Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-04-13
1990-07-03
Hollrah, Glennon H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
71 81, 71 88, 71 90, C07D31196
Patent
active
049392786
DESCRIPTION:
BRIEF SUMMARY
This invention relates to organic compounds having herbicidal properties and plant growth regulating properties, to processes for the preparation of such compounds; to intermediates useful in the preparation of such compounds; to herbicidal compositions and processes utilizing such compounds and to plant growth regulating compositions and processes utilizing such compounds.
The use of certain cyclohexane-1,3-dione derivatives as grass herbicides is known in the art. Thus, for example, the compendium "Agricultural Chemicals - Book II Herbicides 1986-87 Revision" (W. T. Thomson Editor, Thomson Publications, California U.S.A.) describes the cyclohexane-1,3-dione derivatives known commerically as Alloxydim Sodium (methyl-3-[1-(allyloxyimino)butyl]-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3- ene carboxylate), Cloproxydim ((E,E)-2[1-[1-[(3-chloro-2-propenyl)oxy]imino]butyl]-5-[2-(ethylthio)propy l]-3-hydroxy-2-cyclohexen-1-one), Cycloxydim (2-[1-ethoxyimino)butyl]-3-hydroxy-5-[2H-tetrahydrothiopyran-3-yl]-2-cyclo hexen-1-one and Sethoxydim (2-[1-(ethoxyimino)butyl]-5-[2-ethylthio]propyl-3-hydroxy-2-cyclohexen-1-o ne) as selective post-emergent herbicides.
Alloxydim and Sethoxydim have been disclosed in Australian Patent No. 464 655 and Australian Patent Application No. 35,314/78 respectively.
Pyrones of the general Formula (1) have been claimed to show herbicidal activity (Japan Kokai 76 63175 (Chemical Abstracts, 86:72439y)). ##STR2##
We have discovered that compounds similar to the general Formula (1) but which bear substituents at the 6-position other than hydrogen or geminal dimethyl exhibit particularly useful herbicidal activity, with special selectivity for weed grasses in crops, and plant growth regulating activity.
Accordingly, the invention provides a compound of the general Formula (2) ##STR3##
wherein R.sup.1 is selected from the group consisting of: hydrogen; alkyl; alkenyl; alkynyl; cycloalkyl; cycloalkenyl substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, optionally substituted phenyl, optionally substituted heterocycle; optionally substituted phenyl; optionally substituted heterocycle; alkyl sulfonyl; optionally substituted benzene sulfonyl; an acyl group; and an inorganic or organic cation;
R.sup.2 is selected from the group consisting of: alkyl; alkenyl; cycloalkyl; cycloalkenyl; haloalkenyl; alkynyl; haloalkynyl; substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalkyl group is substituted with a substituent selected from the group consisting of halogen, alkoxy, alkylthio, optionally substituted phenyl, and optionally substituted heterocycle; optionally substituted phenyl; and optionally substituted heterocycle;
R.sup.3 is selected from the group consisting of: alkyl; haloalkyl; alkenyl; cycloalkyl; cycloalkenyl; alkynyl; and optionally substituted phenyl;
R.sup.4 is selected from the group consisting of: alkynyl; haloalkyl; haloalkenyl; cycloalkyl; cycloalkenyl; substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, oxo, acyl, alkoxycarbonyl, (alkoxyimino)alkyl, ketal, carboxylic acid, optionally substituted phenyl, and optionally substituted heterocycle; and optionally substituted heterocycle;
R.sup.5 is selected from the group consisting of: alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; cycloalkyl; cycloalkenyl; substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, oxo, acyl, alkoxycarbonyl, (alkoxyimino)alkyl, ketal, carboxylic acid, optionally substituted phenyl, and optionally substituted heterocycle; and optionally substituted hererocycle;
R.sup.4 and R.sup.5 together with the carbon to which they are attached form a substituted or unsubstituted saturated or partially saturated heterocyclic or carbocyclic ring conta
REFERENCES:
patent: 4008067 (1977-02-01), Hirono et al.
CA 86: 72439y, Mikio et al., JP 76/63175, 6-1-1976.
CA 102: 184973y, Watson, 5-20-1983.
Anderson-McKay Janet E.
Liepa Andris J.
Costello James A.
Dunlena Pty. Limited
Hollrah Glennon H.
Trinh Ba K.
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