5-fluoro pyrimidine derivatives

a technology of fluoropyrimidine and derivatives, which is applied in the field of 5fluoropyrimidines and their derivatives, can solve the problems that no single fungicide is useful in all situations, and achieve the effects of convenient use, improved performance and less cos

Inactive Publication Date: 2010-01-28
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

[0003]Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
[0004]The present disclosure relates to 5-fluoro pyrimidine compounds and their use as fungicides. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.
[0176]Additionally, another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and / or treatment of a plant infested by a phytopathogenic organism comprising a compound of Formula I and a phytologically acceptable carrier material.

Problems solved by technology

Generally, no single fungicide is useful in all situations.

Method used

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examples

Preparation of 5-Fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-amine (1)

[0200]

[0201]To a solution of 4-fluorobenzyl alcohol (2.56 g, 20.3 mmol) in 1,4-dioxane (20 mL) was added 60% NaH (0.813 g, 20.3 mmol) in several portions over a period of 10 min. To the magnetically stirred solution was added 4-amino-2-chloro-5-fluoropyrimidine * (2.00 g, 13.6 mmol) and the mixture was stirred at room temperature until gas evolution subsided. The reaction mixture was then heated in a CEM Discover microwave reactor at 120° C. for 90 min. The cooled reaction mixture was partitioned between ethyl acetate and water, the organic phase was concentrated, and the product was purified by column chromatography (hexane / ethyl acetate gradient) to yield 5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-amine (1.66 g, 52% yield) as a white solid: mp 129-131° C.; 1H NMR (300 MHz, CDCl3) δ 7.91 (d, J=2.6 Hz, 1H), 7.42 (m, 2H), 7.03 (m, 2H), 5.27 (s, 2H), 5.05 (br s, 2H); MS (ESI) m / z 238 (M+H)+. *4-Amino-2-chloro-5-fluoropyr...

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Abstract

This present disclosure is related to the field of 5-fluoro pyrimidines and their derivatives and to the use of these compounds as fungicides.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation-in-part application of U.S. patent application Ser. No. 12 / 357,710, filed Jan. 22, 2009, which claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 011,799 filed Jan. 22, 2008, and U.S. Provisional Patent Application Ser. No. 61 / 115,297 filed Nov. 17, 2008.FIELD OF THE INVENTION[0002]This present disclosure is related to the field of 5-fluoro pyrimidines and their derivatives and to the use of these compounds as fungicides.BACKGROUND AND SUMMARY OF THE INVENTION[0003]Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.[0004]The present disclosure relates to 5-fluoro pyrimidine compounds and their use as fungici...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/5377C07D239/02A61K31/505A61K31/506A61K31/501C07D403/12C07D413/04
CPCC07D405/12C07D401/12C07D403/12C07D409/12C07D413/12C07D417/12C07D239/47A01N43/54A01N43/60A01N43/80A01N47/18A01N47/24A01N47/36A01N47/42A01N47/44A01N55/00A01N57/32
Inventor BOEBEL, TIMOTHY A.BRYAN, KRISTYKLITTICH, CARLA J.R.LORSBACH, BETHMARTIN, TIMOTHY P.OWEN, W. JOHNPOBANZ, MARK A.SULLENBERGER, MICHAEL T.WEBSTER, JEFFERY D.YAO, CHENGLIN
Owner DOW AGROSCIENCES LLC
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