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Substituted pyrimidine compound and use thereof

A compound, pyrimidine technology, applied in the field of substituted pyrimidine compounds, can solve the problem of no biological activity report

Active Publication Date: 2014-05-07
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] Patent WO9507278 discloses that the compounds represented by the following general formula have certain bactericidal, acaricidal and / or insecticidal activities, wherein the 209th row of TABLE1 mentions compounds CK8, CK9, CK10, but there is no report of any biological activity;

Method used

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  • Substituted pyrimidine compound and use thereof
  • Substituted pyrimidine compound and use thereof
  • Substituted pyrimidine compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0303] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0304] 1) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine

[0305]

[0306] Slowly add 8.80 g (0.16 mol) of sodium methoxide in methanol solution dropwise to 11.30 g (0.11 mol) of formamidine acetate in 50 ml of methanol solution under stirring at room temperature, and continue stirring at room temperature for 2 h after dropping. Then add 11.17g (0.068mol) intermediate ethyl 2-chloroacetoacetate dropwise to the above solution, and continue to stir the reaction at room temperature for 5-7 hours. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and the pH is adjusted to 5 with hydrochloric acid. ~6, suction filtered to get an orange solid, the aqueous phase was extracted with (3×50ml) ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and precipitated. The residue was dissolved in 50ml of ethyl acetate, left overnight, and filtere...

Embodiment 2

[0310] Embodiment 2: the preparation of intermediate 2-(4-(5-trifluoromethylpyridine-2-oxyl group) phenyl) ethylamine

[0311] 1) Preparation of 2-(4-(5-(trifluoromethyl)pyridine-2-oxyl)phenyl)acetonitrile

[0312]

[0313] Add 18.15g (0.1mol) of 2-chloro-5-trifluoromethylpyridine and 15.96g (0.12mol) of p-hydroxybenzonitrile into 200ml of butanone, add 27.60g (0.2mol) of potassium carbonate, and heat to reflux under stirring , reacted for 4-10 hours, after the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, and 300ml of ethyl acetate was added for extraction. Column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:5) gave 22.50 g of white solid, yield 81%, melting point 48-49°C.

[0314] 2) Preparation of 2-(4-(5-trifluoromethylpyridine-2-oxyl)phenyl)ethylamine

[0315]

[0316] A mixture of 2.78g (0.01mol) 2-(4-(5-trifluoromethylpyridine-2-oxyl group) phenyl) acetonitrile, Raney nicke...

Embodiment 3

[0317] Embodiment 3: Preparation of 4-(2-(5-chloro-6-methylpyrimidine-4-amino)ethyl)phenol

[0318]

[0319] Add 1.13g (0.01mol) 4-hydroxyphenethylamine and 2.02g (0.02mol) triethylamine into 50ml toluene, add 1.63g (0.01mol) 4,5-dichloro-6-methyl dropwise under stirring at room temperature Pyrimidine, continue to react for 4-10 hours. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction. The organic phase is washed with 50ml of saturated saline, desolvated under reduced pressure, and the residue is Analysis (eluent: ethyl acetate and petroleum ether (boiling range: 60-90°C), volume ratio: 1:3) gave 2.10 g of white solid, yield 88%, melting point: 177-179°C.

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Abstract

The invention discloses a substituted pyrimidine compound. The structure of the compound is shown in a general formula (I), wherein each substituent is described in the specification. The compound has broad-spectrum sterilization, insecticidal and mite killing activity, has good prevention and control effects on diseases such as cucumber downy mildew, puccinia sorghi, wheat powdery mildew, rice blast and cucumber gray mold, and particularly has better prevention effects on the cucumber downy mildew, the puccinia sorghi, the rice blast and the like, and also has good prevention and control effects on aphids, tetranychus cinnabarinus, diamondback moths and armyworms, and good effects can be achieved under the condition of small dosage. The compound also has the characteristics of simplicity of a preparation method and the like.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel substituted pyrimidine compound and its application. Background technique [0002] Patents EP0370704 and JP2009161472 disclose the following general formula and specific compounds (numbers in the two patents are respectively compound 47 and compound A), 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 compound (numbered as compound 5 in the literature), and the bioassay results show that it has certain activity against wheat rust and barley powdery mildew. [0003] [0004] Fluoxin [0005] Patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound (numbere...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D403/12C07D239/42A01N43/54A01N43/58A01N47/18A01N47/36A01P3/00A01P7/04A01P7/02
CPCA01N43/54A01N43/58A01N47/18A01N47/36C07D239/42C07D239/60C07D401/12C07D403/12
Inventor 刘长令王立增冯聪朱敏娜兰杰孙旭峰孙芹张金波常秀辉柴宝山李志念周银平王斌宋玉泉
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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