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US 11,634,393 B2Granted
Substituted tolyl fungicides
AssigneeFMC Corporation
InventorsJames Francis Bereznak, Andrew Edmund Taggi, Stephen P. Bolgunas
Life of this patent
Estimating the term…
Abstract
Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein A, Q, R1, R2, R3, R4, W and Y are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
Claims14
A compound selected from Formula 1, tautomers, N-oxides, and salts thereof,
- wherein
- A is a radical selected from the group consisting of
- wherein the bond extending to the right is attached to the ring containing Q and the bond extending to the left is attached to the phenyl ring bearing the Y—N(R3)C(═W)R4 substituent;
- Q is CR6 or N;
- Y is CR7aR7b, O or NR8;
- W is O or S;
- R1 and R2 are each independently halogen, cyano, hydroxy, nitro, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, C2-C6 cyanoalkoxy, C3-C6 cycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl;
- R3 is H, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkoxycarbonyl or C2-C4 haloalkoxycarbonyl;
- R4 is C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylamino or C2-C4 dialkylamino;
- each R5 is independently halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;
- n is 0, 1 or 2;
- R6 is halogen, cyano, hydroxy, nitro, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, C2-C6 cyanoalkoxy, C2-C6 alkoxyalkoxy, C1-C6 alkylamino, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, —ZC(═O)V, CR10a═NOR10b, ON═CR11aR11b, CR12a═NNR12bR12c or -L-J;
- R7a is H, hydroxy, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;
- R7b is H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;
- R8 is H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
- Z is a direct bond, O, S or NH;
- or CH2 optionally substituted with up to 2 substituents independently selected from halogen, methyl or methoxy;
- V is R9 or OR9;
- R9, R10b, R11a and R12c are each H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl or C4-C8 cycloalkylalkyl;
- R10a, R11b, R12a and R12b are each independently H, C1-C3 alkyl or C1-C3 haloalkyl;
- L is a direct bond, CH2, O, S, NR13, OCH2, CH2O, C(═O), S(═O) or S(═O)2;
- J is a 3- to 6-membered nonaromatic carbocyclic ring, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 4 substituents independently selected from R14;
- or
- J is a 3- to 6-membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 4 substituents independently selected from R14;
- R13 is H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
- each R14 is independently halogen, hydroxy, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C(═O)OR15;
- and
- each R15 is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl.
25 more elements
Dependencies are inferred from the claim text.