5-fluoropyrimidinone derivatives

Abstract

This present disclosure is related to the field of 5-fluoropyrimidinones and their derivatives and to the use of these compounds as fungicides.

What is claimed is: 
     
         1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
       
       wherein R 1  is:
 H 
 C 1 -C 6  alkyl optionally substituted with 1-3 R 4 ; 
 C 1 -C 6  alkenyl optionally substituted with 1-3 R 4 ; 
 C 3 -C 6  alkynyl optionally substituted with 1-3 R 4 ; 
 substituted phenyl, substituted benzyl, phenyl or benzyl wherein substituents for the substituted phenyl or the substituted benzyl are selected from the group consisting of: 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
 -(CHR6) m OR 7 ; 
 -(CHR6) m N(R9)R 10 ; 
 —C(═O)R 8 ; 
 —C(═S)R 8 ; 
 —S(O) 2 R 8 ; 
 —C(═O)OR 8 ; 
 —C(═S)OR 8 ; 
 -(CHR6) m N(R 9 )R 10 ; 
 —C(═O)N(R 9 )R 10 ; or 
 —C(═S)N(R 9 )R 10 ; 
 
       wherein m is an integer 1-4; 
       R 2  is:
 H; or 
 C 1 -C 6  alkyl optionally substituted with R 4 ; 
 
       alternatively R 1  and R 2  may be taken together to form:
 ═CR 11 N(R 12 )R 13 ; 
 
       R 3  is:
 C 1 -C 6  alkyl optionally substituted with 1-3 R 4 , 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 optionally substituted with R 14 , C 2 -C 6  haloalkenyl, C 3 -C 6  alkynyl, substituted phenyl, substituted benzyl, phenyl or benzyl wherein substituents for the substituted phenyl or the substituted benzyl are selected from the group consisting of: 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
 -(CHR 6 ) m OR 7 ; 
 -(CHR 6 ) m SR 8 ; or 
 —(CHR 6 ) m N(R 9 )R 10 ; 
 
       R 4  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, halothio, C 1 -C 3  alkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkylaminocarbonyl, hydroxyl, C 3 -C 6  trialkylsilyl, phenyl optionally substituted with 1-3 R 5 , or with 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, halothio, amino, C 1 -C 6  alkylamino, C 2 -C 6  dialkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylcarbonyl, C 1 -C 6  alkylsulfonyl, nitro, hydroxyl, or cyano; 
       R 6  is H, C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkoxycarbonyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 ; 
       R 7  is H, C 1 -C 8  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  trialkylsilyl, C 2 -C 6  trialkylsilylalkyl C 2 -C 6  alkylcarbonyl, C 1 -C 6  alkoxycarbonyl, substituted phenyl, substituted benzyl, phenyl or benzyl wherein substituents for the substituted phenyl or the substituted benzyl are selected from the group consisting of: 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
       R 8  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, substituted phenyl, substituted benzyl, phenyl or benzyl wherein substituents for the substituted phenyl or the substituted benzyl are selected from the group consisting of: 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
       R 9  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxyalkyl, C 2 -C 6  alkylcarbonyl, substituted phenyl, substituted benzyl, phenyl or benzyl wherein substituents for the substituted phenyl or the substituted benzyl are selected from the group consisting of: 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
       R 10  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 5 ; 
       alternatively R 9  and R 10  may be taken together to form 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 11  is H or C 1 -C 4  alkyl; 
       R 12  is H, cyano, hydroxyl, C 1 -C 4  alkyl, C 1 -C 6  alkoxy, 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 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
       alternatively R 11  and R 12  may be taken together to form 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 13  is H, C 1 -C 4  alkyl, C 1 -C 6  alkoxy, 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 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 ; 
       and 
       alternatively R 12  and R 13  may be taken together to form 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 14  is phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 . 
     
     
         2 . A composition for the control of a fungal pathogen including the compound of  claim 1  and a phytologically acceptable carrier material. 
     
     
         3 . The composition of  claim 2  wherein the fungal pathogen is Apple Scab ( Venturia inaequalis ), Leaf Blotch of Wheat ( Septoria tritici ), Leaf Spot of Sugarbeets ( Cercospora beticola ), Leaf Spots of Peanut ( Cercospora arachidicola  and  Cercosporidium personatum ), and Black Sigatoka of Banana ( Mycosphaerella fijiensis ). 
     
     
         4 . (canceled) 
     
     
         5 . The compound of  claim 1 , wherein:
 R 1  is: H;   R 2  is H;   R 3  is —(CHR 6 ) m OR 7 , C 2 -C 6  alkenyl, cyclopropylmethyl, or (tetrahydrofuran-2-yl)methyl,   wherein m is an integer 1-4;   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, halothio, amino, C 1 -C 6  alkylamino, C 2 -C 6  dialkylamino, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylcarbonyl, C 1 -C 6  alkylsulfonyl, nitro, hydroxyl, or cyano;   R 6  is H, C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkoxycarbonyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 ; and   R 7  is H, C 1 -C 8  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  trialkylsilyl, C 2 -C 6  trialkylsilylalkyl C 2 -C 6  alkylcarbonyl, C 1 -C 6  alkoxycarbonyl, benzyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R 5 , 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 5 , biphenyl or naphthyl optionally substituted with 1-3 R 5 .   
     
     
         6 . The compound of  claim 5 , wherein m is 1. 
     
     
         7 . The compound of  claim 5 , wherein R 3  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       cyclopropylmethyl, and (tetrahydrofuran-2-yl)methyl. 
     
     
         8 . The compound of  claim 1 , wherein R 1  and R 2  are taken together to form: CR 11 N(R 12 )R 13 . 
     
     
         9 . The compound of  claim 8 , wherein R 11  is H, R 12  is —CH 3 , and R 13  is —CH 3 . 
     
     
         10 . The compound of  claim 1 , wherein R 3  is —(CHR 6 ) m OR 7 , R 6  is H, m is 1, and R 7  is C 1 -C 6  alkycarbonyl. 
     
     
         11 . The compound of  claim 10 , wherein R 1  and R 2  are each H, or R 1  and R 2  are taken together to form: ═CR 11 N(R 12 )R 13 . 
     
     
         12 . The compound of  claim 1 , wherein R 3  is C 2 -C 6  alkenyl. 
     
     
         13 . The compound of  claim 12 , wherein R 1  and R 2  are each H, or R 1  and R 2  are taken together to form: ═CR 11 N(R 12 )R 13 . 
     
     
         14 . The compound of  claim 1 , wherein R 3  is C 1 -C 6  alkyl substituted with phenyl, wherein the phenyl is substituted with 1-3 R 5 . 
     
     
         15 . The compound of  claim 14 , wherein R 5  is halogen or C 1 -C 6  alkoxy. 
     
     
         16 . The compound of  claim 1 , wherein R 3  is C 1 -C 6  alkyl and R 1  and R 2  are each H, or R 1  and R 2  are taken together to form: ═CR 11 N(R 12 )R 13 . 
     
     
         17 . The compound of  claim 1 , wherein R 3  is cyclopropyl-methyl. 
     
     
         18 . The compound of  claim 1 , wherein R 3  is —(CHR 6 ) m SR 8 , R 6  is H, m is 1, and R 8  is C 1 -C 6  alkyl. 
     
     
         19 . The compound of  claim 1 , wherein R 3  is C 1 -C 6  alkyl optionally substituted with 1-3 R 4 , and R 4  is a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms. 
     
     
         20 . The compound of  claim 1 , wherein R 3  is C 1 -C 6  alkyl and R 1  is —C(═O)-thiophenyl. 
     
     
         21 . The compound of  claim 1 , wherein R 3  is thiophenyl.