EP1423009A2 - Herbicides a base de cetones d'aryle substituees - Google Patents

Herbicides a base de cetones d'aryle substituees

Info

Publication number
EP1423009A2
EP1423009A2 EP02772170A EP02772170A EP1423009A2 EP 1423009 A2 EP1423009 A2 EP 1423009A2 EP 02772170 A EP02772170 A EP 02772170A EP 02772170 A EP02772170 A EP 02772170A EP 1423009 A2 EP1423009 A2 EP 1423009A2
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
cyano
chloro
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Withdrawn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
EP02772170A
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 EP1423009A2 publication Critical patent/EP1423009A2/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Withdrawn legal-status Critical Current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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to new herbicidal active substance combinations which contain known substituted aryl ketones on the one hand and one or more known herbicidally active compounds and / or a compound which improves the tolerance of crop plants on the other hand and, with particularly good success, for weed control in various crop plants or for combating monocotyledons and dicot weeds can be used in the semi and non-selective range.
  • Compounds which improve crop plant tolerance are particularly advantageous as broadly active combination preparations for the selective control of monocotyledon and dicotyledon weeds in crops of useful plants, such as, for example, in cotton, barley, potatoes, corn, rice, soybeans, sunflowers, wheat and sugar cane, but also for Control of monocot and dicot weeds in the semi and non-selective range can be used.
  • the invention relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • a 1 represents a single bond or O (oxygen)
  • A represents a single bond or alkanediyl (alkylene), alkenediyl or alkynediyl,
  • R 1 stands for hydrogen or for optionally substituted alkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or for the grouping -C (Q) -R 2 ,
  • R represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkyl.amino, dialkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, Alkenyl, alkenyloxy, alkenylamino, Alkenyloxya ino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkyl alkyl, cycloalkylalkoxy, Cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,
  • X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally substituted alkyl, alkoxy, alkylthio,
  • Y for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio,
  • n the numbers 0 to 6
  • R 3 stands for hydrogen, halogen or for optionally substituted alkyl, alkylthio or aryl, or - if m stands for 2 optionally together with a second radical R 3 represents oxygen or alkanediyl (alkylene),
  • R 4 for hydroxy, formyloxy, halogen, or for optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfmyl, arylsulfonyl, arylcarbon Arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfmyl or arylalkylsulfonyl,
  • R 5 stands for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
  • R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 7 represents hydroxy, formyloxy, or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
  • R represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
  • R 9 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
  • R 10 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
  • R 11 represents hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
  • 1,3-dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoro- methyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (sulfentrazone), methyl 2- [[[[(4,6-dimethyl-2-pyrimidinyl) amino] -carbonyl] -amino] -sulfonyl] -benzoate (sulfometuron-methyl), N-phosphonomethyl-glycine-trimethylsulfomum (sulfosate), N- (4,6-dimemoxy-pyrimidin-2-yl) -N '- (2- ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-but
  • R1 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
  • 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 Group halogen, hydroxy, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy and (C !
  • R 3 halogen, (C r C 4 ) haloalkyl, (C r C 4 ) haloalkoxy, nitro, (C r C 4 ) alkyl, (C r C) alkoxy, (Cj-C4) alkylsulfonyl, ( C 1 -C4) alkoxycarbonyl or (C 1 -C4) alkylcarbonyl;
  • R 4 is hydrogen or methyl
  • R 5 halogen; Nitro, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C r C4) haloalkoxy, (C 3 - C 6 ) cycloalkyl, phenyl, (C r C 4 ) alkoxy, cyano , (C r C 4 ) alkylthio, (C r C4) alkylsulfinyl, (C1-C 4 ) alkylsulfonyl, (C 1 -C 4 ) alkoxycarbonyl or (Cj-C 4 ) alkylcarbonyl;
  • R 1 is hydrogen, (C r C 6 ) - alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, each of the latter four radicals being unsubstituted or by one or more substituents from the group halogen, (C ⁇ -C4) -Alkyloxy, halogen-
  • R 3 halogen, halogen ⁇ ! -C 4 ) alkyl, halo (C r C 4 ) alkoxy, (C r C 4 ) alkyl, (C r C 4 ) arkoxy, (C r C 4 ) alkylsulfonyl, (C r C 4 ) - alkoxycarbonyl, (C r C 4 ) -
  • R 4 is hydrogen, methyl
  • R 5 halogen, (C r C 4 ) alkyl, halogen (C 1 -C 4 ) alkyl, halogen ⁇ C 4 ) alkoxy,
  • 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. Preferred meanings of the groups listed above in connection with the formula (I) are defined below.
  • a 1 preferably represents a single bond or O (oxygen).
  • a 2 preferably stands for a single bond or for alkanediyl (alkylene), alkenediyl or alkynediyl each having up to 6 carbon atoms.
  • Q is preferably O (oxygen) or S (sulfur).
  • R 1 preferably represents hydrogen, each optionally substituted by cyano, halogen, -CC alkoxy, CC 4 - alkylthio, dC 4 - alkylsulfinyl or CC 4 - alkylsulfonyl substituted alkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl or optionally substituted by cyano or halogen
  • Alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or -CC 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, each optionally by Nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 -
  • R preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 -alkoxy-carbonyl, each optionally by cyano, halogen, C 1 -C 4 -alkoxy, Cj-C 4 - alkylthio, C] -C 4 - alkylsulfinyl or C, -C 4 - alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxyamino or alkylhydrazino, each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino, N- Alkyl-alkoxyamino or dialkylhydrazino, each with 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alken
  • Cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C 1 -C 4 -alkyl, C ⁇ - C 4 haloalkyl, C ⁇ -C 4 -alkoxy, C 4 -haloalkoxy or C ⁇ -C 4 -
  • C ⁇ -C4-haloalkyl C ⁇ -C4 alkoxy, dC 4 haloalkoxy, C] -C 4 - alkylthio, C] -C4 haloalkylthio, C ⁇ -C 4 -alkoxy-carbonyl, C 3 -C 6 - Cycloalkyl or C 3 - C 6 -cycloalkyl-C 4 -alkyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyloxy, heterocyclylalkylthio or heterocyclyl bis, and additionally at least one heteroatom selected from the series nitrogen (N) (but not more than 5 N atoms), oxygen (O) (but not more than 2 O atoms), sulfur (S) (but not more than 2 S atoms), SO or SO 2 and optionally also a group selected from
  • halogen preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or in each case optionally by cy.ano, halogen,
  • Y preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen, -CC 4 alkoxy, C r C 4 - alkylthio, C r C 4 - alkylsulfinyl or C r C 4 -alkyl-sulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.
  • Z preferably represents one of the groupings below
  • m preferably represents the numbers 0 to 3.
  • R 3 preferably represents hydrogen, halogen, represents in each case optionally cyano-, halogen, C ⁇ -C 4 -alkoxy, C 4 - alkylthio, dC 4 - alkylsulfinyl or C ⁇ -C 4 - alkylsulfonyl-substituted alkyl or alkylthio each having 1 to 6
  • R 4 preferably represents hydroxyl, formyloxy, halogen, represents in each case optionally cyano-, halogen, C ⁇ -C 4 -alkoxy, C 4 - alkylthio, C ⁇ -C 4 - alkylsulfinyl or C ⁇ -C 4 - alkylsulfonyl substituted alkoxy, alkylthio , Alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyl oxy or alkylsulfonyloxy having in each case 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyloxy or alkynyloxy having in each case 3 to 6 carbon atoms, represents in each case optionally substituted by nitro, cyano, halo, C ⁇ -C 4 -alkyl, C 4 haloalkyl, -C-C 4
  • R 5 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, each optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl
  • R 6 preferably represents hydrogen, represents optionally cyano-, halogen, C ⁇ -C 4 alkoxy, CC 4 - alkylthio, CC 4 - alkylsulfinyl or C ⁇ -C 4 alkyl sulfonyl-substituted alkyl having 1 to 6 carbon atoms, in each case optionally cyano or halogen substituted alkenyl or alkynyl each having 3 to 6 carbon atoms, each optionally by
  • R 7 preferably represents hydroxyl, formyloxy, each optionally through
  • R 8 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or each optionally by cyano, halogen or -C 4 -
  • R 9 preferably represents hydrogen, represents optionally cyano-, halogen or C ⁇ -C 4 - alkoxy-substituted alkyl, or represents optionally cyano-, halogen or C ⁇ -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
  • R 10 preferably represents hydrogen, alkyl which is optionally substituted by cyano, halogen or -CC alkoxy, or is optionally substituted by cyano, Halogen or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
  • R 1 ' preferably represents hydrogen, cyano, carbamoyl, halogen, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy ,
  • a 1 represents a single bond or O (oxygen).
  • a 2 particularly preferably represents a single bond or methylene
  • R 1 particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i -
  • ⁇ is particularly preferably hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, Ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t- Pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,
  • X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, 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-butylthio,
  • Butylamino dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
  • Y particularly preferably represents hydrogen, nitro, cy, ano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, 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-
  • R 3 particularly preferably represents the numbers 0, 1 or 2.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, 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, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- Butylthio, or for phenyl, or - if m stands for 2 - optionally together with a second radical R 3 for oxygen
  • R 4 particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyl , n- or i
  • R 5 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, in each case optionally by cyano, 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,
  • R 6 particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Ethyl, n- or i-propyl, n-, i-, s- or t-
  • R 7 particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy.
  • R 8 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy Propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio , Ethylthio, n- or i-
  • R 9 particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.
  • R 10 particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy
  • R 11 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or in each case optionally by cyano, fluorine, chlorine,
  • Methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
  • R 1 very particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methyl, n- or i-propyl, n- or i -Butyl, methylthio, ethylthio, n- or i-propylthio, for propenyl, each optionally substituted by fluorine and / or chlorine, butenyl, ethynyl, propynyl or butinyl, for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmefhyl, cyclobutylmethyl,
  • R 2 very particularly preferably represents hydrogen, amino, hydroxyamino, hydrazino, in each case optionally by cyano, fluorine, chlorine, methoxy,
  • X very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfmylmethyl, methylsulfonylmethyl, methoxy , Ethoxy, difluoromethoxy,
  • Y very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, methyl Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
  • n very particularly preferably represents the numbers 0 or 1.
  • R 3 very particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - for the Case that m is 2 - optionally together with a second radical R 3 for oxygen, propane-l, 3-diyl or butane-1,4-diyl.
  • R 4 very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, optionally substituted by fluorine and / or chlorine, Methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, propylnulfonyloxy, ethylsulfonyloxy, ethyl
  • R 5 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, each optionally substituted by fluorine and / or chlorine , n- or i-Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for each cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl.
  • R 6 very 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, methoxy or ethoxy, each in each case optionally propenyl, butenyl, propynyl or substituted by fluorine or chlorine Butinyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine or methyl, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenylmethyl.
  • R 7 very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- which are each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-
  • Methyl, ethyl, n- or i-propyl trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl-methoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.
  • R 8 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • 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 9 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
  • R 10 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
  • R very particularly preferably 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, methoxy or ethoxy , Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
  • a 1 , A 2 , Q, R 1 , R 2 , X, Y and Z each have the meanings given above as preferred, particularly preferred or very particularly preferred.
  • Mixture component of formula (I) is particularly highlighted.
  • the compounds of formula (I) are described in the patent applications given above for the substituted aryl ketones.
  • a 1 , A, R, X, Y and Z have the meaning given above,
  • Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
  • Z has the meaning given above, optionally in the presence of a dehydrating agent, such as dicyclohexyl carbodiimide, and optionally in the presence of one or more reaction auxiliaries, such as triethylamine and trimethylsilyl cyanide, and optionally in the presence of one or more diluents, such as acetonitrile, at temperatures between 0 ° C. and 150 ° C. implements (see the manufacturing examples),
  • a dehydrating agent such as dicyclohexyl carbodiimide
  • reaction auxiliaries such as triethylamine and trimethylsilyl cyanide
  • diluents such as acetonitrile
  • 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
  • clodinafop-propargyl cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop- R-methyl, quizalofop-P-ethyl), carboxylic acid derivatives (e.g. clopyralid, dicamba, fluroxypyr, piclor ⁇ am, triclopyr), benzothiadiazoles (e.g. bentazone), chloroacetamides (e.g. acetochlor, alachlor, butachlor, (S-) dimethenamid,
  • carboxylic acid derivatives e.g. clopyralid, dicamba, fluroxypyr, piclor ⁇ am, triclopyr
  • benzothiadiazoles e.g. bentazone
  • chloroacetamides e.g. acetochlor, alachlor, butachlor, (S
  • Metazachlor Metolachlor, Pretilachlor, Propachlor, Propisochlor
  • Cyclohexanediones e.g. Butroxydim, Clefoxydim, Cycloxydim, Sethoxydim, Tralkoxydim
  • Dinitro-aniline e.g. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin
  • Diifphenylin Triflural Aclonifen, bifenox, fluoroglycofen-ethyl, fomesafen, lactofen, oxyfluorfen
  • ureas e.g.
  • Flufenacet Mefenacet
  • phenoxycarboxylic acid derivatives e.g. 2,4-D, dichloroprop-P, MCPA, MCPB, mecoprop
  • pyrazoles e.g. pyrazolates
  • Pyrazoxyfen Pyrazoxyfen
  • pyridazinones for example norflurazon
  • pyridines for example dithiopyr, thiazopyr
  • pyrimidinyl (thio) benzoates for example bispyribac, pyribenzoxim, pyrithiobac, Pyrimino- bac
  • sulphonylureas for example amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Cyclosulfamuron, Ethoxysulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfuron, Iodosulfuron-methyl-sodium, Imazosulfuron, Metsulfuron-methyl, Nicosul requirementson, Oxasulfuron, Primisulfuron-methyl, ethylsulfosulfuron, Pyrosulfuron, Sul
  • Prosulfocarb, triallates triazines (e.g. ametryn, atrazine, cyanazines, dimexyflam, simazine, terbuthylazine, terbutryn), triazinones (e.g. hexazinones, metamitron, metribuzin), triazoles (e.g. amitrole), triazolinones (e.g.
  • amicarbazone zone sodium, fluc Propoxycarbazone-sodium
  • triazolopyrimidines eg cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam
  • triketones eg mesotrione, sulcorrione
  • uraciles eg bromacil
  • MCPA Mefenacet, Mesosulfuron, Mesotrione, Metolachlor, S-Metolachlor, Metosulam, Metsulfuron-methyl, Metribuzin, Molinate, Naproanilide, Nicosulfuron, OK-701, Oxadiargyl, Oxadiazon, Oxaziclomefone, Oxyfluin, Pendol Pretilachlor, Profoxydim, Propanil, Propoxycarbazone-sodium, Pyraclonil, Pyrazolate, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribenzoxim, Pyributi- carb, Pyriftalid, Pyriminobac-methyl, Qinclorac, Quinoclamine, Simazin, Simetryn, Sulcotronifine, Terburyl, Thuryltrione, Terburyl Tiocarbazil, tritosulfuron.
  • the agents according to the invention preferably contain one or two active ingredients
  • 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 additionally 1, 2 or 3 active ingredients of group 2 and / or an active ingredient of group 3.
  • each of an active ingredient of group 1 and additionally 1, 2 or 3 active ingredients of group 2 and / or a compound of group 3 - are listed in Table 2 below.
  • the names of the active compounds of the formula (I) (active compounds of group 1) are in each case the
  • 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 and are particularly effective in herbicidal activity 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 for the selective control of monocotyledonous and dicotyledonous weeds and that they too can be used to control monocot and dicot weeds in the semi and non-selective range.
  • the herbicidal activity of the active compound combinations according to the invention from compounds of groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
  • 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.
  • 1 to 1 part by weight of active compound of the formula (I) comprises 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 of active compound of group 2.
  • the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate 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 (I) 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 compatibility with crop plants 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.
  • 1 part by weight of active compound of the formula (I) or mixtures thereof with active compounds of group 2 account for 0.001 to 1000 parts by weight, preferably 0.01 to 100
  • Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated 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 transgenic 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 plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhiozomes become.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • 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.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, 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, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products, which go beyond the effects to be expected.
  • transgenic plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which contains them
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important ones are examples of transgenic plants
  • Cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, with corn, soybeans, potatoes, cotton and rapeseed being particularly emphasized.
  • the properties (“traits”) are particularly emphasized of the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b ), Cry ⁇ A (c), CrylLA, CrylTIA, C ⁇ yfflB2, Cry9c Cry2Ab, Cry3Bb and CryJJF 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.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, 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 transgenic plants.
  • “Bt plants” include corn, cotton, soy and potato, which are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rapeseed), IMI® (tolerance against Imidazolinone) and STS® (tolerance to sulfonylureas such as corn).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg 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 those developed in the future
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • 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, furthermore by single- or multi-layer coating.
  • ALS ALS
  • 4-HPPD EDPA
  • EPSP EPSP
  • / or PPO inhibitors such as, for example, acuron plants.
  • the active compounds according to the invention can be used, for example, in the following plants:
  • 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 track systems, on paths and squares, but also for stubble treatment and with the minimum tillage process become. They are also suitable as burners (killing herbs, for example in potatoes) or as defoliants (for example 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.
  • formulations are made in a known manner, e.g. 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.
  • extenders that is to say liquid solvents and / or solid carriers
  • 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, for example 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.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol
  • 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 meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and
  • Silicates as solid carriers for granules are possible: e.g. broken and fractionated natural 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; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, 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.
  • Other additives can be mineral and vegetable oils.
  • 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 ingredient combinations according to the invention are generally used in the form of ready-to-use formulations.
  • the in the drug combination Active ingredients contained in nations can also be mixed in individual formulations during use, ie applied in the form of tank mixes.
  • the new combinations of active ingredients can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and soil conditioners, is also possible.
  • mineral or vegetable oils e.g. the commercial preparation "Rako Binol”
  • ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new active compound 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 usual way, e.g. by pouring, 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.
  • the good herbicidal activity of the new active compound combinations can be seen from the examples below. While the individual active ingredients have weaknesses in the herbicidal action, the combinations consistently show a very good weed action which goes beyond a simple summation of action. 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 II) 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 2 ) are filled with soil (soil) from a rice field and 3 rice plants (variety: Nipponbare, 2-3 leaf stage, height: approx. 15 cm) are planted in the middle of the planters. Seeds 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 amount of active ingredient in the preparation described above is applied to the water surface in the planters using a pipette.
  • the water depth in the planters is kept at 2-3 cm.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
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Abstract

L'invention concerne des agents comprenant a) au moins un composé de formule (I) dans laquelle A, R?1, R2, R3 et R4¿ ont la signification mentionnée dans la description et b) des herbicides connus, comme mentionné dans la description et/ou c) des safeners comme mentionné dans la description. L'invention concerne également leur utilisation pour lutter contre la croissance indésirable de plantes.
EP02772170A 2001-08-30 2002-08-19 Herbicides a base de cetones d'aryle substituees Withdrawn EP1423009A2 (fr)

Applications Claiming Priority (3)

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DE10142334A DE10142334A1 (de) 2001-08-30 2001-08-30 Herbizide auf Basis von substituierten Arylketonen
DE10142334 2001-08-30
PCT/EP2002/009236 WO2003017766A2 (fr) 2001-08-30 2002-08-19 Herbicides a base de cetones d'aryle substituees

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AU (1) AU2002336988A1 (fr)
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CA (1) CA2457411A1 (fr)
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Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10143083A1 (de) * 2001-09-03 2003-03-20 Bayer Cropscience Ag Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern
CN101395164A (zh) * 2006-01-10 2009-03-25 罗伊·J·于 N-(膦酰基烷基)-氨基酸、其衍生物和组合物以及使用方法
WO2009089165A2 (fr) * 2008-01-07 2009-07-16 Auburn University Combinaisons d'herbicides et de phytoprotecteurs
RU2488270C2 (ru) * 2008-02-05 2013-07-27 Ариста Лайфсайенс Норс Америка, Ллс Твердый состав легкоплавкого активного соединения
MX2010008873A (es) * 2008-02-12 2010-08-31 Arysta Lifescience North Ameri Metodo para el control de vegetacion indeseada.
PL2337452T3 (pl) 2008-07-03 2015-05-29 Monsanto Technology Llc Połączenia derywatyzowanych sacharydowych środków powierzchniowo czynnych i środków powierzchniowo czynnych stanowiących tlenek eteroaminy jako adiuwanty do herbicydów
US9078443B1 (en) 2014-01-31 2015-07-14 Fmc Corporation Methods for controlling weeds using formulations containing fluthiacet-methyl and HPPD herbicides

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4780127A (en) * 1982-03-25 1988-10-25 Stauffer Chemical Company Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides
DE3525205A1 (de) * 1984-09-11 1986-03-20 Hoechst Ag, 6230 Frankfurt Pflanzenschuetzende mittel auf basis von 1,2,4-triazolderivaten sowie neue derivate des 1,2,4-triazols
DE3680212D1 (de) * 1985-02-14 1991-08-22 Ciba Geigy Ag Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen.
DE3939503A1 (de) * 1989-11-30 1991-06-06 Hoechst Ag Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden
US5700758A (en) * 1989-11-30 1997-12-23 Hoechst Aktiengesellschaft Pyrazolines for protecting crop plants against herbicides
US5804532A (en) * 1991-01-25 1998-09-08 Rhone-Poulenc Agriculture Limited Herbicidal 2-cyano-1,3-diones
GB9325618D0 (en) * 1993-12-15 1994-02-16 Rhone Poulenc Agriculture New herbicides
PT758324E (pt) * 1994-05-04 2005-07-29 Bayer Cropscience Ag Tiocarboxilamidas aromaticas substituidas e sua utilizacao como herbicidas
GEP20002093B (en) * 1995-02-24 2000-05-10 Basf Ag Pyrazol-4-yl-Benzoyl Derivatives and Herbicides Containing Them
JP3712148B2 (ja) * 1995-08-08 2005-11-02 株式会社エス・ディー・エス バイオテック 水田用除草剤組成物
JP3687933B2 (ja) * 1995-08-08 2005-08-24 株式会社エス・ディー・エス バイオテック 水田用除草剤組成物
KR970707119A (ko) * 1995-09-07 1997-12-01 오쓰카 유지로 트리아졸 유도체, 그를 함유하는 제초제 조성물, 및 그의 사용방법(triazole derivatives, herbicide composition containing the same, and method for using the same)
ES2318868T3 (es) * 1997-01-17 2009-05-01 Basf Se Derivados del benzoilo sustituidos por 3-heterociclilo.
TR200003752T2 (tr) * 1998-06-16 2001-06-21 Basf Aktiengesellschaft Sinerjik etkili herbisit karışımlar
DE19827855A1 (de) * 1998-06-23 1999-12-30 Hoechst Schering Agrevo Gmbh Kombinationen aus Herbiziden und Safenern
DE19846792A1 (de) * 1998-10-10 2000-04-13 Hoechst Schering Agrevo Gmbh Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
FR2785148B1 (fr) * 1998-11-02 2000-12-15 Rhone Poulenc Agrochimie Nouvelles compositions herbicide a base de glyphosate et d'isoxazoles
DE19853827A1 (de) * 1998-11-21 2000-05-25 Aventis Cropscience Gmbh Kombinationen aus Herbiziden und Safenern
SK3162002A3 (en) * 1999-09-08 2002-06-04 Aventis Cropscience Uk Ltd New herbicidal compositions
DE19950943A1 (de) * 1999-10-22 2001-05-17 Aventis Cropscience Gmbh Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Hemmstoffe der Hydroxyphenylpyruvat-Dioxygenase

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03017766A2 *

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AU2002336988A1 (en) 2003-03-10
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US20050090397A1 (en) 2005-04-28
AR036344A1 (es) 2004-09-01
WO2003017766A3 (fr) 2003-11-20
CA2457411A1 (fr) 2003-03-06
DE10142334A1 (de) 2003-03-20

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