[go: up one dir, main page]

WO1991004969A1 - Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them - Google Patents

Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them Download PDF

Info

Publication number
WO1991004969A1
WO1991004969A1 PCT/EP1990/001647 EP9001647W WO9104969A1 WO 1991004969 A1 WO1991004969 A1 WO 1991004969A1 EP 9001647 W EP9001647 W EP 9001647W WO 9104969 A1 WO9104969 A1 WO 9104969A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
alkyl
group
chr
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.)
Ceased
Application number
PCT/EP1990/001647
Other languages
German (de)
French (fr)
Inventor
Rainer SCHÜTZE
Lothar Willms
Klaus Bauer
Hermann Bieringer
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of WO1991004969A1 publication Critical patent/WO1991004969A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • X independently of one another halogen, haloalkyl, CN or NO 2 ,
  • Z is hydrogen or halogen
  • n 0, 1, 2, 3 or 4
  • R 1 independently of one another is hydrogen or C 1 -C 4 alkyl, m 1, 2, 3 or 4,
  • W is a divalent group of the formula -O-, -CO-S- or -CO-O-, R 2 is a group of the formula
  • -CH 2 CH CHR 3 , -CH 2 C ⁇ CR 3 , -CH 2 - Si (R 4 ) (R 5 ) (R 6 ) or
  • -N CR 7 R 8 or tetrahydropyranylmethyl
  • Radicals are unsubstituted or substituted in the ring by C 1 -C 4 alkyl
  • R 3 is hydrogen, C 1 -C 4 alkyl or optionally
  • R 4 , R 5 and R 6 independently of one another are C 1 -C 4 alkyl or phenyl
  • R 7 and R 8 either independently of one another are hydrogen or C 1 -C 4 alkyl or R 7 and R 8 together are C 3 -C 7 - Mean cycloalkyl
  • R 2 -N CR 7 R 8 and W means oxygen, the groups of
  • R 2 -CH 2 CH CHR 3 , -CH 2 C ⁇ CR 3 or tetrahydrofurfuryl
  • EP-A-0 052 798 (GB-A-2 087 890) and EP-A-0 008 624
  • Q is a group of the formulas Q 1 , Q 2 , Q 3 or Q 4 , wherein
  • X halogen in particular fluorine or chlorine, or
  • n 1 or 2
  • R 1 is hydrogen and m is 1 to 4 or
  • R 1 is methyl or ethyl and m 1, W - O- or - CO- O-,
  • R 2 has the meaning given above
  • R 3 is hydrogen
  • R 4 , R 5 , R 6 are each methyl
  • R 7 and R 8 are each methyl or together cyclopentyl or
  • Halogen means fluorine, chlorine, bromine or iodine and preferably represents fluorine, chlorine or bromine.
  • Haloalkyl preferably represents C 1 -C 4 alkyl which is substituted one or more times by halogen, in particular for
  • Substituted phenyl preferably means phenyl which is substituted by one or more radicals from the group C 1 -C 4 alkyl, halogen, haloalkyl, alkoxy,
  • Haloalkoxy or cyano is substituted.
  • Compounds of formula (I) have at least one
  • racemates can be separated into enantiomers by customary methods. However, it is also also possible to directly isolate the pure enantiomers using optically active starting materials,
  • the compounds of formula (I) include both the possible diastereomers, enantiomers, racemates and mixtures thereof. In particular, they include the compounds in the D form in the propionic acid part in the
  • the invention also relates to a method for
  • a a suitable leaving group preferably Cl or Br
  • reaction of the compounds (II) and (III) according to variant a) is preferably carried out in inert aprotic
  • Solvents such as aliphatic or aromatic
  • Hydrocarbons e.g. toluene / xylene
  • acetonitrile e.g. toluene / xylene
  • reaction of the compound (IV) according to variant b) is preferably carried out in inert aliphatic or aromatic hydrocarbons, in particular halogenated hydrocarbons (for example CH 2 Cl 2 , CHCI 3 , CCl 4 ), or ethers (dioxane,
  • the reaction of the heteroaryloxyphenoxypropionic acids (IV) with the alcohols ROH is preferably carried out in inert aliphatic or aromatic solvents.
  • reaction of the compounds of the formulas (II) and (V) according to variant e) can be carried out analogously under the reaction conditions of variant a); likewise the reaction of the intermediate obtained with the
  • Formula (II), as defined by Q stands for substituted 2-haloquinolines, 2-halopyridines, 2-halobenzoxazoles and 2-haloquinoxalines, which are known or analogous
  • Carboxylic acid derivatives with leaving group A are transferred.
  • the compounds of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous harmful plants, the activity generally being higher in the particular D-form of the compounds than in the racemate and
  • the L-form has little or no herbicidal activity.
  • Connections can be checked without being limited to certain types by the name.
  • crops of economically important crops such as wheat, barley, rye, rice, maize, sugar beet, cotton and soybeans are only marginally or not harmed at all.
  • the present compounds are very well suited for the selective control of undesired plant growth in agricultural
  • the compounds of formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. As
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW Emulsions
  • Emulsions oil or water-based dispersions (SC)
  • Microcapsules or waxes are Microcapsules or waxes.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are
  • Spray powders are evenly dispersible in water
  • Preparations containing the active ingredient in addition to a dilution or inert. toff still wetting agents, e.g. polyoxyethylated
  • Alkylphenols polyoxethylated fatty alcohols and fatty amines, alkane or alkylbenzenesulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid
  • alkane or alkylbenzenesulfonates and dispersants e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid
  • Emulsifiable concentrates are made by dissolving the
  • Active ingredient in an organic solvent e.g.
  • Alkylarylsulfonic acid calcium salts such as
  • fatty acid polyglycol esters such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Sorbitan fatty acid esters polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural
  • Clays such as kaolin, bentonite or pyrophyllite or diatomaceous earth.
  • water-dispersible granules can either by
  • Mineral oils on the surface of carriers such as sand, Kaolinite or granulated inert material. Suitable active ingredients can also be used in the production of
  • the agrochemical preparations usually contain
  • active ingredient of the formula (I) 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active ingredient of the formula (I).
  • concentrations of the active ingredients can depend on the type of formulation
  • the active substance concentration in wettable powders is e.g.
  • Concentrates can have the active ingredient concentration about 1 to
  • Dust-like formulations contain about 1 to 25% by weight, mostly 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight, preferably 2 to 20% by weight of active ingredient. at
  • the active ingredient content depends in part on whether the active compound is liquid or solid. In general, the content of the water-dispersible granules is between 10 and 90% by weight.
  • present formulations optionally diluted in a conventional manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, ground or scatter granules as well as sprayable solutions are used before use
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and in a hammer mill
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, and 10 parts by weight of lignosulfonic acid
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight.
  • An emulsifiable concentrate is obtained from 10 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexane as solvent and 10 parts by weight
  • e) A water-dispersible granulate is obtained by
  • Granules produced by conventional methods consist, for example, of
  • Block copolymer 40% EO content
  • organic phase twice more with 0.5 N hydrochloric acid and once with saturated sodium bicarbonate solution.
  • the organic phase is dried over magnesium sulfate and the
  • Crop tolerance was rated according to a key in which the effectiveness is expressed by value numbers from 0-5. Here means:
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in plastic pots in sandy loam soil, covered with soil and in the greenhouse under good conditions
  • Test plants were treated at the three-leaf stage three weeks after sowing.
  • the agents according to the invention also have good herbicidal activity against a broad spectrum in the after-emergence
  • Tubers and rhizomes or young plants or seeds of various rice weeds such as Cyperus species, Eleocharis, Scirpus and
  • Echinochlöa were in closed plastic pots in
  • the compounds according to the invention were poured into the backwater in the form of aqueous suspensions or emulsions, sprinkled into the water as granules or sprayed onto the green parts of the plants. Three weeks later, the herbicide
  • AVFA Avena fatua
  • ALMY Alopecurus myosurides
  • AVFA Avena fatua
  • ALMY Alopecurus myoisurides
  • ORSA Oryza sativa
  • ORSA Oryza sativa

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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to selective herbicides, preferably for combatting monocotyledonous weeds, of formula (I) Q-Y-(1,4-C6H4)-OCH(CH3)-CO-O-(CHR<1>)m-W-R<2>, where Y stands for O or S, Q stands for a group of the formulae Q<1>-Q<4>, where Q<1> stands for quinoline-2-yl, Q<2> stands for quinoxaline-2-yl and Q<3> stands for benzoxazole-2-yl, Q in each case being substituted by (X)n, as well as pyrid-2-yl which is substituted in the 3 position by X and otherwise by Z, and X stands for H, halogen, haloalkyl, CN, NO2, Z stands for H or halogen, n=1 to 4, R<1> stands for H or C1-C4 alkyl, m = 1 to 4, W stands for O, COS or COO, R<2> = CH2CH=XHR<3>, CH2C=CR<3>, CH2SiR<4>R<5>R<6>, -N=CR<7>R<8>, possibly alkyl-substituted tetrahydropyranylmethyl or -furfuryl, R<3> stands for H, C1-C4 alkyl, (subst.) phenyl, R<4>, R<5>, R<6> stand for C1-C4 alkyl or phenyl, R<7>, R<8> each stand for H or C1-C4 alkyl or together denote C3-C7 cycloalkyl, except that Q does not stand for Q<4>, if W=COO, and Q does not stand for Q<1>, Q<2>, if R<2>=-N=CR<7>R<8> and W=O, and Q does not stand for Q<3>, if R<2>=-CH2CH=CHR<3>, CH2C=CR<3> or tetrahydrofurfuryl and m=1-3 and W=COO.

Description

Beschreibung description

Herbizide heterocyclisch substituierte Herbicidal heterocyclically substituted

Phenoxyalkancarbonsäurederivate und Verfahren zu ihrer  Phenoxyalkanecarboxylic acid derivatives and process for their

Herstellung Manufacturing

Gegenstanc der Erfindung sind heterocyclisch substituierte Phenoxyalkancarbonsäurederivate der Formel (I) Contrary to the invention are heterocyclically substituted phenoxyalkane carboxylic acid derivatives of the formula (I)

Figure imgf000003_0001
Figure imgf000003_0001

worin wherein

Y 0 oder S,  Y 0 or S,

Q eine Gruppe der Formel  Q is a group of the formula

( Q1 ) , (Q 1 ),

(Q2), (Q 2 ),

( Q3 ) oder (Q 3 ) or

(Q4)(Q 4 )

Figure imgf000003_0002
worin
Figure imgf000003_0002
wherein

X unabhängig voneinander Halogen, Haloalkyl, CN oder NO2,X independently of one another halogen, haloalkyl, CN or NO 2 ,

Z Wasserstoff oder Halogen und Z is hydrogen or halogen and

n 0, 1, 2 , 3 oder 4 bedeuten, R1 unabhängig voneinander Wasserstoff oder C1-C4-Alkyl, m 1, 2, 3 oder 4, n is 0, 1, 2, 3 or 4, R 1 independently of one another is hydrogen or C 1 -C 4 alkyl, m 1, 2, 3 or 4,

W eine divalente Gruppe der Formel -O-, -CO-S- oder -CO-O-, R2 eine Gruppe der Formel W is a divalent group of the formula -O-, -CO-S- or -CO-O-, R 2 is a group of the formula

-CH2CH=CHR3, -CH2C≡CR3, -CH2- Si (R4) (R5) (R6) oder -CH 2 CH = CHR 3 , -CH 2 C≡CR 3 , -CH 2 - Si (R 4 ) (R 5 ) (R 6 ) or

-N=CR7R8 oder Tetrahydropyranylmethyl oder -N = CR 7 R 8 or tetrahydropyranylmethyl or

Tetrahydrofurfuryl, wobei die letztgenannten zwei  Tetrahydrofurfuryl, the latter two

Reste unsubstituiert oder im Ring durch C1-C4-Alkyl substituiert sind, Radicals are unsubstituted or substituted in the ring by C 1 -C 4 alkyl,

R3 Wasserstoff, C1-C4-Alkyl oder gegebenenfalls R 3 is hydrogen, C 1 -C 4 alkyl or optionally

substituiertes Phenyl,  substituted phenyl,

R4, R5 und R6 unabhängig voneinander C1-C4-Alkyl oder Phenyl, R7 und R8 entweder unabhängig voneinander Wasserstoff oder C1-C4-Alkyl oder R7 und R8 gemeinsam C3-C7-Cycloalkyl bedeuten, R 4 , R 5 and R 6 independently of one another are C 1 -C 4 alkyl or phenyl, R 7 and R 8 either independently of one another are hydrogen or C 1 -C 4 alkyl or R 7 and R 8 together are C 3 -C 7 - Mean cycloalkyl,

wobei für den Fall, daß  in the event that

W= -COO- bedeutet, die Gruppe der Formel Q4 ausgenommen W = -COO- means that the group of the formula Q 4 is excluded

ist und  is and

für den Fall, daß  in case that

R2 -N=CR7R8 und W Sauerstoff bedeutet, die Gruppen der R 2 -N = CR 7 R 8 and W means oxygen, the groups of

Formeln Q1 und Q2 ausgenommen sind und Formulas Q 1 and Q 2 are excluded and

für den Fall, daß  in case that

R2 -CH2CH=CHR3, -CH2C≡CR3 oder Tetrahydrofurfuryl, R 2 -CH 2 CH = CHR 3 , -CH 2 C≡CR 3 or tetrahydrofurfuryl,

m = 1 bis 3 und W = -CO-O- bedeuten, die Gruppe der  m = 1 to 3 and W = -CO-O- mean the group of

Formel Q3 ausgenommen ist. Formula Q 3 is excluded.

Partiell strukturverwandte Herbizide sind bereits aus Partially structurally related herbicides are already out

DE-A-29 14 300 (US-A-4, 482, 373 ), US-A-4 687 849, DE-A-29 14 300 (US-A-4, 482, 373), US-A-4 687 849,

EP-A-0 052 798 (GB-A-2 087 890) und EP-A-0 008 624 EP-A-0 052 798 (GB-A-2 087 890) and EP-A-0 008 624

(CA-A-1 114 382) bekannt. (CA-A-1 114 382).

Von besonderem Interesse sind erfindungsgemäße Verbindungen der Formel (I), worin Of particular interest are compounds of formula (I) according to the invention, wherein

Y Sauerstoff,  Y oxygen,

Q eine Gruppe der Formeln Q1, Q2, Q3 oder Q4, worin Q is a group of the formulas Q 1 , Q 2 , Q 3 or Q 4 , wherein

X Halogen, insbesondere Fluor oder Chlor, oder  X halogen, in particular fluorine or chlorine, or

Trifluormethyl,  Trifluoromethyl,

Z Halogen und Z halogen and

n 1 oder 2 bedeuten, n is 1 or 2,

R1 Wasserstoff und m 1 bis 4 oder R 1 is hydrogen and m is 1 to 4 or

R1 Methyl oder Ethyl und m 1, W - O- oder - CO- O- , R 1 is methyl or ethyl and m 1, W - O- or - CO- O-,

R2 die obengenannte Bedeutung, R 2 has the meaning given above,

R3 Wasserstoff, R 3 is hydrogen,

R4, R5, R6 jeweils Methyl, R 4 , R 5 , R 6 are each methyl,

R7 und R8 jeweils Methyl oder zusammen Cyclopentyl oder R 7 and R 8 are each methyl or together cyclopentyl or

Cyclohexyl  Cyclohexyl

bedeuten. mean.

Die m den Resten R1 - R7 aufgeführten Alkyl-, Alkenyl- oder Alkinylreste können sowohl geradkettig als auch verzweigt sein. "Halogen" bedeutet Fluor, Chlor, Brom oder Jod und steht bevorzugt für Fluor, Chlor oder Brom. Halogenalkyl steht bevorzugt für C1-C4-Alkyl, das ein- oder mehrfach durch Halogen substituiert ist, insbesondere für The m the radicals R 1 - R 7 listed alkyl, alkenyl or alkynyl radicals may be straight-chain or branched both. "Halogen" means fluorine, chlorine, bromine or iodine and preferably represents fluorine, chlorine or bromine. Haloalkyl preferably represents C 1 -C 4 alkyl which is substituted one or more times by halogen, in particular for

Trifluormethyl oder Trichlormethyl. Substituiertes Phenyl bedeutet vorzugsweise Phenyl, das durch ein oder mehrere Reste aus der Gruppe C1-C4-Alkyl, Halogen, Halogenalkyl, Alkoxy,Trifluoromethyl or trichloromethyl. Substituted phenyl preferably means phenyl which is substituted by one or more radicals from the group C 1 -C 4 alkyl, halogen, haloalkyl, alkoxy,

Haloalkoxy oder Cyano substituiert ist. Haloalkoxy or cyano is substituted.

Verbindungen der Formel (I) weisen zumindest ein Compounds of formula (I) have at least one

Asymmetriezentrum im Propionsäureteil auf und können Center of asymmetry in the propionic acid part and can

deshalb als Enantiomerengemisch, z.B. in racemischer Form, oder als reine Enantiomere vorliegen. Die Racemate lassen sich nach üblichen Methoden in Enantiomere trennen. Ebenso ist es jedoch auch möglich, die reinen Enantiomeren direkt unter Verwendung von optisch aktiven Ausgangsstoffen, therefore as a mixture of enantiomers, e.g. are present in racemic form or as pure enantiomers. The racemates can be separated into enantiomers by customary methods. However, it is also also possible to directly isolate the pure enantiomers using optically active starting materials,

herzustellen. In den übrigen Molekülteilen können bei manufacture. In the other parts of the molecule

geeigneter Substituentenbedeutung weitere Asymmetriezentren enthalten sein, so daß mehrere Diastereomere und suitable substituent meaning further asymmetry centers may be included, so that several diastereomers and

Enantiomere möglich sind. Die Verbindungen der Formel (I) umfassen sowohl die möglichen Diastereomere, Enantiomere, Racemate und deren Gemische. Insbesondere umfassen sie die Verbindungen in der D-Form im Propionsäureteil in der im Enantiomers are possible. The compounds of formula (I) include both the possible diastereomers, enantiomers, racemates and mixtures thereof. In particular, they include the compounds in the D form in the propionic acid part in the

Vergleich zum racemischen Gemisch angereicherten Form oder als reine Enantiomere. Comparison to the racemic mixture enriched form or as pure enantiomers.

Gegenstand der Erfindung ist auch ein Verfahren zur The invention also relates to a method for

Herstellung der erfindungsgemäßen Verbindungen der Formel (I), dadurch gekennzeichnet, daß man a) Verbindungen der Formel (II) Q - Hal (II) mit Verbindungen der Formel (III) Preparation of the compounds of formula (I) according to the invention, characterized in that a) compounds of the formula (II) Q - Hal (II) with compounds of the formula (III)

Figure imgf000006_0002
Figure imgf000006_0002

umsetzt oder b) Verbindungen der Formel (IV)  or b) compounds of the formula (IV)

(IV)

Figure imgf000006_0001
Figure imgf000006_0003
(IV)
Figure imgf000006_0001
Figure imgf000006_0003

mit Verbindungen der Formel HO-(CH)m-W-R2, worin with compounds of the formula HO- (CH) m -WR 2 , wherein

A eine geeignete Abgangsgruppe, bevorzugt Cl oder Br,  A a suitable leaving group, preferably Cl or Br,

bedeutet, umsetzt oder c) Verbindungen der genannten Formel (IV), worin K = OH ist,  means, or c) compounds of the formula (IV) mentioned, in which K = OH,

nach bekannten Methoden, z.B. mittels Carbonyldiimidazol, in solche mit aktivierter Carbonylgruppe überführt und diese mit Verbindungen der Formel HO- (CHR1)m-W-R2 zur by known methods, for example by means of carbonyldiimidazole, converted into those with activated carbonyl group and this with compounds of the formula HO- (CHR 1 ) m -WR 2

Verbindung der Formel (I) umsetzt oder d) Verbindungen der Formel (IV), worin A = OH ist, nach an  Reacts compound of formula (I) or d) Compounds of formula (IV), wherein A = OH, according to

sich bekannten Methoden mit Hilfe von Dicyclohexylcarbodiimid (DCC) mit Verbindungen der Formel HO-(CHR1)m-W-R2 in known methods using dicyclohexylcarbodiimide (DCC) with compounds of the formula HO- (CHR 1 ) m -WR 2 in

Gegenwart eines organischen Amins zur Verbindung der  Presence of an organic amine to connect the

Formel (I) umsetzt oder e) Verbindungen der genannten Formel (II) mit Hydrochinon oder 4-Hydroxythiophenol zu Verbindungen der Formel V Implement formula (I) or e) compounds of the formula (II) mentioned with hydroquinone or 4-hydroxythiophenol to give compounds of the formula V.

(V)(V)

Figure imgf000007_0001
Figure imgf000007_0001

umsetzt, die anschließend mit 2-Chlorpropionsäureestern der Formel CH3CH(Cl)CO-O-(CHR1)m-WR2 umgesetzt werden. implemented, which are then reacted with 2-chloropropionic esters of the formula CH 3 CH (Cl) CO-O- (CHR 1 ) m -WR 2 .

Die Umsetzung der Verbindungen (II) und (III) nach Variante a) erfolgt vorzugsweise in inerten aprotischen The reaction of the compounds (II) and (III) according to variant a) is preferably carried out in inert aprotic

Lösungsmitteln, wie aliphatischen oder aromatischen Solvents such as aliphatic or aromatic

Kohlenwasserstoffen (z.B. Toluol/Xylol), Acetonitril, Hydrocarbons (e.g. toluene / xylene), acetonitrile,

Aceton, Dimethylsulfoxid oder Dimethylformamid, bei Acetone, dimethyl sulfoxide or dimethylformamide, at

Temperaturen zwischen 40°C und der Siedetemperatur des Lösungsmittels. Temperatures between 40 ° C and the boiling point of the solvent.

Die Umsetzung der Verbindung (IV) nach Variante b) wird vorzugsweise in inerten aliphatischen oder aromatischen Kohlenwasserstoffen, insbesondere Halogenkohlenwasserstoffen (z.B. CH2Cl2, CHCI3, CCl4), oder Ethern (Dioxan, The reaction of the compound (IV) according to variant b) is preferably carried out in inert aliphatic or aromatic hydrocarbons, in particular halogenated hydrocarbons (for example CH 2 Cl 2 , CHCI 3 , CCl 4 ), or ethers (dioxane,

Tetrahydrofuran) in der Regel bei Rückflußtemperatur Tetrahydrofuran) usually at reflux temperature

durchgeführt. carried out.

Die Umsetzung der Heteroaryloxyphenoxypropionsäuren (IV) mit den Alkoholen ROH erfolgt nach Variante c) bevorzugt in inerten aliphatischen oder aromatischen Lösungsmitteln. According to variant c), the reaction of the heteroaryloxyphenoxypropionic acids (IV) with the alcohols ROH is preferably carried out in inert aliphatic or aromatic solvents.

Die Umsetzung der Heteroaryloxyphenoxypropionsäuren (IV) mit Hilfe von DCC nach Variante d) erfolgt beispielsweise in Gegenwart von 4-N,N-Dimethylaminopyridin (DMAP) in unter den Reaktionsbedingungen inerten aliphatischen oder The reaction of the heteroaryloxyphenoxypropionic acids (IV) with the aid of DCC according to variant d) takes place, for example, in the presence of 4-N, N-dimethylaminopyridine (DMAP) in aliphatic or inert under the reaction conditions

aromatischen Lösungsmitteln. aromatic solvents.

Die Umsetzung der Verbindungen der Formeln (II) und (V) nach Variante e) kann unter den Reaktionsbedingungen von Variante a) analog durchgeführt werden; ebenso die Umsetzung des erhaltenen Zwischenprodukts mit den The reaction of the compounds of the formulas (II) and (V) according to variant e) can be carried out analogously under the reaction conditions of variant a); likewise the reaction of the intermediate obtained with the

2-Chlorpropionsäureestern. Die für die Herstellung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) benötigten Heterocyclen der 2-chloropropionic acid esters. The heterocycles required for the preparation of the compounds of the general formula (I) according to the invention

Formel (II) stehen gemäß der Definition von Q für substituierte 2-Halogenchinoline, 2-Halogenpyridine, 2-Halogenbenzoxazole und 2-Halogenchinoxaline, die bekannt sind oder analog Formula (II), as defined by Q, stands for substituted 2-haloquinolines, 2-halopyridines, 2-halobenzoxazoles and 2-haloquinoxalines, which are known or analogous

bekannten Verfahren hergestellt werden können, z.B. für known methods, e.g. For

Q-Hal mit Q = Q1 bis Q3 aus den entsprechenden Q-Hal with Q = Q 1 to Q 3 from the corresponding

2-Mercaptoverbindungen bzw. 2-OxoVerbindungen durch 2-mercapto compounds or 2-oxo compounds

Halogenierung [s. z.B. Chem. Abstracts 59, 396 f; American Chem. J. 21, 111 (1899)] oder für Q-Hal mit Q = Q4 wie es in EP-A-0 248 968 und dort zitierten Literatur angegeben ist. Halogenation [see eg Chem. Abstracts 59, 396 f; American Chem. J. 21, 111 (1899)] or for Q-Hal with Q = Q 4 as indicated in EP-A-0 248 968 and the literature cited therein.

Die Phenole der Formel (III) (Y = O) lassen sich z.B. durch Alkylierung von Hydrochinon mit den der Formel entsprechenden Chlorpropionsäureestern herstellen (J. Org. Chem. 39, 214 (1974)). The phenols of formula (III) (Y = O) can e.g. by alkylation of hydroquinone with the chloropropionic acid esters corresponding to the formula (J. Org. Chem. 39, 214 (1974)).

Die Thiophenole der Formel (III) (Y = S) sind beispielsweise durch Umsetzung von an der SH- Gruppe geschütztem 4-Hydroxy- thiophenol mit den genannten 2- Chlorpropionsäureestern und Abspaltung der Schutzgruppe zugänglich. The thiophenols of the formula (III) (Y = S) are accessible, for example, by reacting 4-hydroxythiophenol which is protected on the SH group with the 2-chloropropionic acid esters mentioned and by splitting off the protective group.

Die Verbindungen der Formel (IV) sind analog allgemein The compounds of formula (IV) are analogous in general

bekannten Verfahren zugänglich, beispielsweise durch known methods accessible, for example by

Umsetzung von Hydrochinon oder 4-Hydroxythiophenol mit  Implementation of hydroquinone or 4-hydroxythiophenol with

Verbindungen der genannten Formel (II) und anschließender Umsetzung mit entsprechenden 2-Chlorpropionsäureestern, wobei die Produkte nach bekannten Verfahren noch in die  Compounds of formula (II) mentioned and subsequent reaction with corresponding 2-chloropropionic acid esters, the products still being known by known processes in

Carbonsäurederivate mit Abgangsgruppe A überführt werden.  Carboxylic acid derivatives with leaving group A are transferred.

Die erfindungsgemäßen Verbindungen der Formel (I) weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger monokotyler Schadpflanzen auf, wobei die Wirksamkeit in der Regel bei der jeweiligen D-Form der Verbindungen höher als beim Racemat ist und The compounds of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous harmful plants, the activity generally being higher in the particular D-form of the compounds than in the racemate and

die L-Form geringere oder keine herbizide Wirkung hat.  the L-form has little or no herbicidal activity.

Auch schwer bekämpfbare perennierende Unkräuter, die  Also difficult to control perennial weeds that

aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen  from rhizomes, rhizomes or other permanent organs

austreiben, werden durch die Wirkstoffe gut erfaßt. Dabei ist es gleichgültig, ob die Substanzen im Vorsaat-, Vorauflauf oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der monokotylen drive out, are well captured by the active ingredients. It does not matter whether the substances are pre-seeded, pre-emergence or post-emergence procedures. Some representatives of the monocots are examples

Unkrautflora genannt, die durch die erfindungsgemäßen Weed flora called by the inventive

Verbindungen kontrolliert werden können, ohne daß durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Connections can be checked without being limited to certain types by the name.

Auf der Seite der monokotylen Unkrautarten werden z.B. Avena, Apera, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria sowie Cyperusarten aus der annuellen Gruppe und auf seiten der perennierenden Spezies Agropyron, Cynodon, Imperata, Paspalum sowie Sorghum und auch ausdauernde Cyperusarten gut erfaßt. On the side of the monocot weed species, e.g. Avena, Apera, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata, Paspalum as well as Sorghum and also perennial Cyperus species well recorded.

Unter den spezifischen Kulturbedingungen im Reis vorkommende Unkräuter werden von den erfindungsgemäßen Wirkstoffen Weeds occurring in the rice under the specific crop conditions are removed from the active compounds according to the invention

ebenfalls hervorragend bekämpft. also fought very well.

Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das If the compounds according to the invention are applied to the earth's surface before germination, either

Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum KeimblattStadium heran, Prevention of weed seedlings completely or weeds growing up to the cotyledon stage,

stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. however, they stop growing and eventually die completely after three to four weeks.

Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die When the active ingredients are applied to the green parts of the plants in the post-emergence process, there is also a drastic growth stop very quickly after the treatment

Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so daß auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkurrenz sehr früh und Weed plants remain in the growth stage at the time of application or die completely after a certain time, so that weed competition which is harmful to the crop plants very early and

nachhaltig beseitigt wird. is permanently eliminated.

Obgleich die erfindungsgemäßen Verbindungen eine Although the compounds of the invention are one

ausgezeichnete herbizide Aktivität gegenüber monokotylen excellent herbicidal activity against monocots

Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen wie z.B. Weizen, Gerste, Roggen, Reis, Mais, Zuckerrübe, Baumwolle und Soja nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Having weeds, crops of economically important crops such as wheat, barley, rye, rice, maize, sugar beet, cotton and soybeans are only marginally or not harmed at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural

Nutzpflanzungen. Crops.

Die Verbindungen der Formel (I) können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-pnysikalisehen Parameter vorgegeben sind. Als The compounds of formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. As

Formulierungsmöglichkeiten kommen beispielsweise in Frage: Formulation options are possible, for example:

Spritzpulver (WP), emulgierbare Konzentrate (EC), wäßrige Lösungen (SL); Emulsionen (EW) wie Öl-in-Wasser und Wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL); Emulsions (EW) such as oil-in-water and

Wasser-in-Öl-Emulsionen, versprühbare Lösungen oder Water-in-oil emulsions, sprayable solutions or

Emulsionen, Dispersionen auf Öl- oder Wasserbasis (SC), Emulsions, oil or water-based dispersions (SC),

Suspoemulsionen, Stäubemittel (DP), Beizmittel, Granulate (GR) wie Granulate zur Streu- oder Bodenapplikation oder Suspoemulsions, dusts (DP), pickling agents, granules (GR) such as granules for spreading or soil application or

wasserdispergierbare Granulate (WG), ULV-Formulierungen, water-dispersible granules (WG), ULV formulations,

Mikrokapseln oder Wachse. Microcapsules or waxes.

Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray

Drying Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Drying Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind The necessary formulation aids such as inert materials, surfactants, solvents and other additives are

ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen,  also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J .; H.v. Olphen,

"Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley &. Sons, N.Y.; Marsden, "Solvents Guide", 2nd Ed.,  "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley &. Sons, N.Y .; Marsden, Solvents Guide, 2nd Ed.,

Interscience, N.Y. 1950; McCutcheon's "Detergents and  Interscience, N.Y. 1950; McCutcheon's "Detergents and

Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.;  Emulsifiers Annual ", MC Publ. Corp., Ridgewood N.J .;

Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,  Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schoenfeldt,

"Grenzflächenaktive Äthylenoxidaddukte", Wiss.  "Surface-active ethylene oxide adducts", Wiss.

Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,  Publishing company, Stuttgart 1976; Winnacker-Küchler,

"Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986. Auf der Basis dieser Formulierungen lassen sich auch "Chemical technology", volume 7, C. Hauser Verlag Munich, 4th ed. 1986. On the basis of these formulations can also

Kombinationen mit anderen pestizid wirksamen Stoffen, Combinations with other pesticidal substances,

Düngemitteln und/oder Wachstumsregulatoren herstellen, Manufacture fertilizers and / or growth regulators,

z.B. in Form einer Fertigformulierung oder als Tankmix.  e.g. in the form of a finished formulation or as a tank mix.

Spritzpulver sind in Wasser gleichmäßig dispergierbare Spray powders are evenly dispersible in water

Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inert. toff noch Netzmittel, z.B. polyoxyethylierte Preparations containing the active ingredient in addition to a dilution or inert. toff still wetting agents, e.g. polyoxyethylated

Alkylphenole, polyoxethylierte Fettalkohole und Fettamine, Alkan- oder Alkylbenzolsulfonate und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'- disulfonsaures Natrium, dibutylnaphthalin- sulfonsaures Alkylphenols, polyoxethylated fatty alcohols and fatty amines, alkane or alkylbenzenesulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid

Natrium oder auch oleylmethyltaurinsaures Natrium enthalten. Contain sodium or oleylmethyl tauric acid sodium.

Emulgierbare Konzentrate werden durch Auflösen des Emulsifiable concentrates are made by dissolving the

Wirkstoffes in einem organischen Lösungsmittel z.B. Active ingredient in an organic solvent e.g.

Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons

Zusatz von einem oder mehreren Emulgatoren hergestellt. Addition of one or more emulsifiers produced.

Als Emulgatoren können beispielsweise verwendet werden: The following can be used as emulsifiers:

Alkylarylsulfonsaure Calzium-Salze wie Alkylarylsulfonic acid calcium salts such as

Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren  Ca-dodecylbenzenesulfonate or non-ionic emulsifiers

wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,

Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether,

Sorbitanfettsäureester, Polyoxyethylensorbitan- fettsäureester oder Polyoxethylensorbitester. Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural

Tonen wie Kaolin, Bentonit oder Pyrophyllit oder Diatomeenerde.  Clays such as kaolin, bentonite or pyrophyllite or diatomaceous earth.

Granulate zur Streu- oder Bodenapplikation und Granules for spreading or soil application and

wasserdispergierbare Granulate können entweder durch water-dispersible granules can either by

Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g.

Polyvinylalkohol, polyacrylsaurem Natrium oder auch Polyvinyl alcohol, polyacrylic acid sodium or also

Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Mineral oils, on the surface of carriers such as sand, Kaolinite or granulated inert material. Suitable active ingredients can also be used in the production of

Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Fertilizer granules in the usual way - if desired in a mixture with fertilizers - are granulated.

Die agrochemischen Zubereitungen enthalten in der Regel The agrochemical preparations usually contain

0,1 bis 99 Gewichtsprozent, insbesondere 2 bis 95 Gew.-%, Wirkstoff der Formel (I). Dabei können die Konzentrationen der Wirkstoffe in Abhängigkeit vom Formulierungstyp 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active ingredient of the formula (I). The concentrations of the active ingredients can depend on the type of formulation

verschieden sein. to be different.

In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. The active substance concentration in wettable powders is e.g.

etwa 10 bis 95 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren about 10 to 95 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. With emulsifiable

Konzentraten kann die Wirkstoffkonzentration etwa 1 bis Concentrates can have the active ingredient concentration about 1 to

85 Gew.-%, vorzugsweise 5 bis 80 Gew.-% betragen. Staubformige Formulierungen enthalten etwa 1 bis 25 Gew.-%, meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen etwa 0,2 bis 25 Gew.-%, vorzugsweise 2 bis 20 Gew.-% Wirkstoff. Bei 85% by weight, preferably 5 to 80% by weight. Dust-like formulations contain about 1 to 25% by weight, mostly 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight, preferably 2 to 20% by weight of active ingredient. at

Granulaten und speziell wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt. Im allgemeinen liegt der Gehalt bei den in Wasser dispergierbaren Granulaten zwischen 10 und 90 Gew.-%.  Granules and especially water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid. In general, the content of the water-dispersible granules is between 10 and 90% by weight.

Daneben enthalten die genannten Wirkstofformulierungen In addition, the active ingredient formulations mentioned contain

gegebenenfalls die jeweils üblichen Haft-, Netz-,  where applicable, the usual liability, network,

Dispergier-, Emulgier-, Penetrations-, Lösungsmittel,  Dispersing, emulsifying, penetrating, solvent,

Füll- oder Trägerstoffe.  Fillers or carriers.

Zur Anwendung werden die in handelsüblicher Form To be used in the commercial form

vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubformige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung  present formulations optionally diluted in a conventional manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, ground or scatter granules as well as sprayable solutions are used before use

üblicherweise nicht mehr mit weiteren inerten Stoffen  usually no longer with other inert substances

verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die diluted. With the external conditions such as temperature, humidity, the type of herbicide used, among others, varies

erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,01 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,015 und 5 kg/ha. required application rate of the compounds of formula (I). It can fluctuate within wide limits, e.g. between 0.01 and 10.0 kg / ha or more of active substance, but is preferably between 0.015 and 5 kg / ha.

Folgende Beispiele dienen zur Erläuterung der Erfindung: The following examples serve to explain the invention:

A) FORMULIERUNGSBEISPIELE a) Ein Stäubemittel wird erhalten, indem man 10 Gew. -Teile einer Verbindung der Formel (I) und 90 Gew. -Teile Talkum als Inertstoff mischt und in einer Schlagmühle A) FORMULATION EXAMPLES a) A dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and in a hammer mill

zerkleinert. b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I), 64 Gewichtsteile kaolinhaltigen Quarz als Inerstoff, 10 Gewichtsteile ligninsulfonsaures  crushed. b) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, and 10 parts by weight of lignosulfonic acid

Kalium und 1 Gew. -Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer  Potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and mixed in one

Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gewichtsteile einer Verbindung der Formel (I) mit 6 Gew. -Teilen Alkylphenolpolyglykolether (®Triton X 207), 3 Gew. -Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew. -Teilen paraffinischem Mineralöl  Pin mill grinds. c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. -Share paraffinic mineral oil

(Siedebereich z.B. ca. 255 bis über 277°C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 10 Gew.- Teilen einer Verbindung der Formel (I), 75 Gew. -Teilen Cyclohexan als Lösungsmittel und 10 Gew. -Teilen  (Boiling range e.g. approx. 255 to above 277 ° C) mixed and ground in a friction ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 10 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexane as solvent and 10 parts by weight

oxethyliertes Nonylphenol (10 EO) als Emulgator. e) Ein in Wasser dispergierbares Granulat wird erhalten, indem man Ethylated nonylphenol (10 EO) as an emulsifier. e) A water-dispersible granulate is obtained by

75 Gewichtsteile einer Verbindung der Formel (I), 75 parts by weight of a compound of the formula (I),

10 " ligninsulfonsaures Calcium,  10 "calcium lignosulfonic acid,

5 " Natriumlaurylsulfat,  5 "sodium lauryl sulfate,

3 " Polyvinylalkohol und  3 "polyvinyl alcohol and

7 " Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als  7 "kaolin mixes, grind on a pin mill and powder in a fluidized bed by spraying water as

Granulierflüssigkeit granuliert. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man  Granulating liquid granulated. f) A water-dispersible granulate is also obtained by

25 Gewichtsteile einer Verbindung der Formel (I),  25 parts by weight of a compound of the formula (I),

5 " 2,2'-dinaphthylmethan-6,6'-disulfonsaures  5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid

Natrium,  Sodium,

2 " oleolymethyltaurinsaures Natrium,  2 "oleolymethyl tauric acid sodium,

1 " Polyvinylalkohol,  1 "polyvinyl alcohol,

17 " Calciumcarbonat und  17 "calcium carbonate and

50 " Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. g) Ein nach üblichen Methoden hergestelltes Granulat besteht z.B. aus  50 "water homogenized and pre-comminuted on a colloid mill, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle. G) Granules produced by conventional methods consist, for example, of

2 - 15 Gew. -Teilen Wirkstoff der Formel (I) und  2 - 15 parts by weight of active ingredient of the formula (I) and

98 - 85 " " inertes Granulatmaterial, wie  98-85 "" inert granular material, such as

Attapulgit, Bimsstein und Quarzsand. h) Ein emulgierbares Konzentrat wird erhalten aus Attapulgite, pumice stone and quartz sand. h) An emulsifiable concentrate is obtained from

10 Gewichtsteilen Verbindung der Formel (I), 10 parts by weight of compound of the formula (I),

5 " ®Genapol PF 40 (Ethylenoxid-Propylenoxid- 5 "®Genapol PF 40 (ethylene oxide propylene oxide

Blockcopolymer, 40 % EO- Gehalt), Block copolymer, 40% EO content),

3 " Phenylsulfonat Ca 70 (alkylarylsulfonsaures  3 "phenyl sulfonate Ca 70 (alkylarylsulfonic acid

Calcium),  Calcium),

5 '' ®Emulsogen EL 360 (Fettsäurepolyglykolester), 5 '' ®Emulsogen EL 360 (fatty acid polyglycol ester),

40 '' ®Solvesso 200 und 40 '' ® Solvesso 200 and

37 '' N-Methylpyrrolidon.  37 '' N-methyl pyrrolidone.

B) HERSTELLUNGSBEISPIELE: B) PRODUCTION EXAMPLES:

Beispiel 1: Example 1:

2-[4-(6-Chlorchinoxalin-2-yl-oxy)-phenoxy]propionsäure-2- (propin-3-yl-oxy)-ethylester  2- [4- (6-Chloroquinoxalin-2-yl-oxy) phenoxy] propionic acid 2- (propin-3-yl-oxy) ethyl ester

2,6 g (10 mmol) 2-(4-Hydroxyphenoxy)-propionsäure-3- propin-3-yl-oxyethylester werden in 50 ml N,N-Dimethylformamid mit 1,8 g (12 mmol) Kaliumcarbonat und 1,8 g (10 mmol) 2.6 g (10 mmol) of 2- (4-hydroxyphenoxy) propionic acid-3-propin-3-yl-oxyethyl ester are dissolved in 50 ml of N, N-dimethylformamide with 1.8 g (12 mmol) of potassium carbonate and 1.8 g (10 mmol)

2,6-Dichlorchinoxalin versetzt und 4 h unter Rühren auf  2,6-dichloroquinoxaline are added and the mixture is stirred for 4 h

100°C erwärmt. Anschließend wird das DMF unter reduziertem  Heated to 100 ° C. Then the DMF is reduced

Druck abgezogen, der Rückstand in Essigsäureethylester  Stripped pressure, the residue in ethyl acetate

aufgenommen, die organische Phase mit 5-prozentiger  added the organic phase with 5 percent

Natriumhydroxydlosung und anschließend mit Wasser gewaschen, die organische Phase wird mit Magnesiumsulfat getrocknet und der Essigsäureethylester abdestilliert. Der Rückstand wird  Sodium hydroxide solution and then washed with water, the organic phase is dried with magnesium sulfate and the ethyl acetate is distilled off. The backlog will

mit Ether ausgerührt und im Vakuum getrocknet. Man erhält  stirred with ether and dried in vacuo. You get

1,9 g (44.5 % d.Th.) 2-[4-(6-Chlorchinoxalin-2-yloxy)- phenoxy]-propionsäure-2-(propin-3-yloxy)-ethylester vom Schmp.  1.9 g (44.5% of theory) of ethyl 2- [4- (6-chloroquinoxalin-2-yloxy) phenoxy] propionate 2- (propin-3-yloxy), mp.

135-136°C und der Formel:  135-136 ° C and the formula:

Figure imgf000015_0001
Beispiel 2 :
Figure imgf000015_0001
Example 2:

2-[4-(6-Chlorbenzoxazol-2-yl-oxy)-phenoxy]-propionsäure-2- [(tetrahydrofuran-2-yl)-methoxy]ethylester  2- [4- (6-Chlorobenzoxazol-2-yl-oxy) phenoxy] propionic acid 2- [(tetrahydrofuran-2-yl) methoxy] ethyl ester

3,1 g (9,5 mmol) 2-[4-(6-Chlorbenzoxazol-2-yl-oxy)phenoxy]- propionsäure werden in 150 ml trockenem Toluol bei 90°C in Lösung gebracht, dann fügt man 1,3 g (10.9 mmol) 3.1 g (9.5 mmol) of 2- [4- (6-chlorobenzoxazol-2-yl-oxy) phenoxy] propionic acid are dissolved in 150 ml of dry toluene at 90 ° C., then 1.3 is added g (10.9 mmol)

Thionylchor id hinzu, rührt 1 h bei 70°C und destilliert das überschüssige Thionylchlorid unter reduziertem Druck wieder ab. Bei 40°C tropft man zu dieser Lösung ein Gemisch aus 1,4 g (9,6 mmol) 2-[(Tetrahydrofuran-2-yl)-methoxy]ethanol und 1,13 g (11 mmol) Triethylamin hinzu, rührt 2 h bei 40°C, filtriert vom ausgefallenen Pyridiniumchlorid ab. Die  Add Thionylchor id, stir for 1 h at 70 ° C and distill off the excess thionyl chloride under reduced pressure. A mixture of 1.4 g (9.6 mmol) of 2 - [(tetrahydrofuran-2-yl) methoxy] ethanol and 1.13 g (11 mmol) of triethylamine is added dropwise to this solution at 40 ° C., and the mixture is stirred 2 h at 40 ° C, filtered from the precipitated pyridinium chloride. The

organische Phase wird viermal mit 5 prozentiger  organic phase becomes four times with 5 percent

Natriumhydroxidlösung gewaschen, die Toluollösung über  Washed sodium hydroxide solution, the toluene solution over

Magnesiumsulfat getrocknet und dann das Toluol im Vakuum abdestilliert. Als Rückstand erhält man 1, 6 g (36,5 % d.Th.) 2-[4-(6-Chlorbenzoxazol-2-yl-oxy)phenoxy]propionsaure-2-[(2- tetrahydrofuranyl)-methoxy]ethylester als farbloses Öl:  Dried magnesium sulfate and then distilled off the toluene in vacuo. The residue obtained is 1.6 g (36.5% of theory) of 2- [4- (6-chlorobenzoxazol-2-yloxy) phenoxy] propionate 2 - [(2-tetrahydrofuranyl) methoxy] ethyl ester as a colorless oil:

Figure imgf000016_0001
Figure imgf000016_0001

Beispiel 3:  Example 3:

2-[4-(5-Chlorbenzoxazol-2-yl-oxy)-phenoxy]propionsäure-2- (propin-3-yloxy)ethylester  2- [4- (5-Chlorobenzoxazol-2-yl-oxy) phenoxy] propionic acid 2- (propin-3-yloxy) ethyl ester

19,28 g (54 mmol) 2-[4-(5-Chlorbenzoxazol-2-yloxy)-phenoxy]- propionsäure werden in 200 ml Tetrahydrofuran gelöst und dann 9,12 g (53 mmol) 1,1'-Carbonyldiimidazol hinzugefügt. Man rührt 40 min bei Raumtemperatur bis die Gasentwicklung beendet ist, tropft dann 6,17 g (54 mmol) 2-(Propin-3-yloxy)- ethanol hinzu, rührt 5 min bei Raumtemperatur nach, fügt anschließend 1,0 g 50 prozentige Natriumhydridsuspension in Mineralöl hinzu und rührt 12 Stunden bei Raumtemperatur. Das Tetrahydrofuran wird unter reduziertem Druck 19.28 g (54 mmol) of 2- [4- (5-chlorobenzoxazol-2-yloxy) phenoxy] propionic acid are dissolved in 200 ml of tetrahydrofuran and then 9.12 g (53 mmol) of 1,1'-carbonyldiimidazole are added . The mixture is stirred for 40 min at room temperature until the evolution of gas has ceased, then 6.17 g (54 mmol) of 2- (propin-3-yloxy) ethanol are added dropwise, the mixture is stirred for 5 min at room temperature, then 1.0 g of 50 percent is added Add sodium hydride suspension in mineral oil and stir for 12 hours at room temperature. The tetrahydrofuran is made under reduced pressure

abdestilliert, der Rückstand in Essigsäureethylester  distilled off, the residue in ethyl acetate

aufgenommen und die organische Phase viermal mit 5 prozentiger Natriumhydroxidlösung gewaschen. Die Essigesterfraktion wird über Magnesiumsulfat getrocknet und das Lösungsmittel im Vakuum abdestilliert. Der Rückstand wird dann über recorded and the organic phase washed four times with 5 percent sodium hydroxide solution. The ethyl acetate fraction is dried over magnesium sulfate and the solvent is distilled off in vacuo. The backlog is then over

Aluminiumoxid mit Essigsäureethylester/Dichlormethan (1:8) filtriert. Auf diese Weise erhält man 5,3 g (23.6 % d.Th.) 2-[4-(5-Chlorbenzoxazol-2-yl-oxy)-phenoxy]propionsäure-2- (propin-3-yloxy)ethylester als farbloses Öl: Filtered aluminum oxide with ethyl acetate / dichloromethane (1: 8). In this way, 5.3 g (23.6% of theory) of 2- [4- (5-chlorobenzoxazol-2-yl-oxy) phenoxy] propionic acid 2- (propin-3-yloxy) ethyl ester are obtained as colorless Oil:

Figure imgf000017_0001
Figure imgf000017_0001

Beispiel 4:  Example 4:

D-2-[4-(6-Chlorbenzoxazol-2-yl-oxy)-phenoxy]propionsäure-2- [(isopropylidenamino)oxy]ethylester  D-2- [4- (6-chlorobenzoxazol-2-yl-oxy) phenoxy] propionic acid 2- [(isopropylidenamino) oxy] ethyl ester

3,1 g (9,5 mmol) D-2-[4-(6-Chlorbenzoxazol-2-yloxy)phenoxy]- propionsäure werden in 70 ml Essigsäureethylester gelöst, 50 mg 4-N,N-Dimethylaminopyridin und 1,11 g (9,5 mmol) 3.1 g (9.5 mmol) of D-2- [4- (6-chlorobenzoxazol-2-yloxy) phenoxy] propionic acid are dissolved in 70 ml of ethyl acetate, 50 mg of 4-N, N-dimethylaminopyridine and 1.11 g (9.5 mmol)

2-(Isopropylidenaminooxy) ethanol hinzugefügt. Bei 0°C fügt man 2,06 g (10 mmol) Dicyclohexylcarbodiimid hinzu, rührt dann noch 30 min bei 20°C und saugt den ausgefallenen 2- (Isopropylideneaminooxy) ethanol added. At 0 ° C, 2.06 g (10 mmol) of dicyclohexylcarbodiimide are added, the mixture is then stirred for a further 30 min at 20 ° C and the precipitated product is suctioned off

Dicyclohexylharnstoff ab. Anschließend wäscht man die Dicyclohexylurea. Then you wash them

organische Phase noch zweimal mit 0,5 N Salzsäure und einmal mit gesättigter Natriumhydrogencarbonat-Lösung. Die organische Phase wird über Magnesiumsulfat getrocknet und der organic phase twice more with 0.5 N hydrochloric acid and once with saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the

Essigsäureethylester abdestilliert. Man erhält so 1,7 g Distilled off ethyl acetate. This gives 1.7 g

(41,3 % d.Th.) D-2-[4-(6-Chlorbenzoxazol-2-yloxy)-phenoxy]- propionsäure-2-[(isopropylidenamino)oxy]-ethylester vom (41.3% of theory) D-2- [4- (6-chlorobenzoxazol-2-yloxy) phenoxy] propionic acid 2 - [(isopropylidenamino) oxy] ethyl ester of

Schmp. 73°C und Drehwert [α]D 20 = 22,4°C [c = 1, CHCl3]: Mp 73 ° C and rotation value [α] D 20 = 22.4 ° C [c = 1, CHCl 3 ]:

Figure imgf000017_0002
In der folgenden Tabelle 1 sind die Beispiele 1 bis 5 zusammen mit weiteren Beispielen von Verbindungen der genannten Formel (I) aufgeführt, die in analoger Weise erhalten werden.
Figure imgf000017_0002
Examples 1 to 5 are listed in the following Table 1 together with further examples of compounds of the formula (I) mentioned, which are obtained in an analogous manner.

Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001

Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001

BIOLOGISCHE BEISPIELE BIOLOGICAL EXAMPLES

Die Schädigung der Unkrautpflanzen bzw. die The damage to the weed plants or the

Kulturpflanzenverträglichkeit wurde gemäß einem Schlüssel bonitiert, in dem die Wirksamkeit durch Wertzahlen von 0 - 5 ausgedrückt ist. Dabei bedeutet: Crop tolerance was rated according to a key in which the effectiveness is expressed by value numbers from 0-5. Here means:

0 = ohne Wirkung bzw. Schaden 0 = without effect or damage

1 = 0 - 20 % Wirkung bzw. Schaden  1 = 0 - 20% effect or damage

2 = 20 - 40 % Wirkung bzw. Schaden  2 = 20 - 40% effect or damage

3 = 40 - 60 % Wirkung bzw. Schaden  3 = 40 - 60% effect or damage

4 = 60 - 80 % Wirkung bzw. Schaden  4 = 60 - 80% effect or damage

5 = 80 - 100% Wirkung bzw. Schaden  5 = 80 - 100% effect or damage

1. Unkrautwirkung im Vorauflauf 1. Pre-emergence weed action

Samen bzw. Rhizomstücke von monokotylen und dikotylen Seeds or rhizome pieces of monocotyledons and dicotyledons

Unkrautpflanzen wurden in Plastiktöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern oder Emulsionskonzentraten formulierten Weed plants were placed in sandy loam in plastic pots and covered with soil. Formulated in the form of wettable powders or emulsion concentrates

erfindungsgemäßen Verbindungen wurden dann als wäßrige Compounds according to the invention were then as aqueous

Suspensionen bzw. Emulsionen mit einer Wasseraufwandmenge von umgerechnet 600 - 800 1/ha in unterschiedlichen Dosierungen auf die Oberfläche der Abdeckerde appliziert. Suspensions or emulsions with a water application rate of the equivalent of 600 - 800 1 / ha in different dosages applied to the surface of the covering earth.

Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Unkräuter gehalten. Die optische Bonitur der Pflanzen- bzw. Auflaufschaden After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the weeds. The visual assessment of the damage to the plants or the run-up

erfolgte nach dem Auflaufen der Versuchspflanzen von 3 - 4 was done after emergence of the test plants from 3 - 4

Wochen im Vergleich zu unbhandelten Kontrollen. Weeks compared to untreated controls.

Wie die Boniturwerte in Tabelle 2 zeigen, weisen die As the rating values in Table 2 show, the

erfindungsgemäßen Verbindungen eine gute herbizide Compounds according to the invention a good herbicidal

Vorauflaufwirksamkeit gegen ein breites Spektrum von Ungrasern auf. 2. Unkrautwirkung im Nachauflauf Pre-emergence effectiveness against a wide range of grass weeds. 2. Post-emergence weed action

Samen bzw. Rhizomstücke von mono- und dikotylen Unkräutern wurden in Plastiktöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in plastic pots in sandy loam soil, covered with soil and in the greenhouse under good conditions

Wachstumsbedingungen angezogen. Drei Wochen nach der Aussaat wurden die Versuchspflanzen im Dreiblattstadium behandelt. Growth conditions attracted. The test plants were treated at the three-leaf stage three weeks after sowing.

Die als Spritzpulver bzw. als Emulsionskonzentrate The as wettable powder or as emulsion concentrates

formulierten erfindungsgemäßen Verbindungen wurden in formulated compounds according to the invention were in

verschiedenen Dosierungen mit einer Wasseraufwandmenge von umgerechnet 600 - 800 1/ha auf die grünen Pflanzenteile gesprüht und nach ca. 3 - 4 Wochen Standzeit der various doses with a water application rate of the equivalent of 600 - 800 1 / ha sprayed onto the green parts of the plant and after about 3 - 4 weeks of standing

Versuchspflanzen im Gewächshaus unter optimalen Trial plants in the greenhouse under optimal

Wachstumsbedingungen die Wirkung der Präparate optisch im Vergleich zu unbehandelten Kontrollen bonitiert. Growth conditions rated the effect of the preparations optically in comparison to untreated controls.

Die erfindungsgemäßen Mittel weisen auch im Nachauflauf eine gute herbizide Wirksamkeit gegen ein breites Spektrum The agents according to the invention also have good herbicidal activity against a broad spectrum in the after-emergence

wirtschaftlich wichtiger Ungräser auf (Tabelle 3). economically important grasses (Table 3).

3. Kulturpflanzenverträglichkeit 3. Crop tolerance

In weiteren Versuchen im Gewächshaus wurden Samen einer größeren Anzahl von Kulturpflanzen und Unkräutern in sandigem Lehmboden ausgelegt und mit Erde abgedeckt. In further experiments in the greenhouse, seeds of a large number of crop plants and weeds were laid out in sandy loam soil and covered with soil.

Ein Teil der Töpfe wurde sofort wie unter 1. beschrieben behandelt, die übrigen im Gewächshaus aufgestellt, bis die Pflanzen zwei bis drei echte Blätter entwickelt hatten und dann mit den erfindungsgemäßen Substanzen in unterschiedlichen Dosierungen, wie unter 2. beschrieben, besprüht. Some of the pots were immediately treated as described under 1, the rest were placed in the greenhouse until the plants had developed two to three real leaves and then sprayed with the substances according to the invention in different dosages, as described under 2.

Vier bis fünf Wochen nach der Applikation und Standzeit im Gewächshaus wurde mittels optischer Bonitur festgestellt, daß die erfindungsgemäßen Verbindungen zweikeimblättrige Four to five weeks after application and standing in the greenhouse, it was determined by means of an optical rating that that the compounds according to the invention dicotyledonous

Kulturen wie z.B. Soja, Baumwolle, Raps, Zuckerrüben und Cultures such as Soy, cotton, rapeseed, sugar beet and

Kartoffeln im Vor- und Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen ungeschädigt ließen. Einige Substanzen schonten darüber hinaus auch Gramineen-Kulturen wie z.B. Leaving potatoes undamaged in the pre- and post-emergence process even with high active ingredient doses. Some substances also protect Gramineae crops such as

Gerste, Weizen, Roggen, Sorghum-Hirsen, Mais oder Reis. Die Verbindungen der Formel I weisen somit eine hohe Selektivität bei Anwendung zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen auf. Barley, wheat, rye, sorghum, corn or rice. The compounds of the formula I thus have a high selectivity when used to combat undesirable plant growth in agricultural crops.

4. Herbizide Wirkung bei Anwendung in Reis 4. Herbicidal action when used in rice

Knollen und Rhizome bzw. Jungpflanzen oder Samen verschiedener Reisunkräuter wie Cyperus-Arten, Eleocharis, Scirpus und Tubers and rhizomes or young plants or seeds of various rice weeds such as Cyperus species, Eleocharis, Scirpus and

Echinochlöa wurden in geschlossenen Plastiktöpfen in Echinochlöa were in closed plastic pots in

spezielle Reiserde ausgelegt bzw. -gepflanzt und mit Wasser bis zu einer Höhe von 1 cm über dem Boden angestaut. Ebenso wurde mit Reispflanzen verfahren. special rice soil laid out or planted and accumulated with water up to a height of 1 cm above the ground. The same procedure was followed with rice plants.

Im Vorauflaufverfahren, d.h. 3 - 4 Tage nach dem Verpflanzen wurden die erfindungsgemäßen Verbindungen in Form wäßriger Suspensionen oder Emulsionen ins Anstauwasser gegossen, als Granulate ins Wasser gestreut oder auf die grünen Pflanzenteile gesprüht. Jeweils drei Wochen später wurde die herbizide In the pre-emergence process, i.e. 3-4 days after transplanting, the compounds according to the invention were poured into the backwater in the form of aqueous suspensions or emulsions, sprinkled into the water as granules or sprayed onto the green parts of the plants. Three weeks later, the herbicide

Wirkung und eine eventuelle Schadwirkung gegenüber Reis optisch bonitiert.. Die Ergebnisse zeigen, daß sich die Effect and a possible harmful effect vis-à-vis rice. The results show that the

erfindungsgemäßen Verbindungen zur selektiven Compounds according to the invention for selective

Unkrautbekämpfung eignen (Tabelle 4 und 5) . Gegenüber Weed control suitable (Tables 4 and 5). Across from

bisherigen Reisherbiziden zeichnen sich die erfindungsgemäßen Verbindungen dadurch aus, daß sie zahlreiche, insbesondere auch schwer bekämpfbare Problemunkräuter, wie Echinochlöa, wirkungsvoll bekämpfen und dabei von Reis toleriert werden. Tabelle 2 : Previous rice herbicides are characterized in that the compounds according to the invention are effective in combating numerous problem weeds, in particular those which are difficult to control, such as echinochlea, and are thereby tolerated by rice. Table 2:

Herbizide Wirkung der erfindungsgemäßen Verbindungen im Vorauflauf  Pre-emergence herbicidal activity of the compounds according to the invention

Figure imgf000028_0001
Figure imgf000028_0001

Abkürzungen: AVFA = Avena fatua  Abbreviations: AVFA = Avena fatua

ALMY = Alopecurus myosurides  ALMY = Alopecurus myosurides

SEPU = Setaria pumila  SEPU = Setaria pumila

LOMU = Lolium multiflorum  LOMU = Lolium multiflorum

ECCR = Echinochlöa crus-galli Tabelle 3 : ECCR = Echinochlöa crus-galli Table 3:

Herbizide Wirkung der erfindungsgemäßen Verbindungen im Nachauflauf  Post-emergence herbicidal activity of the compounds according to the invention

Figure imgf000029_0001
Figure imgf000029_0001

Abkürzungen: AVFA = Avena fatua Abbreviations: AVFA = Avena fatua

ALMY = Alopecurus myoisurides  ALMY = Alopecurus myoisurides

SEPU = Setaria pumila  SEPU = Setaria pumila

LOMU = Lolium multiflorum  LOMU = Lolium multiflorum

ECCR = Echincichloa crus-galli Tabelle 4 : ECCR = Echincichloa crus-galli Table 4:

Wirkung der erfindungsgemäßen Verbindungen im Reis. Vorauflaufapplikation.  Effect of the compounds according to the invention in rice. Pre-emergence application.

Figure imgf000030_0001
Figure imgf000030_0001

Abkürzungen: ORSA = Oryza sativa  Abbreviations: ORSA = Oryza sativa

ECCR = Echinochlöa crus-galli ECCR = Echinochlöa crus-galli

Tabelle 5 : Table 5:

Wirkung der erfindungsgemäßen Verbindungen im Reis. Nachauflaufapplikation.  Effect of the compounds according to the invention in rice. Post-emergence application.

Figure imgf000031_0001
Fortsetzung Tabelle 5:
Figure imgf000031_0001
Continuation of table 5:

Wirkung der erfindungsgemäßen Verbindungen im Reis. Nachauflaufapplikation.  Effect of the compounds according to the invention in rice. Post-emergence application.

Figure imgf000032_0001
Figure imgf000032_0001

Abkürzungen: ORSA = Oryza sativa  Abbreviations: ORSA = Oryza sativa

ECCR = Echinochlöa crus-galli  ECCR = Echinochlöa crus-galli

Claims

PATENTANSPRÜCHE PATENT CLAIMS Verbindungen der allgemeinen Formel (I) Compounds of the general formula (I)
Figure imgf000033_0001
Figure imgf000033_0001
 worin wherein Y O oder S,  Y O or S, Q eine Gruppe der Formel  Q is a group of the formula (Q1), (Q2), (Q 1 ), (Q 2 ), (Q3) oder (Q 3 ) or (Q4)(Q 4 )
Figure imgf000033_0002
Figure imgf000033_0002
 worin  wherein X unabhängig voneinander Halogen, Haloalkyl, CN oder NO2,X independently of one another halogen, haloalkyl, CN or NO 2 , Z Wasserstoff oder Halogen und Z is hydrogen or halogen and n 0, 1, 2, 3 oder 4 bedeuten,  n is 0, 1, 2, 3 or 4, R1 unabhängig voneinander Wasserstoff oder C1-C4-Alkyl, m 1, 2, 3 oder 4, R 1 independently of one another is hydrogen or C 1 -C 4 alkyl, m 1, 2, 3 or 4, W eine divalente Gruppe der Formel -O-, -CO-S- oder -CO-O-,  W is a divalent group of the formula -O-, -CO-S- or -CO-O-, R2 eine Gruppe der Formel R 2 is a group of the formula -CH2CH=CHR3, -CH2C≡CR3, -CH2- Si (R4) (R5) (R6) oder -CH 2 CH = CHR 3 , -CH 2 C≡CR 3 , -CH 2 - Si (R 4 ) (R 5 ) (R 6 ) or -N=CR7R8 oder Tetrahydropyranylmethyl oder -N = CR 7 R 8 or tetrahydropyranylmethyl or Tetrahydrofurfuryl, wobei die letztgenannten zwei  Tetrahydrofurfuryl, the latter two Reste unsubstituiert oder im Ring durch C1-C4-Alkyl substituiert sind, R3 Wasserstoff , C 1 - C4-Alkyl oder gegebenenfalls Radicals are unsubstituted or substituted in the ring by C 1 -C 4 alkyl, R 3 is hydrogen, C 1 -C 4 alkyl or optionally substituiertes Phenyl ,  substituted phenyl, R4, R5 und R6 unabhängig voneinander C1-C4-Alkyl oderR 4 , R 5 and R 6 independently of one another are C 1 -C 4 alkyl or Phenyl, Phenyl, R7 und R8 entweder unabhängig voneinander Wasserstoff oder C1-C4-Alkyl oder R7 und R8 gemeinsam C3-C7-R 7 and R 8 are either independently hydrogen or C 1 -C 4 alkyl or R 7 and R 8 together are C 3 -C 7 - Cycloalkyl bedeuten, Mean cycloalkyl, wobei für den Fall, daß  in the event that W= -COO- bedeutet, die Gruppe der Formel Q4 ausgenommen ist und W = -COO- means the group of formula Q 4 is excluded and für den Fall, daß  in case that R2 -N=CR7R8 und W Sauerstoff bedeutet, die Gruppen derR 2 -N = CR 7 R 8 and W means oxygen, the groups of Formeln Q1 und Q2 ausgenommen sind und Formulas Q1 and Q 2 are excluded and für den Fall, daß  in case that R2 -CH2CH=CHR3, -CH2C≡CR3 oder Tetrahydrofurfuryl, R 2 -CH 2 CH = CHR 3 , -CH 2 C≡CR 3 or tetrahydrofurfuryl, m = 1 bis 3 und W = -CO-O- bedeuten, die Gruppe der Formel Q3 ausgenommen ist. m = 1 to 3 and W = -CO-O- mean the group of formula Q 3 is excluded. 2. Verbindungen der Formel (I) nach Anspruch 1, 2. Compounds of formula (I) according to claim 1, worin wherein Y Sauerstoff,  Y oxygen, Q eine Gruppe der Formeln Q1, Q 2, Q3 oder Q4, worinQ is a group of the formulas Q 1 , Q 2 , Q 3 or Q 4 , wherein X Halogen oder Trifluormethyl, X halogen or trifluoromethyl, Z Halogen und  Z halogen and n 1 oder 2 bedeuten, n is 1 or 2, R1 Wasserstoff und m 1 bis 4 oder R 1 is hydrogen and m is 1 to 4 or R1 Methyl oder Ethyl und m 1, R 1 is methyl or ethyl and m 1, W -O- oder -CO-O-,  W -O- or -CO-O-, R2 die obengenannte Bedeutung, R 2 has the meaning given above, R3 Wasserstoff R 3 is hydrogen R4,R5,R6 jeweils Methyl, R 4 , R 5 , R 6 are each methyl, R7 und R8 jeweils Methyl oder zusammen Cyclopentyl oderR 7 and R 8 are each methyl or together cyclopentyl or Cyclohexyl Cyclohexyl bedeuten. mean. 3. Verfahren zur Herstellung der nach Anspruch 1 oder 2 definierten Verbindungen der Formel (I), dadurch 3. A process for the preparation of the compounds of formula (I) defined according to claim 1 or 2, thereby gekennzeichnet, daß man a) Verbindungen der Formel (II) Q - Hal (II) mit Verbindungen der Formel (III) characterized that one a) compounds of the formula (II) Q - Hal (II) with compounds of the formula (III)
Figure imgf000035_0001
Figure imgf000035_0001
 umsetzt oder b) Verbindungen der Formel (IV)  or b) compounds of the formula (IV) (IV)(IV)
Figure imgf000035_0002
mit Verbindungen der Formel HO-(CHR1)m-W-R2, worin
Figure imgf000035_0002
with compounds of the formula HO- (CHR 1 ) m -WR 2 , wherein A eine geeignete Abgangsgruppe bedeutet, umsetzt oder c) Verbindungen der genannten Formel (IV), worin A = OH ist, nach bekannten Methoden in solche mit aktivierter  A denotes a suitable leaving group, or c) compounds of the formula (IV) mentioned, in which A = OH, are converted into those with activated by known methods Carbonylgruppe überführt und diese mit Verbindungen der  Converts carbonyl group and this with compounds of Formel HO-(CHR1)m-W-R2 zur Verbindung der Formel (I) Formula HO- (CHR 1 ) m -WR 2 for the compound of formula (I) umsetzt oder d) Verbindungen der Formel (IV), worin A = OH ist, nach an  or d) compounds of the formula (IV) in which A = OH, according to sich bekannten Methoden mit Hilfe von Dicyclohexylcarbodiimid (DCC) mit Verbindungen der Formel HO- (CHR1)m-W-R2 in known methods using dicyclohexylcarbodiimide (DCC) with compounds of the formula HO- (CHR 1 ) m -WR 2 in Gegenwart eines organischen Amins zu Verbindungen der  Presence of an organic amine to compounds of Formel (I) umsetzt oder e) Verbindungen der genannten Formel (II) mit Hydrochinon  Formula (I) or e) compounds of the formula (II) mentioned with hydroquinone oder 4-Hydroxythiophenol zu Verbindungen der Formel V (V)
Figure imgf000035_0003
umsetzt, die anschließend mit 2-Chlorpropionsäureestern der Formel CH3CH(Cl)CO-O-(CHR1)m-WR2 umgesetzt werden. or 4-hydroxythiophenol to compounds of the formula V (V)
Figure imgf000035_0003
implemented, which are then reacted with 2-chloropropionic esters of the formula CH 3 CH (Cl) CO-O- (CHR 1 ) m -WR 2 . 4. Herbizides Mittel, dadurch gekennzeichnet, daß es eine Verbindung der Formel (I) nach Anspruch 1 oder 2 neben 4. Herbicidal agent, characterized in that it is a compound of formula (I) according to claim 1 or 2 in addition Formulierungshilfsmitteln enthält. Contains formulation aids. 5: Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge an einer oder mehreren der Verbindungen der Formel (I) nach Anspruch 1 oder 2 auf die Pflanzen oder die Anbauflächen appliziert. 5: Process for combating undesirable plant growth, characterized in that a herbicidally effective amount of one or more of the compounds of the formula (I) according to Claim 1 or 2 is applied to the plants or the areas under cultivation. 6. Verfahren nach Anspruch 5, dadurch gekennzeichnet, daß die unerwünschten Pflanzen monokotyle Ungräser sind. 6. The method according to claim 5, characterized in that the undesirable plants are monocotyledon grasses. 7. Verfahren nach Anspruch 5 oder 6, dadurch gekennzeichnet, daß die Verbindungen der Formel (I) selektiv gegen 7. The method according to claim 5 or 6, characterized in that the compounds of formula (I) selectively against Schadpflanzen in Nutzpflanzenkulturen eingesetzt werden. Harmful plants are used in crops. 8. Verwendung von Verbindungen der Formel (I) nach 8. Use of compounds of formula (I) after Anspruch 1 oder 2 als Herbizide. Claim 1 or 2 as herbicides. 9. Verwendung nach Anspruch 8, dadurch gekennzeichnet, daß die Herbizide selektiv gegen Ungräser in Nutzpflanzenkulturen eingesetzt werden. 9. Use according to claim 8, characterized in that the herbicides are used selectively against grasses in crops.
PCT/EP1990/001647 1989-10-05 1990-10-01 Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them Ceased WO1991004969A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP3933246.2 1989-10-05
DE3933246 1989-10-05
DE3939095 1989-11-25
DEP3939095.0 1989-11-25

Publications (1)

Publication Number Publication Date
WO1991004969A1 true WO1991004969A1 (en) 1991-04-18

Family

ID=25885837

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/001647 Ceased WO1991004969A1 (en) 1989-10-05 1990-10-01 Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them

Country Status (3)

Country Link
AU (1) AU6540490A (en)
PT (1) PT95503A (en)
WO (1) WO1991004969A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5696119A (en) * 1992-12-15 1997-12-09 The Dupont Merck Pharmaceutical Company (2-quinoxalinyloxy) phenoxypropanoic acids and related derivatives as anticancer agents
WO2006125337A1 (en) * 2005-05-23 2006-11-30 Sinochem Corporation α, β- AND, Ϝ-UNSATURATED CARBOXYLATES AND THE USE AS HERBICIDIDE THEREOF
WO2014060557A3 (en) * 2012-10-19 2014-06-12 Syngenta Participations Ag Liquid agrochemical compositions comprising a polymeric thickener and an alcohol-containing solvent system, and liquid herbicidal compositions having an alcohol-containing solvent system
CN104649995A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 6-chlorobenzoxazole oxygen phenoxypropionic acid allyl ester compound and application thereof as weeding agent

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4042098C2 (en) * 1990-12-28 1993-10-07 Hoechst Ag Process for the preparation of optically active quinoxalinyloxy-phenoxypropionic acid esters

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008624A1 (en) * 1978-07-03 1980-03-19 Ciba-Geigy Ag O-(Pyridyloxy-phenyl)-lactic acid esters, process for their preparation and their use as herbicides and plant growth regulants
EP0052798A1 (en) * 1980-11-26 1982-06-02 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Oxime esters, processes for their preparation, their use and compositions containing these esters
EP0058639A2 (en) * 1981-02-16 1982-08-25 Ciba-Geigy Ag 2-(4-(6-Halogen-quinoxalinyl-2-oxy)-phenoxy)-propionic-acid esters, processes for their preparation and their application as herbicides and plant growth regulators
US4482373A (en) * 1979-04-09 1984-11-13 Hoechst Aktiengesellschaft Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides
US4687849A (en) * 1985-10-04 1987-08-18 Hoffmann-La Roche Inc. [(Isopropylideneamino)oxy]-ethyl-2-[[6-chloroquinoxalinyl)oxy]phenoxy]propionate postemergent herbicide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008624A1 (en) * 1978-07-03 1980-03-19 Ciba-Geigy Ag O-(Pyridyloxy-phenyl)-lactic acid esters, process for their preparation and their use as herbicides and plant growth regulants
US4482373A (en) * 1979-04-09 1984-11-13 Hoechst Aktiengesellschaft Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides
EP0052798A1 (en) * 1980-11-26 1982-06-02 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Oxime esters, processes for their preparation, their use and compositions containing these esters
EP0058639A2 (en) * 1981-02-16 1982-08-25 Ciba-Geigy Ag 2-(4-(6-Halogen-quinoxalinyl-2-oxy)-phenoxy)-propionic-acid esters, processes for their preparation and their application as herbicides and plant growth regulators
US4687849A (en) * 1985-10-04 1987-08-18 Hoffmann-La Roche Inc. [(Isopropylideneamino)oxy]-ethyl-2-[[6-chloroquinoxalinyl)oxy]phenoxy]propionate postemergent herbicide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5696119A (en) * 1992-12-15 1997-12-09 The Dupont Merck Pharmaceutical Company (2-quinoxalinyloxy) phenoxypropanoic acids and related derivatives as anticancer agents
WO2006125337A1 (en) * 2005-05-23 2006-11-30 Sinochem Corporation α, β- AND, Ϝ-UNSATURATED CARBOXYLATES AND THE USE AS HERBICIDIDE THEREOF
WO2014060557A3 (en) * 2012-10-19 2014-06-12 Syngenta Participations Ag Liquid agrochemical compositions comprising a polymeric thickener and an alcohol-containing solvent system, and liquid herbicidal compositions having an alcohol-containing solvent system
US10314305B2 (en) 2012-10-19 2019-06-11 Syngenta Participations Ag Liquid agrochemical compositions comprising a polymeric thickener and an alcohol-containing solvent system, and liquid herbicidal compositions having an alcohol-containing solvent system
CN104649995A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 6-chlorobenzoxazole oxygen phenoxypropionic acid allyl ester compound and application thereof as weeding agent
CN104649995B (en) * 2013-11-25 2017-06-09 沈阳中化农药化工研发有限公司 A kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compound and its application as herbicide

Also Published As

Publication number Publication date
AU6540490A (en) 1991-04-28
PT95503A (en) 1991-08-14

Similar Documents

Publication Publication Date Title
DE3816704A1 (en) HETEROCYCLIC 2-ALKOXYPHENOXYSULFONYL UREAS AND THEIR USE AS HERBICIDES OR PLANT GROWTH REGULATORS
DE3604042A1 (en) IMIDAZOLIDIN (THI) ON DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN PLANT PROTECTION
EP0272594A1 (en) Bicyclic imides, process for their preparation and their use in crop protection
DE3115152A1 (en) &#34;HETEROCYCLIC PHENYL ETHERS AND HERBICIDES CONTAINING THEM&#34;
EP0264865A2 (en) Herbicides containing alpha-iminoanilide, these compounds and process for their preparation
EP0075840B1 (en) Heterocyclic phenyl ethers, process for their preparation and herbicides containing them
EP0496757B1 (en) Process for eradicating rice weeds
EP0470489A1 (en) 4,5,6,7-Tetrahydro-3-aryl-indazoles, process for their preparation and their use as herbicides
DD273436A5 (en) METHOD FOR PRODUCING SUBSTITUTED TETRAHYDROPHTHOLIMIDES AND THEIR USE OF THE HERBIDE
DE3533440A1 (en) N-SUBSTITUTED 3,4,5,6-TETRAHYDROPHTHALIMIDES, METHODS FOR THEIR PRODUCTION AND THEIR USE IN PLANT PROTECTION
WO1991004969A1 (en) Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them
EP0151744B1 (en) 1-acylimidazolinones, process for their preparation and their agricultural application
EP0288960A1 (en) Alkyl-N-aryl-tetrahydrophthalimides, process for their manufacture and their use in protecting plants
DE3018003C2 (en)
EP0303114B1 (en) Heterocyclically substituted sulfamic acid phenyl esters, process for their preparation and their use as herbicides and plant growth regulators
EP0037524A1 (en) Substituted acetanilides, process for their preparation and their utilization as herbicides
EP0171724A2 (en) Phenoxypropanoic acid derivatives, process for their preparation, and their use as herbicides
EP0037526A1 (en) Substituted acetanilides, process for their preparation and their utilization as herbicides
EP0502492A2 (en) Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators
EP0227045B1 (en) Heterocyclic phenyl ethers, process for their preparation and herbicidal compositions containing them
DE3807532A1 (en) Pyrimidine-carboxylic acids, their preparation, and their use as herbicides
DE3402982A1 (en) PHENOXYPROPIONYLOXYALKANPHOSPHONIC ACID ESTER
EP0037527A1 (en) Substituted acetanilides, process for their preparation and their utilization as herbicides
DE2748658A1 (en) HERBICIDES BETA-NAPHTHYL-PHENYL ETHER
EP0107123A1 (en) Aniline derivatives, process for their preparation and their use in combating undesired plant growth

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AT AU BB BG BR CA CH DE DK ES FI GB HU JP KP KR LK LU MC MG MW NL NO RO SD SE SU US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BF BJ CF CG CH CM DE DK ES FR GA GB IT LU ML MR NL SE SN TD TG

NENP Non-entry into the national phase

Ref country code: CA