Substituted pyrazol compound containing pyrimidine, preparation method and use thereof

A compound and pyrazole technology, applied in the field of pyrimidine-containing substituted pyrazole compounds and their preparation, can solve the problems that structural substituted pyrazole compounds have not been reported.

Active Publication Date: 2016-11-30
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 pyrimidine-containing substituted pyrazole compounds having a structure as shown in the general formula I of the present invention have not been reported.

Method used

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  • Substituted pyrazol compound containing pyrimidine, preparation method and use thereof
  • Substituted pyrazol compound containing pyrimidine, preparation method and use thereof
  • Substituted pyrazol compound containing pyrimidine, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0406] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0407] 1) Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine

[0408]

[0409] 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 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 completion of the reaction monitored by TLC, the solvent was evaporated 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 o...

Embodiment 2

[0413] Example 2: Preparation of 4,5-dichlorothieno[2,3-d]pyrimidine

[0414]

[0415] Get 2-amino-3-cyano-4-oxo-5,5-dihydrothiophene and 250ml phosphorus oxychloride (POCl 3 ) into the reaction bottle, slowly add 38ml of N,N-dimethylformamide dropwise at room temperature, and the dropwise addition is completed in about 30 minutes. React at room temperature for 1 hour, then raise the temperature to 75°C for 3 hours. After cooling down to room temperature, the reaction solution was poured into crushed ice and filtered to obtain 89.1 g of a dark gray solid with a yield of 86.9% and a melting point of 160-161°C.

Embodiment 3

[0416] Embodiment 3: the preparation of intermediate 4-chloroquinazoline

[0417] 1) Preparation of quinazolin-4(3H)-one

[0418]

[0419] Take 13.7g (0.1mol) of anthranilic acid and 20ml of formamide in a 250ml three-necked flask, and heat up to 140°C for 5-8 hours. After the completion of the reaction as monitored by TLC, the temperature of the reaction solution was lowered to 100° C., 80 ml of water was added dropwise with stirring, and then cooled to room temperature, filtered and washed with anhydrous ether to obtain 10.96 g of reddish brown, with a yield of 75.1%.

[0420] 2) Preparation of 4-chloroquinazoline

[0421]

[0422] Take 14.6g (0.1mol) of quinazolin-4(3H)-one in a 250ml single-necked bottle, use 50ml of thionyl chloride as a solvent, and raise the temperature to reflux for 4-6 hours. After the reaction was monitored by TLC, after cooling, the reaction solution was poured into water and stirred for 30 min, filtered and washed with anhydrous ether to ob...

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Abstract

The invention discloses a substituted pyrazol compound containing pyrimidine. The structure of the compound is shown as general formula I in the specification, wherein each substituent group is defined as the specification. The compound provided by the invention has broad-spectrum bactericidal, insecticidal and acaricidal activity, and has excellent control effect on cucumber downy mildew, wheat powdery mildew, corn rust, rice blast, cucumber anthracnose and the like. The compound provided by the invention also shows good insecticidal activity.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel substituted pyrazole compound containing pyrimidine, a preparation method and application thereof. Background technique [0002] Patent WO9507278 discloses the general formula of pyrimidine-containing substituted pyrazole compounds shown in the following general formula and the specific compounds CK1 and CK2, which are used as agricultural fungicides, insecticides, and acaricides. [0003] [0004] The following compounds CK3, CK4, and CK5 were retrieved online by Scifinder, but there were no specific references. [0005] [0006] However, the pyrimidine-containing substituted pyrazole compounds with the structure shown in the general formula I of the present invention have not been reported. Contents of the invention [0007] The object of the present invention is to provide a pyrimidine-containing substituted pyrazo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A01N43/56A01P3/00A01P7/02A01P7/04
CPCA01N43/56C07D403/12A01N43/54C07D495/04C07D401/14C07D417/14C07D403/14C07D409/14C07D487/04C07D498/04C07D513/04A01N43/90C07D239/72
Inventor 刘长令孙旭峰王军锋关爱莹李志念张金波班兰凤马森兰杰夏晓丽杨金龙姚忠远
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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