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

A compound having the following formula

• wherein R3 is selected from the group consisting of H, R1, OR1, OC(O)OR1 or OC(O)NR1R6,
• where R1 is selected from the group consisting of C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C3-C8 cycloalkyl, and
• where R6 is selected from the group consisting of H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 alkenyl or C2-C5 alkynyl;
• and
• wherein M is selected from the group consisting of H, C(O)R8, or SO2R9
• where R8 is selected from the group consisting of 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 aryalkenyl, 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,
• wherein alkyl, alkenyl, and alkynyl, include within their scope both straight and branched groups, the terms alkenyl, alkenylene are intended to include groups containing one or more double bonds, and the terms alkynyl, alkynylene are intended to include groups containing one or more triple bonds, cycloalkyl, refers to C3-C14 cycloalkyl groups containing 0-3 heteroatoms and 0-2 unsaturations, the foregoing terms further contemplate either substituted or unsubstituted forms, unless specifically defined otherwise, a substituted form refers to substitution with one or more groups selected from halogen, hydroxy, cyano, nitro, aroyl, aryloxy, aryl, arylthio, hetlroaryl, heteroaryloxy, heteroarylthio, C1-C8 acyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkyhltio, C1-C6 haloalkylthio, carboaryloxy, carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups,
• wherein the term aryl refers to a substituted phenyl or naphthyl group, the term heteroaryl refers to any 5 or 6 membered aromatic ring containing one or more heteroatorns, these heteroaromatic rings may also be fised to other aromatic systems, the foregoing terms further contemplate either substituted or unsubstituted forms, a substituted form refers to substitution with one or more groups selected from nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, aryl, heteroaryl, halogen, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 OC(O)alkyl, OC(O)aryl, C3-C6 OC(O)cycloalkyl, C1-C6 NHC(O)alkyl, C3-C6 NHC(O)cycloalkyl, NHC(O)aryl, NHC(O)heteroaryl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkylsulfinyl, aryloxy, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, C(O)Ry, C(NORX)RY where RY and RX are independently H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, aryl or heteroaryl in which any alkyl or cycloalkyl containing substituent may be substituted with one or more halogens, the terms halogen and halo include chlorine, bromine, fluorine and iodine, the term haloalkyl refers to groups substituted with one or more halogen atoms, the term alkoxy as used herein refers to a straight or branched chain alkoxy group, the term haloalkoxy refers to an alkoxy group substituted with one or more halogen atoms,
• where R9 is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, aryl, or heteroaryl.