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Pyrazole ether compound as well as preparation method and application thereof

A technology of compound and pyrazole ether, applied in the field of fungicide composition, insecticide, pest control, harmful bacteria, pyrazole ether compound and its preparation

Pending Publication Date: 2022-05-20
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many pests and harmful bacteria control agents on the market, due to the continuous expansion of the market, foreign pests and harmful bacteria, drug resistance of pests and harmful bacteria, drug service life, drug economics and people's increasing concern for the environment Pay attention to, scientists need to continuously research and develop new insecticides and fungicides with high efficiency, safety, economy, environmental compatibility and unique mode of action

Method used

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  • Pyrazole ether compound as well as preparation method and application thereof
  • Pyrazole ether compound as well as preparation method and application thereof
  • Pyrazole ether compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1 This example illustrates the preparation method of compound 03 in Table 1 (method A)

[0093]

[0094] Add o-nitrobenzyl bromide (0.10 mol) and azobis Isobutyronitrile (0.80 g) and 15% hydrogen peroxide (0.09 mol). After dropping, continue to react for 2-5h until the reaction is complete. The separated organic layer is washed with 10% sodium sulfite solution and separated to obtain a dichloromethane solution of o-nitrobenzyl bromide, which is directly used in the next reaction.

[0095] 2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)nitrobenzene, at 10-25°C under stirring conditions, base)-3-hydroxyl-1H-pyrazole (0.05mol), the dichloromethane solution of o-nitrobenzyl bromide (0.06mol) obtained in the previous step, tetrabutylammonium bromide (0.80g), water (15g) and To the reaction mixture of dichloromethane (50 mL), a 10% aqueous solution of sodium hydroxide (0.08 mol) was added dropwise. After the addition is complete, react at 50-80°C for 1-3h un...

Embodiment 2

[0099] Example 2 This example illustrates the preparation method of compound 03 in Table 1 (method B)

[0100]

[0101] 2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)-N-methyleneaniline 2-(((1-(4-chlorophenyl) -1H-pyrazol-3-yl)oxy)methyl)aniline (0.02mol), paraformaldehyde (0.022mol), triethylamine (0.5g), toluene (20mL) and ethanol (4mL) in React at 80-95°C for 2-3h, raise the temperature to 100-115°C for 2-3h, concentrate under reduced pressure to obtain the title compound, which is directly used in the next reaction.

[0102] 2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)-N-methylaniline NaBH 4 (0.015mol), 2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)-N-methyleneaniline (10mmol) and ethanol (15mL) in Stir the reaction under reflux until complete, concentrate under reduced pressure to remove most of the ethanol, cool, add dichloromethane, wash with water, dry over anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain the title...

Embodiment 3

[0104] Example 3 This example illustrates the preparation method of compound 19 in Table 1 (method A)

[0105]

[0106] Referring to Example 1, 2-bromomethyl-4-heptafluoroisopropylaniline, 2-(((1-(4-chlorophenyl)- 1H-pyrazol-3-yl)oxy)methyl)-4-heptafluoroisopropylaniline and N-(2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl )oxy)methyl)-4-(heptafluoroisopropyl)phenyl)methyl carbamate.

[0107] N-(2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)-4-(heptafluoroisopropyl)phenyl)-N-methyl Methyl carbamate was cooled in an ice-water bath and stirred, to N-(2-(((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)methyl)-4-(hepta Fluoroisopropyl)phenyl)carbamate (5.0mmol) in N,N-dimethylformamide (15mL) solution, NaH (7.5mmol) was added in batches, after stirring for 15min, iodomethane (7.5 mmol), stirring and reacting for 0.5-2.5 hours, allowed it to naturally warm up to room temperature and react until complete. The reaction mixture was added to ice water, extracted with ethyl acetate, the ...

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PUM

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Abstract

The invention discloses a pyrazole ether compound as shown in a formula (I) as well as a preparation method and application thereof. In the formula, R, R1, R2, R3, R4, R5, W, m and n are defined in the specification. The compound shown in the formula (I) has insecticidal and / or bactericidal biological activity, and particularly has very high activity on diseases such as rust disease and powdery mildew.

Description

technical field [0001] The invention belongs to the field of insecticides and fungicides, and in particular relates to pyrazole ether compounds with insecticide and fungicide biological activity and a preparation method thereof, insecticides and fungicide compositions containing the compounds, and the use of these compounds to control pests, Uses and methods of harmful germs. Background technique [0002] The prevention and control of pests and harmful bacteria is very important in the process of realizing efficient agriculture. The control of pests and harmful bacteria is also very important in the fields of forestry, animal husbandry, sideline, fishery and public health. Although there are many pests and harmful bacteria control agents on the market, due to the continuous expansion of the market, foreign pests and harmful bacteria, drug resistance of pests and harmful bacteria, drug service life, drug economics and people's increasing concern for the environment To pay a...

Claims

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Application Information

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IPC IPC(8): C07D231/22A01N47/20A01N47/30A01P7/00A01P1/00A01P3/00A01P7/02A01P7/04
CPCC07D231/22A01N47/20A01N47/30
Inventor 刘兴平柳爱平王惠峰冯蛟龙欧晓明刘民华何莲杨小龙张再刘双瑾
Owner 湖南海利常德农药化工有限公司
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