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Pyrazol-5-amide derivative containing oxazole structure and preparation method and application thereof

A technology of amides and derivatives, applied in the field of pyrazole-5-amide derivatives and their preparation, to achieve excellent control effects

Active Publication Date: 2019-11-05
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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  • Pyrazol-5-amide derivative containing oxazole structure and preparation method and application thereof
  • Pyrazol-5-amide derivative containing oxazole structure and preparation method and application thereof
  • Pyrazol-5-amide derivative containing oxazole structure and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] 4 mmol of compound IIIa was dissolved in 30 mL of chloroform, then 20 mmol of pyridine was added, and then 6 mmol of intermediate IIa was added thereto under ice-cooling conditions. After the addition was completed, the reaction was continued in ice bath for 9 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 Ia; 1 H NMR (400MHz, CDCl 3 ):δ8.46~8.47(m,1H,Py-H),8.03~8.08(m,2H,Ar-H),7.93(d,J=8.8Hz,2H,Ar-H),7.86~7.88( m,1H,Py-H),7.77(s,1H,Oxazole-H),7.61(s,1H,Oxazole-H),7.45(d,J=8.8Hz,2H,Ar-H),7.34-7.39 (m,1H,Py-H),7.12-7.17(m,2H,Ar-H),6.96(s,1H,NH),6.29(s,1H,Pyrazole-H),5.29(s,2H,CH 2 ), 4.45 (d, J=5.2Hz, 2H, CH 2 ).

Embodiment 2

[0031]

[0032] 3 mmol of compound IIIa was dissolved in 30 mL of dichloromethane, then 2 mL of triethylamine was added, and then 5 mmol of intermediate IIb was added thereto under ice-cooling conditions. After addition, the reaction was heated to reflux for 15 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 ):δ8.46~8.47(m,1H,Py-H),7.86~7.97(m,5H,Py-H,Ar-H and Oxazole-H),7.61(s,1H,Oxazole-H),7.51 (d, J=2.0Hz, 1H, Ar-H), 7.45(d, J=8.4Hz, 2H, Ar-H), 7.32-7.38(m, 2H, Py-H and Ar-H), 6.99( s,1H,NH),6.30(s,1H,Pyrazole-H),5.32(s,2H,CH 2 ), 4.45 (d, J=5.6Hz, 2H, CH 2 ).

Embodiment 3

[0034]

[0035] 6 mmol of compound IIIb was dissolved in 30 mL of DMF, then 15 mmol of DIPEA was added, and then 7 mmol of intermediate IIa was added thereto under ice-cooling conditions. After the addition was complete, the mixture was heated to 80°C 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 ):δ8.46~8.48(m,1H,Py-H),8.01~8.05(m,2H,Ar-H),7.87~7.89(m,1H,Py-H),7.72~7.82(m,3H ,Ar-H and Oxazole-H),7.59(s,1H,Oxazole-H),7.35~7.38(m,1H,Py-H),7.21~7.26(m,1H,Ar-H),7.09~7.15 (m,3H,Ar-H and NH),6.29(s,1H,Pyrazole-H),5.28(s,2H,CH 2 ), 4.45 (d, J=5.6Hz, 2H, CH 2 ).

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Abstract

The invention relates to a pyrazol-5-amide derivative (I) containing an oxazole structure and a preparation method and application thereof. The pyrazol-5-amide derivative (I) is obtained through condensation of chloroformyl pyrazol (II) and oxazole methylamine (III). The pyrazol-5-amide derivative containing the oxazole structure has an effective control effect on harmful insects, and the compoundcan be used for preparing pesticides in the fields of agriculture, gardening and the like.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to a pyrazole-5-amide derivative containing an oxazole structure and a preparation method and use thereof. 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] Substituted pyrazole rings are widely used in agricultural production. Pyrazole compounds have excellent insecticidal and acaricidal activities. Pyrazole heterocycles are widely introduced into pesticide compound molecules, such as pyrazole amide insecticide a...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/76A01P7/04
CPCC07D413/14A01N43/76
Inventor 戴红王杨荀校叶浩张莉芳张敏梁凯郑丹丹曹成江周家华
Owner NANTONG UNIVERSITY
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