Fungicidal Azocyclic Amides

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

• wherein
• R1 is an optionally substituted phenyl, naphthalenyl or 5- or 6-membered heteroaromatic ring;
• A is CHR15 or NR16;
• R15 is H, halogen, cyano, hydroxy, —CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-C4 alkylsulfinylalkyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl, C3-C5 dialkylaminocarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl;
• R16 is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-C4 alkylsulfinylalkyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl, C3-C5 dialkylaminocarbonyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl;
• W is O or S;
• X is a radical selected from
• wherein the bond of X1, X2, X3, X4, X5, X6, X7, X8 or X9 which is identified with “t” is connected to the carbon atom identified with “q” of Formula 1, the bond which is identified with “u” is connected to the carbon atom identified with “r” of Formula 1, and the bond which is identified with “v” is connected to G;
• each R2 is independently C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, halogen, cyano or hydroxy;
• or
• two R2 are taken together as C1-C4 alkylene or C2-C4 alkenylene to form a bridged bicyclic or fused bicyclic ring system;
• or
• two R2 attached to adjacent ring carbon atoms joined by a double bond are taken together as —CH═CH—CH═CH— optionally substituted with 1 to 3 substituents selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen, hydroxy, amino, cyano and nitro;
• G is an optionally substituted 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring;
• J is a 5-, 6- or 7-membered ring, a 8- to 11-membered bicyclic ring system or a 7- to 11-membered spirocyclic ring system, each ring or ring system containing ring members selected from carbon and optionally 1 to 4 heteroatoms selected from up to 2 O, up to 2 S and up to 4 N, and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), S(O)2 and SiR17R18, each ring or ring system optionally substituted with 1 to 5 substituents independently selected from R5;
• each R5 is independently H, halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —NR25R26, 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, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C10 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C6 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 alkylaminoalkyl, C3-C8 dialkylaminoalkyl, C2-C6 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C4-C8 cycloalkylcarbonyl, C2-C6 alkoxycarbonyl, C4-C8 cycloalkoxycarbonyl, C5-C10 cycloalkylalkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C8 cycloalkylaminocarbonyl, C2-C6 haloalkoxyalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, C2-C6 alkoxyalkoxy, C2-C6 alkylcarbonyloxy, C2-C6 haloalkylcarbonyloxy, C4-C8 cycloalkylcarbonyloxy, C3-C6 alkylcarbonylalkoxy, 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 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino or -Z2Q;
• R25 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl or C2-C6 haloalkoxycarbonyl;
• R26 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 haloalkoxycarbonyl or -Z4Q;
• each R17 and R18 is independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C3-C6 halocycloalkyl, C4-C10 cycloalkylalkyl, C4-C7 alkylcycloalkyl, C5-C7 alkylcycloalkylalkyl, C1-C5 haloalkyl, C1-C5 alkoxy or C1-C5 haloalkoxy;
• each Q is independently phenyl, benzyl, naphthalenyl, a 5- or 6-membered heteroaromatic ring or an 8- to 11-membered heteroaromatic bicyclic ring system, each optionally substituted with 1 to 5 substituents independently selected from R7 on carbon atom ring members and R12 on nitrogen atom ring members;
• or
• each Q is independently a 3- to 7-membered nonaromatic carbocyclic ring, a 5-, 6- or 7-membered nonaromatic heterocyclic ring or an 8- to 11-membered nonaromatic bicyclic ring system, each optionally including ring members selected from the group consisting of C(═O), C(═S), S(O), S(O)2 and SiR17R18, and optionally substituted with 1 to 5 substituents independently selected from R7 on carbon atom ring members and R12 on nitrogen atom ring members;
• each R7 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 alkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C4 alkoxyalkyl, C1-C4 hydroxyalkyl, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyloxy, C2-C6 alkylcarbonylthio, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl;
• or
• R5 and R7 are taken together with the atoms linking R5 and R7 to form an optionally substituted 5- to 7-membered ring containing ring members selected from carbon and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O), S(O)2 and SiR17R18;
• R12 is H, C1-C3 alkyl, C1-C3 alkylcarbonyl, C1-C3 alkoxy or C1-C3 alkoxycarbonyl;
• each Z1 and Z2 is independently a direct bond, O, C(═O), S(O)m, CHR20 or NR21;
• each Z4 is independently O, C(═O), S(O)m or CHR20;
• each R20 is independently H, C1-C4 alkyl or C1-C4 haloalkyl;
• each R21 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl or C2-C6 haloalkoxycarbonyl;
• each m is independently 0, 1 or 2;
• and
• n is 0, 1 or 2;
• provided that:
• (a) when R1 is unsubstituted thienyl, X is X1 and the ring containing X is saturated, G is an unsubstituted thiazole ring connected at its 2-position to X and at its 4-position to Z1 in Formula 1, A is CHR15, R15 is H, and J is an isoxazole ring connected at its 4-position to Z1 and substituted at its 5-position with methyl and at its 3-position with meta-substituted phenyl, then Z1 is O, C(═O), S(O)m, CHR20 or NR21;
• (b) when A is NR16, X is X1 or X2, Z1 is a direct bond, and J is phenyl, then J is substituted with at least one R5 other than H, F, Cl, CN, OCH3, CF3 and CH3;
• and
• (c) when A is CHR15, R15 is H, W is O, X is X1, n is 0, G is a thiazole ring connected at its 2-position to X, and at its 4-position to Z1 in Formula 1, and bonded at its 5-position to H, F, Cl or Br, Z1 is a direct bond, and R1 is
• then when J is a substituted phenyl or substituted pyrimidin-4-yl, it is substituted with at least one R5 other than H, SCF3, OCF3, C(CH3)3, S(O)2CF3, OCH3, CF3, Br, cyclopropyl, 1-methylcyclopropyl, OH or CF2CH3, and when J is a 2,3-dihydro-1H-inden-4-yl or 5,6,7,8-tetrahydronaphthalen-2-yl, it is substituted with at least one R5 other than H, CH3 or C(CH3)3.