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EP1423005A1 - Melanges herbicides a base d'arylcetones substituees - Google Patents

Melanges herbicides a base d'arylcetones substituees

Info

Publication number
EP1423005A1
EP1423005A1 EP02758472A EP02758472A EP1423005A1 EP 1423005 A1 EP1423005 A1 EP 1423005A1 EP 02758472 A EP02758472 A EP 02758472A EP 02758472 A EP02758472 A EP 02758472A EP 1423005 A1 EP1423005 A1 EP 1423005A1
Authority
EP
European Patent Office
Prior art keywords
methyl
chlorine
fluorine
ethyl
methoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02758472A
Other languages
German (de)
English (en)
Inventor
Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
Dorothee Hoischen
Klaus-Helmut Müller
Hans-Georg Schwarz
Stefan Herrmann
Kristian Kather
Otto Schallner
Toshio Goto
Shinichi Shirakura
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience 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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1423005A1 publication Critical patent/EP1423005A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Definitions

  • the invention relates to new herbicidal combinations of active compounds which have known substituted aryl ketones on the one hand and one or more herbicidally active herbicides
  • Substituted aryl ketones are known as effective herbicides (cf. DE-A-10001588, WO-A-99/10328; US 6207618, WO-A-01/32636). However, the action of these compounds is not entirely satisfactory under all conditions.
  • alkanediyl alkylene having 1 to 6 carbon atoms
  • R 1 represents one of the groupings below
  • n the numbers 0 to 6
  • R for halogen, for alkyl, alkoxycarbonyl or alkylthio, each optionally substituted by cyano, halogen or C 1 -C 4 alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or for optionally substituted by halogen, Cr alkyl or CrC 4 alkoxy Phenyl, or - if m stands for 2 - optionally together with a second radical R 5 for a carbo- onyl group (C O) or alkanediyl (alkylene) having 2 to 6 carbon atoms,
  • R 6 for hydroxy, formyloxy, halogen, for alkoxy, alkylthio which are each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,
  • R 7 for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or optionally substituted in each case by cyano, halogen or C 1 -C 4 -alkoxy
  • Alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl,
  • R 8 is hydrogen, optionally by cyano, halogen or C 1 -C 4 -
  • R 9 for hydroxy, formyloxy, for alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, each optionally substituted by cyano, halogen or C 1 -C 4 alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano or halogen
  • R 11 for hydrogen, for optionally by cyano, halogen or CrC 4 -
  • R 12 for hydrogen, for optionally by cyano, halogen or -C 4 -
  • R 13 stands for hydrogen, cyano, carbamoyl, halogen, or for each optionally by alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfmyl or alkylsulfonyl, each of which is substituted by cyano, halogen or Cr C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups .
  • R is hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen or dC 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl or C 1 -C 4- Alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylammosulfonyl, each having 1 to 6 carbon atoms in the alkyl groups, and
  • R 4 represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which has 1 to 4 heteroatoms, of which up to 4 nitrogen atoms and, if appropriate - alternatively or additively - 1 to 3 oxygen atoms, Sulfur atoms, -SO-
  • R 1 is hydrogen, (C r C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 5 -C 6 ) cycloalkenyl, phenyl or 3- to 6- membered heterocyclyl with up to three heteroatoms from the group nitrogen, oxygen and sulfur, the six latter radicals optionally being substituted by one or more, identical or different substituents from the group halogen, (C 1 -Cg) alkoxy, (C 1 -C 6 ) -Haloalkoxy, (C r C 2 ) -alkylsulfmyl, (C r C 2 ) -alkylsulfonyl, (C 3 -C 6 ) - cycloalkyl, (C ⁇ -C 4 ) -alkoxycarbonyl, (C ⁇ -C 4 ) -alkylcarbonyl and Phenyl and in the case of
  • R 2 is hydrogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, the three last-mentioned radicals optionally being substituted by one or more, identical or different substituents from the Halogen, hydroxy, (C 1 -C 4 ) alkyl, (C1-C 4 ) alkoxy and (C1 -C 4 ) alkylthio are substituted;
  • R 3 halogen, (C r C 4 ) -haloalkyl, (C 1 -C 4 ) -haloalkoxy, nitro, (C r C 4 ) -alkyl, (C r C 4 ) -alkoxy, (C r C 4 ) - Alkylsulfonyl ; (C 1 -C 4 ) alkoxycarbonyl or (C r C 4 ) alkylcarbonyl;
  • R 4 is hydrogen or methyl; R 5 halogen; Nitro, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, (C 3 - C 6 ) cycloalkyl, phenyl, (C r C 4 ) alkoxy , Cyano, (C1-C4) - alkylthio, (C r C4) -alkylsulfinyl, (C ⁇ -C) -alkylsulfonyl, (C 1 -C) -alkoxycarbonyl or (C 1 - C4) -alkylcarbonyl;
  • R 1 is hydrogen, (C r C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, each of the latter four residues being unsubstituted or by one or more substituents from the group halogen, (C ⁇ ⁇ C4) -Alkyloxy, halogen (-C-Cg) -alkoxy and (C1-C4) - alkylthio and in the case of cyclic radicals also (-CC-C4) alkyl and (-C-C4) -haloalkyl is substituted;
  • R 2 is hydrogen or methyl
  • R 3 halogen, halogen (C 1 -C 4 ) alkyl, halogen (C 1 -C 4 ) alkoxy, (C r C 4 ) alkyl,
  • R 5 halogen, (C r C 4 ) alkyl, halogen (C r C 4 ) alkyl, halogen (C r C 4 ) alkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (C r C 4 ) - alkoxy, cyano, (C r C 4 ) - alkylthio, (C r C 4 ) -alkylsulfmyl, (C r C 4 ) - alkylsulfonyl, (C r C 4 ) -alkoxycarbonyl, (C r C) - alkylcarbonyl,
  • n 1 or 2
  • alkali metal salts especially the sodium salts (known from DE-Al-19 621 522).
  • the compounds involved in the active compound combinations according to the invention optionally contain one or more asymmetrically substituted carbon atoms and can therefore be present in various enantiomeric (R- or S-configured) or diastereomeric forms.
  • the invention relates both to the possible combinations with individual enantiomeric or stereoisomeric forms and with mixtures of the respective possible stereoisomeric forms of the compounds involved.
  • m preferably represents the numbers 0, 1, 2, 3 or 4.
  • A preferably represents alkanediyl (alkylene) having 1 to 3 carbon atoms.
  • R 1 preferably represents one of the groupings below
  • R 2 preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, bromine, CrC 3 alkoxy, C 3 -C 3 -alkylthio, CC 3 alkyl sulfinyl or -Cralkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylammosulfonyl each having 1 to 5 carbon atoms in the alkyl groups.
  • R 3 preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, bromine, CC 3 alkoxy, C! -C 3 alkylthio , C ⁇ -C3-alkyl-sulfmyl or C1-C3-alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylammosulfonyl each having 1 to 5 carbon atoms in the alkyl groups.
  • R 4 preferably represents one of the heterocyclic groupings below
  • each heterocyclic group preferably carries 1 to 3, particularly preferably 1 or 2, substituents,
  • Q oxygen or sulfur
  • Y 1 for hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, for each optionally by cyano, fluorine, chlorine, bromine, -C 3 - alkoxy, Ci-CrAlkylthio, -C-C 3 -AJJiylsulfinyl and / or C 1 -C 3 -alkyl-sulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 5 carbon atoms in the alkyl groups, for each optionally substituted by fluorine or chlorine, alkylamino or dialkylamino, each having up to 5 Carbon atoms in the alkyl groups, for alkenyl, alkynyl, alkenyloxy, alkenylthio or alkenylamino
  • R 5 preferably represents fluorine, chlorine, bromine, for alkyl, alkoxycarbonyl or alkylthio each optionally substituted by cyano, fluorine, chlorine or —C alkoxy, each having 1 to 5 carbon atoms in the alkyl groups, for optionally by fluorine, chlorine, bromine, C1 -C 4 - alkyl or C 1 -C 4 alkoxy-substituted phenyl, or optionally - in the case where m is 2 - together with a second radical R 5 for alkanediyl (alkylene) having 2 to 6 carbon atoms.
  • R 6 preferably represents hydroxyl, formyloxy, or alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 5 carbon atoms in the alkyl groups each optionally substituted by cyano, fluorine, chlorine or -Q B - alkoxy , for in each case optionally substituted by cyano, fluorine, chlorine and / or bromine alkenyloxy or alkynyloxy each having 3 to 5 carbon atoms, or for in each case optionally by
  • R 7 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
  • Alkylsulfonyl or alkoxycarbonyl each with 1 to 5 carbon atoms in the alkyl groups, or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine or C Cs-alkyl.
  • R 8 preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine or d-Cralkoxy alkyl having 1 to 5 carbon atoms, in each case optionally substituted by cyano, fluorine, chlorine and / or bromine alkenyl or alkynyl each having 3 to 5 Carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, fluorine, chlorine, bromine or Q-Cs-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 3 carbon atoms in the alkyl part, or for each optionally containing nitro, Cyano, fluorine, chlorine, bromine, iodine, or (each optionally substituted by fluorine and / or chlorine) C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-substituted phenyl or phenyl-C
  • R 9 preferably represents hydroxyl, formyloxy, alkoxy, alkylcarboxyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 5 carbon atoms in the alkyl groups, each optionally substituted by cyano, fluorine, chlorine or CrCralkoxy, each optionally by cyano, fluorine, Chlorine and / or bromine substituted
  • R 10 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
  • R 11 preferably represents hydrogen, alkyl with 1 to 5 carbon atoms optionally substituted by cyano, fluorine, chlorine or -Cralkoxy or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine or d-Cs-alkyl.
  • R 12 preferably represents hydrogen, alkyl with 1 to 5 carbon atoms optionally substituted by cyano, fluorine, chlorine or C 1 -C 3 -alkoxy or cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine or -Cralkyl ,
  • R 13 preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 5 carbon atoms in each case optionally substituted by cyano, fluorine, chlorine or -Cs-alkoxy in the alkyl groups.
  • n particularly preferably represents the numbers 0, 1, 2 or 3.
  • R particularly preferably represents hydrogen, nitro, cyano, carboxy, carboyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-Propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally with fluorine and / or chlorine, Methoxy, ethoxy, n- or i-propoxy substituted methoxy, ethoxy, n- or i-propoxy, for each optionally substituted by fluorine and / or chlorine tes
  • R particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i -Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally with fluorine and / or chlorine, methoxy, ethoxy, n - or i-propoxy substituted methoxy, ethoxy, n- or i-propoxy, for each methylthio, ethylthio, n- or
  • R particularly preferably represents one of the heterocyclic groupings below
  • Q particularly preferably stands for oxygen.
  • Y 1 particularly preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, in each case optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t
  • Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or - in the event that two adjacent radicals Y 1 and Y 1 are located on a double bond - together with the adjacent radical Y 1 also for a benzo group.
  • R 5 particularly preferably represents fluorine, chlorine, bromine or methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • 1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
  • R 6 particularly preferably represents hydroxy, formyloxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylnulfonyloxy, ethyl i
  • Phenylsulfonyl benzoyloxy, benzoylmethoxy, phenylsulfonyloxy, phenyl methoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.
  • R 7 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally by cyano, fluorine,
  • R 8 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, each for propenyl, butenyl, propynyl or butynyl, optionally substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano,
  • R 9 particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally with cyano, fluorine, Chloro or bromine substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy,
  • R 10 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, Propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
  • R u particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl.
  • R 12 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl.
  • R 13 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine,
  • a particularly preferred “group la” of compounds as active ingredient components of group 1 are those compounds of the formula (I) in which
  • A represents methylene or dimethylene
  • R 1 represents one of the groupings below
  • R 2 for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfmylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio , Methylsulfinyl, ethylsulfinyl, methylsulfony, ethylsulfonyl or dimethylaminosulfonyl,
  • R 3 for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinyhethyl, methylsulfonylmethyl, methoxy,
  • R 4 represents the heterocyclic grouping below, wherein
  • Q oxygen or sulfur
  • Y 1 for hydrogen, chlorine, bromine, iodine, for each methyl, ethyl, n- or i-substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl Propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, for methylamino, Eth
  • Y 2 for hydrogen, amino, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, optionally substituted by fluorine and or chlorine, methoxy or ethoxy, for propenyl or propynyl, for each cyclopropyl, cyclobutyl or cyclopropylmethyl optionally substituted by fluorine and / or chlorine, or for each optionally phenyl or benzyl substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or together with the rest ⁇ l for each propane optionally substituted by methyl and / or ethyl 1,3-diyl (trimethylene) or butane-1,4-diyl (te
  • n 0, 1 or 2
  • R 5 represents methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, methylthio, each optionally substituted by fluorine or chlorine,
  • R 6 for hydroxy, formyloxy, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy each optionally substituted by fluorine, chlorine, methoxy or ethoxy , Propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propyl Propenyloxy
  • R 7 for hydrogen, cyano, fluorine, chlorine, bromine, each for where appropriate
  • R 8 for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenyl or propynyl optionally substituted by fluorine or chlorine, for optionally substituted by fluorine, chlorine, bromine , Methyl or ethyl substituted cyclopropyl, or for each optionally substituted by fluorine,
  • R 9 for hydroxy, formyloxy, for each optionally by cyano, fluorine,
  • R 10 for hydrogen, cyano, fluorine, chlorine, bromine, or for each optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy
  • R 11 represents hydrogen, each represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, or represents cyclopropyl which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl,
  • R 12 stands for hydrogen, for methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for cyclopropyl which is optionally substituted with fluorine, chlorine, bromine, methyl or ethyl, and
  • R 13 represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.
  • Group Ib which is particularly preferred as active ingredient components of Group 1 are those compounds of the formula (I) in which
  • R 1 , R 2 and R 3 have the meanings given above for the compounds of “Group la” and are very particularly preferred and
  • R 4 represents the heterocyclic grouping below
  • Y for hydrogen, for in each case optionally substituted by fluorine and or chlorine, methoxy or ethoxy, methyl, ethyl, n- or i-propyl, for ethenyl, propenyl or propynyl, for in each case optionally substituted by fluorine and / or chlorine cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for phenyl or benzyl optionally substituted in each case by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy.
  • a particularly preferred “active ingredient group 1” group “Group 1c” are those compounds of formula (I) in which
  • R 1 , R 2 and R 3 have the meanings given above for the compounds of “Group la” and are very particularly preferred and
  • R 4 represents the heterocyclic grouping below
  • Y 1 represents hydrogen or methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy and
  • Y for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, for propenyl or propynyl, for each optionally by Fluorine and / or chlorine substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for phenyl or benzyl optionally substituted by fluorine, chlorine, methyl, ethyl, methoxy or ethoxy.
  • a particularly preferred “group ID” as active ingredient components of group 1 are those compounds of the formula (I) in which
  • R 1 , R 2 and R 3 have the meanings given above for the compounds of “Group 1” as being particularly preferred and
  • R 4 represents one of the heterocyclic groupings below
  • Double bond are - together with the adjacent residue ⁇ l also stands for a benzo group
  • Y for hydrogen, for each methyl, ethyl, n- or i- substituted by fluorine and / or chlorine, methoxy or ethoxy
  • R 1 , R 2 , R 3 and R 4 each have the meanings given above as preferred, particularly preferred or very particularly preferred.
  • the compounds of the general formulas (I-Al) to (I-A4), of the general formulas (I-Bl) to (I-B4) and of the general formulas (I-Cl) to (I-C4) become further active ingredients -Components of Group 1 especially highlighted:
  • R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 each have the above as preferred, particularly preferred or meanings given with very particular preference.
  • the active substances of group 2 can be assigned to their chemical structure according to the following active substance classes:
  • Amides e.g. Isoxaben, Picolinafen, Propanil
  • aryl heterocycles e.g. Azafenidin, Benzfendizone, Butafenacil-allyl, Carfentrazone-ethyl, Cinidon-ethyl, Fluazolate, Flumiclorac-pentyl, Flumioxazin, Flupropacil, Fluthiacet-methyl, Oxi-argol, Oxadiazon, oxadiazon, oxadiazon , Pyraflufen-ethyl, pyridate, pyridafol, sulfentrazone, thidiazimin, 4- [4,5-dihydro-4-methyl-5-oxo- (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5-fluoro-benzenecarboth
  • carboxylic acid derivatives e.g. clopyralid, dicamba, fluroxypyr, picloram, Triclopyr
  • benzothiadiazoles e
  • Diphenyl ether e.g. Acifluorfen-sodium, Aclonifen, Bifenen-ethyl, Fluoroglycofen, Fluoroglyofen Lactofen, oxyfluorfen
  • ureas e.g. chlorotoluron, diuron, isoproturon, linuron, metobromuron, metoxuron
  • imidazolinones e.g. imazamethabenz-methyl
  • Imazamox, imazaquin, imazethapyr isoxazoles (e.g. isoxaflutole), nicotinanilides (e.g. diflufenican), nitriles (e.g. bromoxynil, loxynil), organophosphorus compounds (e.g. anilofos, glufosinate-ammonium, glyphosate-isopropylammonamide (sulfo) oxy-oxyacetylammonium, sulfo Flufenacet, Mefenacet), phenoxycarboxylic acid derivatives (e.g.
  • pyrazoles e.g. pyrazolates, pyrazoxyfen
  • pyridazinones e.g. norflurazone
  • pyridines e.g. dithiopyr, thiazopyr
  • pyrimidinyl (thio ) benzoates e.g. bispyribac, pyribenzoxime, pyrithiobac, pyrimino-bac
  • sulfonylureas e.g.
  • Fentrazamides Fentrazamides
  • thiocarbamates e.g. butylates, dimepiperates, EPTC, Esprocarb, Molinate, Orbencarb, prosulfocarb, triallates
  • triazines e.g. ametryn, afrazin, cyanazines, dimexyflam, simazin, terbuthylazine, terbutryn
  • triazinones e.g. Hexazinone, Metamitron, Metribuzin
  • Triazole e.g. Amitrole
  • Triazolinone e.g. Amicarbazone, Flucarbazone-sodium, Propoxycarbazone-sodium
  • Triazolopyrimidine e.g. Cloransulam-methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam (e.g. Mesotrione), Triketone
  • Fentrazamide flufenacet, acetochlor, alachlor, amicarbazone, amidosulfuron,
  • the agents according to the invention preferably contain one or two active substances from group 1 and additionally 1, 2, 3 or 4 active substances from group 2 and / or an active substance from group 3.
  • the agents according to the invention particularly preferably contain an active ingredient of group 1 and additionally 1, 2 or 3 active ingredients of group 2 and / or an active ingredient of group 3.
  • the agents according to the invention very particularly preferably contain an active ingredient of group 1 and one or two active ingredients of group 2 and / or an active ingredient of group 3.
  • Table 2 Examples of combinations consisting of an active ingredient from group 1 and 1, 2 or 3 active ingredients from group 2 and / or a compound from group 3
  • the active compound combinations defined above from the substituted aryl ketones of the formula (I) and the above-mentioned active compounds of group 2 have very good herbicidal activity, with very good crop tolerance, and in different crops, especially in cotton, Barley, potatoes, corn, rice, soybeans, sunflowers, wheat and sugar cane, especially in barley, corn, rice and wheat, especially in rice, can be used to selectively control monocot and dicot weeds and that they can also be used to control monocots and dicot weeds can be used in the semi and non-selective range.
  • the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 to 1 part by weight of active ingredient in group 1 accounts for 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight, active ingredient in group 2.
  • Antidots which are capable of antagonizing the damaging effect of a herbicide on the crop plants, especially the group 3 compounds listed above are suitable, the damaging effect of active compounds of the formula (I) and their salts, optionally also in combination with one or more of the active ingredients of group 2 mentioned above, to be completely removed from the crop plants without impairing the herbicidal activity against the weeds.
  • a preferred embodiment is therefore also a mixture comprising a compound of the formula (T) and / or its salts on the one hand and 2,4-D and or its derivatives on the other hand, optionally in combination with one or more of the active ingredients of group 2 mentioned above.
  • Typical Derivatives of 2,4-D are, for example, their esters.
  • the advantageous effect of the crop plant tolerance of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the abovementioned under (c), compounds which improve tolerance to crop plants (antidots / safeners).
  • all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the fransgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground plant parts and organs of the plants, such as sprout, leaf, flower and root, by way of example
  • Leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhiozomes are listed.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • the preferred fransgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting,
  • Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients are mentioned as examples of fransgenic plants, with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • twins ben the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CrylA), Cry ⁇ A (c), CryllA, CrylllA, Cry ⁇ iB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are generated in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicides
  • Active substances for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the fransgenic plants.
  • “Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. maize,
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and in the case of propagation material, in particular in the case of seeds, by means of single- or multi-layer coating.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Nicotiana, Phaseolus, Pisum, Solanum, Vicia Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriochaimis, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium,
  • the active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and rail systems, on paths and squares, but also for stubble treatment and with the minimum tillage process become. They are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silicic acid, aluminum oxide and silicates, as solid carriers for granulates are possible: eg broken and fractionated natural ones Rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Mineral and vegetable oils can also be used as additives.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • mineral-based or vegetable-compatible oils for example the commercial preparation "Rako Binol”
  • ammonium salts such as ammonium sulfate or ammonium rhodanide in the formulations as further additives.
  • the new active ingredient combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, spraying, dusting or scattering.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • X % damage by herbicide A (active ingredient of the formula I) at p kg / ha
  • Y % damage by herbicide B (active ingredient of the formula H) at q kg / ha
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Emulsifier 1 part by weight of benzyloxypolyglycol ether
  • an active substance preparation 1 part by weight of an active substance combination according to the invention is mixed with the stated amount of solvent and, after addition of the stated amount of the emulsifier, diluted with water to the desired concentration.
  • Planters 500 cm are filled with soil from a rice field. 3 each
  • Rice plants (variety: Nipponbare, 2-3 leaf stage, height: approx. 15 cm) are planted in the middle of the planters. Seeds of Cyperus, Echinochloa, Lindernia, Rotala and Elatine are sown in the same planters. The soil in the vessels is kept moist. After two days, each planter is dammed up to a water depth of 2-3 cm.
  • the necessary amount of active ingredient or formulation is dissolved in several milliliters (2-3 ml) of the solvent (acetone or DMF), if necessary mixed with an emulsifier (1 ml) and diluted with water to the desired concentration.
  • the solvent acetone or DMF
  • Mixtures are produced by mixing a predetermined, dissolved amount of the first active ingredient with the necessary amount of the second active ingredient (and, if desired, with additional active ingredients / formulations or other ingredients) and then diluting it with water to the desired concentration.
  • a surfactant compound (Renex 36) is added to the spray solution in pre and post emergence tests at a concentration of 0.1%.
  • the amount of active ingredient or formulation is chosen so that the desired application rate per ha is achieved.
  • Test plants are grown under controlled conditions (temperature and light). As soon as the plants have reached a height of 5 to 15 cm, the test compound or the combination of test compounds is sprayed on in such a way that the desired amounts of active compound per unit area are applied.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 l of water / ha.
  • the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

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  • 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)
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Abstract

L'invention concerne des agents contenant a) au moins un composé de formule (I), dans laquelle A, R<1>, R<2>, R<3> et R<4> ont la signification indiquée dans la description, b) des herbicides connus tels que ceux indiqués dans la description et/ou c) des phytoprotecteurs connus tels que ceux indiqués dans la description. Cette invention concerne également l'utilisation de ces agents dans la lutte contre la croissance indésirable de plantes.
EP02758472A 2001-08-30 2002-08-19 Melanges herbicides a base d'arylcetones substituees Withdrawn EP1423005A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10142333 2001-08-30
DE10142333A DE10142333A1 (de) 2001-08-30 2001-08-30 Herbizide Mischungen auf Basis von substituierten Arylketonen
PCT/EP2002/009243 WO2003020033A1 (fr) 2001-08-30 2002-08-19 Melanges herbicides a base d'arylcetones substituees

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CA (1) CA2458766A1 (fr)
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AR036385A1 (es) 2004-09-08
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DE10142333A1 (de) 2003-03-20

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