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Preparation and application of pyrazole oxime ether derivative containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure

A technology of trifluoromethylpyrazole and pyrazole oxime ether, which is applied in the field of preparation of pyrazole oxime ether derivatives to achieve excellent control effects

Inactive Publication Date: 2019-08-09
NANTONG UNIVERSITY
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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, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice

Method used

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  • Preparation and application of pyrazole oxime ether derivative containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure
  • Preparation and application of pyrazole oxime ether derivative containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure
  • Preparation and application of pyrazole oxime ether derivative containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] 4mmol of compound IIIa was dissolved in 30mL of acetonitrile, then 10mmol of potassium carbonate was added, and 5mmol of intermediate II was added thereto at room temperature. After the addition was complete, it was heated to reflux for 12 hours. The reaction solution was cooled to room temperature, suction filtered, the mother liquor was concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 )δ:8.51(dd,J 1 =4.8Hz,J 2 =1.6Hz,1H,Py-H),7.95(dd,J 1 =8.0Hz,J 2 =1.6Hz, 1H, Py-H), 7.80(s, 1H, CH=N), 7.75(s, 1H, Pyrazole-H), 7.44~7.47(m, 1H, Py-H), 7.00~7.04( m,2H,Ar-H),6.85~6.89(m,2H,Ar-H),5.08(s,2H,CH 2 ),3.61(s,3H,N-CH 3 ),2.37(s,3H,CH 3 ).

Embodiment 2

[0036]

[0037] 4 mmol of compound IIIb was dissolved in 20 mL of acetonitrile, and 7 mmol of intermediate II and 8 mmol of cesium carbonate were added thereto at room temperature. After the addition, the reaction was heated to reflux for 8 hours. The reaction was stopped, and the reaction solution was rotary evaporated to dryness under reduced pressure, and the resulting residue was separated and purified by column chromatography to obtain the target compound Ib; 1 H NMR (400MHz, CDCl 3 )δ:8.51(dd,J 1 =4.8Hz,J 2 =1.6Hz,1H,Py-H),7.95(dd,J 1 =8.0Hz,J 2 =1.6Hz,1H,Py-H),7.78(s,1H,CH=N),7.76(s,1H,Pyrazole-H),7.44~7.47(m,1H,Py-H),6.85(s, 4H,Ar-H),5.10(s,2H,CH 2 ),3.78(s,3H,OCH 3 ),3.61(s,3H,N-CH 3 ),2.38(s,3H,CH 3 ).

Embodiment 3

[0039]

[0040] 5 mmol of compound IIIc was dissolved in 20 mL of DMF, and 5 mmol of intermediate II and 14 mmol of sodium carbonate were added thereto at room temperature. After the addition was completed, the temperature was raised to 100° C. and reacted for 20 hours. The reaction was stopped, and the reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ic; 1 H NMR (400MHz, CDCl 3 )δ:8.51(dd,J 1 =4.8Hz,J 2 =1.6Hz,1H,Py-H),7.95(dd,J 1=8.0Hz,J 2 =1.6Hz, 1H, Py-H), 7.80(s, 1H, CH=N), 7.75(s, 1H, Pyrazole-H), 7.44~7.47(m, 1H, Py-H), 7.11(d, J=8.4Hz, 2H, Ar-H), 6.79(d, J=8.8Hz, 2H, Ar-H), 5.09(s, 2H, CH 2 ),3.60(s,3H,N-CH 3 ),2.38(s,3H,CH 3 ),2.31(s,3H,CH 3 ).

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Abstract

The invention relates to preparation and application of a pyrazole oxime ether derivative (I) containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure. The pyrazole oxime ether derivative (I) is obtained by condensation of 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole4-methyl chloride (II) with pyrazole hydroxy oxime (III). The pyrazole oxime ether derivative containing 1-(3-chloropyridine-2-yl)-3-trifluoromethylpyrazole structure has effective control effect on harmful insects, and the compound can be used for preparation of pesticides in agriculture, horticulture and other fields.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to the preparation and application of a pyrazole oxime ether derivative containing a 1-(3-chloropyridin-2-yl)-3-trifluoromethylpyrazole structure. Background technique [0002] Pest control has always been the core field of pesticide scientific research, and the widespread use of insecticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice. [0003] Pyrazole oxime ether compounds are also an important class of nitrogen-containing heterocyclic compounds, and its typical compound is pyraclofen, which plays an important role in insecticide in the field of pesticides. ...

Claims

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Application Information

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IPC IPC(8): C07D401/14A01N43/56A01P7/04
CPCA01N43/56C07D401/14
Inventor 朱玥丁颖王杨戴红叶浩石玉军周家华钱宏炜
Owner NANTONG UNIVERSITY
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