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1-phenazinyl(phenyl)(5-pyrimidyl)methanol compound and preparation method and application thereof

A compound, phenazine-based technology, applied in the field of 1-phenazinyl carbinol compound and its preparation, can solve the problems of poor solubility and difficulty in dosage form processing, and achieve good antifungal effect, good solubility and good bactericidal activity Effect

Active Publication Date: 2019-01-04
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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. Our research group has been working on the structural modification and derivatization of phenazine-1-carboxylic acid for several years. It is hoped to find phenazine-1-carboxylic acid analogs with higher activity and better solubility, improve their physical and chemical properties, and make them more suitable for agricultural use

Method used

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  • 1-phenazinyl(phenyl)(5-pyrimidyl)methanol compound and preparation method and application thereof
  • 1-phenazinyl(phenyl)(5-pyrimidyl)methanol compound and preparation method and application thereof
  • 1-phenazinyl(phenyl)(5-pyrimidyl)methanol compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Synthesis of 1-phenazinyl (phenyl) (5-pyrimidinyl) methanol

[0047] 1. Synthesis of phenazinyl-1-formyl chloride:

[0048]

[0049] Add 2.5 g (11.2 mmol) of phenazinyl-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 solid of Shenzimycin completely disappears, continue the reflux reaction for 2 to 3 hours, remove the solvent on a rotary evaporator, add a small amount of dichloromethane to dissolve, and then spin dry, try to take away the excess oxalyl chloride, For the next step.

[0050] 2. Synthesis of phenazin-1-yl (phenyl) ketone:

[0051]

[0052] Add 30ml of anhydrous benzene solution into a single-necked bottle containing phenazinyl-1-formyl chloride, and slowly add 8.4g (22.4mmol) of anhydrous AlCl 3 , reacted at room temperature for 7 hours, and monitored by pointing plate, the ...

Embodiment 2

[0061] Embodiment 2: Synthesis of phenazin-1-yl (4-phenoxy) (5-pyrimidinyl) methanol:

[0062] 1. Synthesis of phenazinyl-1-formyl chloride:

[0063]

[0064] Add 2.5 g (11.2 mmol) of phenazinyl-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 solid of Shenzimycin completely disappears, continue the reflux reaction for 2 to 3 hours, remove the solvent on a rotary evaporator, add a small amount of dichloromethane to dissolve, and then spin dry, try to take away the excess oxalyl chloride, For the next step.

[0065] 2. Synthesis of phenazin-1-yl (4-phenoxyphenyl) ketone:

[0066]

[0067] Add 30ml of anhydrous diphenyl ether solution into a single-necked bottle containing phenazinyl-1-formyl chloride, and slowly add 3.03g (22.6mmol) of anhydrous AlCl 3 , reacted at room temperature for 8h, and monitored by...

Embodiment 3

[0076] Embodiment 3: Synthesis of (2,3-dimethylphenyl) (phenazin-1-yl) (5-pyrimidinyl) methanol

[0077] 1. Synthesis of phenazinyl-1-formyl chloride:

[0078]

[0079] Add 2.5 g (11.2 mmol) of phenazinyl-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 solid of Shenzimycin completely disappears, continue the reflux reaction for 2 to 3 hours, remove the solvent on a rotary evaporator, add a small amount of dichloromethane to dissolve, and then spin dry, try to take away the excess oxalyl chloride, For the next step.

[0080] 2. Synthesis of (2,3-dimethylphenyl)(phenazin-1-yl)methanone:

[0081]

[0082] Add 30ml of anhydrous o-xylene solution into a single-necked bottle equipped with phenazinyl-1-formyl chloride, and slowly add 3.0g (22.6mmol) of anhydrous AlCl 3 , reacted for 12h under ice-bath condition...

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Abstract

The invention provides a 1-phenazinyl(phenyl)(5-pyrimidyl)methanol compound and a preparation method and an application thereof. A general formula of the compound is as shown in the description, wherein Ra is 5-bromopyrimidine and a substituted compound thereof (A) (a formula is as shown in the description), and R is an alkyl, an alkoxy, a cyano-group, an alkoxy, monobromopyridine and a substituted compound thereof; and Rb is a benzene ring and a substituted compound thereof (B) (a formula is as shown in the description), and R is an alkyl, an alkoxy, a halogeno-group, an aryloxy, a cyano-group, and an aryl. The preparation method for the compound comprises the following steps: using an active substructure splicing method, and introducing an ancymidol structure into an azophenylene-1-carboxylic acid structure. The application comprises a process of preparing a sterilization composition containing the compound, and the application further comprises better bactericidal activity of the compound and the sterilization composition for preventing diseases, especially pellicularia sasakii ito, watermelon fusarium wilt, alternaria solani, rice blast, sclerotinia sclerotiorum, fusarium graminearumt, blumeria graminis and the like, in crops caused by fungi.

Description

technical field [0001] The invention relates to the technical field of biological pesticides, in particular to a 1-phenazinyl (phenyl) (5-pyrimidinyl) methanol compound and a preparation method and application thereof. Background technique [0002] Phenazine-1-carboxylic acid (PCA) has broad-spectrum medical bactericidal activity and anti-lung cancer and leukemia activity, and its structure is the compound shown in formula one. Widely present in microbial secretions such as Pseudomonas and Streptomycetes. In recent years, studies have found that phenazine-1-carboxylic acid has resistance to rice sheath blight, watermelon wilt, pepper blight, wheat Take-all, watermelon anthracnose, rapeseed sclerotinia and other pathogens have broad-spectrum agricultural antibacterial activity, harmless to humans, animals and the environment, and are ideal compounds for the development of green pesticides. [0003] [0004] However, phenazine-1-carboxylic acid has poor solubility in almos...

Claims

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Application Information

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IPC IPC(8): C07D403/06A01N43/60A01P3/00
CPCA01N43/60C07D403/06
Inventor 吴清来汤显军
Owner YANGTZE UNIVERSITY
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