Fungicidal compositions and methods, and compounds and methods for the preparation thereof

The acylated aminosalicylamide compound of the Formula I:

• wherein:
• a. m is 1 or 2;
• b. ( )n represents a carbon chain including “n” number of carbon atoms where n is 1 to 11;
• c. q is from 0 to 2n;
• d. each X is independently selected from the group consisting of H, halogen, C1-C4 alkyl, C2-C4 alkenyl, cyclopropyl, cyano, NO2, C1-C4 haloalkyl, hydroxy, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfonyl, C1-C3 alkylsulfinyl, C1-C2 SCOalkyl, C1-C3 NHalkyl, C1-C3 N(alkyl)2, C1-C3 NHCOalkyl, NHC(O)H, C1-C3 N-alkyl COalkyl, C1-C3 NHCONHalkyl, C1-C2 NHCON(alkyl)2, NHC(O)Rx, C(O)Rx, C(O)ORx, and C(O)NRxRx, in which Rx is independently H or C1-C4 alkyl;
• e. Z is selected from the group consisting of H, C1-C2 alkyl, CH3NH and Me2N;
• f. R1 and R2 may be the same or different, but at least one of R1 and R2 must be H or methyl, and each of R1 and R2 is independently selected from the group consisting of H, cyano, C1-C4 alkyl (straight chain or branched), C2-C4 alkenyl (straight chain or branched), aryl, C1-C4 haloalkyl (straight chain or branched), C1-C4 carboalkoxy optionally substituted with one or more of OR6, SR6, NR6R7, halogen or cyano;
• g. R3, R4, and R5 may be the same or different and each of R3-R5 is independently selected from the group consisting of H, halogen, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C6 cycloalkoxy, aryloxy, C(═O)R6 and C(═O)OR6;
• h. each Rq can be the same or different and each Rq is defined as follows:
• i. any or all of Rq are selected from the group consisting of H, halogen, cyano, C1-C4 alkyl (straight chain or branched), C2-C4 alkenyl (straight chain or branched), aryl, C1-C4 haloalkyl (straight chain or branched), C1-C4 alkoxy (straight chain or branched), C1-C4 haloalkoxy (straight chain or branched), C1-C4 carboalkoxy, and C3-C6 cycloalkyl optionally substituted with one or more of OR6 SR6, NR6R7, halogen or cyano;
• ii. any of Rq can be hydroxy provided that no two geminal Rq are both hydroxy;
• iii. any adjacent Rq can be combined as unsaturations in the main chain to form alkenyl or alkynyl bonds as allowed by chemical bonding rules;
• and
• iv. any of geminal Rq can be combined in a double bond to an oxygen;
• i. the number of substituents included as Rq will vary depending on n and q in accordance with chemical bonding rules;
• j. R6 and R7 may be the same or different and each of R6 and R7 is selected from the group consisting of H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, aryl and C1-C4 alkoxyalkyl, except that R7 can not be H;
• k. aryl, as used herein, may be unsubstituted or may have up to three substituents selected from the group consisting of halogen, C1-C4 alkyl, C2-C4 alkenyl, C3-C6 cycloalkyl, cyano, C1-C4 haloalkyl, hydroxy, C1-C3 alkoxy, C1-C3 haloalkoxy and aryloxy;
• and
• l. when stereocenters are formed by various substitution patterns as described herein, all isomers are included in the definitions for the structure of Formula I,
• said acylated aminosalicylamides however not including L-Glutamic acid, N-[3-(formylamino)-2-hydroxybenzoyl]-, dipropyl ester;
• L-Glutamic acid, N-[3-(formylamino)-2-hydroxybenzoyl]-, dibutyl ester;
• L-Aspartic acid, N-[3-(formylamino)-2-hydroxybenzoyl]-, bis(2,2-dimethylpropyl) ester;
• Benzamide, 3-(formylamino)-2-hydroxy-N-pentyl-;
• Benzamide, 3-(formylamino)-2-hydroxy-N-butyl-;
• Benzamide, 3-(formylamino)-2-hydroxy-N-octyl-;
• Benzamide, 3-(formylamino)-2-hydroxy-N-decyl-;
• Benzamide, 3-(formylamino)-2-hydroxy-N-dodecyl-;
• Benzamide, 3-(formylamino)-2-hydroxy-N-hexyl-.