5-fluoro pyrimidine derivatives
This present disclosure is related to the field of 5-fluoro pyrimidines and their derivatives and to the use of these compounds as fungicides.
1. A compound of Formula (I)
wherein R 1 is —N(R 3 )R 4 ;
R 2 is —OR 21 ;
R 3 is: H;
wherein m is 1;
R 4 is: H;
R 20 is independently halogen, cyano, nitro, amino, C 1 -C 6 alkoxyalkoxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio, C 2 -C 6 haloalkenylsulfonyl, C 3 -C 6 alkynylthio, C 3 -C 6 alkynylsulfonyl, C 3 -C 6 haloalkynylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 8 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, C 3 -C 6 trialkylsilyl, 2-[(E)-methoxyimino]-N-methyl-acetamidyl, phenyl, benzyl, benzyloxy, phenoxy,or a 5- or 6-membered heteroaromatic ring wherein each phenyl, benzyl, benzyloxy, phenoxy, or 5- or 6-membered heteroaromatic ring may be optionally substituted with 1-3 substitutents independently selected from R 31 ;
R 21 is:
—(CHR 22 ) m R 23 ;
R 22 is H;
R 23 is:
C 3 -C 6 alkyl; or
phenyl optionally substituted with 1-5 R 20 ;
R 31 is independently halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio, C 2 -C 6 haloalkenylsulfonyl, C 3 -C 6 alkynylthio, C 3 -C 6 alkynylsulfonyl, C 3 -C 6 haloalkynylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 8 dialkylaminocarbonyl, or C 3 -C 6 trialkylsilyl.
2. A compound of Formula (I)
wherein R 1 is —N(R 3 )R 4 ;
R 2 is —OR 21 ;
R 3 is H;
R 4 is H;
R 21 is (—CHR 22 ) m R 23 , M is 1;
R 22 is H;
R 23 is phenyl optionally substituted with 1-5 R 20 ;
R 20 is halogen, cyano, nitro, amino, C 1 -C 6 alkoxyalkoxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkenyl, hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylamino, benzyloxy, or phenoxy, wherein each benzyloxy, phenoxy, may be optionally substituted with 1-3 substitutents independently selected from R 31 ; and
R 31 is halogen, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy.
3. A compound of Formula (I)
wherein R 1 is —N(R 3 )R 4 ;
R 2 is —OR 21 ;
R 3 is H;
R 4 is H;
R 21 is (—CHR 22 ) m R 23 , M is 1;
R 22 is H; and
R 23 is phenyl, p-tolyl, 4-fluoro-phenyl, 4-methoxy-phenyl, 3-methoxy-phenyl, 3 fluoro-phenyl, 3-bromo-phenyl,2,4,6-trimethyl-phenyl, 1-ethyl-2-methoxy-phenyl, 3-benzonitrile, or 3-fluoro-4-methoxy-phenyl.
4. A composition for the control of a fungal pathogen including the compound of claim 1 and a phytologically acceptable carrier material.
5. The composition of claim 4 wherein the fungal pathogen is one Apple Scab ( Venturia inaequalis ), Speckled Leaf Blotch of Wheat ( Septoria tritici ), Leaf spot of sugarbeets ( Cercospora beticola ), Leaf Spot of peanut ( Cercospora arachidicola ), and Black Sigatoka ( Mycosphaerella fijiensis ).
6. 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 1 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a seed adapted to produce at least one of the plant and another plant.
7. A composition for the control of a fungal pathogen including the compound of claim 2 and a phytologically acceptable carrier material.
8. The composition of claim 7 wherein the fungal pathogen is one Apple Scab ( Venturia inaequalis ), Speckled Leaf Blotch of Wheat ( Septoria tritici ), Leaf spot of sugarbeets ( Cercospora beticola ), Leaf Spot of peanut ( Cercospora arachidicola ), and Black Sigatoka ( Mycosphaerella fijiensis ).
9. 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 2 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a seed adapted to produce at least one of the plant and another plant.
10. A composition for the control of a fungal pathogen including the compound of claim 3 and a phytologically acceptable carrier material.
11. The composition of claim 10 wherein the fungal pathogen is one Apple Scab ( Venturia inaequalis ), Speckled Leaf Blotch of Wheat ( Septoria tritici ), Leaf spot of sugarbeets ( Cercospora beticola ), Leaf Spot of peanut ( Cercospora arachidicola ), and Black Sigatoka ( Mycosphaerella fijiensis ).
12. 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 3 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a seed adapted to produce at least one of the plant and another plant.
13. The compound of claim 3 , wherein R 23 is p-tolyl.