Heterocyclic ketone-containing N-substituted phenyl pyrazole compound, preparation method thereof and application thereof in prevention and control of plant diseases and insect pests

A technology of phenylpyrazoles and compounds, applied in the field of N-substituted phenylpyrazoles and its preparation and control of plant diseases and insect pests, to achieve good insecticidal effect

Inactive Publication Date: 2012-10-17
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the continuous expansion of the application scale of pesticides, problems such as the resistance of organically synthesized insecticides and fungicides during use have become more prominent. The key to solving these problems is to find and develop new low-toxic insecticides with new targets. , Fungicide

Method used

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  • Heterocyclic ketone-containing N-substituted phenyl pyrazole compound, preparation method thereof and application thereof in prevention and control of plant diseases and insect pests
  • Heterocyclic ketone-containing N-substituted phenyl pyrazole compound, preparation method thereof and application thereof in prevention and control of plant diseases and insect pests
  • Heterocyclic ketone-containing N-substituted phenyl pyrazole compound, preparation method thereof and application thereof in prevention and control of plant diseases and insect pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of 3-(2-((1-phenyl-2H-pyrazole-3-oxyl)methyl)phenyl)oxazolinone-2-one (compound 1)

[0027]

[0028] Add 0.48g (3.0mmol) of compound (III-1), 0.62g (4.5mmol) of potassium carbonate, and 20mL of anhydrous acetone into a 100mL four-neck flask, stir for 0.5h at the reflux temperature of acetone (56°C), and then add 0.77g (3.00mmol) of compound (II-1) was dissolved in 15mL of acetone. After continuing to react at this temperature for 12h, it was left to cool and added 50mL of water to quench the reaction. Ethyl acetate (50mL×3) was extracted, the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain a yellow viscous liquid, which was separated and purified by column chromatography (silica gel filled, petroleum ether / ethyl acetate) to obtain a white solid with a yield of 88.5% and a melting point of 105-106°C.

[0029] NMR data ( 1 HN...

Embodiment 2

[0030] Example 2: 3-(2-((1-(4-chlorophenyl)-2H-pyrazole-3-oxyl group) methyl) phenyl) oxazolone-2-one (compound 2) synthesis

[0031]

[0032] Add 0.58g (3.0mmol) of compound (III-2), 0.62g (4.5mmol) of potassium carbonate, and 20mL of anhydrous acetonitrile into a 100mL four-neck flask, stir for 0.5h at the reflux temperature of acetonitrile (76°C), and then add 0.77g (3.00mmol) of compound (II-1) was dissolved in 15mL of acetonitrile. After continuing to react at this temperature for 18h, it was left to cool and added 50mL of water to quench the reaction. Ethyl acetate (50mL×3) was extracted, the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain a yellow viscous liquid, which was separated and purified by column chromatography (silica gel filled, petroleum ether / ethyl acetate) to obtain a white solid with a yield of 86.0% and a melting point of 138-139...

Embodiment 3

[0034] Example 3: 3-(2-((1-(3-chlorophenyl)-2H-pyrazole-3-oxyl)methyl)phenyl)oxazolinone-2-one (compound 3) synthesis

[0035]

[0036]0.58g (3.0mmol) of compound (III-3), 0.62g (4.5mmol) of potassium carbonate, and 20mL of anhydrous N,N-dimethylformamide were added to a 100mL four-necked flask, and dissolved in N,N-dimethylformamide Stir for 0.5 h at the reflux temperature (115° C.) of dimethylformamide, then add 0.77 g (3.00 mmol) of compound (II-1) in 15 mL of N,N-dimethylformamide solution, and continue the reaction at this temperature for 20 h. Let cool and add 50 mL of water to quench the reaction. Ethyl acetate (50mL×3) was extracted, the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain a yellow viscous liquid, which was separated and purified by column chromatography (silica gel filled, petroleum ether / ethyl acetate) to obtain a white solid wit...

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Abstract

The invention discloses a heterocyclic ketone-containing N-substituted phenyl pyrazole compound, a preparation method thereof and application thereof in prevention and control of plant diseases and insect pests. A series of heterocyclic ketone-containing N-substituted phenyl pyrazole compound is obtained by performing etherification of substituted aryl pyrazole serving as a raw material and benzyl halogen-containing heterocyclic ketone under the action of an acid-catcher. The compound of the kind has excellent sterilizing and insecticidal activity and is applied in the prevention and control of diseases and insect pests for various plants.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides. Specifically, it relates to an N-substituted phenylpyrazole compound containing a heterocyclic ketone and its preparation and application for preventing and controlling plant diseases and insect pests. technical background [0002] At present, the control of pests and diseases has always been the core field of pesticide scientific research. The widespread use of pesticides has effectively controlled most pests and fungi, reducing the major losses caused by pests and diseases in agriculture. However, with the continuous expansion of the application scale of pesticides, problems such as the resistance of organically synthesized insecticides and fungicides during use have become more prominent. The key to solving these problems is to find and develop new low-toxic insecticides with new targets. , Bactericide. [0003] Methoxyacrylate compounds are a class of substances with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12A01N43/76A01N43/824A01P3/00A01P7/04A01P7/02
Inventor 朱红军李钰皓张湘宁李玉峰颜章伟刘睿倪珏萍
Owner NANJING TECH UNIV
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