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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

• the invention relates to new herbicidal, synergistic active substance combinations which contain known substituted aryl ketones on the one hand and one or more known herbicidally active compounds on the other hand and, if appropriate, additionally contain a nerbinding which improves the tolerance of crop plants and with particularly good
• Success can be used to control weeds in various crops or to control monocot and dicot weeds in the semi and non-selective range.
• Substituted aryl ketones are known to be effective herbicides (cf. WO-A-96/26200,
• the invention relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
• A represents a single bond or alkanediyl having 1 to 6 carbon atoms
• R 1 represents one of the groupings below
• n the numbers 0 to 6
• R 5 for halogen each optionally by cyano, halogen or
• R 6 for hydroxyl, formyloxy, halogen, for alkoxy, alkylthio which are each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, Alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, for alkenyloxy or alkynyloxy each optionally substituted by cyano or halogen, or for each optionally substituted by nitro, cyano, halogen, d- -Alkyl, Ci-C4-haloalkyl, Ci- C 4 -alkoxy or - -haloalkoxy substituted phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyl
• R 7 for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy
• Alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl,
• R 8 for hydrogen, for optionally by cyano, halogen or -C 4 -
• Cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety or represents in each case optionally substituted by nitro, cyano, halo, C ⁇ -C alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C C haloalkoxy phenyl or phenyl-C 1 -C -alkyl, R 9 for hydroxy, formyloxy, for alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or C 4 -C alkoxy, for each optionally substituted by cyano or halogen
• R 10 for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or Ci - alkoxy stands,
• R 11 for hydrogen, for optionally by cyano, halogen or dC 4 -
• R 12 for hydrogen, for optionally by cyano, halogen or C ! -C 4 -
• R 13 represents hydrogen, cyano, carbamoyl, halogen, or each optionally substituted by alkyl, alkoxy, alkoxycarbonyl, alkylthio optionally substituted by cyano, halogen or Ci-C 4 alkoxy, Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups,
• R 2 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for in each case optionally by for optionally by
• R 3 for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, -C4-alkylthio, CrC 4 -alkylsulfinyl or -C4-alkylsulfonyl , Alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl 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 optionally - alternatively or additively - 1 to 3 oxygen atoms, sulfur atoms, Contains -SO groups, -S ⁇ 2 groups, -CO groups and / or -CS groups,
• m preferably represents the numbers 0, 1, 2, 3 or 4.
• A preferably represents a single bond or 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, if appropriate, in each case
• R 3 preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, bromine, -Ca-alkoxy, d-Cs-alkylthio, C 1 -C 3 alkylsulfinyl or -CC 3 alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl 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 3, particularly preferably 2, and very particularly preferably 1 substituent.
• Alkyl part or for phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino which is optionally substituted by fluorine, chlorine, bromine, iodine, C1-C4-alkyl or C1-C4-alkoxy, 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 represents a benzo group, and
• R 5 preferably represents fluorine, chlorine, bromine, alkyl or alkylthio, each of which is optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C 3 -alkoxy, each having 1 to 5 carbon atoms, optionally by fluorine, chlorine, bromine, C. 1 -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, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 5 carbon atoms in each of which is optionally substituted by cyano, fluorine, chlorine or C 1 -C 3 -alkoxy Alkyl groups, for alkenyloxy or alkynyloxy each optionally substituted by cyano, fluorine, chlorine and / or bromine, each having 3 to 5 carbon atoms, or for each optionally by
• R preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
• Alkylsulfonyl or alkoxycarbonyl each with 1 to 5 carbon atoms in the alkyl groups, or for cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine or dd-alkyl.
• R 8 preferably represents hydrogen, each alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine or dC 3 -alkoxy, and in each case alkenyl or alkynyl which is optionally substituted by cyano, fluorine, chlorine and / or bromine 3 to 5 carbon atoms, each for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, fluorine, chlorine, bromine or dd-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 3
• R 9 preferably represents hydroxyl, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 5 carbon atoms in the alkyl groups, each of which is optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C 3 -alkoxy in each case optionally substituted by cyano, fluorine, chlorine and / or bromine, alkenyloxy or alkynyloxy each having 3 to 5 carbon atoms, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, iodine or (in each case optionally substituted by fluorine and / or chlorine ) d- C 4 -alkyl or C 1 -C 4 -alkoxy substituted phenylalkoxy, phenylcarbonyloxy, phenylcarbonylalkoxy or phenyl
• R 10 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
• R u preferably represents hydrogen, alkyl optionally substituted by cyano, fluorine, chlorine, bromine or dC 3 -alkoxy having 1 to 5 carbon atoms or cycloalkyl optionally substituted by cyano, fluorine, chlorine, bromine or dd-alkyl having 3 to 6 carbon atoms.
• R 12 preferably represents hydrogen, alkyl which has 1 to 5 carbon atoms and is optionally substituted by cyano, fluorine, chlorine, bromine or dC 3 -alkoxy or cycloalkyl which is optionally substituted by cyano, fluorine, chlorine, bromine or C 1 -C 3 -alkyl with 3 to 6 carbon atoms.
• R 13 preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, bromine or C 1 -C 3 -
• n particularly preferably represents the numbers 0, 1, 2 or 3.
• R particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfmyl, 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 methylthio, ethylthio
• R 3 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 optionally substituted by fluorine
• R particularly preferably represents one of the heterocyclic groupings below
• Y 2 preferably represents hydrogen, hydroxyl, amino, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, which are each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, for each optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, ethynyl, propynyl or propenyloxy, for each optionally substituted by fluorine and / or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclo - hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, or for each optionally by fluorine, chlorine
• R 5 particularly preferably represents fluorine, chlorine, bromine or methyl, ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, for phenyl optionally substituted by fluorine, chlorine, methyl or methoxy, or optionally also - for the Case that m is 2 - together with a second radical R 5 for ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
• a second radical R 5 for ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) or butane-1,4-diyl (
• R 6 particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl-thio, methylsulfinyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy,
• 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, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano, flu
• R 9 particularly preferably stands for hydroxyl, formyloxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n- 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, each optionally by cyano, fluorine
• 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 11 particularly preferably represents hydrogen, in each case optionally through
• R 12 particularly preferably represents hydrogen, in each case optionally by
• R 13 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine,
• Bromine or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
• a group of compounds which is particularly preferred as active ingredient components of group 1 are those compounds of the formula (I) in which
• n 0, 1 or 2
• A represents methylene
• R 1 represents one of the groupings below
• R for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy,
• R 3 for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylthio , Methylsulfinyl, ethylsulfinyl, methylsulfony, ethylsulfonyl or dimethylaminosulfonyl,
• R 4 represents the heterocyclic grouping below
• Q oxygen or sulfur
• Y 1 for hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylenesulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, Methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-prop
• Benzylamino 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 represents a benzo group, and
• R> 5 for in each case optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, for phenyl, or optionally also - in the event that m represents 2 - together with a second radical R 5 represents ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene),
• R 6 for hydroxyl, 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 Propenyl
• R 7 for hydrogen, cyano, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, each optionally substituted by fluorine, chlorine, methoxy or ethoxy , n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, R 8 for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy
• R 10 for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- which is optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy 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 11 for hydrogen each optionally by fluorine, chlorine, bromine,
• R 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, 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.
• a further particularly preferred group as active ingredient components are also those compounds of the formula (I) in which
• R, R and R have the meanings given above as being particularly preferred and
• R> 4 represents one of the heterocyclic groupings below
• Y 1 for hydrogen, cyano, fluorine, chlorine, bromine, for each substituted by fluorine, chlorine, methoxy or ethoxy
• Methyl, ethyl, n- or i-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, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, for ethenyl, propenyl, ethynyl, propynyl, propenyloxy, propenylthio or propenylamino, each optionally substituted by fluorine and / or chlorine, for each optionally Cyclopropyl
• Y 2 for hydrogen, hydroxy, amino, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy , for propenyl or propynyl, for cyclopropyl, cyclobutyl or cyclopropylmethyl, each optionally substituted by fluorine and / or chlorine, or for in each case optionally phenyl or benzyl substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or together with an adjacent radical Y 1 or Y 2 for each optionally by methyl and / or ethyl-substituted propane-1,3-diyl
• a further particularly preferred group of compounds as active ingredient components of group 1 are also those compounds of formula (I) in which
• R 1 , R 2 and R 3 have the meanings given above as being particularly preferred and
• R 4 represents the heterocyclic grouping below
• Y 2 for hydrogen, hydroxy, amino, for each methyl optionally substituted by fluorine and / or chlorine, methoxy or ethoxy,
• R 1 , R 2 , R 3 and R 4 each preferably have the meanings given as being very particularly preferred.
• R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R s , R 9 , R 10 , R 11 , R 12 and R 13 preferably have the meanings given above as being particularly preferred ,
• the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
• the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
• 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, oxadiazon, oxadisargyl, profluazole, pyraflufen-ethyl, pyridate, pyridafol, sulfentrazone, thidiazimin, 4- [4,5-dihydro-4-memyl-5-oxo (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5 -fluoro-ber_zolcarbothioamide), aryloxyphenoxypropionates (e.g.
• 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, picloram, triclopyr), benzothiadiazoles (e.g. bentazone), chloroacetamides (e.g.
• acetochlor alachlor, butachlor, (S-) dimethenamid, metazachlor, metolachlor, pretilachlor, propachlor, propisydimione (e.g. , Clefoxydim, Cycloxydim, Sethoxydim, Tralkoxydim), Dinitro-aniline (e.g. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Trifluralin), Diphenylether (e.g. Acifluorfen-sodium, Aclonifen, Bifenox, Fluoroglycofen-ethyl,
• Diphenylether e.g. Acifluorfen-sodium, Aclonifen, Bifenox, Fluoroglycofen-ethyl
• Fomesafen, lactofen, oxyfluorfen), ureas e.g. chlorotoluron, diuron, isoproturon, linuron, metobromuron, metoxuron
• imidazolinones e.g. imazamethabenz-methyl, imazamox, imazaquin, imazethapyr
• isoxazole e.g. isoxaflanilufen
• Nitriles e.g. bromoxynil, loxynil
• organophosphorus compounds e.g. anilofos, glufosinate-ammonium, glyphosate-isopropylammonium,
• Sulfosates Sulfosates
• oxyacetamides e.g. flufenacet, mefenacet
• phenoxycarboxylic acid derivatives e.g. 2,4-D, dichloroprop-P, MCPA, MCPB, mecoprop
• pyrazoles e.g. pyrazolates, pyrazoxyfen
• pyridazinones e.g. norflurazone
• pyridines e.g. dithiopyr, Thiazopyr
• pyrimidinyl (thio) benzoates e.g. bispyribac, pyribenzoxime, pyrithiobac, pyriminobac
• sulfonylureas e.g. amidosulfuron, azimsulfuron, bensulfuron-methyl
• Triazolopyrimidine e.g. Cloransulam- methyl, diclosulam, florasulam, flumetsulam, metosulam), triketones (eg mesotrione, sulcotrione), uracile (eg bromacil).
• BAS-145138 Benoxacor, dichlormid, Furilazole, MON-13900 and R-29148.
• the agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally one active substance from group 3.
• the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
• each of an active ingredient from group 1 and one or two active ingredients from group 2 - or from one active ingredient from group 1, one or two active ingredients from group 2 and a compound from 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 taken from Table 1.
• Table 2 Examples of combinations consisting of a group 1 active ingredient and a group 2 active ingredient
• 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, corn, rice, soybeans, sunflowers, wheat and sugar cane, especially in barley, corn, rice and wheat, especially in rice, can be used to selectively control monocotyledon and dicotyledon weeds and that they can also be used to control monocotyledon and dicotyledonous weeds Weeds in the semi and non-selective range can be used.
• 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 part by weight of active ingredient of the formula (I) comprises 0.001 to 1000 parts by weight, preferably 0.002 to 500 parts by weight and particularly preferably 0.01 to 100 parts by weight of active ingredient of group 2.
• Antidotes that are capable of the harmful effects of a herbicide on the crop to antagonize plants are suitable, the damaging effect of active substances of formula (I) and their salts, optionally also in combination with one or more of the above-mentioned active substances of group 2, approximately on the crop plants to be completely canceled without affecting 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, if appropriate in combination with one or more of the active substances of group 2 mentioned above.
• Typical derivatives of 2,4-D are, for example their esters.
• 2,4-D is a known herbicide.
• 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 above (c) mentioned compounds which improve the tolerance of the crop plants (antidots / safeners).
• plants and parts of plants can be treated.
• Plants are understood here to mean all plants and plant populations, such as desired and undesirable 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 sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhiozomes.
• the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
• 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 using the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and on propagation material, in particular on seeds by wrapping one or more layers .
• the customary treatment methods for example by dipping, spraying, evaporating, atomizing, scattering, spreading and on propagation material, in particular on seeds by wrapping one or more layers .
• those plants are emphasized which tolerate so-called ALS, 4-HPPD, EPSP and / or PPO inhibitors, such as, for example, acuron plants.
• the active substances according to the invention can e.g. can be used in the following plants:
• Dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
• Dactyloctenium Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Pous, Sagaria, Setaria, Rottboell. Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum,
• Oryza Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
• 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 powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules
• natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
• synthetic rock powders such as highly disperse silica, aluminum oxide and silicates
• emulsifying and / or foaming agents are possible: e.g. non-ionic 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 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 used in individual formulations mixed in the application, ie applied 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 or vegetable oils which are compatible with plants (e.g. the commercial preparation "Rako Binol") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
• the new active substance 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
• the effect of the combination is super-additive, that is, it shows a synergistic effect.

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