N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-9840475-B2
Application number	US-201615072035-A
Country	US
Kind code	B2
Filing date	Mar 16, 2016
Priority date	Dec 28, 2012
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

This present disclosure is related to the field of to N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-di-hydropyrimidme-1(2H)-carboxamide compounds and their derivatives and to the use of these compounds as fungicides. This application claims the benefit of U.S. Provisional Patent Application Ser. No. 61/746,837 filed Dec. 28, 2012, which is expressly incorporated by reference herein. Background and Summary of the Invention 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.

First claim

What is claimed is:

1. A composition for the control of a fungal disease comprising a compound selected from the group consisting of:

and a phytologically acceptable carrier material.

2. A compound of Formula I:

wherein R1 is —C(═O)N(R 4 )R 5 ;
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 6 , 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 6 ;
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 6 , 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 6 ;
R 4 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 6 , 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 6 ;
R 5 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, or benzyl, wherein the benzyl may be optionally substituted with 1-3 R 6 ; and
R 6 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, cyano, hydroxyl or nitro, or an optical isomer, a salt, or a hydrate thereof.

3. The compound of claim 2 , wherein R 4 is phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 6 .

4. The compound of claim 2 , wherein R 5 is H.

5. The compound of claim 2 , wherein R 2 is methyl.

6. The compound of claim 2 , wherein R 3 is H.

7. A compound of Formula I:

wherein R 1 is —C(═S)N(R 4 )R 5 ;
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 6 , 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 6 ;
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 6 , 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 6 ;
R 4 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 6 , 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 6 ;
R 5 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl, or benzyl, wherein the benzyl may be optionally substituted with 1-3 R 6 ; and
R 6 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, cyano, hydroxyl or nitro,

or an optical isomer, a salt, or a hydrate thereof.

8. The compound of claim 7 , wherein R 4 is phenyl or benzyl, wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 6 .

9. The compound of claim 7 , wherein R 5 is H.

10. The compound of claim 7 , wherein R 2 is methyl.

11. The compound of claim 7 , wherein R 3 is H.

12. The compound of claim 3 , wherein R 6 is independently selected from C 1 alkyl, halo, C 1 alkoxy, C 1 haloalkyl, and cyano.

13. A composition for the control of at least one fungal disease, wherein the composition comprises a fungicidally effective amount of the compound of claim 2 and a phytologically acceptable carrier material.

14. the composition of claim 13 , wherein the fungal disease is Septoria tritici.

15. The compound of claim 8 , wherein R 4 is phenyl and each R 6 is independently selected from C 1 alkyl, halo, C 1 alkoxy, C 1 haloalkyl, and cyano.

16. A composition for the control of at least one fungal disease, wherein the composition comprises a fungicidally effective amount of the compound of claim 7 and a phytologically acceptable carrier material.

17. the composition of claim 16 , wherein the fungal disease is Septoria tritici.

18. A method for the control and prevention of fungal attack on a plant, the method comprising the steps of:
applying the composition of claim 1 to at least one surface 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.

19. A method for the control and prevention of fungal attack on a plant, the method comprising the steps of:
applying a fungicidally effective amount of at least one of the compounds of Formula I of claim 2 to at least one surface 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.

20. A method for the control and prevention of fungal attack on a plant, the method comprising the steps of:
applying a fungicidally effective amount of at least one of the compounds of Formula I of claim 7 to at least one surface 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.

Assignees

• Adama Makhteshim Ltd

Inventors

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

Classifications

• A01N43/54

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

• A01N47/30

  Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl · CPC title

• C07D239/47 Primary

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

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title