Triazoline ketone ether-substituted compound and application thereof

A technology of triazolone ethers and compounds, which is applied in the field of substituting triazolone ether compounds, and can solve problems such as different structures

Active Publication Date: 2015-01-14
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although all the compounds disclosed in the above-mentioned patents have certain similarities with the compounds of the present invention, there are still significant differences in their structures

Method used

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  • Triazoline ketone ether-substituted compound and application thereof
  • Triazoline ketone ether-substituted compound and application thereof
  • Triazoline ketone ether-substituted compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0133] Example 1: Preparation of Compound 70

[0134]

[0135] 1) Preparation of 4-methylphenylisocyanate

[0136] Weigh 14.85 g (0.05 mol) of triphosgene and put it into a 1000 ml three-neck flask equipped with a mechanical stirrer, a thermometer, and a tail gas absorption device, add 150 ml of 1,2-dichloroethane, and then control the temperature for 0-5 ℃. While stirring at this temperature, 5.35 g (0.05 mol) of p-methylaniline solution (dissolved in 100 ml of 1,2-dichloroethane) was slowly added dropwise. A large amount of insoluble matter appeared during the dropwise addition. After dropping, the temperature of the reaction solution was raised to reflux for reaction. After the reaction solution was clarified, the reaction was completed, and the reaction solution was precipitated to obtain 6.52 grams of a red oily substance.

[0137] 2) Preparation of intermediate 2,2-dimethyl-N-(4-methylphenyl)hydrazide

[0138] Dissolve 10 g of 4-methylphenylisocyanate in 75 ml of ...

example 2

[0146] Example 2: Preparation of Compound 500

[0147]

[0148] 1) Preparation of intermediate 2,4-dihydro-5-methoxy-2-methyl-4-(4-methylphenyl)-3H-1,2,4-triazol-3-one

[0149] Dissolve 8.25 g of 5-chloro-2,4-dihydro-2-methyl-4-(4-methylphenyl)-3H-1,2,4-triazol-3-one in 80 mL of methanol 14.0 ml of 30% (mass fraction) sodium methoxide / methanol solution was added, and the reaction was refluxed for 3 hours. After the completion of the reaction as monitored by TLC, the reaction solution was poured into 100 milliliters of saturated brine, extracted with ethyl acetate, the extract was dried with anhydrous magnesium sulfate and precipitated under reduced pressure, column chromatography (the volume ratio of ethyl acetate and sherwood oil was 1: 5) Purified to obtain 5.2 g of white solid.

[0150] 2) Preparation of Intermediate II-2

[0151] Dissolve 6.7 g of 2,4-dihydro-5-methoxy-2-methyl-4-(4-methylphenyl)-3H-1,2,4-triazol-3-one in 100 ml Add 6.53 g of NBS and 0.05 g of azobi...

Embodiment 3

[0162] Example 3: 30% Compound 84 wettable powder

[0163] Compound 84 30%

[0164] Sodium Lauryl Sulfate 2%

[0165] Sodium lignosulfonate 3%

[0166] Naphthalenesulfonic acid formaldehyde condensate 5%

[0167] Light Calcium Carbonate Top up to 100%

[0168] Compound 84 and other components were fully mixed, and pulverized by a superfine pulverizer to obtain a 30% wettable powder product.

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Abstract

The invention discloses a triazoline ketone ether-substituted compound which has a structure shown in a general formula I in the description. In the formula, the definition of each substitutional group is shown in the description. The compounds in the general formula I can be used for preventing and treating diseases caused by various pathogenic bacteria on various plants, such as oomycetes, basidiomycetes, ascomycetes, adelomycetes and the like; in addition, the compounds have high biological activity, so that favorable effect at lower dosage can be obtained, particularly the compounds have better effect for the activity of the diseases of blumeria graminis and the like. Therefore, the invention also discloses application of the compounds in the general formula I to the fields of agriculture and the like as bactericides.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a substituted triazolone ether compound and its application. Background technique [0002] Triazolone ether compounds have good fungicidal activity. Patent FR2773155 refers to the following compounds as fungicides: [0003] [0004] Patent WO9823155 relates to the following compounds as fungicides: [0005] [0006] Despite numerous patents, there is a constant need to develop new fungicidal compounds to control harmful pathogens in agriculture, civil and animal technology. Although all the compounds disclosed in the above-mentioned patents have certain similarities with the compounds of the present invention, there are still significant differences in their structures. Contents of the invention [0007] The object of the present invention is to provide a kind of substituted triazolone ether compound which can control harmful bacteria in a very small ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12A01N43/653A01P3/00
Inventor 刘长令姜美峰李志念李淼杨瑞秀杨吉春
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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