comprehensively finally selects the synthetic route disclosed by the present invention, and enumerates the test method for selecting the synthetic route below, in order to illustrate that the synthetic route finally selected by the present invention is the most Excellent choice:

[0044] 1. Synthesis of ethyl hydroxycyclopentyl carboxylate

[0045] 1.1 Ethyl hydroxycyclopentyl carboxylate is obtained by hydrolyzing and es...

Embodiment 3

[0101] Embodiment three: a kind of spirolide compound provided by the present invention, its chemical structural formula is:

[0102]

[0103] The method for preparing the above-mentioned compound comprises the following steps, (1) using cyclopentanone as a raw material, after carrying out cyanohydrinization reaction, hydrolyzing and esterifying the cyano group to obtain ethyl hydroxycyclopentyl formate: cyclopentanol, catalyst sodium pyrosulfate, The water is stirred and dissolved, the molar ratio of cyclopentanone and sodium cyanide is 1:0.95, the quality of the catalyst sodium pyrosulfate accounts for 0.3% of the reaction system quality, the reaction temperature is 30°C, and sodium cyanide is added dropwise in the mixed solution Aqueous solution, stirring, layering, the upper organic phase that obtains is cyclopentanyl cyanohydrin, the quality of water used can be as the criterion that can dissolve raw material,

[0104] The chemical reaction equation is:

[0105]

...

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Abstract

The invention discloses a volution lactone compound. The chemical structural formula of the volution lactone compound is shown in the specification. A preparing method of the volution lactone compound includes the steps that (1) cyclopentanone serves as a raw material and is subjected to a cyanohydrintion reaction, then cyano groups are hydrolyzed and esterified, and hydroxyl-cyclopentanecarboxylic acid ethyl ester is obtained; (2) a sulfonation reaction is carried out; (3) a butt joint ring formation reaction is carried out; (4) an alkylation reaction is carried out, wherein the cyclizing product obtained in the step (3), a reaction solvent and a catalyst are mixed, 3-bromopropylene is added into the mixed liquid, the solvent is removed in a pressure-reduction mode after reacting, water and benzene are added, extracting and layering are carried out, an organic phase substance is obtained, solvent pressure-reduction removing and filtering are carried out, and the final product volution lactone compound is obtained. The volution lactone compound has the advantage that a pesticide good in pest killing effect, long in lasing period and low in toxicity is obtained.

Description

technical field [0001] The invention belongs to the technical field of pesticides, in particular to a spirolide compound, its synthesis method and its application. Background technique [0002] The importance of pesticides to the production of agriculture, animal husbandry, fishery and forestry is obvious to all. Pesticides are developing dynamically-humans continue to use advanced science and technology to develop new varieties with better performance and eliminate old varieties to meet the needs of the development of agriculture, animal husbandry, fishery and forestry. For a period of time, pesticides will still be dominated by chemical synthesis. In the past 30 years, the speed of updating pesticide varieties has been accelerating, and the trend of updating is that the activity is increasing and the toxicity is decreasing, and will continue to develop in this direction. In order to optimize the structure of pesticide varieties in our province and my country, and for the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/94A01N43/12A01P7/00A01P7/02A01P7/04
CPCC07D307/94A01N43/12
Inventor 李源于乐祥李磊石隆平孙富江
Owner 山东东方农药科技实业有限公司
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