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Pyrazolyl pyrilamine compound and use thereof

A pyrazolyl pyrimidine amine compound technology, applied in the field of pyrazolyl pyrimidine amine compounds, can solve the problems that the structure of pyrazolyl pyrimidine amine compounds has not been reported.

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

[0004] 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 pyrilamine compound and use thereof
  • Pyrazolyl pyrilamine compound and use thereof
  • Pyrazolyl pyrilamine compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0321] Example 1: Preparation of 4,5-dichlorothieno[2,3-d]pyrimidine

[0322]

[0323] Take 2-amino-3-cyano-4-oxy-4,5-dihydrothiophene and 250ml phosphorus oxychloride (POCl 3 ) In the reaction flask, slowly add 38ml of dimethylformamide (DMF) dropwise at room temperature, and the addition is completed in about 30 minutes. React at room temperature for 1 hour, and then increase to 75°C for 3 hours. After cooling to room temperature, the reaction solution was poured into crushed ice and filtered to obtain 89.1 g of dark gray solid with a yield of 86.9% and a melting point of 160-161°C.

Embodiment 2

[0324] Example 2: Intermediate 2-(1-(2,4-Dichlorophenyl)-1H-pyrazol-4-yl)ethylamine

[0325] 1) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole

[0326]

[0327] Take 21.35g (0.1mol) 2,4-dichlorophenylhydrazine hydrochloride and 16.4g (0.1mol) 1,1,3,3-tetramethoxypropane in a 250ml three-necked flask, and 100ml of 95% ethanol aqueous solution as The solvent is heated to reflux for 3-5 hours. After the reaction was monitored by TLC, most of the ethanol was evaporated under reduced pressure, sodium carbonate aqueous solution was added to the remaining liquid, the aqueous phase was extracted with (3×100ml) ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered and desolventized . The residue was separated by column chromatography (eluent was ethyl acetate and petroleum ether, the volume ratio was 1:10) to obtain 18.06 g of yellow solid, with a yield of 84.8%.

[0328] 2) Preparation of 1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde

[03...

Embodiment 3

[0343] Example 3: Preparation of compound 66

[0344]

[0345] Take 2.05g (0.01mol) 4,5-dichlorothieno[2,3-d]pyrimidine and 2.56g (0.01mol) 2-(1-(2,4-dichlorophenyl)-1H-pyrazole -4-yl) ethylamine was added to 50ml of ethanol, 2.02g (0.02mol) of triethylamine was added with stirring at room temperature, heated to reflux, reacted for 5 hours, TLC monitored the reaction, the solvent was evaporated under reduced pressure, and (3× 50ml) ethyl acetate extraction, the organic phase was washed with 50ml saturated brine, and the solvent was removed under reduced pressure, and the residue was column chromatographed (eluent: ethyl acetate and petroleum ether (boiling range 60-90℃), volume ratio 1 :3) 3.56 g of white solid was obtained, the yield was 83.8%, and the melting point was 131.6°C.

[0346] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 2.97(2H,t),3.81-3.98(2H,q),6.65(1H,s),6.72(1H,t),7.32-7.48(2H,m),7.52(1H,t) ), 7.60 (1H, d), 7.64 (1H, s), 8.57 (1H, s).

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Abstract

The present invention discloses a pyrazolyl pyrilamine compound, the compound has a structure as shown in formula (I), and the substituent groups in the (I) are as defined in the specification. The pyrazolyl pyrilamine compound has good control effects on downy mildew of cucumber, puccinia polysra, wheat powdery mildew and other diseases, and is especially better in the control effect on the downy mildew of cucumber.

Description

Technical field [0001] The invention belongs to the field of agricultural fungicides, and specifically relates to a novel pyrazolylpyrimidinamine compound and its use. Background technique [0002] Patent WO9507278 discloses the general formula of pyrazolyl pyrimidinamine compounds shown in the following general formula and specific compounds CK1 and CK2, which are used as agricultural fungicides, insecticides, and acaricides. [0003] [0004] However, the pyrazolylpyrimidinamine compounds with the structure shown in the general formula I of the present invention have not been reported. Summary of the invention [0005] The purpose of the present invention is to provide a pyrazolyl pyrimidinamine compound that can control a variety of pathogens in a small dose, which can be used in agriculture or other fields to prepare drugs for preventing and treating pathogens. [0006] The technical scheme of the present invention is as follows: [0007] The present invention provides a pyrazolyl...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D513/04C07D403/12C07D401/14C07D417/14A01P3/00
Inventor 孙旭峰柴宝山王军锋杨吉春王斌王立增张金波关爱莹刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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