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Pyrazole oxime ether compound containing pyrazole biphenyl structure, and preparation method and application thereof

A technology of pyrazole biphenyl and pyrazole oxime ether, which is applied in the fields of organic chemistry and pesticides to achieve excellent control effects

Active Publication Date: 2017-07-14
安徽先胜达农药有限公司
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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 containing pyrazole biphenyl structure, and preparation method and application thereof
  • Pyrazole oxime ether compound containing pyrazole biphenyl structure, and preparation method and application thereof
  • Pyrazole oxime ether compound containing pyrazole biphenyl structure, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] 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 14 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 ): δ7.91(d, J=2.4Hz, 1H, Pyrazole-H), 7.82(s, 1H, CH=N), 7.72(d, J=2.0Hz, 1H, Pyrazole-H), 7.63(d ,J=8.4Hz,2H,Ar-H),7.38(d,J=8.4Hz,2H,Ar-H),7.16-7.20(m,1H,Ar-H),6.90(d,J=7.6Hz ,1H,Ar-H),6.66-6.70(m,2H,Ar-H),6.46(t,J=2.4Hz,1H,Pyrazole-H),5.03(s,2H,CH 2 ),3.59(s,3H,N-CH 3 ),2.38(s,3H,CH 3 ),2.31(s,3H,CH 3 ).

Embodiment 2

[0047]

[0048] 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 was completed, the reaction was heated to reflux for 13 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 ): δ7.91(d, J=2.4Hz, 1H, Pyrazole-H), 7.81(s, 1H, CH=N), 7.72(d, J=1.6Hz, 1H, Pyrazole-H), 7.63(d ,J=8.4Hz,2H,Ar-H),7.38(d,J=8.4Hz,2H,Ar-H),7.08(d,J=8.4Hz,2H,Ar-H),6.77(d,J =8.8Hz, 2H, Ar-H), 6.46(t, J=2.0Hz, 1H, Pyrazole-H), 5.03(s, 2H, CH 2 ),3.59(s,3H,N-CH 3 ),2.37(s,3H,CH 3 ),2.30(s,3H,CH 3 ).

Embodiment 3

[0050]

[0051] 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 complete, the temperature was raised to 90° C. and reacted for 16 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 ): δ7.91(d, J=2.4Hz, 1H, Pyrazole-H), 7.82(s, 1H, CH=N), 7.72(d, J=1.6Hz, 1H, Pyrazole-H), 7.64(d ,J=8.8Hz,2H,Ar-H),7.35(d,J=8.8Hz,2H,Ar-H),7.16(d,J=8.4Hz,2H,Ar-H),6.89(d,J =9.2Hz, 2H, Ar-H), 6.46(t, J=2.0Hz, 1H, Pyrazole-H), 4.98(s, 2H, CH 2 ),3.61(s,3H,N-CH 3 ),2.36(s,3H,CH 3 ).

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Abstract

The invention relates to a pyrazole oxime ether compound (I) containing a pyrazole biphenyl structure, and a preparation method and application thereof. The pyrazole oxime ether compound (I) containing the pyrazole biphenyl structure is formed by condensing tetrazole biphenyl methyl chloride (II) and pyrazolyl hydroxyoxime (III). The pyrazole oxime ether compound (I) containing the pyrazole biphenyl structure has an effective control effect on harmful insects. The compound is used for preparing insecticides in the fields such as agriculture and gardening.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to a pyrazole oxime ether compound containing a pyrazole biphenyl 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] 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 insecticides a...

Claims

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Application Information

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IPC IPC(8): C07D231/20A01P7/04
Inventor 戴红石玉军姚炜宋婵钱宏炜王祥龙张周韩旭东
Owner 安徽先胜达农药有限公司
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