2-aldoximino-5-fluoropyrimidine derivatives

A compound of Formula I:

• wherein R1 is:
• H;
• C1-C6 alkyl optionally substituted with R4;
• C1-C6 alkenyl optionally substituted with R4;
• C3-C6 alkynyl optionally substituted with R4;
• phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R5, a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R5;
• —(CHR6)mOR7;
• —C(═O)R8;
• —C(═S)R8;
• —C(═O)OR8;
• —C(═S)OR8;
• —(CHR6)mN(R9)R10;
• —C(═O)N(R9)R10;
• or
• —C(═S)N(R9)R10;
• m is an integer from 1 to 3;
• R2 is:
• H;
• or
• C1-C6 alkyl optionally substituted with R4;
• alternatively R1 and R2 may be taken together to form:
• ═CR11N(R12)R13;
• R3 is independently C1-C6 alkyl, C1-C6 cycloalkyl, C1-C5 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkylaminocarbonyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylaminocarbonyl, benzyl, phenyl, or 5- or 6-membered heteroaromatic ring, wherein each (hetero)aryl, phenyl, benzyl, or 5- or 6-membered heteroaromatic ring may be optionally substituted with 1 to 3 substituents independently selected from R5;
• R4 is independently halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C3 alkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, or C2-C6 alkylaminocarbonyl;
• R5 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, amino, C1-C6 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, or C2-C6 alkylcarbonyl, nitro, or cyano;
• R6 is H, C1-C6 alkyl, C1-C6 alkoxy, phenyl or benzyl wherein each of the phenyl or benzyl may be optionally substituted with 1 to 3 substituents independently selected from R5;
• R7 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or benzyl may be optionally substituted with 1 to 3 R5, or a 5- or 6-membered saturated or unsaturated ring containing 1 to 3 heteroatoms wherein each ring may be optionally substituted with 1 to 3 substituents independently selected from R5;
• R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1 to 3 R5, or a 5- or 6-membered saturated or unsaturated ring containing 1 to 3 heteroatoms wherein each ring may be optionally substituted with 1 to 3 substituents independently selected from R5;
• R9 is H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R5, or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R5;
• R10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, benzyl, wherein the benzyl may be optionally substituted with 1-3 R5
• alternatively R9 and R10 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 R5;
• R11 is H or C1-C4 alkyl;
• R12 is H, C1-C4 alkyl, C1-C6 alkoxy, C2-C6, alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R5;
• alternatively R11 and R12 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 R5;
• R13 is H, C1-C4 alkyl, C1-C6 alkoxy, C2-C6, alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R5;
• alternatively R12 and R13 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 R5.