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Fluorine-containing pyrimidine compound and application

A technology of compounds and pyrimidines, which is applied in the field of fluoropyrimidine compounds, and can solve the problems that the structure of fluoropyrimidine compounds has not been reported.

Active Publication Date: 2014-05-07
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0030] In the prior art, there is no report on the structure of fluoropyrimidine compounds as shown in the general formula I of the present invention

Method used

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  • Fluorine-containing pyrimidine compound and application
  • Fluorine-containing pyrimidine compound and application
  • Fluorine-containing pyrimidine compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0370] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-difluoromethylpyrimidine

[0371] 1) Preparation of ethyl 2-chloro-4,4-difluoroacetoacetate

[0372]

[0373] Slowly add 177.46 g (1.33 mol) of sulfuryl chloride in 200 ml of dichloromethane solution dropwise to 200.00 g (1.20 mol) of ethyl 4,4-difluoroacetoacetate in 300 ml of dichloromethane under stirring at room temperature, and add for about 3 hours. After completion, a large amount of gas was generated, and the stirring reaction at room temperature was continued for 5-7 hours. After the reaction was monitored by TLC, the dichloromethane solvent and excess sulfuryl chloride were evaporated under reduced pressure to obtain 240 g of a light yellow liquid.

[0374] 2) Preparation of 4-hydroxy-5-chloro-6-difluoromethylpyrimidine

[0375]

[0376] Take 71.9g (0.70mol) of formamidine acetate in a 1000ml there-necked flask, add 150ml of methanol, stir at 5-10°C, take 64.6g (120mol) of sodium methoxide, co...

Embodiment 2

[0380] Embodiment 2: Preparation of intermediate 2-(4-(5-(trifluoromethyl)pyridine-2-oxyl)phenyl)ethylamine

[0381] 1) Preparation of 2-(4-(5-(trifluoromethyl)pyridine-2-oxyl)phenyl)acetonitrile

[0382]

[0383] Add 18.15g (0.1mol) of 2-chloro-5-trifluoromethylpyridine and 15.96g (0.12mol) of p-hydroxybenzonitrile into 200ml of butanone, add 27.60g (0.2mol) of potassium carbonate, and heat to reflux under stirring , reacted for 4-10 hours, after the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, and 300ml of ethyl acetate was added for extraction. Column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:4) gave 22.50 g of white solid, yield 81%, melting point 48-49°C.

[0384] 2) Preparation of 2-(4-(5-(trifluoromethyl)pyridine-2-oxyl)phenyl)ethylamine

[0385]

[0386] A mixture of 2.78g (0.01mol) 2-(4-(5-(trifluoromethyl)pyridine-2-oxyl)phenyl)acetonitrile, Raney nickel (1.0g), 25% ...

Embodiment 3

[0387] Example 3: Preparation of intermediate 2-(4-(3,5,6-tri(chloro)pyridine-2-oxyl)phenyl)ethylamine hydrochloride

[0388] 1) Preparation of N-Boc-4-hydroxyphenethylamine

[0389]

[0390] Dissolve 11.3g (0.1mol) of 4-hydroxyphenethylamine in 80ml of tetrahydrofuran, add 10.08g (0.12mol) of sodium bicarbonate and 50ml of water in turn, and add 21.80g (0.1mol) of di-tert-butyl dicarbonate dropwise under stirring at room temperature After dropping the ester, continue to react for 4-10 hours. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction. Column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:4) gave 17.15 g of white solid, yield 81%, melting point 48-49°C.

[0391] 2) Preparation of N-Boc-2-(4-(3,5,6-trichloropyridine-2-oxyl)phenyl)ethylamine

[0392]

[0393] Add 2.37g (0.01mol) N-Boc-4-hydroxyphenethylamine and 2.17g (0....

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Abstract

The invention discloses a fluorine-containing pyrimidine compound has a structural general formula I as shown in the specification, wherein definitions of substituents in the formula are as shown in the specification. The compound shown as the general formula I has broad-spectrum bactericidal and insecticidal activity in the field of agriculture. The compound shown as the general formula I has a good prevention effect on various germs such as cucumber downy mildew, wheat powdery mildew, puccinia sorghi, rice blast and cucumber gray mold, and particularly, still has the good prevention and control effect on the cucumber downy mildew, the puccinia sorghi and the wheat powdery mildew at a lower dosage. At the same time, a part of compound has better insecticidal activity, and can be used for preventing and controlling various insect pests such as diamondback moths, myzus persicae, armyworms and tetranychus cinabarinus boisdu.

Description

technical field [0001] The invention belongs to the field of agricultural sterilization and insecticide. It specifically relates to a fluorine-containing pyrimidine compound and its use. Background technique [0002] Patents EP0370704 and JP2009161472 disclose the following general formula and specific compounds (numbers in the two patents are respectively compound 47 and compound A), which have bactericidal and insecticidal activities. Now it has been developed as a commercial fungicide, the common name in English is diflumetorim, and the common name in Chinese is fluoxazil; It has certain activity against wheat rust and barley powdery mildew. [0003] [0004] Patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound (numbered as compound 7 in JP11012253), the common name of the compound in English is Flufenerim, and the common name in Chinese is pyrimethanil. [0005] [0006] EP0665225, JP10036355, US5498612 have rep...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D401/12A01N43/54A01P7/02A01P7/04A01P3/00
CPCA01N43/54C07D239/42C07D401/12
Inventor 刘长令任兰会单中刚王立增王斌张金波孙芹孙旭峰冯聪李志念宋玉泉
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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