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US 8,133,847 B2Granted
Pyrido[2,3-B]pyrazine derivatives useful as herbicidal compounds
AssigneeSyngenta Limited
InventorsNeil Brian Carter, Matthew Robert Cordingley, Patrick Jelf Crowley, Michael Drysdale Turnbull
Life of this patent
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Abstract
The present invention relates to a method of controlling plants or inhibiting plant growth which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a compound of formula (I) wherein R1, R2, R3, R4 and R5 are as defined in claim 1; or salts or N-oxides thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to herbicidal compositions comprising compounds of formula (I) and to certain novel pyrido[2,3-b]pyrazines.
Claims16
A method of controlling plants which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a compound of formula (I)
- wherein
- R1 and R2 are independently hydrogen, C1-C4alkyl, C1-C4haloalkyl, halo, cyano, hydroxy, C1-C4alkoxy, C1-C4alkylthio, aryl or aryl substituted by one to five R6, which may be the same or different, or heteroaryl or heteroaryl substituted by one to five R6, which may be the same or different;
- R3 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C10cycloalkyl, C3-C10cyclo-alkyl-C1-C6alkyl-, C1-C10alkoxy-C1-C6alkyl-, C1-C10cyanoalkyl-, C1-C10alkoxycarbonyl-C1-C6alkyl-, N—C1-C3alkyl-aminocarbonyl-C1-C6alkyl-, N,N-di-(C1-C3alkyl)-aminocarbonyl-C1-C6alkyl-, aryl-C1-C6alkyl- or aryl-C1-C6alkyl- wherein the aryl moiety is substituted by one to three R7, which may be the same or different, or heterocyclyl-C1-C6alkyl- or heterocyclyl-C1-C6alkyl- wherein the heterocyclyl moiety is substituted by one to three R7, which may be the same or different;
- R4 is aryl or aryl substituted by one to five R8, which may be the same or different, or heteroaryl or heteroaryl substituted by one to four R8, which may be the same or different;
- R5 is hydroxy, R9-oxy-, R10-carbonyloxy-, tri-R11-silyloxy- or R12-sulfonyloxy-,
- each R6, R7 and R8 is independently halo, cyano, nitro, C1-C10alkyl, C1-C4haloalkyl, C2-C10alkenyl, C2-C10alkynyl, hydroxy, C1-C10alkoxy, C1-C4haloalkoxy, C1-C10alkoxy-C1-C4alkyl-, C3-C7cycloalkyl, C3-C7cycloalkoxy, C3-C7cycloalkyl-C1-C4alkyl-, C3-C7cycloalkyl-C1-C4alkoxy-, C1-C6alkylcarbonyl-, formyl, C1-C4alkoxycarbonyl-, C1-C4alkylcarbonyloxy-, C1-C10alkylthio-, C1-C4haloalkylthio-, C1-C10alkylsulfinyl-, C1-C4haloalkylsulfinyl-, C1-C10alkylsulfonyl-, C1-C4haloalkylsulfonyl-, amino, C1-C10alkylamino-, di-C1-C10alkylamino-, C1-C10alkylcarbonylamino-, aryl or aryl substituted by one to three R13, which may be the same or different, heteroaryl or heteroaryl substituted by one to three R13, which may be the same or different, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to three R13, which may be the same or different, heteroaryl-C1-C4alkyl- or heteroaryl-C1-C4alkyl- wherein the heteroaryl moiety is substituted by one to three R13, which may be the same or different, aryloxy- or aryloxy-substituted by one to three R13, which may be the same or different, heteroaryloxy- or heteroaryloxy-substituted by one to three R13, which may be the same or different, arylthio- or arylthio-substituted by one to three R13, which may be the same or different, or heteroarylthio- or heteroarylthio-substituted by one to three R13, which may be the same or different;
- R9 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or aryl-C1-C4alkyl- or aryl-C1-C4alkyl-wherein the aryl moiety is substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy;
- R10 is C1-C10alkyl, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C10alkyl-, C1-C10 haloalkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C4alkoxy-C1-C10alkyl-, C1-C4alkylthio-C1-C4alkyl-, C1-C10alkoxy, C2-C10 alkenyloxy, C2-C10 alkynyloxy, C1-C10alkylthio-, N—C1-C4alkyl-amino-, N,N-di-(C1-C4alkyl)-amino-, aryl or aryl substituted by one to three R14, which may be the same or different, heteroaryl or heteroaryl substituted by one to three R14, which may be the same or different, aryl-C1-C4alkyl- or aryl-C1-C4alkyl- wherein the aryl moiety is substituted by one to three R14, which may be the same or different, heteroaryl-C1-C4alkyl- or heteroaryl-C1-C4alkyl- wherein the heteroaryl moiety is substituted by one to three R14, which may be the same or different, aryloxy- or aryloxy-substituted by one to three R14, which may be the same or different, heteroaryloxy- or heteroaryloxy-substituted by one to three R14, which may be the same or different, arylthio- or arylthio-substituted by one to three R14, which may be the same or different, or heteroarylthio- or heteroarylthio-substituted by one to three R14, which may be the same or different;
- each R11 is independently C1-C10alkyl or phenyl or phenyl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy;
- R12 is C1-C10alkyl or phenyl or phenyl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy;
- each R13 is independently halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy;
- and
- each R14 is independently halo, cyano, nitro, C1-C10alkyl, C1-C4haloalkyl, C1-C10alkoxy, Cr C4alkoxycarbonyl-, C1-C4haloalkoxy, C1-C10alkylthio-, C1-C4haloalkylthio-, C1-C10alkylsulfinyl-, C1-C4haloalkylsulfinyl-, C1-C10alkylsulfonyl-, C1-C4haloalkylsulfonyl-, aryl or aryl substituted by one to five substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy, or heteroaryl or heteroaryl substituted by one to four substituents independently selected from halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy;
- or salts or N-oxides thereof.
11 more elements
A compound of formula (Ia)
- wherein R1, R2 and R4 are as defined for compounds of formula (I);
- or salts or N-oxides thereof, provided that if R1 and R2 are hydrogen, R4 is not 4-bromo-2,6-difluoro-phenyl, 2-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 2-chloro-6-fluoro-phenyl, 4-chloro-2-fluoro-phenyl, 4-chloro-2-methyl-phenyl, 2-chloro-phenyl, 5-chloro-2-trifluoromethyl-phenyl, 2,4-dichloro-phenyl, 2,6-dichloro-phenyl, 2,6-difluoro-4-cyano-phenyl, 2,6-difluoro-4-methoxy-phenyl, 2,6-difluoro-4-methyl-phenyl, 2,3-difluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,4-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2-fluoro-4-methyl-phenyl, 2-fluoro-phenyl, 2-fluoro-6-methoxy-phenyl, 2-fluoro-6-methyl-phenyl, 4-fluoro-2-methyl-phenyl, 4-fluoro-2-trifluoromethyl-phenyl, 5-fluoro-2-trifluoromethyl-phenyl, 2,3,4,5,6-pentafluoro-phenyl, 2,3,5,6-tetrafluoro-phenyl, 2,3,4-trifluoro-phenyl, 2,4,6-trifluoro-phenyl, 2,5,6-trifluoro-phenyl or 2,4,6-trimethyl-phenyl.
A compound of formula (Ia)
- wherein R1, R2 and R4 are as defined for compounds of formula (I);
- or salts or N-oxides thereof, provided that if R1 and R2 are hydrogen, R4 is not 2-bromo-4,6-difluoro-phenyl, 4-bromo-2,6-difluoro-phenyl, 2-bromo-6-fluoro-phenyl, 2-bromo-phenyl, 2-chloro-4,6-difluoro-phenyl, 2-chloro-4-fluoro-phenyl, 2-chloro-6-fluoro-phenyl, 4-chloro-2-fluoro-phenyl, 2-chloro-6-methyl-phenyl, 4-chloro-2-methyl-phenyl, 2-chloro-phenyl, 2-chloro-6-trifluoromethyl-phenyl, 5-chloro-2-trifluoromethyl-phenyl, 2,4-dichloro-6-fluoro-phenyl, 2,6-dichloro-4-fluoro-phenyl, 2,4-dichloro-phenyl, 2,6-dichloro-phenyl, 2,6-difluoro-4-cyano-phenyl, 2,4-difluoro-6-methoxy-phenyl, 2,6-difluoro-4-methoxy-phenyl, 2,4-difluoro-6-methyl-phenyl, 2,6-difluoro-4-methyl-phenyl, 2,3-difluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,4-difluoro-6-trifluoromethyl-phenyl, 2,6-dimethoxy-phenyl, 2,4-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,6-di(trifluoromethyl)-phenyl, 2-fluoro-6-methoxy-phenyl, 2-fluoro-4-methyl-phenyl, 2-fluoro-6-methyl-phenyl, 4-fluoro-2-methyl-phenyl, 2-fluoro-phenyl, 2-fluoro-6-trifluoromethyl-phenyl, 4-fluoro-2-trifluoromethyl-phenyl, 5-fluoro-2-trifluoromethyl-phenyl, 2-methoxy-phenyl, 2,3,4,5,6-pentachloro-phenyl, 2,3,4,5,6-pentafluoro-phenyl, 2,3,5,6-tetrafluoro-phenyl, 2,3,6-trichlorophenyl, 2,4,6-trichlorophenyl, 2-trifluoromethyl-phenyl, 2,3,4-trifluoro-phenyl, 2,4,6-trifluoro-phenyl, 2,5,6-trifluoro-phenyl or 2,4,6-trimethyl-phenyl.
A compound of formula (Ib)
- wherein R1, R2 and R4 are as defined for compounds of formula (I) and R5 is R9-oxy, R10-carbonyloxy, tri-R11-silyloxy or R12-sulfonyloxy;
- or salts or N-oxides thereof.
A compound of formula (Ic)
- wherein R1, R2 and R4 are as defined for compounds of formula (I) and R3 is C1-C10 alkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C6alkyl-, C1-C10alkoxy-C1-C6alkyl-, C1-C10 cyanoalkyl-, C1-C10 alkoxycarbonyl-C1-C6alkyl-, N—C1-C3alkyl-aminocarbonyl-C1-C6alkyl-, N,N-di-(C1-C3alkyl)-aminocarbonyl-C1-C6alkyl-, aryl-C1-C6alkyl or aryl-C1-C6alkyl substituted with one to three substituents R7, which may be the same or different, or heterocyclyl-C1-C6alkyl or heterocyclyl-C1-C6alkyl substituted with one to three substituents R7, which may be the same or different;
- and R5 is R9-oxy, R10-carbonyloxy, tri-R11-silyloxy or R12-sulfonyloxy;
- or salts or N-oxides thereof.
A compound of formula (Id)
- wherein R1, R2 and R4 are as defined for compounds of formula (I) and R3 is C1-C10 alkyl, C2-C10alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl-C1-C6alkyl-, C1-C10 alkoxy-C1-C6alkyl-, C1-C10 cyanoalkyl-, C1-C10 alkoxycarbonyl-C1-C6alkyl-, N—C1-C3alkyl-aminocarbonyl-C1-C6alkyl-, N,N-di-(C1-C3alkyl)-aminocarbonyl-C1-C6alkyl-, aryl-C1-C6alkyl or aryl-C1-C6alkyl substituted with one to three substituents R7, which may be the same or different, or heterocyclyl-C1-C6alkyl or heterocyclyl-C1-C6alkyl substituted with one to three substituents R7, which may be the same or different;
- or salts or N-oxides thereof.
A compounds of formula (5)
- wherein R1 and R2 are as defined for compounds of formula (I) and R17 is C1-C6alkyl;
- or salts or N-oxides thereof.
A compound of formula (6)
- wherein R1 and R2 are as defined for compounds of formula (I);
- or salts or N-oxides thereof.
A herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I) in addition to formulation adjuvants.
A herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I), one or more further herbicides and optionally one or more safeners.
Dependencies are inferred from the claim text.