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US 6,521,622 B1Granted
Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
AssigneeDow AgroSciences LLC
InventorsMichael J. Ricks, William H. Dent, III, Richard B. Rogers, Chenglin Yao, Bassam S. Nader, John L. Miesel, Gina M. Fitzpatrick, Kevin G. Meyer, Noormohamed M. Niyaz, Irene M. Morrison, Robert P. Gajewski
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Abstract
Heterocyclic aromatic amides having a hydroxy group adjacent to the amide functionality are useful as antifungal agents, particularly for plants.
Claims34
A compound of Formula I:
- wherein:
- (a)
- represents a 5- or 6-membered heterocyclic aromatic ring in which
- (i) each of X1-X4 is independently O, S, NR′, N, CR″ or a bond;
- (ii) no more than one of X1-X4 is O, S or NR′;
- (iii) no more than one of X1-X4 is a bond;
- (iv) when any one of X1-X4 is S, O or NR′, one of the adjacent X1-X4 must represent a bond;
- and
- (v) at least one of X1-X4 must be O, S, NR′ or N;
- wherein
- R′ is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, hydroxy, acyloxy, C1-C6 alkoxymethyl, CHF2, cyclopropyl or C1-C4 alkoxy;
- and,
- R″ is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, aryl, C1-C3 NHC(O)alkyl, NHC(O)H, C1-C3 haloalkylthio, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl or nitro wherein adjacent R″ substituents may form a ring or adjacent R′ and R″ substituents may form a ring;
- (b) Z is O, S or NORZ in which RZ is H or C1-C3 alkyl;
- and
- (c) A represents
- in which
- Q1, Q2 are O or S;
- W is O, CH2, CHR6, or a bond;
- R1 is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl or heteroaryl;
- R3 is H, R1, OR1, OC(O)OR1 or OC(O)NR1R6;
- R6 is independently C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 alkenyl or C2-C5 alkynyl.
19 more elements
A compound of Formula I:
- wherein:
- (a)
- represents a 5- or 6-membered heterocyclic aromatic ring in which
- (i) each of X1-X4 is independently O, S, NR′, N, CR″ or a bond;
- (ii) no more than one of X1-X4 is O, S or NR′;
- (iii) no more than one of X1-X4 is a bond;
- (iv) when any one of X1-X4 is S, O or NR′, one of the adjacent X1-X4 must represent a bond;
- and
- (v) at least one of X1-X4 must be O, S, NR′ or N;
- wherein
- R′ is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, hydroxy, acyloxy, C1-C6 alkoxymethyl, CHF2, cyclopropyl or C1-C4 alkoxy;
- and,
- R″ is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, aryl, C1-C3 NHC(O)alkyl, NHC(O)H, C1-C3 haloalkylthio, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl or nitro wherein adjacent R″ substituents may form a ring or adjacent R′ and R″ substituents may form a ring;
- (b) Z is O, S or NORZ in which RZ is H or C1-C3 alkyl;
- and
- (c) A represents
- where *=point of attachment
- in which
- Q1, Q2 are O or S;
- W is O, CH2, CHR6, or a bond;
- R1 is C2-C8 alkynyl, C3-C8 cycloalkyl, aryl or heteroaryl;
- R3 is OC(O)R1;
- R6 is independently C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C5 alkynyl.
20 more elements
Dependencies are inferred from the claim text.