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Pyrimidine-containing substituted azole compounds and application thereof

A technology of azole compounds and compounds, applied in the fields of chemicals, applications, and organic chemistry for biological control, which can solve problems such as unreported structural compounds

Pending Publication Date: 2018-03-09
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] In the prior art, the structure of the compound shown in the general formula I of the present invention has not been reported

Method used

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  • Pyrimidine-containing substituted azole compounds and application thereof
  • Pyrimidine-containing substituted azole compounds and application thereof
  • Pyrimidine-containing substituted azole compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0400] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0401] 1) Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine

[0402]

[0403] 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

[0407] Example 2: Preparation of 4,5-dichlorothieno[2,3-d]pyrimidine

[0408]

[0409] 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

[0410] Embodiment 3: the preparation of intermediate 4-chloroquinazoline

[0411] 1) Preparation of quinazolin-4(3H)-one

[0412]

[0413] 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%.

[0414] 2) Preparation of 4-chloroquinazoline

[0415]

[0416] 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 pyrimidine-containing substituted azole compounds with a structure as shown in a formula 1 in the description. In the formula 1, the definition of each substituent is enclosedin the description. The compounds disclosed by the invention have broad-spectrum bactericidal function and insecticidal and acaricidal activities, and have excellent control efficacy on cucumber downymildew, puccinia polysora, cucumber anthracnose and the like, in particular on cucumber downy mildew and puccinia polysora. Part of the compounds show certain insecticidal cavity on myzus persicae and tetranychus cinnabarinus at the same time. The pyrimidine-containing substituted azole compounds can be used for preparing bactericidal, insecticidal and acaricidal agents.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a pyrimidine-containing substituted azole compound and its application. Background technique [0002] WO 2003049739 reported that the following pyrimidine-containing substituted azole compounds can inhibit the activity of protein kinases, thereby having a therapeutic effect on diseases caused by related protein kinases, such as diabetes, tumors, and stroke. [0003] [0004] Both WO 2015187089 and WO 2014084778 reported the following pyrimidine-containing substituted thiadiazole compounds, which have therapeutic, anti-inflammatory and anti-tumor effects on autoimmune diseases, respectively. [0005] [0006] In the prior art, there is no report on the compound with the structure represented by the general formula I of the present invention. Contents of the invention [0007] The object of the present invention is to provide a...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D417/14C07D417/12C07D401/14C07D495/04C07D487/04C07D513/04C07D498/04A01N43/90A01N43/78A01N43/653A01N43/647A01N43/836A01N43/828A01N43/824A01P7/02A01P7/04A01P3/00A01P5/00
CPCA01N43/647A01N43/653A01N43/78A01N43/82A01N43/90C07D401/14C07D403/12C07D417/12C07D417/14C07D487/04C07D495/04C07D498/04C07D513/04
Inventor 刘长令孙旭峰王军锋姚忠远兰杰杨金龙张俊龙关爱莹
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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