EP0573460A4 - HERBICIDE PYRONES. - Google Patents

HERBICIDE PYRONES.

Info

Publication number
EP0573460A4
EP0573460A4 EP19920904717 EP92904717A EP0573460A4 EP 0573460 A4 EP0573460 A4 EP 0573460A4 EP 19920904717 EP19920904717 EP 19920904717 EP 92904717 A EP92904717 A EP 92904717A EP 0573460 A4 EP0573460 A4 EP 0573460A4
Authority
EP
European Patent Office
Prior art keywords
alkyl
optionally substituted
phenyl
compounds
group
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP19920904717
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0573460A1 (en
Inventor
Andris Juris Liepa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dunlena Pty Ltd
Original Assignee
Dunlena Pty Ltd
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 Ltd filed Critical Dunlena Pty Ltd
Publication of EP0573460A1 publication Critical patent/EP0573460A1/en
Publication of EP0573460A4 publication Critical patent/EP0573460A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems

Definitions

  • the present invention relates to organic compounds having herbicidal properties a plant growth regulating properties; to herbicidal compositions and processes utilisin such compounds and to plant growth regulating compositions and processes utilisin such compositions.
  • R is substituted phenyl
  • R 1 is H, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfonyl, alkoxy, all ylthio, acyl, (un)substituted phenylalkyl or PhS0 2
  • R 2 is alkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or (un)substituted phenylalkyl
  • R 3 is alkyl, fluoroalkyl, alkenyl, alkynyl, or phenyl.
  • Watson et al teach that tetrahydropyran-2,4-dione derivatives which are substituted the 6-position with a substituted phenyl group exhibit particularly useful herbicidal activity.
  • R 1 is lower alkyl
  • R 2 is lower alkyl, lower alkenyl or lower alkynyl
  • R 3 is H or lower alkyl
  • R 4 is lower alkyl or phenyl
  • R 3 forms cycloalkylene of 4 to 5 carbon atoms by combining with R 4 ;
  • R 5 and R 7 are selected from the group consisting of H and lower alkyl; R 6 is lower alkyl;
  • R 8 is H or lower alkyl; and R 9 is lower alkyl.
  • the above compounds are substituted in the 5 and/ or 6- positions of the pyran rin by one or two alkyl groups
  • R ! is H
  • R 2 is substituted alkyl wherein the alkyl group is substituted by optionally substitute phenyl and optionally substituted heterocycle;
  • R 3 is alkyl
  • R 4 and R 5 together with the carbon to which they are attached form a substituted o unsubstituted saturated or partially saturated heterocyclic or carbocyclic ring containing 3 or more ring atoms; etc.
  • the last mentioned spirocyclic analogues are stated as being a preferred subgenus.
  • Further preferred are compounds in which R 1 is H, R 2 is alkyl, alkenyl or haloalke (specifically ethyl, allyl, 2-chloroallyl and 3-chloroallyI) and R 3 is ethyl or n-propyi.
  • WO 8800945 at Tables 1-4 lists 91 individual spirocyclic compounds, all with R 2 as ethyl, allyl or chloroallyl only.
  • the compounds of the invention are substantially more effective against monocotyledonous plants or grass species than against dicotyledonous plants or broad-leaved species.
  • certain of the compounds show selective herbicidal activity against wild grasses in monocotyledonous crop species and hence may be used for selective control of wild grass in graminaceous crops
  • the application emphasises th use of the disclosed compounds for control of grass weeds in broadleaf crops witho damage to the broadleaf crop.
  • PCT/AU89/00191 also in the name of the present applicants, describes herbicidal pyrones that are similar to those described in WO8800945, but which have an additional substituent, R 6 , on the pyrone ring.
  • the compounds described in PCT7AU89/00191 are of the general formula:
  • substituted groups R 1 to R 5 are similar to those described in WO 8800945, and, R 6 is selected from alkyl, alkoxy, alkylthio, halogen or substituted alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio or halogen.
  • Preferred values for the oxime capping group R 2 are alkyl, alkenyl, alkynyl and haloalkenyi; specifically preferred are ethyl, propargyl, allyl, 2-chloroallyl and 3-chloroallyl.
  • PCT/AU89/00191 includes 15 examples relating to spirocyclic derivatives, but the oxime capping groups shown are restricted to ethyl, allyl or chloro allyl.
  • R 7 , R 8 and R 9 are independentiy H, halogen, C C 4 alkyl, C , alkoxy, C alkylthio, C : -C 4 alkylsulfinyl, C -C 4 alkylsulfonyl,
  • C j -Q haloalkyl, C C 4 haloalkoxy, nitro, cyano, C j -C 4 alkoxycarbonyl, C C ⁇ alkylaminocarbonyl, C-,-C 6 dialkylaminocarbonyl, aminocarbonyl, phenyl, amino, - alkylamino, or C ⁇ -Cg dialkylamino.
  • R 2 includes a phenyl group itself substituted with an optionally substituted phenyl group which is linked either directly or via a small group, for example by a methylene, oxy or thio bridge, are highly active and more selective pre-emergent and/or post-emergent herbicides or plant growth regulators which are particularly useful for controlling certain grass weeds in dryland and paddy rice. Accordingly, the invention provides a compound of Formula (1):
  • A is a C alkylene or C Q alkenylene group optionally substituted with 1-4 CfQ alkyl substituents;
  • X is O, S, SO, S0 2 , NR 10 or a single bond
  • R 1 is H, Q-Q alkyl, Q-C 4 alkenyl, Q-Q alkynyl, Q-Q cycloalkyl, Q-Q cycloalkenyl, Q-Q alkylcarbonyl, phenylcarbonyl, phenyl optionally substitut with 1-3 substituents selected from the group consisting of halogen, Q-C 4 alk
  • R 2 is Q-Q alkyl, Q-Q alkenyl, Q-Q alkynyl, Q-Q haloalkyl, Q- Q alkylthio, Q cycloalkyl, Q-Q cycloalkenyl, phenyl optionally substituted with 1-3 substituents selected from the group consisting of halogen, Q-Q alkyl, Q- alkylthio, nitro, cyano, Q-Q haloalkyl, amino, and Cf Q haloalkoxy, Q-Q alkoxyalkyl, Q-Q alkylthioalkyl, or Q-Q alkyl substituted with a substituent selected from the group consisting of phenyl, phenoxy and thiophenoxy where the aromatic ring of said substituents may be substituted with 1-3 substituents selected from halogen, Q-Q alkyl, Q-Q alkoxy, Q-Q alkylthio, nitro, cyano, amino, Cf Q
  • R 3 and R 4 are independently H or Q-Q alkyl
  • R 5 and R 6 are independently H, Cf Q alkyl, Q-Q alkenyl, Q-Q alkylthioalkyl, Q-Q haloalkyl, Q-Q haloalkenyi or Q-Q cycloalkyl wherein the alkyl, alkenyl and cycloalkyl groups are optionally substituted with 1-3 substituents selected from the group consisting of OR 12 , NR 13 R 14 , NR 15 C(0)(Q-Q alkyl), NR 18 S0 2 Q-Q alkyl), NR 21 C(0)(Q- Q alkyl), C(OR 16 )(OR 17 )R 22 , C(SR 19 )(SR 20 )R 23 , Cf Q alkoxycarbonyl and phenyl which may be substituted with a substituent selected from halogen, Cf Q alkyl, Q-Q alkoxy, Cf Q alkylthio, nitro, cyano, Q- Q haloalkyl and Q
  • R 7 , R* and R 9 are independentiy H, halogen, Q-Q alkyl, Q-Q alkoxy, Q-Q alkylthio, Cf Q alkylsulfinyl, Cf Q alkylsulfonyl, Cf Q haloalkyl, Cf Q haloalkoxy, nitro, cyano, Cf Q alkoxycarbonyl, Q- Q alkylaminocarbonyl, Q"Q dialkylaminocarbonyl, aminocarbonyl; amino; Cf Q alkylamino, Q-Q alkylamino; or benzenesulfonyl, benzoyl, benzyl, benzyloxy, pyridyl, phenoxy, phenylthio, phenylamino or phenyl group said group optionally substituted wit 1-3 substituents selected from the group consisting of halogen, Q-Q alkyl, Cf C 4 alkoxy, and CF
  • ⁇ o is H, Cf C 4 alkyl or phenyl optionally substituted with 1-3 substituents select from the group consisting of halogen, Q-Q alkyl, Q- Q alkoxy, Cf Q alkylt Q-Q haloalkyl and Cf Q haloalkoxy;
  • M is Li + , Na + , K + , NH 4 ⁇ or N(R ⁇ ) 4 + where R 11 is Q-Q alkyl;
  • R is H, Q-Q alkyl, C(0)(Q- Q alkyl)or C0 2 (Q- Q alkyl);
  • R 13 , R 15 , R 18 , R 21 , R 22 and R 23 are independentiy H or CfQ alkyl
  • R 14 , R 16 , R 17 , R 19 and R 20 are independentiy CfQ alkyl
  • R 16 and R 17 taken together may be -(CH** ⁇ - or -(CH ⁇ -; and R 19 and R 20 taken together may be -(CH 2 ) 2 - or -(CH 2 ) 3 -.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl”, denotes straight chain or branched alkyl, e.g. meth 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”, denote fluorine, chlorine, bromine or iodine. Further, when used in compound words such "haloalkyl” said alkyl may be partially halogenated or fully substituted with halogen atoms which may be the same or different. Examples of haloalkyl include CH 2 CH 2 CF 2 CF 3 and CH 2 CHFC1.
  • Alkylcarbonyl denotes acetyl, propionyl, and the different butyryl isomers.
  • Alkoxycarbonyl denotes methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, and the different butoxycarbonyl isomers.
  • the total number of carbon atoms in a substituent group is indicated by the Ci-Cj prefix where i and j are numbers from 1 to 10.
  • Q-Q alkylthioalkyl would designate -CH j SCH ⁇ -CH- j SQH., - ⁇ CH- j S ⁇ or -CH(CH 3 )SCH 3
  • Q- alkoxyalkyl would represent -CH 2 OCH 3 through to -(CH 2 ) 4 ⁇ CH 3 or -CH 2 0(CH 2 ) 3 C and the various structural isomers embraced therein.
  • R 1 is hydrogen the compounds of the invention may undergo tautomerisation. All tautomeric forms are included in the scope of thi invention.
  • Preferred groups of compounds of general Formula (1) for reasons including ease synthesis and greater herbicidal efficacy, include the following:
  • R 2 is Q-Q alkyl, Q-Q haloalkyl, Q-Q alkenyl or Q-Q alkynyl .
  • A is CfQ alkylene or Q-Q alkenylene optionally substituted with CH 3 or QH 5 ;
  • R 7 , R 8 and R 9 are independently H, CI, Br, F, CfQ alkyl, CfQ alkoxy, Cf alkylthio, Cf Q haloalkyl, CfQ haloalkoxy, nitro, cyano or CfQ alkoxycarbonyl; or benzenesulfonyl, benzoyl, benzyl, benzyloxy, phenoxy, phenyl, phenylthio or phenylamino optionally substituted with 1-3 substituent selected from the group consisting of halogen, Q- Q alkyl, Q- Q alkoxy, or
  • R 7 , R 8 , or R 9 is an optionally substituted benzenesulfonyl, benzoyl, benzyl, benzyloxy, phenoxy, phenyl, phenylthio or phenylamino group;
  • R 10 is H or CH
  • NHPh or N(Me)Ph provided that at least one of R 7 , R 8 , or R 9 is an optionally substituted benzenesulfonyl, benzoyl, benzyl, benzyloxy, phenoxy, phenyl, phenylthio or phenylamino group.
  • R 5 and R 6 are independently Q- Q alkyl, Q-Q alkenyl, Q-Q alkynyl, Cf Q alkylthio or Q-Q alkylthioalkyl.
  • R 1 is H, Li + , Na+ or K+;
  • R 2 is CH 3 , QH 5 , n-QH 7 or n-QH 9 ;
  • R 3 and R 4 are independentiy H or CH 3 ; and
  • R 7 , R 8 and R 9 are independentiy H, CI, Br, F, CH 3 , QH 5 , OCH 3 , OQH 5 , SCH 3 , SQH 5 , CF 3 , CHF Z CF 2 CF 3 , OCHF OCF 3 , OCH 2 CF 3 ,
  • R 7 , R 8 , or R 9 is an optionally substituted benzenesulfonyl, benzoyl, benzyl, benzyloxy, phenoxy, phenyl, phenylthio or phenylamino group.
  • R 3 and R 4 are independently H, CH 3 or QH 5 ; and R 7 , R 8 and R 9 are independentiy H, CI, Br, F, CH 3 , QH 5 , OCH 3 , OQH 5 , SCH 3 , SQH 5 , CF 3 , CHF CF 2 CF 3 , OCHF OCF 3 , OCH 2 CF 3 , NO CN, CO,CH 3 , Ph, S0 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph provided that at least one of R 7 , R 8 , or R 9 is an optionally substituted benzenesulfonyl, benzoyl, benzyl, benzyloxy, phenoxy, phenyl, phenylthio or phenylamino group.
  • the compounds of the invention may be prepared by a method similar to that disclosed in WO8800945, with appropriate alteration of starting reagents.
  • the compounds of the invention may be prepared from the dianion of an acetoacetate ester by condensation with an appropriate ketone(cf. Hukin,S.N., and Weller, L. Can J Chem, 1974, 52, 2157) followed by cyclization with or without intermediate hydrolysis to novel tetrahydro-2H.-pyran-2,4-diones.
  • the pyrandiones their tautomeric 4-hydroxy-5,6-dihydro-2H.-pyran-2-one equivalents can also be obtained by customary methods described in the literature.
  • the 6,6-disubstituted pyran-2,4-diones thus obtained may be acylated on oxygen and the enol esters isomerized (Fries rearrangement) to give novel C-substituted products.
  • C-acylated derivatives may be reacted with O-substituted hydroxylamines which ma in turn be generated in situ from appropriate precursors, to afford derivatives of th general Formula(l) wherein R 1 is hydrogen.
  • Compounds of the invention of Formula(l) wherein R 1 is not hydrogen may be prepared by standard synthetic procedures.
  • compounds of the inventi of Formula(l) wherein R 1 is is an organic or inorganic cation may be prepared fro compounds of the invention of Formula(l) wherein R 1 is hydrogen by reacting these latter compounds with an appropriate inorganic or organic base.
  • T ether extracts were washed with water (50 ml); and the combined aqueous phases were acidified to pH 1-2 with cone, hydrochloric acid and extracted with ether (100 ml). (At this stage of some reactions a first crop of the pyrandione crystallized from the ether solution and was recovered by filtration.) The ether solution was then evaporated and the residual water removed from the product mixture by azeotropic distillation with ethanol/be zene and then with benzene. The residue was either chromatographed (Si0 2 , dichloromethane) or, in some instances, crystallization of t pyrandione was achieved by diluting a concentrated benzene solution (ca.
  • 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 pla growth.
  • Rates of application for compounds of this invention are determined by a number o factors. These factors include formulation selection, method of application, amount vegetation present, growing conditions, etc. In general, the subject compounds shoul be applied at rates of 0.05 to 10 kg/ha with a preferred rate range of 0.1 to 2 kg/h One skilled in the art can easily determine application rates necessary for the desir level of weed control.
  • the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound Formula (1) as hereinbefore defined with at least one other herbicide.
  • the invention provides a met-hod for regulating t 5 growth of a plant comprising applying to the plant, to the seed of the plant, or to growth medium of the plant an effective amount of a compound of Formula (1) a hereinbefore defined.
  • Rates of application of these compounds can be influenced by many factors of the 10 environment and should be determined under actual use conditions.
  • Weed grasse graminaceous crops can normally be killed when treated at a rate of from less tha 0.1 to about 20 kg active ingredient/ha.
  • the compounds of this invention can be mixed with fungicides, bactericides, 15 acaricides, nematicides, insecticides, or other biologically active compounds in orde to achieve desired results with a minimum expenditure of time, effort and material. 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. ft, 0
  • 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 thes may be applied directly. Sprayable formulations can be extended in suitable medi 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 ingredients(s) and at least one of (a) about 0.1% to 20% surfactants(s) and about 5% to 99% solid or liquid inert diluent(s). More specifically, they will conta these ingredients in the following approximate proportions:
  • compositions may be in the form of dusting powders or granules comprisi the active ingredient and a solid diluent or carrier therefor, for example, kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fulle earth, gypsum, Hewitt's earth, diatomaceous earth, and China clay.
  • the compositi may also be in the form of dispersible powders or grains comprising a wetting age to facilitate the dispersion in liquids of the powder or grains which may contain al solid diluents, fillers and suspending agents.
  • compositions for dressing seed may contain an agent (for example a mineral oil) for assisting the adhesi of the composition to the seed.
  • 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 trichloroethylene amongst others. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0 °C.
  • 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 ar prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granul and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
EP19920904717 1991-02-15 1992-02-14 HERBICIDE PYRONES. Withdrawn EP0573460A4 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AUPK462091 1991-02-15
AU4620/91 1991-02-15
AU9973/91 1991-12-11
AUPK997391 1991-12-11

Publications (2)

Publication Number Publication Date
EP0573460A1 EP0573460A1 (en) 1993-12-15
EP0573460A4 true EP0573460A4 (en) 1994-03-17

Family

ID=25644004

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920904717 Withdrawn EP0573460A4 (en) 1991-02-15 1992-02-14 HERBICIDE PYRONES.

Country Status (7)

Country Link
EP (1) EP0573460A4 (cs)
JP (1) JPH06505240A (cs)
CN (1) CN1065660A (cs)
BR (1) BR9205641A (cs)
PT (1) PT100129A (cs)
TW (1) TW221430B (cs)
WO (1) WO1992014736A1 (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19716591A1 (de) * 1996-08-05 1998-03-05 Bayer Ag 2- und 2,5-substituierte Phenylketoenole

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3560789A (en) * 1988-05-04 1989-11-29 Dunlena Pty. Limited Selective pyrone herbicides
AU7161391A (en) * 1990-01-22 1991-08-05 Dunlena Pty. Limited Herbicidal pyrones

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No further relevant documents disclosed *
See also references of WO9214736A1 *

Also Published As

Publication number Publication date
TW221430B (cs) 1994-03-01
PT100129A (pt) 1993-08-31
EP0573460A1 (en) 1993-12-15
CN1065660A (zh) 1992-10-28
JPH06505240A (ja) 1994-06-16
BR9205641A (pt) 1994-06-07
WO1992014736A1 (en) 1992-09-03

Similar Documents

Publication Publication Date Title
US4744815A (en) 4-benzoyl-1-alkyl (alkenyl) - pyrazoles, composition containing them, herbicidal method of using them, and intermediate in their preparation
US5089046A (en) Aryl and heteroaryl diones
AU2001286294B2 (en) Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives
US4640706A (en) Cyclohexenonecarboxylic acid derivatives with herbicidal and plant growth regulating properties
US4432786A (en) Thienylmethoxyiminoalkyl cyclohexanedione herbicides
US5006150A (en) Substituted heterocyclohexane-3,5-diones
KR940011137B1 (ko) 시클로헥산 제초제
DK153835B (da) Cyclohexan-1,3-dion-derivater, herbicid og fremgangsmaade til bekaempelse af uoenskede planter
EP0573460A4 (en) HERBICIDE PYRONES.
KR0172959B1 (ko) 시클로헥세논 옥심에테르, 이들의 제조 및 제초제로서의 이들의 용도
US4758262A (en) Herbicidal propylene oxide derivatives
US6239076B1 (en) Herbicidal 2-(5-isoxazolinyl methyloxyphenyl)-4,5,6,7-tetrahydro -2H-indazole derivatives
KR950003497B1 (ko) 제초성 시클로헥산-1,3-디온 유도체와 그 제조방법
AU1266892A (en) Herbicidal pyrones
US5399542A (en) Substituted benzoxazinone cyclohexanediones and their herbicidal uses
WO1993010081A1 (en) Herbicidal 2(substituted oxime)-cyclohexan-1,3-dione derivatives
AU7161391A (en) Herbicidal pyrones
WO1991010658A1 (en) Herbicidal pyrones
JPH01500433A (ja) 除草性ピロン類
GB2140803A (en) Herbicidal tetrahydropyran-2,4-dione derivatives
US6096930A (en) Herbicidal cyclohexane-1,3-dione derivatives and their preparation process
EP0497453A1 (en) Herbicidal bicyclic ethers
EP0252629A1 (en) Herbicidal cyclohexane-1,3-dione derivatives
US4032323A (en) Isothiazole derivatives
HU182561B (en) Herbicide compositions containing 2-phenyl-5,6-dihydro-4-pyron derivatives and process for producing the active agents

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19930915

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): ES IT

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19940611