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

Patent metadata

Field	Value
Publication number	US-9622474-B2
Application number	US-201314655562-A
Country	US
Kind code	B2
Filing date	Dec 23, 2013
Priority date	Dec 28, 2012
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

This present disclosure is related to the field of N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylates and their derivatives and to the use of these compounds as fungicides. Also provided are methods of controlling a fungal disease such as Septoria tritici , comprising administering an effective amount of the fungicide compound to at lease one surface associated with the plant, seed or soil.

First claim

What is claimed is:

1. A compound of Formula I:

wherein R 1 is —C(═O)OR 4 or —C(═S)OR 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, 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 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 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, cyano, or nitro,
or an optical isomer, a salt, or a hydrate thereof.

2. A composition for the control of at least one fungal disease, said composition including a fungicidally effective amount of the compound of claim 1 and a phytologically acceptable carrier material.

3. The composition of claim 2 wherein the fungal disease is Septoria tritici.

4. 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 clam 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.

5. The method of claim 4 , wherein the fungicidally effective amount of the compound is applied to a surface in the range of about 0.01 g/m 2 to about 0.45 g/m 2 of the compound.

6. The compound of claim 1 , wherein R 1 is —C(═O)OR 4 .

7. The compound of claim 6 , wherein R 4 is phenyl.

8. The compound of claim 7 , wherein the phenyl substituted with methyl.

9. The compound of claim 7 , wherein the phenyl is substituted with methoxy.

10. The compound of claim 1 , wherein R 2 is C1-C6 alkyl.

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

12. The compound of claim 1 , wherein R 3 is H.

13. The compound of claim 1 , wherein. R 3 is C2-C6 alkoxycarbonyl.

14. The compound of claim 13 , wherein R 3 is a phenoxycarbonyl.

15. The compound of claim 1 , wherein the compound is in the form of a salt and wherein the salt is a hydrochloride, hydrobromide, or hydroiodide.

16. A composition for the control of at least one fungal disease, said composition including a fungicidally effective amount of the compound of claim 6 and a phytologically acceptable carrier material.

17. A composition for the control of at least one fungal disease, said composition including a fungicidally effective amount of the compound of claim 11 and a phytologically acceptable carrier material.

18. A composition for the control of at least one fungal disease, said composition including a fungicidally effective amount of the compound of claim 12 and a phytologically acceptable carrier material.

19. The composition of claim 16 wherein the fungal disease is Septoria tritici.

20. 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 claim 16 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.

Assignees

• Adama Makhteshim Ltd

Inventors

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

Classifications

• A01N47/22

  O-Aryl or S-Aryl esters thereof · CPC title

• C07D239/47 Primary

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

• A01N43/54 Primary

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

• A61K31/513

  having oxo groups directly attached to the heterocyclic ring, e.g. cytosine · CPC title