Novel quinazoline (sulfur) ketone compound and application

A ketone compound, quinazoline technology, applied in the chemical, application, organic chemistry and other directions for biological control, can solve problems such as applications that have not been reported in the literature

Inactive Publication Date: 2014-12-03
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the quinazoline (thio) ketone compound of the present invention and its application as an agricultural fungicide have not been reported in the literature

Method used

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  • Novel quinazoline (sulfur) ketone compound and application
  • Novel quinazoline (sulfur) ketone compound and application
  • Novel quinazoline (sulfur) ketone compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0252] Example 1: Preparation of compound 11

[0253]

[0254] Add 0.30g (0.001mol) of benzylamine (II-1) and 0.12g (0.0012mol) of triethylamine into 20mL of dichloromethane, and add 0.21g (0.0011mol) of 1,3-dimethyl- A solution of 4-chloro-5-pyrazolecarboxylic acid chloride in 10 mL of dichloromethane. After dripping, continue to stir the reaction at room temperature for 1 hour. TLC monitors the completion of the reaction. Pour the reaction mixture into 20 mL of water. Separate the organic layer. Wash with 10 mL of dilute hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine, dry with anhydrous magnesium sulfate, and desolvate under reduced pressure. The residue is separated by column chromatography to obtain a pure product of 0.37 g, yield 82.0%, melting point 158-159°C .

Embodiment 2

[0255] Example 2: Preparation of compound 12

[0256] method 1:

[0257]

[0258] Add 0.30 g (0.001 mol) of benzylamine (II-1) and 0.12 g (0.0012 mol) of triethylamine to 20 mL of dichloromethane, and add 0.23 g (0.0011 mol) of 1-methyl-3-ethyl dropwise with stirring at room temperature A 10mL dichloromethane solution of 4-chloro-5-pyrazolecarboxylic acid chloride, and then continue to stir and react at room temperature for 1 hour,

[0259] After the reaction was monitored by TLC, the reaction mixture was poured into 20 mL of water, and the organic layer was separated. The organic layer was washed with 10 mL each of 5% diluted hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and desolvated under reduced pressure. The residue was separated by column chromatography to obtain 0.40 g of pure product, the yield was 85.0%, and the melting point was 159-160°C.

[0260] Method 2:

[0261] 1) Preparation of intermedi...

Embodiment 3

[0267] Example 3: Preparation of compound 34

[0268]

[0269] Add 0.32g (0.001mol) of benzylamine (II-1) and 0.12g (0.0012mol) of triethylamine into 20ml of dichloromethane, and add dropwise 0.23g (0.0011mol) of 1-methyl-3- (Trifluoromethyl)-1H-pyrazole-4-carboxylic acid chloride in 10ml of dichloromethane. After dripping, continue to stir the reaction at room temperature for 1 hour. TLC monitors the reaction to the end. Pour the reaction mixture into 30ml of water and shake to separate the organic The organic phase was washed successively with dilute hydrochloric acid, sodium bicarbonate aqueous solution and saturated brine, and then dried to obtain the product, which was washed with ethyl acetate to obtain a white solid. The pure product was obtained by column chromatography, 0.41g, and the yield was 86.0%. Melting point 179-180°C.

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Abstract

The invention discloses a quinazoline (sulfur) ketone compound with a broad-spectrum bactericidal activity. The structure of the compound is as shown in the general formula (I), and each substituent group in the formula is as defined in the specification. The compound has a broad-spectrum bactericidal activity and has an excellent effect of preventing and curing diseases such as cucumber downy mildew, puccinia polysra and the like. By applying a low dosage of the compound, a good effect can be achieved. The compound provided by the invention has characteristics of simple preparation method and the like.

Description

Technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a novel quinazoline (thio) ketone compound and its use. Background technique [0002] Patent WO2005049589 discloses the use of the following compounds a, b, c, and d as lipid-lowering drugs. [0003] [0004] Patent US5985884 and WO9741097 reported that compounds e, f, and g have good curative effects on diabetes. [0005] [0006] However, the quinazoline (thio) ketone compound of the present invention and its application as an agricultural fungicide have not been reported in the literature. Summary of the invention [0007] The purpose of the present invention is to provide a quinazoline (thio) ketone compound with a novel structure, which can be used in agriculture or other fields to prepare drugs for preventing and treating germs. [0008] The technical scheme of the present invention is as follows: [0009] The present invention provides a quinazoline (thio) ketone co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D417/12A01N43/56A01N43/78A01P3/00
CPCC07D403/12A01N43/56A01N43/78C07D417/12
Inventor 刘长令王立增王军锋薛有仁周继中王秀丽关爱莹
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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