Pyrazolyl pyrimidinamine compounds and application thereof

A technology for pyrazolyl pyrimidine amine and compound, which is applied in the field of pyrazolyl pyrimidine amine compounds, and can solve the problems that the structure of pyrazolyl pyrimidine amine compounds has not been reported and the like

Active Publication Date: 2015-06-17
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the pyrazolyl pyrimidine amine compounds with structures such as the general formula I of the present invention have not been reported

Method used

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  • Pyrazolyl pyrimidinamine compounds and application thereof
  • Pyrazolyl pyrimidinamine compounds and application thereof
  • Pyrazolyl pyrimidinamine compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0384] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0385] 1) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine

[0386]

[0387] 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, 11.17 g (0.068 mol) of intermediate ethyl 2-chloroacetoacetate was added dropwise to the above solution, and the stirring reaction at room temperature was continued for 5-7 hours. After the reaction was monitored by TLC, the solvent was distilled off under reduced pressure, and the pH was adjusted to 5-6 with hydrochloric acid, and an orange-yellow solid was obtained by suction filtration. The aqueous phase was extracted with (3×50ml) ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and dissolve. The residue was dissolved in 50ml of e...

Embodiment 2

[0391] Example 2: Intermediate 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)ethylamine

[0392] 1) Preparation of 1-(4-chlorophenyl)-1H-pyrazole

[0393]

[0394] Take 17.9g (0.1mol) of p-chlorophenylhydrazine hydrochloride and 16.4g (0.1mol) of 1,1,3,3-tetramethoxypropane in a 250ml three-necked flask, 100ml of 95% ethanol aqueous solution as a solvent, and heat up to Reflux reaction for 3-5 hours. After the reaction was monitored by TLC, evaporate most of the ethanol under reduced pressure, add aqueous sodium carbonate solution to the residue, extract the aqueous phase with (3×100ml) ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, and precipitate . The residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether, volume ratio: 1:10) to obtain 15.19 g of a yellow solid, with a yield of 85.1%.

[0395] 2) Preparation of 1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde

[0396]

[0397] Take 185ml (2.4mol) of...

Embodiment 3

[0411] Example 3: Intermediate 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)ethylamine

[0412] 1) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole

[0413]

[0414] Take 21.35g (0.1mol) 2,4-dichlorophenylhydrazine hydrochloride and 16.4g (0.1mol) 1,1,3,3-tetramethoxypropane in a 250ml three-necked bottle, and 100ml95% ethanol aqueous solution as Solvent, warming up to reflux for 3-5 hours. After the reaction was monitored by TLC, evaporate most of the ethanol under reduced pressure, add aqueous sodium carbonate solution to the residue, extract the aqueous phase with (3×100ml) ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, and precipitate . The residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether, volume ratio: 1:10) to obtain 18.06 g of a yellow solid, with a yield of 84.8%.

[0415] 2) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde

[0416]

[0417] Take 185ml (2.4mol) of...

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Abstract

Disclosed are pyrazolyl pyrimidinamine compounds with structures as shown in Formula I. The definitions of each of the substituents can be seen in the description. The compounds of present invention have a broad spectrum of bactericidal, insecticidal and acaricidal activity, and have good control effect on downy mildew of cucumber, powdery mildew of wheat, corn rust, anthracnosis of cucumber and the like, and especially have better control effect on downy mildew of cucumber, powdery mildew of wheat and anthracnosis of cucumber. The compounds of present invention also show good insecticidal activity, part of the compounds, at very low doses, have excellent control effect on diseases caused by Plutella xylostella, armyworm, Myzus persicae, Tetranychus cinnabarinus etc.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel pyrazolyl pyrimidine amine compound and its application. Background technique [0002] Patent WO9507278 discloses the general formula of pyrazolylpyrimidine amine compounds shown in the following general formula and the specific compounds CK1 and CK2 as agricultural fungicides, insecticides and acaricides. [0003] [0004] Searched by Scifinder, the compounds closest to the present invention are CK3, CK4, and CK5, but there are no relevant references. [0005] [0006] However, the pyrazolylpyrimidine amine compound with the structure shown in the general formula I of the present invention has not been reported. Contents of the invention [0007] The object of the present invention is to provide a kind of pyrazolyl pyrimidine amine compound that can control various germs, pests and mites at a very small dose, which c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D401/14C07D417/14A01N43/56A01N43/78A01P3/00A01P7/02A01P7/04A01P5/00
CPCA01N43/56A01N43/78C07D401/14C07D403/12C07D417/14C07D403/14
Inventor 刘长令孙旭峰赵杰王立增李轲轲张金波陈宣明关爱莹宋玉泉兰杰
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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