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Substituted six-membered heterocyclic compound containing pyrimido ring and its preparation method and use

A technology for six-membered heterocycles and compounds, which is applied in the field of substituted six-membered heterocycles containing pyrimido rings and their preparation, and can solve problems such as compounds that have not been reported

Active Publication Date: 2020-08-11
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] But its structure is far from the substituted six-membered heterocyclic compound containing pyrimido ring shown in general formula I of the present invention, and the compound shown in general formula I of the present invention has not been reported yet

Method used

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  • Substituted six-membered heterocyclic compound containing pyrimido ring and its preparation method and use
  • Substituted six-membered heterocyclic compound containing pyrimido ring and its preparation method and use
  • Substituted six-membered heterocyclic compound containing pyrimido ring and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0354] Embodiment 1: Preparation of intermediate 2-((3-methylisoxazolo[5,4-d]pyrimidin-4-yl)amino)ethanol

[0355] 1) Preparation of 5-amino-3-methylisoxazole-4-cyano

[0356]

[0357] Dissolve 14g (0.2 mol) of hydroxylamine hydrochloride in 80mL of 10% sodium hydroxide, add 27.2g (0.2 mol) of (1-ethoxyethylene) malononitrile, add a small amount of ice to keep the temperature below 50°C, and continue at room temperature After stirring for 1.5 hours, the solid was filtered, washed with water, and recrystallized from absolute ethanol to obtain 16.5 g of a solid product.

[0358] 2) Preparation of 4-chloro-3-methylisoxazolo[5,4-d]pyrimidine

[0359]

[0360] Phosphorus oxychloride (POCl 3 ) 40mL and N,N-dimethylformamide 1mL were added to the reaction flask, stirred at room temperature for 1 hour, added 5-amino-3-methylisoxazole-4-cyano group (451mg, 3.66mmol), and heated to React at 160°C for 15-36 hours, and distill the reaction solution under reduced pressure to obtai...

Embodiment 2

[0364] Embodiment 2: the preparation of compound 7-33

[0365]

[0366] Add 0.16 g of 60% sodium hydride into the reaction flask, wash with petroleum ether, add 5 ml of N,N-dimethylformamide, and then add 2-((3-methylisoxazolo[5,4 -d] pyrimidin-4-yl)amino)ethanol 0.39g (2mmol), stirred at room temperature for 2 minutes, then added intermediate 2,3-dichloro-5-trifluoromethylpyridine 0.43g (2mmol), stirred at 60°C React for 2 hours. After the reaction was monitored by TLC, the reaction solution was poured into 50 ml of saturated brine, extracted three times with 100 ml of ethyl acetate, and dried. After precipitation, purification by column chromatography gave 0.36 g of an oily product, namely compound 7-33.

[0367] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):8.51(s,1H),8.34(s,1H),7.90(d,1H),5.83(s,1H),4.71(t,2H),4.16(q,2H),2.64( s, 3H).

[0368] Other compounds of the present invention can be prepared with reference to the above examples.

[0369] ...

Embodiment 3

[0379] Embodiment 3: Determination of bactericidal activity

[0380] The in vitro antibacterial activity or in vivo protective effect test is carried out on various fungal diseases of plants by using the compound sample of the present invention. See the following examples for the results of the bactericidal activity assay.

[0381] (1) Determination of in vitro bactericidal activity

[0382] The determination method is as follows: the high-throughput screening method is used, that is, the sample of the compound to be tested is dissolved in a suitable solvent (the type of solvent is such as acetone, methanol, DMF, etc., and is selected according to its dissolving ability for the sample), and the required concentration is prepared. Liquid to be tested. In an ultra-clean working environment, the liquid to be tested is added to the microwells of a 96-well culture plate, and then the suspension of pathogenic bacteria propagules is added to it, and the treated culture plate is pla...

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Abstract

The invention discloses a substituted six-membered heterocyclic compound containing pyrimidine rings. The structure is shown in a formula I: (the formula I is shown in the description), and the definition of each substation group is shown in the description. The substituted six-membered heterocyclic compound has the advantages that the broad-spectrum bacteria-killing and insect-killing activity isrealized; the good preventing and controlling effect is realized for cucumber downy mildew, wheat powdery mildew, puccinia polysora, rice blast, cucumber anthracnose and the like; meanwhile, the goodinsect-killing activity is realized.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides and insecticides, and specifically relates to a novel pyrimido ring-containing substituted six-membered heterocyclic compound and its preparation method and application. Background technique [0002] Patent JP 59036683 A discloses the use of isoxazolopyrimidine compounds represented by the following general formula as agricultural acaricides. [0003] [0004] However, its structure is far from the pyrimido ring-containing substituted six-membered heterocyclic compound represented by the general formula I of the present invention, and the compound represented by the general formula I of the present invention has not been reported yet. Contents of the invention [0005] The purpose of the present invention is to provide a pyrimido ring-containing substituted six-membered heterocyclic compound that can control various germs, pests and mites, and its preparation method and use in agricultu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D498/04A01N43/90A01P3/00A01P7/04
CPCA01N43/90C07D487/04C07D498/04
Inventor 李淼杨吉春赵杰杨帆张俊龙孙金强孙庚刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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