Preparation and application of difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure

A technology of difluoromethylpyrazoles and compounds, applied in the field of pesticides, to achieve excellent control effects

Active Publication Date: 2016-07-13
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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  • Preparation and application of difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure
  • Preparation and application of difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure
  • Preparation and application of difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of product Ia

[0024]

[0025] Add intermediate III (10mmol) and IVa (10mmol) into 30mL of toluene, raise the temperature to reflux, and use a water separator to continuously take out the water generated by the reaction until no water is produced. After cooling down, concentrate to dryness under reduced pressure. Then the concentrate was dissolved in 30mL chloroform, cooled to 0°C in an ice-water bath, 20mmol N-bromosuccinimide (NBS) was slowly added to the above solution in batches, the reaction was continued at 0°C for 1 hour, and then triethyl Amine 2mL, continue stirring reaction at room temperature for 2 hours, add appropriate amount of water to the reaction mixture, separate the chloroform layer, extract the water phase with chloroform once, combine the chloroform layers, dry over anhydrous sodium sulfate, column chromatography (petroleum ether / acetic acid Ethyl ester=10 / 1) isolated white solid product Ia in 65% yield. 1 HNMR (400M...

Embodiment 2

[0026] Embodiment 2: the synthesis of product Ib

[0027]

[0028] Add intermediate III (10mmol) and IVb (11mmol) to 35mL toluene, raise the temperature to reflux, use a water separator to continuously take out the water generated by the reaction until no water is produced, and after cooling down, concentrate to dryness under reduced pressure. Then the concentrate was dissolved in 25mL chloroform, cooled to 0°C in an ice-water bath, and 25mmol N-bromosuccinimide (NBS) was slowly added to the above solution in batches, and the reaction was continued at 0°C for 1.5 hours, and then triethyl Amine 2mL, continue stirring reaction at room temperature for 2 hours, add appropriate amount of water to the reaction mixture, separate the chloroform layer, extract the water phase with chloroform once, combine the chloroform layers, dry over anhydrous sodium sulfate, column chromatography (petroleum ether / acetic acid Ethyl ester=10 / 1) isolated white solid product Ib with a yield of 55%. ...

Embodiment 3

[0029] Embodiment 3: the synthesis of product Ic

[0030]

[0031] Add intermediate III (10mmol) and IVc (11mmol) into 20mL of toluene, raise the temperature to reflux, and use a water separator to continuously take out the water generated by the reaction until no water is produced. After cooling down, concentrate to dryness under reduced pressure. Then the concentrate was dissolved in 30mL chloroform, cooled to 0°C in an ice-water bath, 22mmol N-bromosuccinimide (NBS) was slowly added to the above solution in batches, the reaction was continued at 0°C for 1 hour, and then triethyl Amine 2.5mL, continue to stir and react at room temperature for 3 hours, add an appropriate amount of water to the reaction mixture, separate the chloroform layer, extract the aqueous phase with chloroform once, combine the chloroform layers, dry over anhydrous sodium sulfate, and perform column chromatography (petroleum ether / Ethyl acetate = 10 / 1) was isolated to obtain the white solid product ...

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Abstract

The invention relates to difluoromethyl pyrazole compound (I) comprising 1,3,4-oxadiazole structure and a preparation method and application thereof.The compound is obtained by dehydration and cyclization of pyrazole hydrazine intermediate (II) comprising furan groups.The difluoromethyl pyrazole compound comprising 1,3,4-oxadiazole structure is effective in controlling harmful insects and is useful in the preparation of insecticides for agricultural field, gardening field and other fields.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a difluoromethylpyrazole compound containing a 1,3,4-oxadiazole 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 compounds play an important role in the design, synthesis and commercial application of modern pesticide molecules. In recent years, fluorine-containing pyrazole pesticides have been further developed. A new generation of fungi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A01N43/824A01P7/04
CPCA01N43/82C07D413/14
Inventor 戴红石玉军何海兵李阳金仲超肖瑶袁艳方源
Owner 安徽先胜达农药有限公司
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