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Preparation and application of pyrazole oxime compound containing 1-methyl-3-difluoromethyl-5-chloropyrazole unit

A technology of difluoromethyl and clopyrazole, applied in the field of preparation of pyrazole oxime compounds, to achieve good insecticidal effect

Active Publication Date: 2020-02-28
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 compound containing 1-methyl-3-difluoromethyl-5-chloropyrazole unit
  • Preparation and application of pyrazole oxime compound containing 1-methyl-3-difluoromethyl-5-chloropyrazole unit
  • Preparation and application of pyrazole oxime compound containing 1-methyl-3-difluoromethyl-5-chloropyrazole unit

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Add 4mmolIIa, 20mmol pyridine and 30mL acetonitrile into a reaction flask. Under stirring in an ice bath, a mixed solution of 5 mmol of Intermediate III and 5 mL of acetonitrile was added thereto. After the addition was completed, the mixture was heated to reflux and stirred for 18 hours. The solvent was removed under reduced pressure, and the resulting crude product was separated by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 )δ: 8.03(s, 1H, CH=N), 6.85~7.12(m, 5H, Ar-HandCHF 2 ),3.93(s,3H,CH 3 ),3.66(s,3H,CH 3 ),2.51(s,3H,CH 3 ).

Embodiment 2

[0033]

[0034] Add 3 mmol IIb, 18 mmol 4-dimethylaminopyridine (DMAP) and 20 mL DMF into a reaction flask. Under stirring in an ice bath, a mixture of 3 mmol of III and 5 mL of DMF was added thereto. After the addition is complete, heat to 90°C and react for 20 hours. After removing the solvent, the resulting crude product was separated by column chromatography to obtain the target substance Ib; 1 HNMR (400MHz, CDCl 3 )δ: 8.07(s, 1H, CH=N), 7.48(d, J=8.8Hz, 2H, Ar-H), 6.85~7.13(m, 3H, Ar-HandCHF 2 ),3.93(s,3H,CH 3 ),3.64(s,3H,CH 3 ),2.52(s,3H,CH 3 ).

Embodiment 3

[0036]

[0037] Add 6mmolIIc, 30mmol triethylamine and 20mL tetrahydrofuran into a reaction flask. Under stirring at room temperature, a mixed solution of 10 mmol of Intermediate II and 5 mL of tetrahydrofuran was added thereto. After the addition was complete, the mixture was stirred in an ice bath for 12 hours. The solvent was removed under reduced pressure, and the resulting crude product was separated by column chromatography to obtain the target object Ic; 1 HNMR (400MHz, CDCl 3 )δ: 8.16(s, 1H, CH=N), 6.77~7.24(m, 6H, Ar-HandCHF 2 ),3.92(s,3H,CH 3 ),3.83(s,3H,CH 3 ).

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PUM

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Abstract

The invention relates to preparation and application of a pyrazole oxime compound (I) containing a 1-methyl-3-difluoromethyl-5-chloropyrazole unit. The pyrazole oxime compound is prepared through a reaction of 1,3-disubstituent-5-aryloxypyrazol oxime (II) with 1-methyl-3-difluoromethyl-5-chloropyrazol-4-formyl chloride (III). The pyrazole oxime compound (I) containing the 1-methyl-3-difluoromethyl-5-chloropyrazole unit has an effective prevention and treatment effect on harmful insects, and can be used for preparing insecticides used in the fields of agriculture, horticulture and the like.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to the preparation and application of pyrazole oxime compounds containing 1-methyl-3-difluoromethyl-5-chloropyrazole units. 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 compounds are a class of important heterocyclic compounds, which are widely used in agricultural production, and the representative compound is pyraclofen. [0004] [0005] Pyrazole units are also important heterocyclic ske...

Claims

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Application Information

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IPC IPC(8): C07D231/20A01N43/56A01P7/04
CPCA01N43/56C07D231/20
Inventor 戴红王杨郑丹丹张敏施磊张燕张海军荀校王雨阳冯浩
Owner NANTONG UNIVERSITY
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