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Pyrazolyl acrylonitrile compound as well as preparation method and application thereof

A technology of pyrazolyl acrylonitrile and compounds, applied in the field of pesticides, can solve the problems of agricultural production loss, loss of sensitivity to various types of pesticides, etc., and achieve the effect of high-efficiency acaricidal activity and safe preparation method

Active Publication Date: 2022-04-19
SHENYANG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Because the selectivity produced by the application of pesticides will cause pests, pest mites and other harmful organisms to develop resistance, once the pests develop resistance, it will lead to a decrease in their sensitivity to a certain type or type of pesticide, or even multiple types of pesticides. Further lead to the reduction or even complete loss of the control effect, thus causing heavy losses to agricultural production

Method used

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  • Pyrazolyl acrylonitrile compound as well as preparation method and application thereof
  • Pyrazolyl acrylonitrile compound as well as preparation method and application thereof
  • Pyrazolyl acrylonitrile compound as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0067] 2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)-3-(2-chloro-ethoxy)-formyloxyacrylonitrile Synthesis of (Z / E)

[0068] (1) Synthesis of intermediate crude product (2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)-3-hydroxyacrylonitrile):

[0069] In a 250mL three-necked reaction flask equipped with a magnetic stirrer, thermometer, water separator and condenser, add 7.4g of ethyl 1,3,4-trimethylpyrazole-5-carboxylate, 7.6g of p-tert-butyl Phenylacetonitrile, 4mL ethylene glycol ethyl ether and 100mL n-heptane, stirred at room temperature for 0.5h, heated to 135°C for 1h, then added dropwise 12.4g of 30% sodium methoxide solution, and continued to reflux for 5h after the dropwise addition; The reaction solution was cooled to room temperature, poured into 250 mL of ice water, extracted three times with 100 mL of ethyl acetate, then adjusted the aqueous phase to pH=5 with 30% hydrochloric acid, extracted three times with 100 mL of ethyl acetate, and extracted ...

Embodiment 2～16

[0073] According to the preparation method of Example 1, the pyrazolylacrylonitrile compounds of Examples 2-16 were prepared by using the corresponding acid chlorides and the intermediate crude product prepared in Example 1.

[0074] Specifically: in Example 2, reacting phenyl chloroformate with the intermediate crude product to prepare Compound No.3 and No.4; in Example 3, reacting cyclohexanecarbonyl chloride with the intermediate crude product to prepare Compound No.5 and No.6 In embodiment 4, 4-ethynyl-benzoyl chloride is reacted with intermediate crude product to prepare compound No.7 and No.8; In embodiment 5, phenylpropyloyl chloride is reacted with intermediate crude product to prepare compound No.9 and No. .10; in embodiment 6, cyclohexa-3-ene-1-formyl chloride is reacted with intermediate crude product to prepare compound No.11 and No.12; in embodiment 7, cyclopentacarbonyl chloride is reacted with intermediate crude product to prepare compound No.13 and No.14; Compo...

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Abstract

The invention belongs to the technical field of pesticides, and discloses a pyrazolyl acrylonitrile compound as well as a preparation method and application thereof. According to the invention, novel acyl fragments such as cyclohexyl formyl, ethynyl benzoyl, phenylpropioyl and phenoxy formyl are introduced into the active structure cyenopyrafen of a commercial acaricide cyenopyrafen, so that a series of novel pyrazolyl acrylonitrile compounds which are not reported in literatures are obtained. A biological activity determination result shows that compared with a commercial acaricide cyenopyrafen, the compound has more efficient acaricidal activity, can be used for preparing insecticides and acaricides in the fields of agriculture, forestry, horticulture and the like, can also be used for pest control in the fields of sanitation, storage, animal husbandry and the like, and has the advantages of being low in dosage, good in activity and the like. In addition, the preparation method of the compound is safe, simple and feasible.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a pyrazolyl acrylonitrile compound and a preparation method and application thereof. Background technique [0002] Because the selectivity produced by the application of pesticides will cause pests, pest mites and other harmful organisms to develop resistance, once the pests develop resistance, it will lead to a decrease in their sensitivity to a certain type or type of pesticide, or even multiple types of pesticides. Further lead to the reduction or even complete loss of control effect, thereby causing heavy losses to agricultural production. Therefore, it is necessary to continuously develop new compounds with agricultural biological activities such as insecticide and acaricide to meet the needs of pest resistance management and agricultural production. In addition, as people pay more and more attention to physical health and environmental protection, higher standards are r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12A01N43/56A01P7/02A01P7/04
CPCC07D231/12A01N43/56
Inventor 秦培文徐婧纪明山
Owner SHENYANG AGRI UNIV
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