Aminodiacyloxylamide derivative, preparation method, and application thereof

A technology of aminobisacyloxyamide and derivatives is applied in the application field of active ingredients to achieve the effects of low preparation cost, simple operation and high reaction efficiency

Active Publication Date: 2017-07-04
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few mature studies on aminoacyloxyamide fungicides, so it is particularly necessary to research and develop new aminoacyloxyamide fungicides with better antibacterial activity.

Method used

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  • Aminodiacyloxylamide derivative, preparation method, and application thereof
  • Aminodiacyloxylamide derivative, preparation method, and application thereof
  • Aminodiacyloxylamide derivative, preparation method, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] preparation of

[0024] Add 4-chloro-o-azidobenzoic acid (VI) (1mmol), p-chloroacetophenone aldehyde (V) (1mmol) and methyl acetate isonitrile (IV) (1mmol) to a 50mL flask, and react at 30°C , the reaction solvent is water, after reacting for 12 hours, add triphenylphosphine (1.2mmol), continue to stir at 30 ℃ for 3 hours, after the reaction is completed, the reaction solution is extracted with dichloromethane, dried, and then The solvent dichloromethane was removed, and the residue was subjected to column chromatography to obtain 0.264 g of white crystals, with a yield of 67%.

[0025] Elemental analysis: found value C% 51.73 H% 3.55 N% 7.40

[0026] Calculated value C% 51.59 H% 3.67 N% 6.38

[0027] 1 H NMR (CDCl 3 ,600MHz)δ(ppm)8.96(t,J=6.0Hz,1H,NH),8.11(d,J=8.4Hz,2H,Ar-H),8.04(d,J=8.8Hz,1H,Ar-H) H), 7.66(d, J=8.0Hz, 2H, Ar-H), 6.88(t, J=2.8Hz, 3H, NH 2 ,CH),6.67-6.60(m,2H,Ar-H),3.95(d,J=5.6Hz,2H,CH 2 ),3.61(s,3H,CH 3 ).

[0028] HRMS Calculated for [C 19...

Embodiment 2

[0030] preparation of

[0031] Add 4-chloro-o-azidobenzoic acid (VI) (1mmol), p-methylacetophenone aldehyde (V) (1mmol) and methyl acetate isonitrile (IV) (1mmol) in a 50mL flask, at 30°C Reaction, the reaction solvent is water, after 12 hours of reaction, add triphenylphosphine (1.2mmol), continue to stir at 30 ℃ for 3 hours, after the reaction is completed, the reaction solution is extracted with dichloromethane, dried, and then The dichloromethane was removed as the solvent, and the residue was subjected to column chromatography to obtain 0.260 g of white crystals, with a yield of 62%.

[0032] Elemental analysis: found value C% 57.59 H% 4.65 N% 6.80

[0033] Calculated C% 57.35 H% 4.57 N% 6.69

[0034] 1 H NMR (DMSO, 400MHz) δ (ppm) 9.06 (s, 1H, NH), 8.10 (t, J = 9.6Hz, 3H, Ar-H), 7.48 (d, J = 7.6Hz, 2H, Ar-H ),6.98(s,3H,NH 2 ,CH),6.72(s,2H,Ar-H),4.05(s,2H,CH 2 ),3.71(s,3H,CH 3 ),2.50(s,3H,CH 3 ).

[0035] HRMS Calculated for [C 20 h 19 ClN 2 o 6 +H]+:419.10...

Embodiment 3

[0037] preparation of

[0038] Add o-azidobenzoic acid (VI) (1mmol), p-isooctylacetophenone aldehyde (V) (1mmol) and ethyl acetate isonitrile (IV) (1mmol) in the 50mL flask, react at 30°C, The reaction solvent is water. After 12 hours of reaction, triphenylphosphine (1.2 mmol) was added and stirred for 3 hours at 30°C. After the reaction was completed, the reaction solution was extracted with dichloromethane, dried, and then removed under reduced pressure. The dichloromethane was removed from the solvent, and the residue was subjected to column chromatography to obtain 0.278 g of a light yellow oily liquid, with a yield of 56%.

[0039] Elemental Analysis: Found C% 67.93 H% 7.40 N% 5.77

[0040] Calculated value C% 67.72 H% 7.31 N% 5.64

[0041] 1 HNMR (CDCl 3 ,400MHz)δ(ppm)8.93(t,J=6.4Hz,1H,NH),8.13-6,69(m,11H,8Ar-H,NH 2 ,CH),4.09-0.80(m,24H,CH,7CH 2 ,3CH 3 ).

[0042] HRMS Calculated for [C 28 h 36 N 2 o 6 +H]+: 497.2652, Found: 497.2690.

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Abstract

The invention provides an aminodiacyloxylamide derivative which has bactericidal activity and contains an amino group. The general formula of the aminodiacyloxylamide derivative is represented as (I), wherein R1 is a methyl group, an ethyl group and an isohexyl group; R2 is chlorine, an isooctyl group and an n-heptyl group; and R3 is hydrogen or chlorine. A preparation method includes the steps of: 1) performing a reaction to azide-carboxylic acid and keto-aldehyde and isonitrile at 30 DEG C, reaction solvent being water; 2) after the reaction is carried out for 24 h, adding triphenylphosphine, continuously performing the reaction for 2-5 h; and 3) after the reaction is finished, extracting the reaction liquid with dichloromethane, drying the reaction liquid and removing the solvent, dichloromethane, under reduced pressure, and performing column chromatography to the residual substance to produce the target compound (I). The compound has good inhibition activity on penicillium digitatum and penicillium italicum, and can be used as a bactericide.

Description

technical field [0001] The invention relates to aminobisacyloxyamide derivatives and their application as active ingredients of fungicides. Background technique [0002] Aminoacyloxyamide compounds are a very important class of compounds, especially aminobisacyloxyamide derivatives. According to literature reports, this type of compound has good biological activities such as anti-inflammatory, bactericidal, and anti-cancer, so it has been widely used in pharmacology. attention of scientists and chemists. Fungicides are an important part of pesticides and play an important role in the history of pesticide development. However, there are still relatively few mature studies on aminoacyloxyamide fungicides, so it is particularly necessary to research and develop new aminoacyloxyamide fungicides with better antibacterial activity. In view of the good bactericidal activity of aminoacyloxy amides, especially amides containing two acyloxy groups in the molecule. It is of great si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/80C07C231/12A01N37/18A01P3/00
CPCA01N37/18C07C231/12C07C235/80
Inventor 王龙朝飞郑开波张诺诺李德江
Owner CHINA THREE GORGES UNIV
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