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N-pyrazolyl carboxanilide compound, intermediate, composition, preparation method and application

A technology of pyrazolyl carboxanilide and compounds, which is applied in the preparation of amino compounds, organic compounds, botany equipment and methods, etc., and can solve the problems of large dosage and narrow application range

Inactive Publication Date: 2017-11-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved in the present invention is to overcome defects such as large dosage and narrow application range of pyrazole amide fungicides in the prior art, and provide N-pyrazolyl carboxanilide compounds, intermediates, compositions, Preparation method and application

Method used

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  • N-pyrazolyl carboxanilide compound, intermediate, composition, preparation method and application
  • N-pyrazolyl carboxanilide compound, intermediate, composition, preparation method and application
  • N-pyrazolyl carboxanilide compound, intermediate, composition, preparation method and application

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Embodiment 1

[0123] Example 1 3-(difluoromethyl)-nitrogen-(3-fluoro-2-(1,3 dimethylbutyl)phenyl)-1-methyl-1H-pyrazole-4-carboxamide Preparation (SIOC-FF-184)

[0124]

Embodiment 1-a

[0125] Embodiment 1-a (preparation of 2-amino-6-fluoroacetophenone)

[0126]

[0127] Add raw material 2-amino-6-fluorobenzonitrile (78g, 0.57mol) and 300ml of anhydrous tetrahydrofuran into the three-necked flask, add ice salt bath to -10°C, add methylmagnesium bromide (205g, 1.72mol) dropwise, add After completion, the temperature was raised to 60° C., and the reaction was carried out overnight. After completion, quench the reaction with 10% hydrochloric acid, adjust the pH of the solution to acidity, and heat to reflux for 2 h. After being cooled to room temperature, sodium hydroxide was added to adjust the pH of the solution to alkaline, extracted with ethyl acetate, the organic phase was washed with water, dried over anhydrous sodium sulfate, evaporated to dryness, separated by flash column chromatography (ethyl acetate:petroleum ether (volume Ratio)=1:10), the product 12g was obtained.

[0128] 1 H NMR (400MHz, CDCl 3 )δ7.17-7.09(m,1H),6.40(d,J=8.4Hz,1H),6.36-6.28...

Embodiment 1-b

[0130] Embodiment 1-b (preparation of 2-(2-amino-6-fluorophenyl)-4-methyl-2-pentanol)

[0131]

[0132] The raw material 2-amino-6-fluoroacetophenone (12g, 78.4mmol) was dissolved in 50ml of anhydrous tetrahydrofuran, cooled to 0°C in an ice bath, and isobutylmagnesium bromide (37.9g, 235.3mmol) was added dropwise. Raised to room temperature for 2h. After the end, it was slowly poured into water and extracted with ethyl acetate. The organic phase was washed twice with water, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 10 g of crude product. Feed directly without purification.

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Abstract

The invention discloses an N-pyrazole formyl aniline compound expressed by the formula I in the specification, an intermediate, a compound, a preparation method and application. The N-pyrazole formyl aniline compound is good in bactericidal activity effect, wide in bacteriocidal spectrum and low in drug dosage, and has remarkable effect for preventing and controlling rice sheath blight. The preparation method for the N-pyrazole formyl aniline compound is simple, low in cost, high in production efficiency and suitable for industrial production.

Description

technical field [0001] The invention relates to N-pyrazolylcarboxanilide compounds, intermediates, compositions, preparation methods and applications. Background technique [0002] Amide compounds are an important class of compounds with fungicidal activity. Since the first amide fungicide carboxin was successfully developed and marketed by Lilailu Company (now Kejuya Company) in 1966, the synthesis and bactericidal activity research of amide compounds has always been an important issue in the field of pesticides and even medicine. A research hotspot, there are a large number of amide compounds and varieties with novel structures reported. Similarly, since Knott discovered that antipyrine containing a pyrazole ring has analgesic, anti-inflammatory and antipyretic effects in 1883 and Thampson reported that 2-pyrazol-5-one can inhibit crop growth in 1946, pyrazole compounds have been Because of its high-efficiency biological activity, it has attracted the attention of people...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/14C07D231/16A01N43/56A01P3/00C07C225/22C07C221/00C07C211/52C07C209/70
CPCA01N43/56C07C209/70C07C211/52C07C221/00C07C225/22C07D231/14C07D231/16
Inventor 吕龙冯骁唐庆红芦昕婷
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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