Aromatic amides having a fungicidal activity, their agronomic compositions and relative preparation method

An amide having general formula (I):

• wherein:
• R1 represents a C1-C12 alkoxyl, a C1-C12 haloalkoxyl, a C3-C18 cycloalkoxyl, a —NR4R5 group;
• R2 represents a C2-C13 acyl, a C2-C12 alkanoyloxyalkyl C1-C12, a C2-C12 haloalkanoyloxyalkyl C1-C12, a C1-C12 alkoxy-C1-C12-alkanoyloxyalkyl C1-C12, a C1-C12 haloalkoxy-C1-C12-alkanoyloxyalkyl C1-C12, a C3-C18 cycloalkoxy-C1-C12-alkanoyloxyalkyl C1-C12, an aryloxy C1-C12 alkanoyloxyalkyl C1-C12, a benzyloxy C1-C12 alkanoyloxyalkyl C1-C12, a C4-C18 cycloalkanoyloxyalkyl C1-C12, a C1-C12 aroyloxyalkyl, a C1-C12 benzoyloxyalkyl, a C1-C12 heterocyclylcarbonyloxyalkyl, a C1-C12 alkyloxyalkyl C1-C12, a C1-C12 haloalkyloxyalkyl C1-C12, a C1-C12 alkoxy-C1-C12-alkyloxyalkyl C1-C12, a C1-C12 haloalkoxy-C1-C12-alkyloxyalkyl C1-C12, a C3-C18 cycloalkoxy C1-C12-alkyloxyalkyl C1-C12, an aryloxy C1-C12-alkyloxyalkyl C1-C12, a benzyloxy C1-C12-alkyloxyalkyl C1-C12, a C3-C18 cycloalkyloxyalkyl C1-C12, a C1-C12 aryloxyalkyl, a C1-C12 benzyloxyalkyl;
• a C1-C12 heterocyclyloxyalkyl, a C4-C12 alkanoylthioalkyl C1-C12, a C2-C12 haloalkanoylthioalkyl C1-C12, a C4-C18 cycloalkanoylthioalkyl C1-C12, a C1-C12 aroylthioalkyl, a C1-C12 benzoylthioalkyl;
• a C1-C12 heterocyclylcarbonylthioalkyl, a C1-C12 alkylthioalkyl C1-C12, a C1-C12 haloalkylthioalkyl C1-C12, a C1-C12 alkoxy-C1-C12-alkylthioalkyl C1-C12, a C1-C12 haloalkoxy-C1-C12-alkylthioalkyl C1-C12, a C3-C18 cycloalkoxy C1-C12-alkylthioalkyl C1-C12, a C1-C12 aryloxy alkylthioalkyl C1-C12, a C1-C12 benzyloxy alkylthioalkyl C1-C12, a C3-C18 cycloalkylthioalkyl C1-C12, a C1-C12 benzylthioalkyl, a C1-C12 arylthioalkyl, a C1-C12 heterocyclylthioalkyl, a C2-C12 alkanoylaminoalkyl C1-C12, a C2-C12 haloalkanoylaminoalkyl C1-C12, a C4-C18 cycloalkanoylaminoalkyl C1-C12, a C1-C12 aroylaminoalkyl, a C1-C12 benzoylaminoalkyl, a C1-C12 heterocyclylcarbonylaminoalkyl, a C1-C12 heterocyclylaminoalkyl, a C4-C18 cycloalkylaminoalkyl C1-C12, a tetrahydropyranyl, a C1-C12 trimethylsilyloxyalkyl, a C1-C12 trimethylsilyl-ethoxyalkyl;
• R1 and R2 together with the carbon atoms to which they are bound can form a 1,3-oxazole ring;
• R3 represents a hydrogen atom, a C1-C12 alkyl, a C3-C18 cycloalkyl;
• R4 and R5, the same or different, represent a hydrogen atom, an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, a C1-C12 alkyl, a formyl, a C2-C13 acyl, a C2-C13 haloalkylcarbonyl, a benzyl group, an aroyl group, a C2-C13 alkoxycarbonyl, a C1-C12 alkoxyalkyl C1-C12;
• a C1-C12 alkanoyloxyalkyl C1-C12, a C1-C12 haloalkanoyloxyalkyl C1-C12, a C3-C18 cycloalkanoyloxyalkyl C1-C12, a C1-C12 aroyloxyalkyl, a C1-C12 heterocyclylcarbonyloxyalkyl, a C1-C12 aryloxyalkyl, a C1-C12 heterocyclyloxyalkyl, a C1-C12 alkanoylthioalkyl C1-C12, a C1-C12 halo-alkanoylthioalkyl C1-C12, a C3-C18 cycloalkanoylthioalkyl C1-C12, a C1-C12 aroylthioalkyl, a C1-C12 heterocyclylthioalkyl, a C1-C12 arylthioalkyl, a C1-C12 alkanoylaminoalkyl C1-C12, a C1-C12 haloalkanoylaminoalkyl C1-C12, a C3-C18 cycloalkanoylaminoalkyl C1-C12, a C1-C12 aroylaminoalkyl, a C1-C12 heterocyclylaminoalkyl;
• A represents a direct bond or a C1-C12 alkyl;
• Y represents an oxygen or sulfur atom;
• Z represents an oxygen or sulfur atom;
• X represents a halogen atom, a CN group, a NO2 group;
• n represents a number ranging from 0 to 3;
• G represents a C3-C18 cycloalkyl containing from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C3-C18 cycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C6-C20 bicycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S, a C6-C20 bicycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, adamantyl, said cyclic groups being optionally substituted with 1 to 3 groups, the same or different, selected from the group consisting of C1-C6 alkyl, C3-C12 cycloalkyl, benzyl and with the possibility of incorporating in said cyclic structure one or more groups selected from the group consisting of:
• C═O, C(═O)O, C(═O)S, C(═S)O, C(═S)S, C(═O)NR3;
• with the proviso that
• if R1 represents a —NR4R5 group wherein R4 is a hydrogen atom and R5 is an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, a formyl, a C2-C13 acyl, a C2-C13 alkoxycarbonyl, and R2 and R3 represent a hydrogen atom, and Y is an oxygen atom, G cannot be a C3-C12 cycloalkyl, a C3-C12 cycloalkenyl and a C3-C8 cycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S.