3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides

Patent metadata

Field	Value
Publication number	US-9642368-B2
Application number	US-201314655570-A
Country	US
Kind code	B2
Filing date	Dec 23, 2013
Priority date	Dec 31, 2012
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

This present disclosure is related to the field of 3-alkyl-5-fluoro-4-substituted-imino-3,4-5 dihydropyrimidin-2(1H)-ones 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 1 -C 6 alkyl optionally substituted with 1-3 R 4 ;
—C(═O)R 5 ;
—C(═O)OR 5 ;
—CH 2 OC(═O)R 5 ; or
—(CHR 8 ) n R 7 ;

R 2 is:
C 1 -C 6 alkyl optionally substituted with 1-3 R 6 ;
—C(═O)R 7 ;
—C(═O)OR 7 ; or
—(CHR 8 ) n R 7 ;
wherein n is an integer from 1-3;

R 3 is —S(O) 2 R 9 ;
R 4 is independently C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 1 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkylaminocarbonyl, hydroxyl, deuterium, or C 3 -C 6 trialkylsilyl;
R 5 is 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, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 10 , or with a 5- or 6-membered saturated or unsaturated ring system, or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R 10 , biphenyl or naphthyl optionally substituted with 1-3 R 10 ;
R 6 is independently halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkylaminocarbonyl, hydroxyl, deuterium, or C 3 -C 6 trialkylsilyl;
R 7 is 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, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 10 , or with a 5- or 6-membered saturated or unsaturated ring system, or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R 10 , biphenyl or naphthyl optionally substituted with 1-3 R 10 ;
R 8 is H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;
R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, amino, C 1 -C 6 alkylamino, C 2 -C 6 dialkylamino, a phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 10 , 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 10 , or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R 10 , biphenyl or naphthyl optionally substituted with 1-3 R 10 ; and
R 10 is independently halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 6 alkylamino, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkylaminocarbonyl, C 2 -C 6 dialkylamino, hydroxy, cyano, or nitro.

2. A compound according to claim 1 , wherein R 4 is independently C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, hydroxyl, or deuterium.

3. A compound according to claim 1 , wherein R 5 is 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 10 .

4. A compound according to claim 1 , wherein R 6 is independently halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, or deuterium.

5. A compound according to claim 1 , wherein R 7 is 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 10 .

6. A compound according to claim 1 , wherein R 10 is independently halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, cyano, or nitro.

7. A compound according to claim 1 , wherein R 9 is phenyl optionally substituted with 1-3 R 10 , or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms optionally substituted with 1-3 R 10 .

8. A compound according to claim 7 , wherein R 10 is independently halogen, C 1 -C 6 , alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy.

9. A compound according to claim 1 , wherein R 1 is C 1 -C 3 alkyl.

10. A compound according to claim 1 , wherein R 2 is C 1 -C 3 alkyl, —C(═O)R 7 , or —C(═O)OR 7 .

11. A compound according to claim 10 , wherein R 7 is C 1 -C 3 alkyl or phenyl.

12. A compound according to claim 11 , wherein R 1 is C 1 -C 3 alkyl.

13. A compound according to claim 1 wherein R 9 is selected from the group consisting of:

14. A compound according to claim 13 , wherein R 2 is C 1 -C 3 alkyl, —C(═O)R 7 , or —C(═O)OR 7 .

15. A compound according to claim 14 , wherein R 7 is C 1 -C 3 alkyl or phenyl.

16. A compound according to claim 15 , wherein R 1 is C 1 -C 3 alkyl.

17. A compound according to claim 1 , wherein R 1 is: C 1 -C 6 alkyl optionally substituted with 1-3 R 1 ;
—C(═O)R 5 ; or
—CH 2 OC(═O)R 5 ;
R 2 is: C 1 -C 6 alkyl optionally substituted with 1-3 R 6 ; —C(═O)R 7 ; —C(═O)OR 7 ; or —(CHR 8 ) n R 7 ;
R 3 is —S(O) 2 R 9 ;
R 4 is hydroxyl, or deuterium;
R 5 is C 1 -C 6 alkyl, or phenyl;
R 6 is deuterium;
R 7 is C 1 -C 6 alkyl, or phenyl optionally substituted with 1-3 R 10 ;
R 8 is H; n is 1
R 9 is C 1 -C 6 alkyl, or a phenyl optionally substituted with 1-3 R 10 , 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 10 ; and
R 10 is independently halogen, C 1 -C 6 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, or cyano.

18. A composition for the control of a fungal pathogen, comprising;
at least one compound of claim 1 ; and
a phytologically acceptable carrier material, wherein said composition is effective for the control of at least one pathogenic fungus.

19. The composition of claim 18 , wherein the pathogenic fungus is Septoria tritici.

20. A method for treating a plant, comprising the steps of:
applying a fungicidally effective amount of at least one of the compounds of claim 1 to at least one surface, selected from the group of surfaces consisting of: at least one portion of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, a seed, and agricultural equipment.

21. The method of claim 20 , wherein the fungicidally effective amount of at least one of the compounds of claim 1 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 of claim 1 .

Assignees

• Adama Makhteshim Ltd

Inventors

• Lorsbach Beth
• Ross Ronald
• Owen W John
• Webster Jeffery D
• Stelzer Lindsay
• Yao Chenglin
• Leplae Jr Paul R
• Galliford Chris V

Classifications

• C07D417/12 Primary

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

• C07D403/12

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

• A01N43/54 Primary

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

• C07D239/47

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

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title