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WO1992008696A1 - Herbicides - Google Patents

Herbicides Download PDF

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Publication number
WO1992008696A1
WO1992008696A1 PCT/AU1991/000529 AU9100529W WO9208696A1 WO 1992008696 A1 WO1992008696 A1 WO 1992008696A1 AU 9100529 W AU9100529 W AU 9100529W WO 9208696 A1 WO9208696 A1 WO 9208696A1
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compound
formula
alkyl
compounds
j6hz
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PCT/AU1991/000529
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English (en)
Inventor
Kevin Norman Winzenberg
Andris Juris Liepa
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Dunlena Pty. Limited
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Publication of WO1992008696A1 publication Critical patent/WO1992008696A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/42—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to organic compounds having herbicidal properties and plant growth regulating properties; to herbicidal compositions and processes utilizing such compounds and to plant growth regulating compositions and processes utilizing such compositions.
  • R is H, C 1 -C 6 alkyl
  • R 1 is R 2 , OR 3 , NR 3 R 4 ;
  • R 2 is optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl;
  • R 3 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, optionally substituted phenyl, optionally substituted benzyl;
  • R 4 is H, C 1 -C 6 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 6 alkoxy or NR 3
  • R 4 is a pyrrolidine, piperidine or morpholine ring;
  • R 6 is C 1 -C 6 cycloalkyl
  • R 7 is H, optionally halogenated C 1 -C 6 alkyl, C 3 -C 6 alkenyl, halogenoalkenyl or alkynyl.
  • the present invention seeks to provide novel compounds which have herbicidal activity, as well as agriculturally useful compositions of these compounds and methods of using these compounds as pre-emergent and/or post-emergent herbicides and plant growth regulators.
  • the invention provides compounds of the formula (1) or isomeric and/or tautomeric forms thereof:
  • R 1 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl or M;
  • R 2 is C 1 -C 4 alkyl
  • R 3 is C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyl with 1-3 halogen substituents, C 2 -C 4 alkynyl, phenyl optionally substituted with 0-3 substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkythio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro, cyano, phenyl (optionally substituted with 0-3 substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro, and cyano) and
  • phenoxy (optionally substituted with 0-3 substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro, and cyano);
  • R 4 and R 5 are independently H, or C 1 -C 4 alkyl, C 2 -C 4 alkenyl;
  • R 6 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl substituted with an optionally substituted phenyl group wherein the substituent on the phenyl group is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, and C 1 -C 4 haloalkoxy, phenyl, phenyl optionally substituted with 1-3 substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, and C 1 -C 4 haloalkoxy;
  • X is -SO 2 R 7 , -CONR 7 R 8 , -COR 7 , -CO 2 R 7 , -SO 2 NR 7 R 8 , -CSNR 7 R 8 ;
  • R 7 and R 8 are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl;
  • M is Li + , Na + , K + , NH 4 + , or N(R 11 ) 4 + where R 11 is C 1 -C 4 alkyl.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl”, denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl or hexyl isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropyloxy, and the different butyloxy isomers.
  • Alkenyl denotes straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, 3-propenyl, etc.
  • Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl, and the different butynyl isomers.
  • Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl, propylsulfonyl, and the different butylsulfonyl isomers.
  • Alkylthio, alkylsulfinyl, alkylamino, etc. are defined in an analogous manner.
  • Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine.
  • halogen-substituted groups such as “haloalkyl” or “haloalkoxy” the alkyl moieties may be partially halogenated or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • Alkylcarbonyl denotes acetyl, propionyl, and the different butyryl isomers.
  • Alkoxycarbonyl denotes methoxycarbonyl, ethoxycarbonyl,
  • C 2 -C 3 alkylthioalkyl would designate -CH 2 SCH 3 , -CH 2 SC 2 H 5 , -CH 2 CH 2 SCH 3 or -CH(CH 3 )SCH 3
  • C 2 -C 5 alkoxyalkyl represents -CH 2 OCH 3 through to -(CH 2 ) 4 OCH 3 or -CH 2 O(CH 2 ) 3 CH 3 and the various structural isomers embraced therein.
  • Alkylene denotes methylene (-CH 2 -), propylene and butylene;
  • R 1 is hydrogen the compounds (1) of the invention may undergo tautomerisation. All tautomeric forms are included in the scope of this invention.
  • the compounds of the invention may be prepared by reduction of amines of formula (2) wherein R 4 , R 5 , R 6 and n are as defined above and R 9 is hydrogen or C 1 -C 6 alkyl. Compounds of formula (2) are readily obtainable by customary methods described in the literature.
  • the cyclohexanediones (5) thus obtained may be acylated on oxygen and the enol esters isomerized (Fries rearrangement) to give the novel C-substituted products (6).
  • the C-acylated derivatives (6) may be reacted with O-substituted hydroxylamines which may in turn be generated in situ from appropriate precursors, to afford derivatives of the general Formula (1) wherein R 1 is hydrogen.
  • R 1 is not hydrogen
  • compounds of the invention of Formula (1) wherein R 1 is an organic or inorganic cation may be prepared from compounds of the invention of Formula (1) wherein R 1 is hydrogen by reacting these latter compounds with an appropriate inorganic or organic base.
  • R 7 R 8 NCSCl 55.mmol in dichloromediane (50 ml) followed by a solution of sodium hydroxide (55 mmol) in water (20 ml). The mixture was stirred for 1-24 h at 0 °C.
  • Cpd 3.5 ⁇ 13.7, s, OH; 8.20, d, J8Hz, 2H; 7.49, d, J8Hz, 2H; 5.13, s, OCH 2 ; 4.25-3.85, m, CHMe; 3.05-1.37, m, 11H; 1.80, s, NMe or SO 2 Me; 1.70, s, NMe or SO 2 Me; 1.17, d, J6Hz, CHMe; 0.94, t, J6Hz, CH 2 Me.
  • Cpd 3.12 ⁇ 15..2, s, OH; 4.04, q, J7Hz, OCH 2 ; 3.82, quintet, J7Hz, NCH; 2.95-1.95, m, 7H; 2.82, s, SO 2 Me; 2.67, s, NMe; 1.75-1.30, m, 6H; 1.30, t, OCH 2 Me; 0.82, t, J7Hz, 2Me.
  • Cpd 4.4 ⁇ 15.1; s, OH; 4.05, q, J7Hz, OCH 2 ; 4.2-3.8, m, NCH; 3.50-1.85, m, 11H; 2.63, s, NMe; 1.85-1.3, m, 4H; 1.28, t, J7Hz, OCH 2 Me; 1.16, d, J7Hz, CHMe; 1.07, t, J7Hz, N(CH 2 Me) 2 ; 0.94, t, J7Hz, CH 2 CH 2 Me.
  • Cpd 6.8 ⁇ 15.3 s, OH; 4.06, q, J7Hz, OCH 2 ; 3.50-3.20, m, NCH 2 ; 3.05-2.80, m, 2H; 2.99, s, NMe; 2.75-1.97, m, 7H; 1.85-1.25, m, 2H; 1.26, t, J7Hz, OCH 2 Me; 1.13, t, J7Hz, COCH 2 Me; 0.94, t, J7Hz, CH 2 CH 2 Me.
  • Cpd 6.9 ⁇ 14.0, s, OH; 4.07, q, J7Hz, OCH 2 ; 3.50-3.20, m, NCH 2 ; 3.05, s, NMe; 3..03-2.2, m, 8H; 1.80-1.30, m, 2H; 1.28, t, J7Hz, OCH 2 Me; 1.12, d, J7Hz, CHMe 2 ; 0.95, t, J7Hz, CH 2 CH 2 Me.
  • Cpd 6.28 ⁇ 14.8,s, OH; 4.08, q, J7Hz, OCH 2 CH 3 ; 3.30-1.30, m, 14H; 1,29, t, J7Hz, COMe or OCH 2 Me; 1.18, d, J6Hz, 2CHMe; 1.15, t, J6Hz, COMe or OCH 2 Me; 0.94, t, J6Hz, CH 2 CH 2 Me.
  • CH CH 2 ; 4.48, d, J6Hz, OCH 2 ; 3.70-1.20, m, 11H; 2.97, s, NMe; 0.94, t, J6Hz, CH 2 CH 2 Me.
  • Cpd 6.50 ⁇ 4.06, q, J7Hz, OCH 2 Me; 3.45-3.20, m, 2H; 3.05-1.30, m, 9H; 3.00, s, NMe; 2.06, s, COMe; 1.28, t, J6Hz, OCH 2 Me; 0.93, t, J6Hz, CH 2 Me.
  • Cpd 9.3 ⁇ 12.2, s, OH; 8.20, d, J9Hz, 2H; 7.50, d, J9Hz, 2H; 5.13, s, OCH 2 ; 3.64, broad d, J6Hz, NCH 2 ; 3.07, s, NMe 2 ; 3.02-2.75, m, 2H; 2.99, s, NMe; 2.70-2.00, m, 5H; 1.80-1.31, m, 2H; 0.95, t, J7Hz, CH 2 Me.
  • Test results indicate that the compounds of the invention are highly active pre-emergent and/or post-emergent herbicides or plant growth regulants.
  • These compounds are particularly useful for controlling certain grass and broadleaf weeds in small grain cereals such as wheat (Triticum aestivum) and barley (Hordeum vulgare), examples of which include, but are not limited to, Centurk wheat, Era wheat, Igri barley and Klages barley.
  • Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as wild oats (Avena fatua), black grain (Alopecurus myosoides), crabgrass (Digitaria sanguinalis), foxtails (Setaria spp.) and Italian ryegrass (Lolium multiflorum).
  • Some of these compounds are useful for controlling certain grass and broadleaf weeds in dryland and paddy rice (Orysa sativa), examples of which include, but are not limited to, Indica and Japonica varieties of the crop. Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as barnyardgrass
  • these compounds also have utility for broad-spectrum pre- and/or post-emergence weed control in areas where control of all vegetation is required. Alternatively, these compounds are useful to regulate plant growth.
  • Rates of application for compounds of this invention are determined by a number of factors. These factors include formulation selection, method of application, amount of vegetation present, growing conditions, etc. In general, the subject compounds should be applied at rates of 0.05 to 10 kg/ha with a preferred rate range of 0.1 to 2 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
  • a further embodiment of the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound of formula (1) as hereinbefore defined with at least one other herbicide.
  • the invention provides a method for regulating the growth of a plant comprising applying to the plant, to the seed of the plant, or to the growth medium of the plant an effective amount of a compound of Formula (1) hereinbefore defined. Rates of application of these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Weed grasses in graminaceous crops can normally be killed when treated at a rate of from less than 0.1 to about 20 kg active ingredient/ha.
  • the compounds of this invention can also be mixed with fungicides, bactericides, acaricides, nematicides, insecticides, or other biologically active compounds. Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type are well known to those skilled in the art.
  • Useful formulation of the compounds within the scope of this invention can be prepared in conventional ways. They include dusts, granules, pellets, solutions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from one litre to several hundred litres per hectare. High strength compositions are primarily used as intermediates for further formulations.
  • the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier therefor, for example, kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewill's earth, diatomaceous earth, and China clay.
  • the compositions may also be in the form of dispersible powders or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also solid diluents, fillers and suspending agents.
  • Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • compositions for dressing seed may contain an agent (for example a mineral oil) for assisting the adhesion of the composition to the seed.
  • an agent for example a mineral oil
  • aqueous dispersions or emulsions may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s).
  • Suitable solvents are acetone, ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes and
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill.
  • Suspensions are prepared by wet milling (see, for example, Littler, US Pat. No. 3,060,084).
  • Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques.

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention se rapporte à des composés représentés par la formule (1) ou à des formes isomères et/ou tautomères de ces composés. Dans la formule (1), R1 représente H, ou un groupe choisi parmi un certain nombre de groupes spécifiés, ou M; R2 représente alkyle C¿1?-C4; R?3¿ représente alkyle C¿1?-C4, ou un groupe choisi parmi un certain nombre de groupes spécifiés; R?4 et R5¿ représentent séparément H, ou alkyle C¿1?-C4, ou alcényle C2-C4; R?6¿ représente hydrogène ou un groupe choisi parmi un certain nombre de groupes spécifiés; X représente -SO¿2?R?7, -CONR7 R8, -COR7, -CO¿2R7, -SO2NR?7R8, -CSNR7R8; R7 et R8¿ représentent séparément hydrogène, alkyle C¿1?-C6, cycloalkyle C3-C6; ou R?7 et R8¿ forment, avec l'azote auquel ils sont liés, une chaîne fermée hétérocyclique de 5 à 7 éléments; n vaut 0, 1, 2, 3, 4 ou 5; à condition que, lorsque n est égal à 0, X ne représente pas COR7, CO2R7 ou CONR7R8; et M représente Li?+, Na+, K+, NH¿4+, ou N(R11)4?+ où R11¿ représente alkyle C¿1?-C4. L'invention décrit des procédés servant à préparer ces composés, des compositions contenant ces composés qui sont dotées d'une action herbicide et d'une action de régulation de la croissance végétale, ainsi que des procédés utilisant ces composés qui servent à réguler la croissance végétale et à produire une action sélective destinée à empêcher, à endommager ou à détruire les mauvaises herbes dans une culture.
PCT/AU1991/000529 1990-11-20 1991-11-20 Herbicides WO1992008696A1 (fr)

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AUPK3433 1990-11-20
AUPK343390 1990-11-20

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5674812A (en) * 1994-03-31 1997-10-07 Basf Aktiengesellschaft 5(sulfo-/carbamoylmethyl)cyclohexenone oxime ethers
US5739085A (en) * 1994-05-05 1998-04-14 Basf Aktiengesellschaft O-(oximino)ethylcyclohexenone oxime ethers and their use as herbicides
US6303816B1 (en) * 1997-02-04 2001-10-16 Eli Lilly And Company Sulphonamide derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1138688A (en) * 1987-02-09 1988-08-11 Ciba-Geigy Ag Novel cyclohexanediones

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1138688A (en) * 1987-02-09 1988-08-11 Ciba-Geigy Ag Novel cyclohexanediones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5674812A (en) * 1994-03-31 1997-10-07 Basf Aktiengesellschaft 5(sulfo-/carbamoylmethyl)cyclohexenone oxime ethers
US5739085A (en) * 1994-05-05 1998-04-14 Basf Aktiengesellschaft O-(oximino)ethylcyclohexenone oxime ethers and their use as herbicides
US6303816B1 (en) * 1997-02-04 2001-10-16 Eli Lilly And Company Sulphonamide derivatives
US6596716B2 (en) 1997-02-04 2003-07-22 Eli Lilly And Company 2-propane-sulphonamide derivatives
US7135487B2 (en) 1997-02-04 2006-11-14 Eli Lilly And Company Sulphonamide derivatives

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