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Preparation method and application of pyrazole oxime ether compounds containing 5-aryloxazole structure

A technology of pyrazole oxime ether and aryl oxazole, which is applied in the field of preparation and application of pyrazole oxime ether compounds, can solve problems such as cross-resistance, and achieve excellent control effects

Active Publication Date: 2019-06-14
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 scale of pesticide use and the gradual increase in the use time, pests gradually began to develop resistance to traditional pesticides, and even cross-resistance

Method used

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  • Preparation method and application of pyrazole oxime ether compounds containing 5-aryloxazole structure
  • Preparation method and application of pyrazole oxime ether compounds containing 5-aryloxazole structure
  • Preparation method and application of pyrazole oxime ether compounds containing 5-aryloxazole structure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Dissolve 5 mmol of compound IIIa in 30 mL of DMF, then add 15 mmol of 4-dimethylaminopyridine (DMAP), add 4 mmol of intermediate IIa to it at room temperature, heat to 120°C, and react for 28 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 ):δ7.85(s,1H,CH=N),7.59~7.62(m,2H,Ar-H),7.25(s,1H,Oxazole-H),7.04~7.23(m,4H,Ar-H ),6.90(s,1H,Ar-H),6.75~6.78(m,1H,Ar-H),5.10(s,2H,CH 2 ),3.63(s,3H,CH 3 ),2.38(s,3H,CH 3 ).

Embodiment 2

[0036]

[0037] Dissolve 5 mmol of compound IIIb in 25 mL of 2-butanone, then add 15 mmol of sodium bicarbonate, add 6 mmol of intermediate IIa to it at room temperature, heat to 35°C, and react for 15 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 Ib; 1 H NMR (400MHz, CDCl 3 ):δ7.85(s,1H,CH=N),7.59~7.62(m,2H,Ar-H),7.21~7.24(m,3H,Ar-H and Oxazole-H),7.09~7.13(m ,2H,Ar-H),6.81(d,J=9.2Hz,2H,Ar-H),5.09(s,2H,CH 2 ),3.59(s,3H,CH 3 ),2.34(s,3H,CH 3 ).

Embodiment 3

[0039]

[0040] 4mmol of compound IIIc was dissolved in 30mL of acetonitrile, then 8mmol of potassium carbonate was added, and 5mmol of intermediate IIa was added thereto at room temperature. After the addition was complete, the temperature was raised to reflux for 9 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 Ic; 1 H NMR (400MHz, CDCl 3 ):δ7.85(s,1H,CH=N),7.59~7.62(m,2H,Ar-H),7.37(d,J=8.8Hz,2H,Ar-H),7.24(s,1H, Oxazole-H), 7.09~7.14(m, 2H, Ar-H), 6.75(d, J=9.2Hz, 2H, Ar-H), 5.08(s, 2H, CH 2 ),3.58(s,3H,CH 3 ),2.34(s,3H,CH 3 ).

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Abstract

The invention relates to a preparation method and an application of pyrazole oxime ether compounds (I) containing a 5-aryloxazole structure. The pyrazole oxime ether compounds (I) containing the 5-aryloxazole structure are obtained through condensing 5-aryloxazol-2-methyl chloride (II) and pyrazole oxime (III). The pyrazole oxime ether compounds (I) containing the 5-aryloxazole structure have an effective prevention and control effect on harmful insects, and can be used for preparing pesticides in the fields of agriculture and gardening.

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 compound containing a 5-aryl oxazole structure Background technique [0002] Prevention and suppression of pests is the core content of the scientific research field of pesticides. Widespread use of various types of insecticides keeps pest infestations under control. However, with the continuous expansion of the scale of pesticide use and the gradual increase in the use time, pests gradually began to develop resistance to traditional pesticides, and even cross-resistance. In addition, with the continuous emergence of new insect pests, the continued research and development of new pesticides has become an inevitable choice. [0003] Nitrogen-containing heterocyclic compounds are widely used in agricultural production. As an important class of nitrogen-containing heterocyclic compounds, pyrazole oxime ether compounds hav...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/76A01P7/04
Inventor 戴红王杨叶浩周钱李宏石玉军姚炜丁颖钱宏炜孙洋
Owner NANTONG UNIVERSITY
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