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Substituent oxadiazole compound and application thereof

A technology of oxadiazoles and compounds, which is applied in the field of substituted oxadiazoles and can solve the problems that the bactericidal activity of substituted oxadiazoles has not been reported.

Active Publication Date: 2019-07-26
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, the substituted oxadiazole compounds and their fungicidal activity as shown in the present invention have not been reported

Method used

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  • Substituent oxadiazole compound and application thereof
  • Substituent oxadiazole compound and application thereof
  • Substituent oxadiazole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0154] Embodiment 1: the preparation of compound 1

[0155]

[0156] 0.30 g (1.31 mmol) of 4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)aniline (intermediate II-1, can refer to the methods reported in WO2017081309, WO2017081311, WO2017081312, etc. prepared), 0.30 g (2.88mmol)

[0157]Cyclopropylformyl chloride, 0.39 g (3.86 mmol) of triethylamine and 15 ml of dichloromethane were placed in a reaction flask and stirred at room temperature for 5 hours. After the completion of the reaction as monitored by TLC, precipitation under reduced pressure and purification of the residue by column chromatography (eluent is ethyl acetate and petroleum ether, the volume ratio is 1:20~1:10) to obtain 0.43 g of oil, namely compound 1 .

Embodiment 2

[0158] Embodiment 2: the preparation of compound 2

[0159]

[0160] 0.51 g (2.23 mmol) 4-(5-trifluoromethyl-1, 2, 4-oxadiazol-3-yl) aniline (intermediate II-1), 0.19 g (2.44 mmol) acetyl chloride, 0.27 g (2.67 mmol) of triethylamine and 15 ml of dichloromethane were placed in a reaction flask and stirred at room temperature for 5 hours. After the completion of the reaction as monitored by TLC, precipitation under reduced pressure and purification of the residue by column chromatography (eluent: ethyl acetate and petroleum ether, volume ratio: 1:20~1:10) yielded 0.19 g of a white solid, the intermediate V-1.

[0161] Place 0.19 g (0.70 mmol) of the above-mentioned white solid (intermediate V-1), 0.15 g (1.44 mmol) of cyclopropanecarbonyl chloride, 0.11 g (1.39 mmol) of pyridine and 20 ml of toluene in a reaction flask, and heat up to Reflux and stir the reaction for 8 hours. After the completion of the reaction as monitored by TLC, precipitation under reduced pressure an...

Embodiment 3

[0162] Embodiment 3: the preparation of compound 8

[0163]

[0164] 0.30 g (1.23 mmol) of 4-(5-trifluoromethyl-1, 2, 4-oxadiazol-3-yl) benzylamine (intermediate II-2, can refer to reports such as WO2017055469, WO2017085100, WO2017103219, etc. method), 0.28 g (2.69mmol)

[0165] Cyclopropylformyl chloride, 0.37 g (3.66 mmol) of triethylamine and 15 ml of dichloromethane were placed in a reaction flask and stirred at room temperature for 4 hours. After the completion of the reaction as monitored by TLC, precipitation under reduced pressure and purification of the residue by column chromatography (eluent: ethyl acetate and petroleum ether, volume ratio: 1:20-1:10) yielded 0.41 g of a white solid, namely compound 8 .

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PUM

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Abstract

The invention discloses a substituent oxadiazole compound with a novel structure. As shown in a general formula I, substituent groups in the formula are defined in the specification. The compound in the general formula I has excellent bactericidal activity and has good control effects on various diseases, particularly soybean rust, at lower dosage, so that the compound in the general formula I isapplied to the field of agriculture and other fields and serves as a sterilizing agent.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a substituted oxadiazole compound and its application. Background technique [0002] 专利WO2017081309A1, WO2017081310A1, WO2017081311A1, WO2017081312A1,WO2018015449A1, WO2018015458A1, WO2017055469A1, WO2017085098A1,WO2017085100A1, WO2017103219A1及WO2017178245A1中涉及3-芳基(杂芳基)-5-三氟甲基噁二唑衍生物及它们在防除植物 Use in pathogenic microorganisms. [0003] In the prior art, there are no reports on the substituted oxadiazole compounds and their fungicidal activity as shown in the present invention. Contents of the invention [0004] The object of the present invention is to provide a substituted oxadiazole compound and its application. [0005] To achieve the above object, the technical scheme of the present invention is as follows: [0006] A substituted oxadiazole compound, as shown in general formula I: [0007] [0008] In the formula: [0009] A 1 Choose from N or CR 1 ,...

Claims

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Application Information

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IPC IPC(8): C07D271/06C07D413/04A01N43/836A01P3/00
CPCC07D271/06C07D413/04A01N43/82
Inventor 张立新张静张石鑫康卓
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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