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

The present invention relates to compounds of Formula I: wherein: a) represents a 6-membered heterocyclic aromatic ring in which X1 is N and X2, X3 and X4 are each independently CR''; R'' is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, 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 wherein adjacent R'' substituents may form a ring; b) Z is O, S or NORZ in which RZ is H or C1-C3 alkyl; and c) A represents (i) C3-C14 cycloalkyl, containing 1 or 3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C1-C6 alkylthio, arylthio, heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 acyloxy, aryl, heteroaryl, C1-C6 acyl, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1 -C6 alkyl groups, or (ii) C6-C14 bi- or tricyclic ring system, containing 1-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C1-C6 alkylthio, arylthio, heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 acyloxy, aryl, heteroaryl, C1-C6 acyl, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups; which are useful as antifungal agents, particularly for plants.