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Phenazine-1-carboxamide compounds and their applications

A technology of formamides and compounds, applied in the chemical field, can solve the problems of difficult formulation processing, poor solubility of phenazine-1-carboxylic acid, etc., and achieve broad-spectrum insecticidal effect

Active Publication Date: 2021-04-13
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, phenazine-1-carboxylic acid has poor solubility in almost all solvents, and it is difficult to process dosage forms. Little research has been done to create new pesticides

Method used

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  • Phenazine-1-carboxamide compounds and their applications
  • Phenazine-1-carboxamide compounds and their applications
  • Phenazine-1-carboxamide compounds and their applications

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0051] The synthetic method of phenazine-1-carboxamide compound of the present invention comprises the following steps:

[0052]

[0053] Below in conjunction with specific example, further set forth the present invention. It should be understood that these examples are only for illustrating the present invention and are not intended to limit the scope of the present invention. The experimental methods that do not indicate the specific implementation conditions in the following examples are usually in accordance with conventional conditions, or in accordance with the conditions suggested by the manufacturer. Percentages and parts are by mass unless otherwise indicated.

[0054] Next, taking N-(2-chloro-4-trifluoromethylphenyl)phenazine-1-carboxamide as an example, the synthesis method of the phenazine-1-carboxamide compounds of the present invention will be described.

example 1

[0055] Example 1: Synthesis of N-(2-chloro-4-trifluoromethylphenyl)phenazine-1-carboxamide:

[0056] 1) Synthesis of phenazine-1-formyl chloride:

[0057]

[0058] Add 2.5 g (11.2 mmol) of phenazine-1-carboxylic acid, 30 ml of dichloromethane into a 100 ml single-port reaction flask, drop 1 to 2 drops of DMF, slowly add 3.0 g of oxalyl chloride (to prevent flushing), and then heat to reflux Reaction until the phenazine-1-carboxylic acid completely disappears, continue to reflux for 2 to 3 hours, remove the solvent on a rotary evaporator, add a small amount of dichloromethane to dissolve, and then spin dry to take away the excess oxalyl chloride as much as possible clean, and then add a certain amount of dichloromethane to dissolve it for use in the next step.

[0059] 2) Synthesis of phenazine-1-carboxylic acid:

[0060]

[0061]Add 2.0g (10.0mmol) of 2-chloro-4-trifluoromethylaniline and 30ml of dichloromethane into a 100mL three-necked flask, cool in an ice-water bat...

example 2

[0062] Example 2: Synthesis of N-(3-chloropyridin-4-yl)phenazine-1-carboxamide:

[0063]

[0064] Add 1.3g (10.0mmol) of 3-chloro-4-aminopyridine and 30ml of dichloromethane into a 100mL three-necked flask, cool in an ice-water bath to 0-5°C, and add dropwise the phenazine-1-methanol prepared in step 1). Acyl chloride (11.2mmol) dichloromethane solution, after dropwise addition, keep warm at 0-5°C for 1 hour, monitor by pointing plate, the reaction is complete. Remove the solvent, add 50ml of dichloromethane to dissolve, fully wash the organic layer with 5% hydrochloric acid aqueous solution, separate the organic layer, then wash the organic layer with 5% aqueous sodium hydroxide solution, separate the organic layer, and dry with anhydrous sodium sulfate After 1 hour, suction filtration was performed, and the filtrate was desolvated to obtain 3.15 g of the above-mentioned amide. Yield 94%. m.p.206.2~208.1℃, 1 H NMR (600MHz, CDCl 3 )δ:13.52(s,1H),9.12(dd,J=8.4,1.8Hz,1H),...

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Abstract

The present invention provides a kind of phenazine-1-carboxamide compound and application thereof, belonging to the field of chemistry. The general formula of this type of compound has the following structure: wherein: R is C 4 -C 10 Alkyl, C 3 -C 10 Alkenyl, C 3 -C 10 Alkynyl, C 3 -C 10 ester group, amide group, cyano group, aldehyde group, ketone group and one or more saturated or unsaturated hydrocarbon groups, alkoxy groups, halogens, fluoromethyl groups, nitro groups, cyano groups, ester groups, ketone groups, Aldehyde substituted phenyl, substituted pyridyl, substituted furyl, substituted pyrazolyl, substituted thiazolyl, substituted thienyl; R' is hydrogen, methyl, ethyl, ethyl acetate; n Any value from 0-10. The phenazine-1-carboxamide compound with novel structure of the present invention can be used for preventing and treating diseases on crops.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a synthesis method and application of phenazine-1-carboxamide compounds. Background technique [0002] The natural product phenazine-1-carboxylic acid (PCA) (Formula 1) has a unique chemical structure and excellent agricultural fungicidal activity, and is effective against rice sheath blight, watermelon wilt, pepper blight, wheat take-all, watermelon anthracnose, Rapeseed sclerotinia and other pathogenic bacteria have broad-spectrum agricultural antibacterial activity, which is harmless to humans, animals and the environment. It is a safe, efficient and environmentally friendly microbial source green pesticide. Using phenazine-1-carboxylic acid as the lead compound, research on the creation of new highly active pesticides is also on the rise, among which phenazine-1-carboxylic acid amides are the best among their highly active analogues, such as Li Rongxiu et al. (Bioorganic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/46C07D401/12C07D413/12C07D409/12A01N43/60A01N43/80A01P3/00
CPCA01N43/60A01N43/80C07D241/46C07D401/12C07D409/12C07D413/12
Inventor 吴清来秦川李俊凯
Owner YANGTZE UNIVERSITY
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