Aryl pyridine/pyrimidine compound and application thereof

A kind of technology of aryl pyridine compounds, applied in the field of aryl pyridine compounds

Active Publication Date: 2015-03-18
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The compounds reported in the prior art are quite different from the compounds of the present invention in structure

Method used

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  • Aryl pyridine/pyrimidine compound and application thereof
  • Aryl pyridine/pyrimidine compound and application thereof
  • Aryl pyridine/pyrimidine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0556] Example 1: Preparation of 2-methyl-5-cyano-6-(4-chlorophenyl)-nicotinoyl chloride

[0557] 1) Preparation of 2-methyl-5-cyano-6-hydroxy-nicotinic acid ethyl ester

[0558]

[0559] Add 100.0g (0.54mol) ethyl 2-ethoxymethylene acetoacetate and 45.2g (0.54mol) cyanoacetamide into a three-necked flask containing 150mL ethanol, and then add 36.5g (0.54mol) ethanol to it Sodium was reacted at room temperature for 5 hours. After the reaction was monitored by TLC, the solvent was removed under reduced pressure, the residue was poured into water, and the pH was adjusted to 2 with 20% hydrochloric acid. A large amount of solid precipitated out, filtered with suction, the filter cake was washed with water, and air dried to give white Solid 50.8g, yield: 45.9%.

[0560] 2) 2-Methyl-5-cyano-6-chloro-nicotinic acid ethyl ester

[0561]

[0562] Put 50.8g (0.25mol) 2-methyl-5-cyano-6-hydroxy-nicotinic acid ethyl ester into a 1000mL single-necked flask, add 200mL oxalyl chloride to it, heat ...

example 2

[0572] Example 2: Preparation of intermediate 2-phenyl-4-methyl-5-pyrimidinecarbonyl chloride

[0573] 1) Preparation of 2-phenyl-4-methyl-5-carboxylic acid ethyl ester pyrimidine

[0574]

[0575] Add 18.6g (0.1mol) 2-ethoxymethylene acetoacetate and 15.6g (0.54mol) benzamidine into a three-necked flask containing 200mL ethanol solution, and add 6.8g (0.1mol) sodium ethoxide to it After reacting at room temperature for 5 hours, after TLC monitoring the reaction, the solvent was removed under reduced pressure, the residue was poured into water, and the pH was adjusted to 2 with 20% hydrochloric acid. A large amount of solid precipitated out, filtered by suction, the filter cake was washed with water, and air dried to obtain a white solid 15.6g, yield: 64.5%.

[0576] 2) Preparation of 2-phenyl-4-methyl-5-carboxypyrimidine

[0577]

[0578] Put 10.0g (0.041mol) of intermediate 2-phenyl-4-methyl-5-carboxylic acid ethyl pyrimidine into a 250mL three-necked flask, add 80mL of methanol to...

example 3

[0582] Example 3: Preparation of 1-(3-chloropyridin-2-yl)piperazine hydrochloride

[0583]

[0584] Add 5.0 g (0.027 mol) of N-Boc-piperazine into a 150 mL reaction flask containing 40 mL of N,N-dimethylformamide, and then add 3.7 g (0.027 mol) of potassium carbonate to it, raise the temperature to 40°C, and stir A solution of 4.0 g (0.027 mol) of 2,3-dichloropyridine (commercially available) in N,N-dimethylformamide was added dropwise to it, the addition was completed in 15 minutes, and the reaction was maintained at 80°C for 4 hours. After the reaction was monitored by TLC, the reaction solution was poured into water, a white solid was precipitated out, filtered to obtain 5.5 g of a white solid, the yield: 68.8%.

[0585]

[0586] Put 5.0g (0.017mol) 4-(3-chloropyridin-2-yl)piperazine-1-tert-butyl carbonate into a 250mL single-necked flask, add 50mL tetrahydrofuran, and then add 3.4g (0.034mol ) Concentrated hydrochloric acid, react at room temperature for 4h. After the reactio...

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Abstract

Disclosed in the present invention is aryl pyridine (pyrimidine) compound having a structure as shown by the general formula (I) below, wherein the substituents in the formula are as defined in the description. The compound of formula I displays relatively high activities on harmful insects, mites and eggs in the fields of agriculture, and civil and animal technology, especially having better activities on harmful mites such as Tetranychus cinnabarinus etc., and can obtain very good effects at a very low dose.

Description

Technical field [0001] The invention belongs to the field of agricultural acaricides. Specifically, it relates to an arylpyrimidine compound and its use as acaricides in agriculture or other fields. Background technique [0002] Chinese patent CN1938292 relates to cyclic amine compounds represented by the following general formula as acaricides: [0003] [0004] The US patent US2007004750 relates to a piperazine-containing compound represented by the following general formula as an insecticide and fungicide: [0005] [0006] Chinese patent CN101332198 reports the application of a 6-aryl-3-substituted carbonyl-pyridine compound and its salt as an anti-tumor drug. Its general formula is: [0007] [0008] Among them, X is selected from oxygen or nitrogen atoms. [0009] The compounds reported in the prior art have very different structures from the compounds of the present invention. Summary of the invention [0010] The purpose of the present invention is to provide an arylpyrimidine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/85A01N43/60A01P7/02
CPCA01N43/60C07D213/85A01N59/00A01N43/40A01N43/54A01N43/78A01N47/06A01N47/40C07D213/74C07D295/04C07D317/62C07D401/12C07D401/14C07D403/12C07D417/12
Inventor 刘长令徐英宋玉泉关爱莹李轲轲谢勇杨吉春杨帆
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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