Preparation and application of pyrazole oxime ester compound containing 2-chloropyridine structure

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

Active Publication Date: 2016-08-24
SHANGHAI RUN BIOTECH CO LTD
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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...

Method used

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  • Preparation and application of pyrazole oxime ester compound containing 2-chloropyridine structure
  • Preparation and application of pyrazole oxime ester compound containing 2-chloropyridine structure
  • Preparation and application of pyrazole oxime ester compound containing 2-chloropyridine structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] In a 100mL four-necked flask, add 4mmol II a, 3mL pyridine and 20mL dichloromethane. Under stirring at room temperature, 5 mmol of III in dichloromethane solution (10 mL) was slowly added dropwise thereto. After dropping, continue to stir at room temperature for 12 hours. The solvent was distilled off under reduced pressure, 60 mL of dichloromethane was added to the residue, washed with saturated brine, dried over anhydrous magnesium sulfate, precipitated, separated and purified by column chromatography to obtain the target compound Ia with a yield of 51%; 1 H NMR (400MHz, CDCl 3 ): δ8.53(d, J=4.0Hz, 1H, Py-H), 8.09~8.11(s, 2H, CH=N and Py-H), 7.40(d, J=8.0Hz, 1H, Ar- H),7.32~7.36(m,1H,Py-H),7.25~7.29(m,1H,Ar-H),7.18~7.21(m,1H,Ar-H),6.80(d,J=8.0Hz ,1H,Ar-H),3.65(s,3H,N-CH 3 ),2.52(s,3H,CH 3 ).

Embodiment 2

[0029]

[0030] In a 100mL four-necked flask, add 3mmol II b, 5mL triethylamine and 25mL dichloromethane. Under stirring at room temperature, 4.2 mmol of III in dichloromethane solution (15 mL) was slowly added dropwise thereto. After dropping, continue to stir at room temperature for 16 hours. The solvent was distilled off under reduced pressure, 60 mL of dichloromethane was added to the residue, washed with saturated brine, dried over anhydrous magnesium sulfate, precipitated, separated and purified by column chromatography to obtain the target compound Ib with a yield of 53%; 1H NMR (400MHz , CDCl 3 ): δ8.53(d, J=4.8Hz, 1H, Py-H), 8.14(s, 1H, CH=N), 8.10(d, J=7.6Hz, 1H, Py-H), 7.33~7.36 (m,1H,Py-H),7.08~7.25(m,3H,Ar-H),6.87~6.91(m,1H,Ar-H),3.69(s,3H,N-CH 3 ),2.49(s,3H,CH 3 ).

Embodiment 3

[0032]

[0033] In a 100mL four-neck flask, add 5mmol II c, 10mmol sodium bicarbonate and 20mL acetonitrile. Under stirring at room temperature, 6 mmol of III in acetonitrile solution (15 mL) was slowly added dropwise thereto. After dropping, the reaction was heated to reflux for 14 hours. The solvent was distilled off under reduced pressure, 50 mL of dichloromethane was added to the residue, washed with saturated brine, dried over anhydrous magnesium sulfate, precipitated, separated and purified by column chromatography to obtain the target compound Ic with a yield of 63%; 1 H NMR (400MHz, CDCl 3 ): δ8.52(d, J=4.0Hz, 1H, Py-H), 8.14(s, 1H, CH=N), 8.09(d, J=8.0Hz, 1H, Py-H), 7.30~7.35 (m,3H,Py-H and Ar-H),6.99(d,J=8.0Hz,2H,Ar-H),3.63(s,3H,N-CH 3 ),2.49(s,3H,CH 3 ).

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PUM

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Abstract

The invention relates to a pyrazole oxime ester compound (I) containing a 2-chloropyridine structure and a preparation method and application of the pyrazole oxime ester compound (I). The pyrazole oxime ester compound (I) containing the 2-chloropyridine structure is obtained through condensation of oxime and 2-chloronicotinyl chloride, wherein oxime contains pyrazole. The pyrazole oxime ester compound containing the 2-chloropyridine structure has effective prevention and treatment effects on harmful insects and can be used for preparing pesticides in the fields such as agriculture and gardening.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a pyrazole oxime ester compound containing a 2-chloropyridine 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] The pyrazole oxime structure is a common class of insecticide active fragments, and its representative compounds are such as pyraclofen: [0004] [0005] Pyridine rings are common active fragments in drug molecules and pesticide molec...

Claims

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Application Information

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IPC IPC(8): C07D401/12A01N43/56A01P7/00A01P7/04
CPCA01N43/56C07D401/12
Inventor 戴红李宏戴宝江石玉军金仲超肖瑶曹琳陈佳
Owner SHANGHAI RUN BIOTECH CO LTD
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