Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation

A compound of Formula I:

• wherein:
• (a) X1 is N;
• X2, X3, and X4 are CR″, where R″ is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, substituted or unsubstituted aryl, C1-C3 NHC(O)alkyl, NHC(O)H, C1-C3 haloalkylthio, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl or nitro;
• (b) Z is O, S or NORZ in which RZ is H or C1-C3 alkyl;
• (c) A is a C3-C14 cycloalkyl, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, C1-C6 alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, C1-C6 acyl, substituted or unsubstituted carboaryloxy, substituted or unsubstituted carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups;
• (d) M is Si(t-Bu)Me2, Si(Ph)Me2, SiEt3, SiMe3, C(Z)R8, SO2R9 where R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, alkoxyalkyl, haloalkyl, alkoxyalkenyl, haloalkenyl, alkoxyalkynyl, haloalkynyl, substituted and unsubstituted arylalkyl, substituted and unsubstituted arylalkenyl, substituted and unsubstituted arylalkynyl, substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, C1-C6 thioalkoxy, substituted and unsubstituted arylalkoxy, substituted and unsubstituted arylalkenyloxy, substituted and unsubstituted arylalkynyloxy, substituted and unsubstituted aryloxy, substituted and unsubstituted heteroaryloxy, amino unsubstituted or substituted with one or two C1-C6 alkyl groups, and R5 is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

A compound of Formula I:

• wherein:
• (a) X1 is N;
• X2, X3, and X4 are CR″, where R″ is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, substituted or unsubstituted aryl, C1-C3 NHC(O)alkyl, NHC(O)H, C1-C3 haloalkylthio, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl or nitro;
• (b) Z is O, S or NORZ in which RZ is H or C1-C3 alkyl;
• (c) A is a C6-C14 bi- or tricyclic ring system, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, C1-C6 alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 acyloxy, aryl, heteroaryl, C1-C6 acyl, carboaryloxy, carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups;
• and
• (d) M is Si(t-Bu)Me2, Si(Ph)Me2, SiEt3, SiMe3, C(Z)R8, SO2R9 where R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, alkoxyalkyl, haloalkyl, alkoxyalkenyl, haloalkenyl, alkoxyalkynyl, haloalkynyl, substituted and unsubstituted arylalkyl, substituted and unsubstituted arylalkenyl, substituted and unsubstituted arylalkynyl, substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, C1-C6 thioalkoxy, substituted and unsubstituted arylalkoxy, substituted and unsubstituted arylalkenyloxy, substituted and unsubstituted arylalkynyloxy, substituted and unsubstituted aryloxy, substituted and unsubstituted heteroaryloxy, amino unsubstituted or substituted with one or two C1-C6 alkyl groups, and R9 is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.