Substituted aryl pyridine compounds and use thereof

An arylpyridine and compound technology, which is applied in the field of agricultural bactericidal, insecticide, and acaricide, and can solve problems such as unreported structural compounds.

Active Publication Date: 2016-02-24
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, the structure of the compound shown in the general formula I of the present invention has not been reported

Method used

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  • Substituted aryl pyridine compounds and use thereof
  • Substituted aryl pyridine compounds and use thereof
  • Substituted aryl pyridine compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0382] Example 1: Preparation of 4,5-dichlorothieno[2,3-d]pyrimidine

[0383]

[0384] Take 2-amino-3-cyano-4-oxyl-4,5-dihydrothiophene and 250mL phosphorus oxychloride (POCl 3 ) into the reaction flask, slowly add 38mL N,N-dimethylformamide (DMF) dropwise at room temperature, and the dropwise addition is completed in about 30 minutes. React at room temperature for 1 hour, then raise the temperature to 75°C for 3 hours. After cooling down to room temperature, the reaction solution was poured into crushed ice and filtered to obtain 89.1 g of a dark gray solid with a yield of 86.9% and a melting point of 160-161°C.

Embodiment 2

[0385] Embodiment 2: Preparation of 2-methyl-6-(4-chlorophenyl)-3-pyridineethylamine

[0386] 1) Preparation of 3-dimethylamino-1-(4-chlorophenyl)-2-propene-one

[0387]

[0388] Put 40.0g (0.26mol) of p-chloroacetophenone into a 500mL single-necked bottle, add 200mL of N,N-dimethylformaldehyde into it, raise the temperature to reflux, and react for 7h. After the completion of the reaction as monitored by TLC, cool to room temperature, distill off the methanol and excess N,N-dimethylformaldehyde generated by the reaction under reduced pressure, a large amount of yellow solid precipitates after cooling, filter with suction, and wash the filter cake with petroleum ether for 2-3 Second, air drying and vacuum drying (70-80° C.) gave 43 g of a yellow solid with a purity of 98.2% and a yield of 79.3%.

[0389] 2) Preparation of ethyl 2-methyl-6-(4-chlorophenyl)nicotinate

[0390]

[0391] Put 24.0g (0.18mol) of ethyl acetoacetate into a 500mL three-neck flask, add 100mL of a...

Embodiment 3

[0404] Embodiment 3: Preparation of 2-methyl-6-(4-chlorophenyl)-3-pyridylbenzylamine

[0405] 1) Preparation of IV-4-1

[0406]

[0407] Put 15.6g (0.062mol) of 2-methyl-3-(chloromethyl)-6-(4-chlorophenyl)-pyridine into a 500mL three-necked flask, and add 200mL of N,N-dimethylformaldehyde Amide, then add 12.0g (0.062mol) phthalimide potassium salt to it, raise the temperature to 50°C, react for 2h, after the reaction is monitored by TLC, cool to room temperature, pour the reaction solution into water, there is a white solid Precipitate, filter with suction, and air-dry to obtain 20.0 g of white solid, purity: 96.2%, yield: 89.1%.

[0408] 2) Preparation of 2-methyl-6-(4-chlorophenyl)-3-pyridylbenzylamine

[0409]

[0410] Put 20.0g (0.055mol) of M-16 into a 500mL three-neck flask, add 200mL of ethanol to it, and then dropwise add 8.0g (0.17mol) of hydrazine hydrate to it, stir at room temperature for a period of time, then gradually raise the temperature to reflux for ...

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Abstract

The invention discloses substituted aryl pyridine compounds with the structure represented by general formula I shown in the description. All substituent groups in the formula I are defined as in the description. The compounds of general formula I have broad-spectrum bactericidal and insecticidal activity in the agriculture field, have very good control effects on cucumber downy mildew, wheat powdery mildew, corn rust, rice blast and other various pathogens, and especially still have very good control effects on the cucumber downy mildew, wheat powdery mildew and the rice blast under a low dosage. Parts of the compounds have good insecticidal activity, and can be used to control diamondback moths and carminespider mites.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and in particular relates to a substituted arylpyridine compound and its application. Background technique [0002] Patent WO9404527 discloses that pyridineethoxy and pyridylethylamino pyridyl derivatives of quinoline and quinazoline represented by the following general formula and specific compound KC1 have insecticidal, acaricidal, nematicidal and fungicidal activities. [0003] [0004] In the prior art, there is no report on the compound with the structure represented by the general formula I of the present invention. Contents of the invention [0005] The object of the present invention is to provide an arylpyridine compound that can control various germs, pests and mites in a very small dose, which can be used in agriculture or other fields to prepare medicines for preventing and controlling germs and pests and mites. [0006] Technical scheme of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D513/04C07D401/12C07D417/14C07D409/14A01N43/90A01N43/54A01N43/78A01P3/00A01P7/02A01P7/04
Inventor 刘长令徐英王军锋孙旭峰班兰凤谢勇李志念孙庚
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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