1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives

Patent metadata

Field	Value
Publication number	US-9271497-B2
Application number	US-201314655568-A
Country	US
Kind code	B2
Filing date	Dec 23, 2013
Priority date	Dec 28, 2012
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

This present disclosure is related to the field of 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-ones and their derivatives and to the use of these compounds as fungicides. Fungicides are compounds, of natural or synthetic origin, which act to protect and/or 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. The present disclosure relates to 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one compounds and their use as fungicides. The compounds of the present disclosure may offer protection against fungi and fungi like organisms including ascomycetes, basidiomycetes, deuteromycetes, and oomycetes.

First claim

What is claimed is:

1. A compound of Formula I:

wherein R 1 is —C(═O)R 4 or —C(═S)R 4 ;
R 2 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkylcarbonyl, arylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, —S(O) 2 R 5 , phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 , or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms, wherein each ring may be optionally substituted with 1-3 R 5 ;
R 3 is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, arylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 , or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms, wherein each ring may be optionally substituted with 1-3 R 5 ;
R 4 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 , or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms, wherein each ring may be optionally substituted with 1-3 R 5 ; and
R 5 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, amino, C 1 -C 6 alkylamino, C 2 -C 6 alkoxycarbonyl, or C 2 -C 6 alkylcarbonyl, hydroxyl, cyano, or nitro.

2. The compound of Formula I, wherein the compound of Formula (I) is selected from the group consisting of:

3. A composition for the control of a fungal disease, a comprising a composition for the control of at least one fungal disease, said composition including a fungicidally effective amount of the compound of Formula I and a phytologically acceptable carrier material.

4. The composition of claim 3 wherein the fungal disease is Septoria tritici.

5. A method for the control and prevention of fungal attack on a plant, the method including the steps of:
applying a fungicidally effective amount of at least one of the compounds of Formula (I) of claim 1 to at least one surface selected from the group of surfaces selected from the group consisting of: a portion of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, any surface adjacent to a plant, any surface in contact with a plant, a seed, and equipment used in agriculture.

6. The method of claim 5 , wherein the fungicidally effective amount Formula I is applied to a surface in the range of about 0.01 g/m 2 to about 0.45 g/m 2 of Formula I.

7. The method of claim 5 , wherein the wherein the compound of Formula (I) is selected from the group consisting of:

Assignees

• Dow Agrosciences Llc

Inventors

• Lorsbach Beth
• Owen W John
• Stelzer Lindsay
• Yao Chenglin

Classifications

• A61P31/10

  Antimycotics · CPC title

• A01N43/54 Primary

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D239/47 Primary

  One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine · CPC title