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Preparation method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure

A technology of methyl pyrazole and pyrazole oxime ether is applied in the field of pesticides to achieve the effect of excellent control effect

Active Publication Date: 2017-02-22
NANTONG UNIVERSITY +1
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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 method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure
  • Preparation method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure
  • Preparation method and application of pyrazole oxime ether compound containing 4-Cl-3-ethyl-1-methylpyrazole structure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] 4 mmol of compound IIa was dissolved in 20 mL of acetonitrile, then 8 mmol of anhydrous potassium carbonate and 6 mmol of intermediate III were added, and the temperature was raised to reflux for 12 hours. After the reaction solution was cooled to room temperature, it was filtered with suction to remove the solid, the mother liquor 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 ): δ7.71(s, 1H, CH=N), 7.07-7.11(m, 1H, Ar-H), 6.67-6.99(m, 3H, Ar-H), 4.96(s, 2H, CH 2 ),3.90(s,3H,OCH 3 ),3.78(s,3H,N-CH 3 ),3.61(s,3H,N-CH 3 ), 2.61 (q, J=7.6Hz, 2H, CH 2 ),2.34(s,3H,CH 3 ), 1.22(t, J=7.6Hz, 3H, CH 3 ).

Embodiment 2

[0035]

[0036] Dissolve 10mmol of compound IIb in 30mL of acetonitrile, then add 15mmol of anhydrous potassium carbonate and 13mmol of intermediate III, and react under reflux for 16 hours. After the reaction solution was cooled to room temperature, it was filtered with suction to remove the solid, the mother liquor was rotary 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 ): δ7.73(s, 1H, CH=N), 6.82(s, 4H, Ar-H), 4.98(s, 2H, CH 2 ),3.79(s,3H,OCH 3 ),3.78(s,3H,N-CH 3 ),3.59(s,3H,N-CH 3 ),2.62(q,J=7.6Hz,2H,CH 2 ),2.35(s,3H,CH 3 ), 1.22(t, J=7.6Hz, 3H, CH 3 ).

Embodiment 3

[0038]

[0039] Dissolve 6mmol of compound IIc in 25mL of dry DMF, then add 10mmol of anhydrous potassium carbonate and 9mmol of intermediate III, heat up to 85°C, and react for 18 hours. After cooling the reaction solution to room temperature, it was poured into 80 mL of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, separated and purified by column chromatography to obtain the target compound Ic. 1 H NMR (400MHz, CDCl 3 ): δ7.76(s, 1H, CH=N), 7.18(d, J=8.8Hz, 2H, Ar-H), 6.90(d, J=9.2Hz, 2H, Ar-H), 4.95(s ,2H,CH 2 ),3.78(s,3H,N-CH 3 ),3.60(s,3H,N-CH 3 ), 2.61 (q, J=7.6Hz, 2H, CH 2 ),2.35(s,3H,CH 3 ), 1.22(t, J=7.6Hz, 3H, CH 3 ).

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Abstract

The invention relates to a pyrazole oxime ether compound (I) containing a 4-Cl-3-ethyl-1-methylpyrazole structure, a preparation method thereof and the application thereof. The pyrazole oxime ether compound (I) is prepared through the condensation reaction of pyrazole oxime (II) and 4-Cl-5-methyl chloride-3-ethyl-1-methylpyrazole (III). The pyrazole oxime ether compound (I) containing the 4-Cl-3-ethyl-1-methylpyrazole structure has the control effect on harmful insects. The above compound can be used for preparing pesticides in the fields of agriculture, gardening and the like.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a pyrazole oxime ether compound containing a 4-chloro-3-ethyl-1-methylpyrazole structure and a preparation method and application 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 oxime compounds are an important class of nitrogen-containing heterocyclic compounds, and their representative compounds, such as pyraflux, play an important role in killing insects in the field of pesticides. ...

Claims

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Application Information

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IPC IPC(8): C07D231/20A01N43/56A01P7/00A01P7/04
CPCA01N43/56C07D231/20
Inventor 戴红石玉军仲苏林葛书山曹雄飞方源洪宇叶林玉
Owner NANTONG UNIVERSITY
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