Fungicidal heterocyclic amines

A compound selected from Formula 1, or an N-oxide or salt thereof,

• wherein
• R1 is H, halogen, cyano, hydroxy, amino, nitro, —CHO or —C(═O)NH2;
• or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C3-C8 cycloalkoxy, C2-C8 alkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C6 alkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, GA, GN or naphthalenyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, GA, GN and phenyl;
• R2 is H, cyano, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl or C3-C10 alkoxyalkoxyalkyl;
• or
• R1 and R2 are taken together with the nitrogen to which they are attached to form a 3- to 7-membered ring, containing ring members in addition to the nitrogen selected from the group consisting of C(R8)2, O, S, NR3, —C(R8)═C(CR8)—, —C(R8)═N—, —N═N—, C(═O), C(═S), C(═NR4), S(═O)p(═NR4)q and SiR5aR5b;
• each GA is independently a benzoyl, phenoxy or phenylsulfonyl or a 5- or 6-membered heteroaromatic ring;
• each GN is independently a 3- to 7-membered nonaromatic carbocyclic or heterocyclic ring, containing ring members selected from the group consisting of C(R8)2, O, S, NR3, —C(R8)═C(CR8)—, —C(R8)—N—, —N═N—, C(═O), C(═S), C(═NR4), S(═O)p(═NR4)q and SiR5aR5b;
• each R3 is independently H, cyano, hydroxy, —C(═O)NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C4-C10 dialkylaminoalkyl, C3-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C10 alkylcarbonyl, C2-C10 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C10 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C10 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C8 alkoxyalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C5 trialkylsilyl or C3-C5 halotrialkylsilyl;
• each R4 is independently H, cyano, amino, hydroxy, C1-C6 alkyl, C3-C10 cycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C1-C6 alkoxy, phenyl or benzoyl;
• each R5a and R5b is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 alkylcycloalkyl, C5-C12 alkylcycloalkylalkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
• G is benzoyl, phenoxy, phenylethynyl, phenylsulfonyl or —(CR6aR6b)nGB;
• GB is a phenyl ring, naphthalenyl or 5- to 6-membered heteroaromatic ring, each ring optionally substituted with 1 to 5 substituents independently selected from R7;
• each R6a and R6b is independently H, halogen, —C(═O)OH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 cycloalkylalkyl, C4-C8 alkylcycloalkyl, C5-C12 alkylcycloalkylalkyl, C1-C6 haloalkyl, C2-C8 alkoxycarbonyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
• or
• R6a and R6b in geminal configuration are taken together with the carbon atom to which they are attached to form a 3- to 7-membered ring, containing ring members in addition to the carbon atom selected from the group consisting of C(R8)2, O, S, NR3, —C(R8)═C(CR8)—, —C(R8)═N—, —N═N—, C(═O), C(═S), C(═NR4), S(═O)p(═NR4)q and SiR5aR5b;
• R7 is halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —SO2NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl or thienyl;
• each R8 is independently H, halogen, CN, C1-C3 alkyl or C1-C3 alkoxy;
• X is N or CR9c;
• Y is N or CR9d;
• W is N;
• Z is N;
• each R9a, R9b, R9c, R9d, R9e and R9f is independently H, halogen, nitro, CN, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;
• n is an integer selected from 0 through 6;
• and
• p and q are independently 0, 1 or 2 in each instance of S(═O)p(═NR4)q, provided that the sum of p and q is 0, 1 or 2;
• provided that:
• (a) when R1 is hydroxy, then R2 is other than hydroxy;
• and
• (b) at least one of X or Y is N.