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1-phenazinyl (phenyl) (5-pyrimidinyl) methanol compound and its preparation method and application

A compound and phenazine-based technology, applied in the field of 1-phenazine-based methanol compounds and their preparation, can solve the problems of poor solubility and difficult formulation processing, and achieve good antifungal effect, good solubility, and good bactericidal activity Effect

Active Publication Date: 2020-10-09
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-pyrimidinyl) methanol compound and its preparation method and application
  • 1-phenazinyl (phenyl) (5-pyrimidinyl) methanol compound and its preparation method and application
  • 1-phenazinyl (phenyl) (5-pyrimidinyl) methanol compound and its preparation method and application

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, drop 1 to 2 drops of DMF into a 100 ml single-neck reaction flask, slowly add 3.0 g of oxalyl chloride (to prevent flooding), then heat to reflux The reaction was carried out until the solid of suzinomycin completely disappeared, and the reflux reaction was continued for 2 to 3 hours. The solvent was dried on a rotary evaporator, and a small amount of dichloromethane was added to dissolve it. Then spin to dry, and take away the excess oxalyl chloride as much as possible. for use in the next step.

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

[0051]

[0052] Add 30 ml of anhydrous benzene solution to the single-necked bottle containing phenazine-1-formyl chloride, slowly add 8.4 grams (22.4 mmol) of anhydrous AlCl 3 , the reaction w...

Embodiment 2

[0061] Example 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, drop 1 to 2 drops of DMF into a 100 ml single-neck reaction flask, slowly add 3.0 g of oxalyl chloride (to prevent flooding), then heat to reflux The reaction was carried out until the solid of suzinomycin completely disappeared, and the reflux reaction was continued for 2 to 3 hours. The solvent was dried on a rotary evaporator, and a small amount of dichloromethane was added to dissolve it. Then spin to dry, and take away the excess oxalyl chloride as much as possible. for use in the next step.

[0065] 2. Synthesis of phenazine-1-yl(4-phenoxyphenyl)methanone:

[0066]

[0067] Add 30 ml of anhydrous diphenyl ether solution to the single-necked bottle containing phenazine-1-formyl chloride, slowly add 3.03 g (22.6 mmol) of anhydrous AlCl...

Embodiment 3

[0076] Example 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, drop 1 to 2 drops of DMF into a 100 ml single-neck reaction flask, slowly add 3.0 g of oxalyl chloride (to prevent flooding), then heat to reflux The reaction was carried out until the solid of suzinomycin completely disappeared, and the reflux reaction was continued for 2 to 3 hours. The solvent was dried on a rotary evaporator, and a small amount of dichloromethane was added to dissolve it. Then spin to dry, and take away the excess oxalyl chloride as much as possible. for use in the next step.

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

[0081]

[0082] Add 30 ml of anhydrous o-xylene solution to the single-necked bottle containing phenazine-1-formyl chloride, slowly add 3.0 g (22.6 mmol) of anhydr...

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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 a compound shown in formula 1. It is widely present in the secretions of microorganisms such as Pseudomonads and Streptomycetes. In recent years, studies have found that phenazine-1-carboxylic acid has resistance to rice sheath blight, watermelon wilt, pepper blight, wheat The broad-spectrum agricultural antibacterial activity of pathogenic bacteria such as total rot, watermelon anthracnose, and rape sclerotinia is harmless to humans, animals and the environment. It is an ideal compound for the development of green pesticides. [0003] [0004] However, phenazine-1-carboxylic acid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A01N43/60A01P3/00
CPCA01N43/60C07D403/06
Inventor 吴清来汤显军
Owner YANGTZE UNIVERSITY
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