Vinyl cyanide compounds, preparation and application thereof

A technology of acrylonitrile and compounds, applied in the field of pesticides, can solve the problems of ecosystem damage, high toxicity of pesticides, residues, etc.

Active Publication Date: 2009-02-18
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the long-term use of insecticides, some harmful organisms have developed serious resistance, which is usually difficult to eliminate with conventional insecticides; moreover, due to the high toxicity of some insecticides, they are easily destroyed without decomposition. Long-term residues, thereby causing damage to the ecosystem; therefore, it has long been desired to develop high-efficiency, low-toxicity and low-residue insecticides

Method used

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  • Vinyl cyanide compounds, preparation and application thereof
  • Vinyl cyanide compounds, preparation and application thereof
  • Vinyl cyanide compounds, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Synthesis of 2-(4-tert-butylphenyl)-3-(2,3-dihydro-2,7-dimethyl-6-benzofuryl)-3-hydroxyacrylonitrile

[0058] At 50°C, a solution formed by dissolving 5.0g of 4-tert-butylphenylacetonitrile in 15ml of THF was added dropwise to a suspension formed by 3.0g of 50% sodium hydride in 50ml of THF, and the resulting product was stirred for 30 minutes, then At 50°C, a solution of 6.5 g of 2,3-dihydro-2,7-dimethyl-6-benzofuranoyl chloride dissolved in 15 ml of THF was added dropwise, and then stirred overnight at room temperature. The reaction mixture was desolvated under reduced pressure and poured into water, added 5.0 g of hydrochloric acid and stirred for 30 minutes, extracted with 100 ml of chloroform, the organic layer was washed with saturated brine and dried with anhydrous sodium sulfate, and desolvated under reduced pressure to obtain 6.5 g of brown viscous things.

Embodiment 2

[0059] Example 2: 2-(4-tert-butylphenyl)-3-(2,3-dihydro-2,7-dimethyl-6-benzofuryl)-3-isobutyryloxypropene Nitrile synthesis

[0060] A solution consisting of 0.5g of isobutyryl chloride and 5ml of chloroform was slowly added dropwise under stirring and cooling in an ice-water bath to 1.0g of 2-(4-tert-butylphenyl)-3-(2,3-dihydro-2, 7-dimethyl-6-benzofuryl)-3-hydroxyacrylonitrile, 0.6g triethylamine and 20ml chloroform in the mixed solution. After the dropwise addition, the temperature of the reaction mixture was raised to about 30°C, and the stirring was continued at this temperature, and the chromatographic tracking was carried out until the reactant was basically converted completely, which took about 5-6 hours. The resulting reaction mixture was poured into water (30 ml), and the layers were separated upon standing. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and precipitated under reduced pressure. The residue was the title com...

Embodiment 3

[0062] According to the method described in Example 2, the corresponding acid chloride, sulfonyl chloride, phosphorus oxychloride and 2-(4-tert-butylphenyl)-3-(2,3-dihydro-2,7 -Dimethyl-6-benzofuryl)-3-hydroxyacrylonitrile Synthesis of other acrylonitrile compounds described in Table 1 were prepared. Such as reacting acetyl chloride with the compound obtained in Example 1 to prepare No.1 compound; reacting isovaleryl chloride with the compound obtained in Example 1 to prepare No.2 compound; reacting benzoyl chloride with the compound obtained in Example 1 to prepare No.3 compound (±) cis-trans-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropanyl formyl chloride reacts with the compound obtained in Example 1 to prepare No.4 compound; Propionyl chloride and Example Compound No.5 was prepared by reacting the compound obtained in 1; Compound No.7 was prepared by reacting t-valeryl chloride with the compound obtained in Example 1; Compound No.8 was prepared by reacting methanesulfonyl ...

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Abstract

The present invention discloses an acrylonitrile compound, a preparation method thereof, and a pest prevention and curing agent with the compound as an active constituent. The compound has structural characteristics as shown in Formula (I). In the preparation method, under the condition with alkaline, an organic solvent at the temperature between minus 10 DEG C and 150 DEG C is used for the reaction between benzofuran acyl chloride or pyrazole acyl chloride and substituted benzyl cyanide, so as to produce an intermediate, the produced intermediate reacts with acyl chloride, and the (I) can be separated. The compound can be used as an active constituent in a pest prevention and curing agent. The present invention has the advantages that the compound has excellent prevention and curing effects on harmful insects and acarus category, the activity of the compound is high, the consumption is low and the security is excellent.

Description

technical field [0001] The invention belongs to the field of pesticides and relates to a novel acrylonitrile compound. The invention also relates to a preparation method of the compound and a pest control agent using the compound as an active ingredient. The novel acrylonitrile compound of the invention can be used as an insecticide and acaricide applied in the fields of agriculture, gardening, animal husbandry and sanitation. Background technique [0002] Acrylonitrile derivatives occupy a very important position in the research and development of pesticides, and many of them have been developed as pesticides. Japanese Patent JP53-92769 discloses 2'-chloro-3-hydroxyl-2-(4-phenyl - the use of 2-thiazolyl)-cinnamonitrile as an insecticide, the use of this compound as an aquatic organism adhesion inhibitor is disclosed in the patent WO95 / 29591. Japanese Patent JP60-11452 discloses the use of 2-(4-chlorophenyl)-3-(3-pyridyl)-3-oxopropionitrile as an insecticide, and Japanese P...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80C07D231/16C07F9/09A01N43/08A01N43/56A01P7/00
Inventor 刘丽张湘宁马亚芳马海军曾霞郭丽琴施娟娟李长乐王娜倪珏萍
Owner JIANGSU PESTICIDE RES INST
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