Substituted pyrimidinamine compound and use thereof

A technology of pyrimidine amines and compounds, applied in the fields of chemicals, applications, and organic chemistry for biological control, which can solve the problems that the structure of pyrimidine ethylamine or propylamine compounds has not been reported.

Active Publication Date: 2015-01-21
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In the prior art, the substituted pyrimidineethylamine or propylamine compounds with

Method used

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  • Substituted pyrimidinamine compound and use thereof
  • Substituted pyrimidinamine compound and use thereof
  • Substituted pyrimidinamine compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0453] Example 1: Preparation of intermediate 4,5-dichloro-6-methylpyrimidine (II-1)

[0454] 1) Preparation of ethyl 2-chloro-acetoacetate

[0455]

[0456] Slowly add 34.26g (0.25mol) sulfonyl chloride solution in dichloromethane to 30.00g (0.23mol) of ethyl acetoacetate in 80ml of dichloromethane under stirring at room temperature. After about 1.5 hours, a large amount of gas will be produced. , continue to stir the reaction at room temperature for 5-7 hours, after the reaction is monitored by TLC, dichloromethane solvent and excess sulfuryl chloride are evaporated under reduced pressure to obtain 30 g of light yellow liquid.

[0457] 2) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine

[0458]

[0459] Slowly add 8.80g (0.16mol) sodium methoxide methanol solution dropwise to 11.30g (0.11mol) formamidine acetate solution in 50ml methanol under stirring at room temperature, and stir at room temperature for 2h after dropping. Then add 11.17g (0.068mol) ethyl 2-chl...

Embodiment 2

[0463] Embodiment 2: the preparation of intermediate 2-(4-(4-methylbenzyloxy)phenyl)ethylamine

[0464] 1) Preparation of 2-(4-(4-methylbenzyloxy)phenyl)acetonitrile

[0465]

[0466] Add 14.05g (0.1mol) of 4-methylbenzyl chloride and 15.96g (0.12mol) of p-hydroxyphenylacetonitrile into 200ml of butanone, add 27.60g (0.2mol) of potassium carbonate, heat to reflux under stirring, and react for 4-10 hours , after the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, extracted with 300ml of ethyl acetate, washed with 5% aqueous sodium hydroxide solution and 50ml of saturated saline successively, and the residue after precipitation was separated by column chromatography to obtain a white solid 18.70 g, yield 79.0%, melting point 85-87°C.

[0467] 2) Preparation of 2-(4-(4-methylbenzyloxy)phenyl)ethylamine

[0468]

[0469] A mixture of 2.37g (0.01mol) of the intermediate 2-(4-(4-methylbenzyloxy)phenyl)acetonitrile, Raney nickel (1.0g), 25% a...

Embodiment 3

[0470] Embodiment 3: Preparation of 2-(4-(2-methylbenzyloxy)phenyl)ethylamine hydrochloride

[0471] 1) Preparation of N-Boc-4-hydroxyphenethylamine

[0472]

[0473] Dissolve 11.3g (0.1mol) of 4-hydroxyphenethylamine in 80ml of tetrahydrofuran, add 10.08g (0.12mol) of sodium bicarbonate and 50ml of water in sequence, and add 21.80g (0.1mol) of di-tert-butyl dicarbonate dropwise under stirring at room temperature Esters, dropwise, continue to react for 4-10 hours, after TLC monitors the reaction, evaporate the solvent under reduced pressure, extract (3×50ml) ethyl acetate, wash with saturated brine 50ml, and the residue after precipitation is separated by column chromatography 17.15 g of white solid was obtained, the yield was 80.5%, and the melting point was 67-68°C.

[0474] 2) N-Boc-2-(4-(2-methylbenzyloxy)phenyl)ethylamine

[0475]

[0476] Add 2.37g (0.01mol) N-Boc-4-hydroxyphenethylamine and 1.41g (0.01mol) 2-methylbenzyl chloride into 50ml butanone, add 2.76g (0...

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Abstract

The invention discloses a substituted pyrimidinamine compound with broad-spectrum bactericidal, insecticidal and acaricidal activity. The structure of the compound is shown as general formula (I) in the specification. All substituent groups in the formula are defined as the specification. The compound provided by the invention has broad-spectrum bactericidal, insecticidal and acaricidal activity, has excellent control effect on cucumber downy mildew, puccinia polysra, wheat powdery mildew, Phyricularia oryzae, cucumber gray mold and other diseases, especially has better control effect on cucumber downy mildew, puccinia polysra, Phyricularia oryzae and the like, and also has good control effect on diamondback moth, armyworm, aphid and Tetrangychus cinnabarinus. The compound can achieve a good effect under a low dosage.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel substituted pyrimidine amine compound and its application. Background technique [0002] Patents EP0370704 and JP2009161472 disclose the following general formula and specific compounds, which have bactericidal and insecticidal activities. Now it has been developed into a commercial fungicide, the common name in English is diflumetorim, and the common name in Chinese is fluoxamethanil. Pesticide Science.1999,55:896-902 also discloses the following specific compounds, and bioassay results show that they have certain activity against wheat rust and barley powdery mildew. [0003] [0004] Patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound, the English common name of which is Flufenerim, and the Chinese common name is pyrimethanil. [0005] [0006] WO02094832 discloses...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D401/12C07D403/12C07D417/12A01N43/58A01N43/54A01N43/78A01P7/02A01P7/04A01P3/00
CPCA01N43/54A01N43/58A01N43/78C07D239/42C07D401/12C07D403/12C07D417/12
Inventor 王立增孙旭峰兰杰张金波王斌关爱莹周继中杨帆宋玉泉刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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