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Azophenylene-1-bishydrazide carboxylate compound and bactericidal composition comprising compound

A technology of carboxylic acid dihydrazide and composition, which is applied in the field of biopesticides, can solve the problems of difficult dosage form processing and poor solubility, and achieve good bactericidal effect, high biological activity, and broad-spectrum bactericidal activity

Inactive Publication Date: 2017-05-10
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The natural product phenazine-1-carboxylic acid (PCA) has a unique chemical structure and excellent agricultural fungicidal activity, and is a safe, efficient, and environmentally friendly microbial source green pesticide, but phenazine-1-carboxylic The solubility in solvents is very poor, and it is difficult to process formulations, and so far, there are very few researches on the creation of new pesticides based on the structural modification and modification of phenazine-1-carboxylic acid (PCA)

Method used

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  • Azophenylene-1-bishydrazide carboxylate compound and bactericidal composition comprising compound
  • Azophenylene-1-bishydrazide carboxylate compound and bactericidal composition comprising compound
  • Azophenylene-1-bishydrazide carboxylate compound and bactericidal composition comprising compound

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preparation example Construction

[0032] The synthetic method of phenazine-1-carboxylic acid dihydrazide compound of the present invention comprises the following steps:

[0033]

[0034] Taking N-tert-butyl-N'-(2-methylbenzoyl) phenazine-1-carboxylhydrazide as an example below, set forth the synthetic method of phenazine-1-carboxylic acid dihydrazide compounds of the present invention .

Embodiment 1

[0036] N-tert-butyl-N'-(2-methylbenzoyl)phenazine-1-carboxhydrazide (R in general formula (I) is substituted phenyl (A), R1 is CH 3 , R2, R3, R4 and R5 are H) synthetic steps are as follows:

[0037] (1) Synthesis of 2-methylphenylformyl chloride:

[0038]

[0039] Add 2.05g (15.0mmol) of 2-methylbenzoic acid into a 100mL single-port reaction flask, slowly add 15mL of thionyl chloride dropwise under stirring, then heat to reflux until the solid disappears completely, continue to reflux for 2 to 3 hours, and then Remove the solvent on a rotary evaporator, 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.

[0040] (2) Synthesis of N-tert-butyl-N'-2-methylphenylcarbohydrazide:

[0041]

[0042] Add 4.20g (21.0mmol) of 20% sodium hydroxide solution into a 100mL three-necked flask, cool in an ice-water bath to 0-5°C, add 2.60g...

example 265

[0072] Example 2 65% wettable powder

[0073]

[0074]

[0075] The components are mixed together and pulverized in a pulverizer until the granules are on par.

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Abstract

The invention discloses an azophenylene-1-bishydrazide carboxylate compound. The azophenylene-1-bishydrazide carboxylate compound is characterized by being represented by a general formula (I), wherein the structural formula is as shown in the specification, and R is substituted phenyl containing one or more saturated or unsaturated hydrocarbyl groups, alkoxy, halogens, fluorine-containing methyl, nitro, cyano, ester group, keto and formyl group, substituted pyridyl, substituted furyl, substituted pyrazolyl, substituted thiazolyl and substituted thienyl. The compound disclosed by the invention simultaneously has broad spectrum insecticidal and bacterial activities, and can be used for controlling diseases caused by multiple pathogenic bacteria such as oomycete, basidiomycetes, ascomycetes, imperfect fungi and the like on various crops.

Description

technical field [0001] The invention relates to the technical field of biological pesticides, in particular to a phenazine-1-carboxylic acid bishydrazide compound and a bactericidal composition containing the compound. Background technique [0002] Phenazine-1-carboxylic acid (PCA), as an important microbial metabolite, widely exists in microbial secretions such as Pseudomonas and Streptomycetes, and has It has broad-spectrum medical bactericidal activity and anti-lung cancer and leukemia activity, and its structure is the compound shown in formula one. In 1996, the team of Professor Xu Yuquan of Shanghai Jiaotong University isolated the secretion of Pseudomonas strain M18 (Pseudomonas sp.) from the soil in the suburbs of Shanghai and found substances with strong agricultural antibacterial activity, one of which was identified as phenazine-1 -carboxylic acid. Studies have found that phenazine-1-carboxylic acid has a relatively stable structure and has broad-spectrum agricu...

Claims

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Application Information

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IPC IPC(8): C07D241/46A01N43/60A01P3/00A01P7/04
CPCC07D241/46A01N43/60
Inventor 吴清来柳豪熊志鹏李俊凯
Owner YANGTZE UNIVERSITY
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