WO1989012041A1 - Derives de 1,3-dicetones bicycliques a action herbicide - Google Patents

Derives de 1,3-dicetones bicycliques a action herbicide Download PDF

Info

Publication number
WO1989012041A1
WO1989012041A1 PCT/AU1989/000237 AU8900237W WO8912041A1 WO 1989012041 A1 WO1989012041 A1 WO 1989012041A1 AU 8900237 W AU8900237 W AU 8900237W WO 8912041 A1 WO8912041 A1 WO 8912041A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
compound
carboxylate
formula
indene
Prior art date
Application number
PCT/AU1989/000237
Other languages
English (en)
Inventor
Andris Juris Liepa
Kevin Norman Winzenberg
Original Assignee
Dunlena Pty. Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dunlena Pty. Limited filed Critical Dunlena Pty. Limited
Publication of WO1989012041A1 publication Critical patent/WO1989012041A1/fr

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

Definitions

  • This invention reUtes to organic compounds having herbicidal
  • Patent No. 464655 and Australian Patent Application No. 35,314/78 respectively.
  • R 1 is sheeted from the group consisting of: hydrogen; alkyl; alkenyl; alkynyl; cycloalkyl; cycloalkenyl substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalky, group is substituted with a substituent selected from the group consisting of
  • R 2 is selected from the group consisting of: alkyl; alkenyl;
  • R 3 is Elected from the group consisting of: alkyl; alkenyl;
  • alkynyl and optionally substituted phenyl
  • n 1,2,3,4,5;
  • 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, alkyl thio, oxo, acyl, alkoxycarbonyl, ketal, optionally substituted phenyl, and optionally substituted heterocycle; optionally substituted phenyl; and optionally substituted heterocycle; with the proviso that when n is 4 not all of the eight substituents R and R 11 are hydrogen.
  • R 4 is selected from the group consisting of: alkyl; alkenyl; alkynyl; substituted alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, optionally substituted phenyl, and optionally substituted heterocycle; optionally substituted phenyl; and optionally substituted heterocycle.
  • alkyl alkenyl and alkynyl include straightchain and branched-chain structures.
  • heterocycle means a mono- or polycyclic heterocyclic ring structure that contains one or more heteroatoms and may or may not be aromatic. Suitable heteroatoms are nitrogen, oxygen, and sulphur.
  • the heterocyclic ring preferably has more than three atoms in the ring.
  • suitable heterocycle groups are thiophenyl, benzofuranyl, furanyl, morpholino, and pyridyl.
  • alkenyl, and alkynyl mean lower alkyl, alkenyl and alkynyl. More preferably alkyl, alkoxy, alkylthio, haloalkyl, alkyl sulphonyl or substituted alkyl groups contain 1 to 6 carbon atoms and alkenyl, alkynyl, haloalkenyl, or haloalkynyl groups contain 2 to 6 carbon atoms.
  • Formula (1) of the invention may undergo tautomerism and exist in any one of five forms as shown below.
  • R 1 is other than hydrogen a compound of Formula (1) may be obtained as a mixture with an isomeric compound of Formula (1b) where R 1 , R 2 , R 3 , R 4 , R and R 11 , and n are as defined above.
  • R 1 particularly preferred choices for R 1 include hydrogen and the alkali metal cations.
  • R 2 examples include alkyl, alkenyl and haloalkenyl. Particularly preferred choices for R 2 include ethyl, ally! and 2- and 3-chloroallyl.
  • R 3 Particularly preferred choices for R 3 include ethyl and n-propyl.
  • n 3.
  • compositions may consist of the isomers separately or in mixtures in any possible ratio.
  • herbicidal compounds of formula (1) of the invention are the alkyl 3aH-indene-3a-carboxylate derivatives (1.1-1.9) (Table 1) and methyl 3,5-dioxo-4-(1-(2-propenyl)oxyimino)butylbicyclo[4.2.0]octane-1-carboxylate (1.10). *
  • the compounds of this invention may be prepared from 3,5-dimeth oxybenzoic acid (2) by reduction with an alkali metal in liquid ammonia followed by addition of an appropriate electrophile (cf. Aust. J. Chem., 1981, 34, 675). (Reaction Scheme 1).
  • the 1-substituted 3,5-dimethoxy-2,5-cyclohexadiene-1-carboxylic acid derivatives of Formula (4) thus obtained may be converted to the ester derivatives of Formula (5) by standard literature methods.
  • the esters of Formula (5) may be prepared by reaction of compounds of Formula (4) with an alcohol in the presence of an acid.
  • esters of Formula (5) may be prepared by a three step method involving reduction of esters of 3,5-dimethoxybenzoic acid with an alkali metal in liquid ammonia followed by addition of an appropriate electrophile followed by treatment with aqueous acid (Reaction Scheme 2).
  • Reaction of compounds of Formula (5) with lithium diisopropyl amide provides the novel bicyclic derivatives of Formula (6), which afford the bicyclic 1,3-diketone derivatives of Formula (7) on treatment with aqueous acid.
  • the enol derivatives of Formula (7) may be acylated on oxygen and the enol ester intermediates thus obtained isomerized (Fries rearrangement) to give the novel C-acylated products of Formula (8).
  • the C-acylated derivatives may be reacted with O-substituted hydroxyl amines to afford derivatives of the general Formula (1) wherein R 1 is hydrogen.
  • Compounds of the invention of Formula (1) wherein R 1 is not hydrogen may be prepared by standard synthetic procedures.
  • compounds of the invention of Formula (1) wherein R 1 is an inorganic or organic 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. From such reactions a mixture of isomeric compounds of Formula (1) and Formula (1b) may be obtained. Esterification of the vinylogous acid in compounds of Formula (1) wherein R 1 is hydrogen provides further herbicidal and growth regulating derivatives; from such reactions a mixture of isomeric compounds of Formula (1) and Formula (1b) may also be obtained.
  • post-emergence application or to the soil before the emergence of the plant (pre-emergence application).
  • the compounds of Formula (1) may be used on their own to inhibit the growth of, severely damage, or kill plants but are preferably used in the form of a composition comprising a compound of the invention in admixture with an inert carrier comprising a solid or liquid diluent.
  • the invention provides plant growth inhibiting, plant damaging, or plant killing compositions comprising a compound of Formula (1) as hereinbefore defined and an inert carrier therefore.
  • compositions of the invention may comprise, in addition to one or more compounds of the invention, one or more compounds not of the invention but which possess biological activity.
  • the compounds of the invention are in general substantially more effective against monocotyledonous plants or grass species than against dicotyledonous plants or broad-leaved species.
  • the herbicidal use of the compounds of the invention alone may not be sufficient to protect a crop.
  • the invention provides a herbicidal composition
  • a herbicidal composition comprising a mixture of at least one herbicidal compound of Formula (1) as hereinbefore defined with at least one other herbicide.
  • Certain of the compounds of Formula (1) exhibit useful plant growth regulating activity. For example, while certain compounds of Formula (1) shown selective herbicidal activity against wild grasses in crops of cultivated plants, at some rates of application they exhibit plant growth regulating effects in said crops. Certain of the compounds of Formula (1)
  • (1) may be used for selective control of wild grass in graminaceous crops.
  • Plant growth regulating effects may be manifested in a number of ways. For example, suppression of apical dominance, stimulation auxiliary bud growth, stimulation of early flowering and seed formation, enhancement of flowering and increase in seed yield, stem thickening, stem shortening and tillering. Plant growth regualting effects shown by compounds of the invention include, for example, tillering and stem shortening in crops such as wheat and barley.
  • the invention provides a process for regulating the growth of a plant which process comprises applying to the plant, to the seed of the plant, or to the growth medium of the plant, an effective amount of a compound Formula (1), as hereinbefore defined.
  • the compounds of Formula (1) may be applied directly to the plant (post-emergence application) or to the seed or soil before the emergence of the plant (pre-emergence) application.
  • the compounds of Formula (1) may be used on their own to regulate the growth of plants but in general are preferably used in the form of a composition comprising a compound of the invention in admixture with a carrier comprising a solid or liquid diluent.
  • the invention provides plant growth regulating compositions comprising a compound of Formula (1) as hereinbefore defined and an inert carrier therefor.
  • compositions of the present invention may be in the form of solids, liquids or pastes.
  • the compositions include both dilute compositions which are ready for immediate use and concentrated compositions which may require dilution before use. Therefore, the concentration of the active ingredient in the compositions of the present invention will vary depending on the type of formulation and whether the composition is ready for use such as, for example, a dust formulation or an aqueous emulsion or whether the composition is a concentrate such as, for example, an emulsifiable concentrate or a wettable powder, which is suitable for dilution before use.
  • the present invention includes both types of composition, accordingly the compositions to the present invention comprise from 1ppm to 99% by weight of active ingredient.
  • the solid compositions may be in the form of powders, dusts, pellets, grains, and granules wherein the active ingredient is mixed with a solid diluent.
  • Powders and dusts may be prepared by mixing or grinding the active ingredient with a solid carrier to give a finely divided composition.
  • Granules, grains and pellets may be prepared by bonding the active ingredient to a solid carrier, for example, by coating or impregnating the preformed granular solid carrier with the active ingredient or by agglomeration techniques.
  • solid carriers include: mineral earths and clays such as, for example, kaolin, betonite, kieselguhr, Fuller's earth, Attaclay, diatomaceous earth, talc, chalk, dolomite, limestone, lime, calcium carbonate, powdered magnesia, magnesium oxide, magnesium sulfate, gypsum, calcium sulfate, pyrophllite, silicic acid, silicates and silica gels; fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate and urea; natural products of vegetable origin such as, for example, grain meals and flours, bark meals, wood meals, nutshell meals and cellulosic powders; and synthetic polymeric materials such as, for example, ground or powdered plastics and resins.
  • mineral earths and clays such as, for example, kaolin, betonite, kieselguhr, Fuller's earth, Attaclay, di
  • the solid compositions may be in the form of dispersible or wettable dusts, powders, granules or grains wherein the active ingredient and the solid carrier are combined with one or more surface active agents which act as wetting, emulsifying and/or dispersing agents to facilitate the dispersion of the active ingredient in liquid.
  • surface active agents include those of the cationic, anionic and non-ionic type.
  • Cationic surface active agents include quaternary ammonium compounds, for example, the long chain alkyl ammonium salts such as cetyltrimethylammonium bromide.
  • Anionic surface active agents include: soaps or the alkali metal, alkaline earth metal and ammonium salts of fatty acids; the alkali metal, alkaline earth metal and ammonium salts of aryl sulfonic acids including the salts of naphthalenesulfonic acids such as butyl naphtha!
  • enesulfonic acid the di- and tri-isopropylnaphthalenesulfonic acids
  • the salts of the condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde the salts of the condensation products of sulfonated naphthalene and naphthalene derivatives with phenol and formaldehyde
  • the salts of alkyl aryl benzenesulfonic acids such as dodecylbanzenesulfonic acid
  • the alkali metal, alkaline earth metal and ammonium salts of the long chain mono esters of sulfuric acid or alkylsulfates such as lauryl sulfate and the mono esters of sulfuric acid with fatty alcohol glycol ethers.
  • Nonionic surface active agents include: the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol; the condensation products of ethylene oxide with phenols and alkylphenols such as isooctyl phenol, octylphenol and nonylphenol; the condensation products of ethylene oxide with castor oil; the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitan monolaurate, and their condensation products with ethylene oxide; ethylene oxi de/propylene oxide block copolymers; lauryl alcohol polyglycol ether acetal; and the l eci thi ns.
  • the l iqui d composi tions may compri se a solution or di spersion of the acti ve i ngredient in a l i quid carrier optional ly contai ni ng one or more surface acti ve agents which act as wetti ng, emul si fyi ng and/or di spersi ng agents.
  • liquid carriers include: water; mineral oil fractions such as, for example, kerosene, solvent naphtha, petroleum, coal tar oils and aromatic hydrocarbons such as, for example, paraffin, cyclohexane, toluene, the xylenes, tetrahydronaphthalene and alkylated naphthalenes; alcohols such as, for example, methanol, ethanol, propanol, isopropanol, butanol, cyclohexanol and propylene glycol; ketones such as, for example, cyclohexanone and isophorone; and strongly polar organic solvents such as, for example, N,N-dimethylformamide, dimethyl sulfoxide,N-methyl pyrrolidone and sulfolane.
  • mineral oil fractions such as, for example, kerosene, solvent naphtha, petroleum, coal tar oils and aromatic hydrocarbons such as, for example, paraffin, cycl
  • a preferred liquid composition comprises an aqueous suspension, dispersion or emulsion of the active ingredient which is suitable for application by spraying, atomizing or watering.
  • aqueous compositions are generally prepared by mixing concentrated compositions with water.
  • Suitable concentrated compositions include emulsion concentrates, pastes, oil dispersions, aqueous suspensions and wettable powders.
  • the concentrates are usually required to withstand storage for prolonged periods and after such storage to be capable of dilution with water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • the concentrates conveniently contain from 20 to 99%, preferably 20 to 60%, by weight of active ingredient.
  • Emulsions or emulsifiable concentrates of the salts are conveniently prepared by dissolving the active ingredient in an organic solvent containing one or more surface active agents used in the formulation and the salts generated in situ by the use of the appropriate organic or inorganic base.
  • compositions of the invention will depend to a large extent on the type of composition used and the facilities available for its application.
  • Solid compositions may be applied by dusting or any other suitable means for broadcasting or spreading the solid.
  • Liquid compositions may be applied by spraying, atomizing, watering, introduction into the irrigation water, or any other suitable means for broadcasting or spreading the liquid.
  • the rate of application of the compounds of the invention will depend on a number of factors including, for example, the compound chosen for use, the identity of the plants whose growth is to be inhibited, the formulations selected for use and whether the compound is to be applied for foliage or root uptake. As a general guide, however, an application rate of from 0.005 to 20 kilograms per hectare is suitable while from 0.01 to 5.0 kilograms per hectare may be preferred.
  • Methyl 3,5-Dioxobicyclo[4.2.0]octane-1-carboxylate was obtained from the hydrolysis of (6.5).
  • Methyl 5,7-Dioxo-6-propionyl-1,2,3,4,5,6,7,7a-octahydro-3aH-indene-3a-carboxylate (8.4) was obtained as an oil from the reaction of (7.1) with propanoic anhydride.
  • Methyl 5,7-Dioxo-6-(1-ethoxyimino)butyl-2-methyl-1,2,3,4,5,6,7,7a-octahydro-3aH-indene-3a-carboxylate (1.6) was obtained as a yellow oil from the reaction of (8.3) with O-ethylhydroxylamine hydrochloride.
  • the post-emergence herbicidal activities of the compounds (1.1-1.10) of the invention were assessed by the following procedure.
  • the pre-emergence herbicidal activities of the compounds of the invention were assessed by the following procedure.
  • test species used are as described in Example 5.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention décrit des composés représentés par la formule (1a), (1b) ou (1c) ou des formes isomères ou tautomères de ces composés; où W représente l'hydrogène ou l'un des groupes (alpha) et (beta); R1, R2, R3, R4, R et R'' représentent divers substituents; et n est égal à 1, 2, 3, 4 ou 5; ainsi que des compositions herbicides et des procédés mettant en oeuvre de tels composés.
PCT/AU1989/000237 1988-05-31 1989-05-29 Derives de 1,3-dicetones bicycliques a action herbicide WO1989012041A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPI8532 1988-05-31
AUPI853288 1988-05-31

Publications (1)

Publication Number Publication Date
WO1989012041A1 true WO1989012041A1 (fr) 1989-12-14

Family

ID=3773119

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1989/000237 WO1989012041A1 (fr) 1988-05-31 1989-05-29 Derives de 1,3-dicetones bicycliques a action herbicide

Country Status (2)

Country Link
EP (1) EP0422040A4 (fr)
WO (1) WO1989012041A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7182974A (en) * 1973-08-15 1975-09-04 Nippon Soda Co., Ltd. Cyclohexane derivatives
GB1455200A (en) * 1973-12-24 1976-11-10 Nippon Soda Co 2-hydroxyliminoalkyl-2-cyclohexene-1-one derivatives
EP0126713A2 (fr) * 1983-05-18 1984-11-28 Ciba-Geigy Ag Dérivés de l'acide cyclohexanedione-carboxylique ayant une activité herbicide et une activité régulatrice de la croissance des plantes
EP0219343A2 (fr) * 1985-10-14 1987-04-22 Dunlena Pty. Limited Dérivés de cyclohexane-1,3-dione à activité herbicide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7182974A (en) * 1973-08-15 1975-09-04 Nippon Soda Co., Ltd. Cyclohexane derivatives
GB1461170A (en) * 1973-08-15 1977-01-13 Nippon Soda Co Substituted cyclohexane-1,3-dione derivatives
GB1455200A (en) * 1973-12-24 1976-11-10 Nippon Soda Co 2-hydroxyliminoalkyl-2-cyclohexene-1-one derivatives
EP0126713A2 (fr) * 1983-05-18 1984-11-28 Ciba-Geigy Ag Dérivés de l'acide cyclohexanedione-carboxylique ayant une activité herbicide et une activité régulatrice de la croissance des plantes
EP0219343A2 (fr) * 1985-10-14 1987-04-22 Dunlena Pty. Limited Dérivés de cyclohexane-1,3-dione à activité herbicide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 85, No. 24, issued 1976, July 5 (Columbus, Ohio, U.S.A.) SAWAKI, MIKIO et al. "2-Cyclohexen-1-one Derivatives" see page 481, column 1, the Abstract No. 176958n *
See also references of EP0422040A4 *

Also Published As

Publication number Publication date
EP0422040A1 (fr) 1991-04-17
EP0422040A4 (en) 1991-08-07

Similar Documents

Publication Publication Date Title
US4440566A (en) Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones
US5089046A (en) Aryl and heteroaryl diones
PL140539B1 (en) Plant growth controlling herbicide and method of obtaining novel derivatives of cyclohexanodionocarboxylic acid
US5468878A (en) Cyclohexanedione derivatives
EP0066195B1 (fr) Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour combattre la croissance indésirable de plantes
EP0136647B1 (fr) Dérivés de cyclohexénone, leur procédé de préparation et leur utilisation pour lutter contre la croissance de plantes non désirées
EP0107156B1 (fr) Dérivés de la cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour lutter contre la croissance végétale indésirable
EP0218233B1 (fr) Dérivés de cyclohexénones, leur procédé de préparation et leur utilisation pour combattre la croissance des plantes indésirables
HU212476B (en) Herbicidal compositions containing cyclohexenone-oxymethers, process for preparation of active ingredients and method for combating weeds
EP0103143A2 (fr) Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour lutter contre la croissance des plantes indésirables
EP0135838B1 (fr) 3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
EP0137174B1 (fr) Dérivés de cyclohexane-1,3-dione, procédé de leur préparation et leur utilisation pour combattre les mauvaises herbes
EP0131875B1 (fr) Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur usage pour combattre la croissance de plantes indésirables
EP0088299B1 (fr) Dérivés du cyclohexane 1,3-dione procédé de préparation et utilisation dans la lutte contre les mauvaises herbes
US5131945A (en) Certain glyoxyl-cyclohexendiones as herbicides
EP0225290B1 (fr) Epoxydes herbicides
WO1989012041A1 (fr) Derives de 1,3-dicetones bicycliques a action herbicide
US4606753A (en) 4-substituted-2-oxabicyclo[2.2.1]heptane ether herbicides
HU212605B (en) Selective herbicidal compositions containing salicylic acid derivatives, process for producing the active ingredient and method for weed control
US4309566A (en) Plant regulator
US4588821A (en) 2-oxabicyclo[2.2.1]heptan-6-ol ether herbicides
US4939278A (en) Herbicidal pyrones
US5086187A (en) Herbicidal pyrones
EP0219343A2 (fr) Dérivés de cyclohexane-1,3-dione à activité herbicide
USRE32489E (en) Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR GB IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1989906690

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1989906690

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1989906690

Country of ref document: EP