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Trifluoromethylpicolinamide-containing compound and preparation method and application thereof

A technology of trifluoromethyl pyridine amide and trifluoromethyl pyridine, which is applied in the field of organic chemical synthesis, can solve the problems of poor environmental compatibility, and the herbicide is not easily degraded, and achieves low toxicity, convenient operation and good environmental compatibility. Effect

Inactive Publication Date: 2018-10-09
上海凯爱网络科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems that many existing herbicides are difficult to degrade and have poor environmental compatibility, the present invention provides a compound containing trifluoromethyl pyridine amide and its preparation method and application

Method used

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  • Trifluoromethylpicolinamide-containing compound and preparation method and application thereof
  • Trifluoromethylpicolinamide-containing compound and preparation method and application thereof
  • Trifluoromethylpicolinamide-containing compound and preparation method and application thereof

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preparation example Construction

[0022] In one embodiment, the preparation method at least includes the following steps:

[0023] Using 2-trifluoromethylpyridine-3-carboxylic acid and aminoacetonitrile hydrochloride to carry out condensation acylation reaction under the conditions of organic solvent, alkali and condensing agent to obtain trifluoromethylpyridine amides compounds.

[0024] The above-mentioned preparation method is further explained below:

[0025] Preferably, the molar ratio of the 2-trifluoromethylpyridine-3-carboxylic acid to aminoacetonitrile hydrochloride is 1:1.0-1.2, so as to ensure the sufficient progress of the condensation reaction.

[0026] Preferably, the organic solvent is dichloromethane or chloroform.

[0027] Preferably, the condensing agent is at least one of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 1-hydroxybenzotriazole (HOBt) .

[0028] Preferably, the base is triethylamine or N,N-diisopropylethylamine, which provides a basic environment for th...

Embodiment 1

[0034] Preparation of structural formula I containing trifluoromethylpyridine amides

[0035] 2-trifluoromethylpyridine-5-carboxylic acid (0.191g, 1.0mmol) and aminoacetonitrile hydrochloride (0.081g, 1.0mmol) were dissolved in 25mL of dichloromethane, triethylamine (0.202g, 2.0mmol) was added ), then added EDC (0.287mg, 1.5mmol), HOBt (0.20g, 1.5mmol), and reacted at 25°C for 3h. Washing (20ml*1), drying with anhydrous sodium sulfate, precipitation to obtain a crude product, the crude product was purified by column chromatography to obtain a white solid, m.p.83-85°C, yield: 88%. 1H NMR (300MHz, DMSO) δ: 9.76-9.53 (m, 1H, pyridine), 9.16 (s, 1H, pyridine), 8.48 (d, J=9.2Hz, 1H, pyridine), 8.08 (d, J=9.2 Hz, 1H, pyridine), 4.39 (d, J=7.6Hz, 2H, CH2).

Embodiment 2

[0037] Preparation of structural formula II containing trifluoromethylpyridine amides

[0038] 2-trifluoromethylpyridine-3-carboxylic acid (0.191g, 1.0mmol) and aminoacetonitrile hydrochloride (0.081g, 1.0mmol) were dissolved in 25mL of dichloromethane, triethylamine (0.202g, 2.0mmol) was added ), then added EDCI (0.287mg, 1.5mmol), HOBt (0.20g, 1.5mmol), reacted at 25°C for 2.5h, TLC detected that the reaction was complete, the reaction solution was washed with water (20ml*2), washed with saturated brine (20ml *1), dried over anhydrous sodium sulfate, and precipitated to obtain a crude product, which was obtained by column chromatography as an off-white solid, m.p.90-93°C, yield: 79.5%. 1H NMR (300MHz, DMSO) δ9.43(s, 1H, NH), 8.83(d, J=4.3Hz, 1H, pyridine), 8.07(d, J=7.6Hz, 1H, pyridine), 7.90-7.70( m, 1H, pyridine), 4.37 (d, J=7.2Hz, 2H, CH2).

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Abstract

The invention relates to the technical field of organic chemical synthesis and specifically discloses a trifluoromethylpicolinamide-containing compound and a preparation method and application thereof. The preparation method comprises that 2-trifluoromethylpyridine-3-carboxylic acid and aminoacetonitrile hydrochloride undergo a condensation acylation reaction in the presence of an organic solvent,a base and a condensing agent to produce the trifluoromethylpicolinamide-containing compound. The trifluoromethyl and amide bond at the ortho position and meta position of a pyridine ring have two structures shown in the formulas I and II and the two structures have low toxicity to the beneficial organism, can be easily degraded, have good environmental compatibility and herbicidal activity and can produce good effects of preventing dicotyledon weeds.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to compounds containing trifluoromethyl pyridine amides and their preparation methods and applications. Background technique [0002] Pyridinamide compounds have a wide range of biological activities, such as insecticide, fungicide and herbicide. In recent years, in the field of sterilization, there have been fungicides and insecticides on the market. In 2002, BASF first registered the succinate dehydrogenase inhibitor (SDHI) fungicide-Boscalid (A), boscalid It is a broad-spectrum, systemic fungicide, which can control diseases caused by Ascomycetes and Deuteromycetes on fruits, vegetables and other crops. [0003] [0004] Fluonicamid (flonicamid) (B) is a new type of pyridine amide insecticide developed by Japan Ishihara Industry on the basis of fungicides and herbicides with reference to the structure of trifluoromethylpyridine. It exerts its effect by hind...

Claims

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Application Information

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IPC IPC(8): C07D213/82A01N43/40A01P13/00
CPCA01N43/40C07D213/82
Inventor 徐立勇
Owner 上海凯爱网络科技有限公司
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