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Pyrazole oxime ether compound having oxazole biphenylyl structure as well as preparation method and application thereof

A technology of pyrazole oxime ether and azole biphenyl, which is applied in the field of pyrazole oxime ether compounds and their preparation, and achieves excellent control effects

Inactive Publication Date: 2018-12-21
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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  • Pyrazole oxime ether compound having oxazole biphenylyl structure as well as preparation method and application thereof
  • Pyrazole oxime ether compound having oxazole biphenylyl structure as well as preparation method and application thereof
  • Pyrazole oxime ether compound having oxazole biphenylyl structure as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Dissolve 4mmol of compound IIIa in 30mL of acetonitrile, then add 10mmol of potassium carbonate, add 5mmol of Intermediate II to it at room temperature, heat to reflux for 14 hours after addition. The reaction solution was cooled to room temperature, filtered with suction, the mother liquor was concentrated under reduced pressure, and the resulting residue was separated and purified by column chromatography to obtain the target compound Ia; 1 H NMR(400MHz, CDCl 3 )δ:7.92(s,1H,Oxazole-H),7.83(s,1H,CH=N),7.59(d,J=8.4Hz,2H,Ar-H),7.35(s,2H,Ar-H ),7.33(s,1H,Oxazole-H),7.24(t,J=8.0Hz,1H,Ar-H),6.78~6.82(m,1H,Ar-H),6.61~6.67(m,2H, Ar-H),5.00(s,2H,CH 2 ), 3.60(s, 3H, N-CH 3 ),2.36(s,3H,CH 3 ).

Embodiment 2

[0037]

[0038] 4mmol of compound IIIb was dissolved in 20mL of acetonitrile, and 7mmol of intermediate II and 8mmol of cesium carbonate were added to it at room temperature. After the addition, the reaction was heated and refluxed for 13 hours. The reaction was stopped, the reaction solution was evaporated to dryness 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 )δ:7.92(s,1H,Oxazole-H),7.83(s,1H,CH=N), 7.60(d,J=8.4Hz,2H,Ar-H),7.33(t,J=15.2Hz, 3H,Ar-H and Oxazole-H), 7.21(t,J=16.4Hz,1H,Ar-H), 7.06~7.08(m,1H,Ar-H), 6.89(t,J=4.0Hz,1H ,Ar-H),6.75~6.78(m,1H,Ar-H),4.99(s,2H,CH 2 ), 3.60(s, 3H, N-CH 3 ),2.35(s,3H,CH 3 ).

Embodiment 3

[0040]

[0041] Dissolve 5mmol of compound IIIc in 20mL of DMF, add 5mmol of intermediate II and 14mmol of sodium carbonate to it at room temperature, after the addition, heat up to 50°C and react for 16 hours. The reaction was stopped, the reaction solution was 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:7.92(s,1H,Oxazole-H), 7.83(s,1H,CH=N), 7.60(d,J=8.4Hz,2H,Ar-H), 7.35(s,1H,Oxazole-H ), 7.32(d,J=8.0Hz,2H,Ar-H),7.22(d,J=8.0Hz,1H,Ar-H),7.15(t,J=16Hz,1H,Ar-H),7.04 (t,J=4.0Hz,1H,Ar-H),6.80(q,J=10.4Hz,1H,Ar-H),4.99(s,2H,CH 2 ), 3.60(s, 3H, N-CH 3 ),2.35(s,3H,CH 3 ).

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Abstract

The invention relates to a pyrazole oxime ether compound (I) having an oxazole biphenylyl structure as well as a preparation method and application thereof. The pyrazole oxime ether compound (I) is obtained through condensation of oxazole biphenyl methyl chloride (II) and pyrazol hydroxime (III), wherein the pyrazole oxime ether compound (I) having the oxazole biphenylyl structure has an effectiveprevention and control effect on harmful insects, and the compound can be used for preparing pesticides in the field of agriculture, gardening and the like. The formula (1) is shown in the description.

Description

Technical field [0001] The invention relates to the field of chemical pesticides, in particular to a pyrazole oxime ether compound containing an oxazole biphenyl structure and a preparation method and application thereof. Background technique [0002] The prevention and control of pests has always been the core area of ​​pesticide scientific research, and the widespread use of pesticides has enabled most pests to be effectively controlled. However, with the continuous expansion of pesticide application scale, the problem of resistance of traditional pesticide varieties 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] The oxazole group has a broad spectrum of biological activity and is widely used in the fields of pesticides and medicine. In recent years, many compounds with oxazole structure reported in the literature have good insectici...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/76A01P7/02A01P7/04
CPCC07D413/12A01N43/76
Inventor 沈爱宝丁颖吴锦明戴红姚炜石玉军郑丹丹李玲
Owner NANTONG UNIVERSITY
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