Phenazine-1-carboxylic acid bisamide compounds and application thereof

A technology of carboxylic acid bisamides and compounds, which is applied in the field of pesticide compound preparation, can solve the problems that it is difficult to develop into diversified dosage forms, and achieve a broad-spectrum bactericidal effect

Active Publication Date: 2018-01-26
上海沪联生物药业(夏邑)股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its solubility problem, phenazine-1-carboxylic acid makes it difficult to be developed into a variety of dosage forms, and so far, n

Method used

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  • Phenazine-1-carboxylic acid bisamide compounds and application thereof
  • Phenazine-1-carboxylic acid bisamide compounds and application thereof
  • Phenazine-1-carboxylic acid bisamide compounds and application thereof

Examples

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preparation example Construction

[0030] The synthetic method of phenazine-1-carboxylic acid bisamide compound of the present invention comprises the following steps:

[0031]

[0032] 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.

[0033] The synthesis method of the phenazine-1-carboxylic acid bisamide compound of the present invention is described below with the synthesis conditions and methods of some example compounds.

example 1

[0034] Example 1: N-(2-phenacylethylamino)phenazine-1-carboxamide (R is a substituted phenyl group (A) in the general formula (I), R 1 , R 2 , R 3 , R 4 and R 5 For the synthesis of H):

[0035] 1) Synthesis of phenazine-1-formyl chloride:

[0036]

[0037] Add 2.5 g (11.2 mmol) of phenazine-1-carboxylic acid, 30 ml of dichloromethane, 1-2 drops of DMF into a 100 ml single-port reaction flask, slowly add 3.0 g of oxalyl chloride (to prevent flushing), and then heat to reflux React until the solid of Shenzimycin completely disappears, continue the reflux reaction for 2-3 hours, remove the solvent on a rotary evaporator, add a small amount of dichloromethane to dissolve, and then spin dry to remove excess oxalyl chloride as much as possible. Then add a certain amount of dichloromethane to dissolve and use in the next step.

[0038] 2) Synthesis of phenazine-1-carboxylic acid methyl ester:

[0039]

[0040] Add 50mL of anhydrous methanol into a 100mL three-necked fla...

example 2

[0051] Example 2: Synthesis of N-(2-butyrylethylamino) phenazine-1-carboxamide (R is a saturated C3 substituted linear alkane group in general formula (I):

[0052] 1) Synthesis of butyryl chloride:

[0053]

[0054] Add 0.88g (10.0mmol) of benzoic acid into a 100ml single-port reaction flask, slowly add 15ml of thionyl chloride dropwise under stirring, then heat and reflux until the solid disappears completely, continue the reflux reaction for 2-3 hours, and place on a rotary evaporator Remove the solvent, add a small amount of toluene to dissolve, and then spin dry to remove excess thionyl chloride as much as possible. Then add a certain amount of dichloromethane to dissolve and use in the next step.

[0055] 2) Synthesis of N-(2-butyrylethylamino)phenazine-1-carboxamide:

[0056]

[0057] In a 100mL three-necked flask, add 2.66g (10.0mol) of N-(2-phenacylethylamino)phenazine-1-carboxamide and 50mL of dichloromethane, stir to completely dissolve the solid, and cool t...

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Abstract

The invention provides phenazine-1-carboxylic acid bishydrazide compounds and an application thereof, and belongs to the technical field of preparation of pesticide compounds; the general formula of the compounds has the following structure defined in the specification, wherein R is saturated C2-C6 straight-chain or branched-chain alkyl, unsaturated C2-C6 alkyl, halogen substituted C2-C6 hydrocarbonyl, C3-C8 cycloalkyl, and substituted phenyl containing one or more saturated or unsaturated hydrocarbonyl, alkoxy, halogen, fluorine-containing methyl, nitryl, cyano group, ester group, ketone group and formyl group, substituted pyridyl, substituted furyl, substituted pyrimidyl, substituted pyrazolyl, substituted thiazolyl, substituted thienyl, substituted imidazolyl or substituted triazolyl. The phenazine-1-dihydrazine carboxylic acid compounds have novel structure, can be used for prevention and treatment of diseases on crops and weeds and have market application prospects.

Description

technical field [0001] The invention relates to a phenazine-1-carboxylic acid bisamide compound and its use as a fungicide and a herbicide, and belongs to the technical field of pesticide compound preparation. Background technique [0002] Phenazine-1-carboxylic acid (PCA), the structure of which is the compound shown in Formula 1. The earliest research reported that it was found in the synthesis of dyes, and then it was widely studied as dye intermediates or color filter reagents. Phenazine-1-carboxylic acid is light yellow needle-like crystal at room temperature, soluble in ether, benzene and chloroform, etc., almost insoluble in water. In the 1850s, scientists began to isolate and extract phenazine-1-carboxylic acid from the metabolites of Streptomyces chromogenus sp. and Pseudomonads fluorescens, and found that it can inhibit a variety of fungal pathogens that can cause plant diseases. It also has broad-spectrum medical bactericidal activity and anti-lung cancer and le...

Claims

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Application Information

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IPC IPC(8): C07D241/46C07D401/12C07D403/12A01P3/00A01P13/00
Inventor 李俊凯朱祥吴清来余林花
Owner 上海沪联生物药业(夏邑)股份有限公司
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