WO2011018486A2 - Composition herbicide active comprenant des benzoxazinones - Google Patents

Composition herbicide active comprenant des benzoxazinones Download PDF

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WO2011018486A2
WO2011018486A2 PCT/EP2010/061718 EP2010061718W WO2011018486A2 WO 2011018486 A2 WO2011018486 A2 WO 2011018486A2 EP 2010061718 W EP2010061718 W EP 2010061718W WO 2011018486 A2 WO2011018486 A2 WO 2011018486A2
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methyl
inhibitors
compositions
group
salts
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WO2011018486A3 (fr
Inventor
Liliana Parra Rapado
William Karl Moberg
Trevor William Newton
Thomas Seitz
Anja Simon
Bernd Sievernich
Matthias Witschel
Helmut Walter
Richard Roger Evans
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BASF SE
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BASF SE
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    • 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
    • A01N43/72—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
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • Herbicidally active composition comprising benzoxazinones
  • the present invention relates to herbicidally active compositions comprising at least one benzoxazinone of formula I and at least one further compound selected from herbicidally active compounds and safeners.
  • crop protection compositions it is desirable in principle to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for the crop protection composition to control the harmful plants effectively, but at the same time to be compatible with the useful plants in question. Also desirable is a broad spectrum of activity allowing the simultaneous control of harmful plants. Frequently, this cannot be achieved using a single herbicidally active compound.
  • Benzoxazinones of formula I have been described for example in WO 02/066471 and EP 0640 600.
  • WO 09/115490 is directed to herbicidal compositions comprising pyroxasulfone and PPOs.
  • WO 10/66677 discloses herbicidal compositions comprising thaxtomines of formula I and PPOs of formulae II, III or IV.
  • compositions which are highly active against unwanted harmful plants.
  • compositions should have good compatibility with useful plants.
  • compositions according to the invention should have a broad spectrum of activity.
  • the present invention relates to herbicidally active compositions comprising:
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • R 2 is hydrogen, Nhb, d-C ⁇ -alkyl or Cs-C ⁇ -alkynyl;
  • R 3 is hydrogen or halogen
  • R 4 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl,
  • X is O or S
  • Y is O or S; and at least one further active compound selected from
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • mitose inhibitors b8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • bromobutide chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb
  • the invention relates in particular to compositions in the form of herbicidally active crop protection compositions comprising a herbicidally effective amount of an active compound combination comprising at least one benzoxazinone compound of formula I and at least one further compound selected from the herbicides B and the safeners C, as defined above, and also at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.
  • the invention also relates to compositions in the form of a crop protection composition formulated as a 1 -component composition comprising an active compound combination comprising at least one benzoxazinone compound of formula I and at least one further active compound selected from the herbicides B and the safeners C, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.
  • the invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one benzoxazinone compound of formula I, a solid or liquid carrier and/or one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.
  • compositions according to the invention comprising at least one benzoxazinone compound of formula I and at least one herbicide B have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum.
  • the herbicidal activity to be expected for mixtures based on the individual compound can be calculated using Colby's formula (see below). If the activity observed exceeds the expected additive activity of the individual compounds, synergism is said to be present.
  • the time frame within which the desired herbicidal action can be achieved, may be expanded by the compositions according to the invention comprising at least one benzoxazinone compound of formula I and at least one herbicide B and optionally a safener C. This allows a more flexibly timed application of the compositons according to the present invention in comparison with the single compounds.
  • compositions according to the invention comprising both at least one
  • benzoxazinone compound of formula I and at least one of the compounds mentioned under C also have good herbicidal activity against harmful plants and better
  • compositions according to the invention comprising at least one benzoxazinone compound of formula I, at least one herbicide B and at least one of the compounds mentioned under C have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum, and show better compatibility with useful plants than compositions comprising only one compound I and one herbicide B.
  • the invention furthermore relates to a method for controlling unwanted vegetation, in particular where crop plants are cultivated, for example in crops of the following crop plants: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • the invention also relates to a method for the desiccation or defoliation of plants. In the last-mentioned method, it is of no importance whether the herbicidally active
  • the organic moieties mentioned in the definition of the variables R 1 to R 11 are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, i.e. all alkyl, can be straight-chain or branched, the prefix C n -Cm denoting in each case the possible number of carbon atoms in the group.
  • C-i-Cs-alkyl CH 3 , C 2 H 5 , n-propyl, and CH(CHs) 2 ;
  • Ci-C3-haloalkyl a Ci-C3-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloro- methyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, penta
  • Ci-C4-haloalkyl a Ci-C3-haloalkyl radical as mentioned above, and also, for example, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1- (bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl,
  • nonafluorobutyl 1 ,1 ,2,2,-tetrafluoroethyl and 1-trifluoromethyl-1 ,2,2,2-tetrafluoroethyl;
  • Ci-C ⁇ -haloalkyl Ci-C4-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;
  • C3-C6-alkenyl for example 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1- dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1-ethyl-1- propenyl, 1-ethyl-2-
  • C3-C6-haloalkenyl a Cs-C ⁇ -alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloro- prop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2- en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3- bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3- tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl; C3-C6-alkynyl: for example
  • - C3-C6-haloalkynyl a Cs-C ⁇ -alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example
  • Ci-C3-alkoxy methoxy, ethoxy, propoxy, 1-methylethoxy
  • Ci-C4-alkoxy Ci-C3-alkoxy as mentioned above, and also, for example butoxy, 1-methylpropoxy, 2-methylpropoxy and 1 ,1-dimethylethoxy;
  • Ci-C ⁇ -alkoxy Ci-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1-dimethylpropoxy, 1 ,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1-dimethylbutoxy, 1 ,2- dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
  • the composition comprises as active compound A or component A at least one, preferebly exactly one,
  • benzoxazinone compound of formula 1.1 corresponds to benzoxazinone compounds of formula I wherein R 1 and R 2 are d-C ⁇ -alkyl, R 3 is halogen, R 4 is Cs-C ⁇ -alkynyl, X is S and Y is
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of the formula 1.2 (corresponds to compounds of formula I, wherein R 3 is C 3 -C6-haloalkynyl
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • d-C ⁇ -alkyl preferably CH3;
  • R 2 is hydrogen, NH2, Ci-C6-alkyl or C 3 -C6-alkynyl,
  • d-C ⁇ -alkyl preferably CH3;
  • R 3 is hydrogen or halogen
  • halogen more preferably F
  • X is O or S
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of the formula 1.3 (corresponds to compounds of formula I, wherein R 2 is NH2 or Cs-C ⁇ -alkinyl)
  • R 1 is hydrogen or Ci-C 6 -alkyl
  • Ci-C ⁇ -alkyl preferably CH3;
  • R 3 is hydrogen or halogen
  • halogen more preferably F
  • R 4 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, Cs-Ce-haloalkenyl, C 3 -C 6 -alkynyl, Ci-C 6 -alkoxy or C 3 -C 6 -cycloalkyl-Ci-C 6 - alkyl,
  • X is O or S
  • Y is O or S
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of the formula 1.4 (corresponds to compounds of formula I, wherein Y is S)
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • d-C ⁇ -alkyl preferably CH3;
  • R 2 is hydrogen, NH2, d-C ⁇ -alkyl or Cs-C ⁇ -alkynyl,
  • d-C ⁇ -alkyl preferably CH3;
  • R 3 is hydrogen or halogen
  • halogen more preferably F
  • R 4 is hydrogen, d-C ⁇ -alkyl, d-C ⁇ -haloalkyl, Cs-C ⁇ -cycloalkyl, Cs-C ⁇ -alkenyl,
  • X is O or S
  • Preferred compounds of the formula I which, as component A, are constituent of the composition according to the invention are the compounds 1.1 to 1.4 as defined above; in particular the compounds 1.1.1 , 1.2.1 , I.2.2, 1.3.1 , 1.3.2 and 1.4.1 listed below 1.1.1 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5- dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione,
  • the composition contains as component A the benzoxazinone of formula 1.1.1. According to a further particular preferred embodiment of the invention the composition contains as component A the benzoxazinone of formula 1.2.1.
  • composition contains as component A the benzoxazinone of formula I.2.2.
  • the composition contains as component A the benzoxazinone of formula 1.3.1.
  • the composition contains as component A the benzoxazinone of formula 1.3.2.
  • the composition contains as component A the benzoxazinone of formula 1.4.1.
  • the benzoxazinone compounds of the formula 1.1 are known from WO 02/066471.
  • benzoxazinone compounds of formulae 1.2, 1.3 and I.4 are novel and likewise form also part of the subject-matter of the present invention. Therefore the invention furthermore relates to benzoxazinone compounds of formulae I.2, 1.3 and 1.4:
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • R 2 is hydrogen, NH 2 , Ci-C 6 -alkyl or C 3 -C 6 -alkynyl;
  • R 3 is hydrogen or halogen
  • X is O or S
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • R 3 is hydrogen or halogen
  • R 4 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C3-C6-haloalkenyl, Cs-C ⁇ -alkynyl, Ci-C ⁇ -alkoxy or C3-C6-cycloalkyl-Ci-C6- alkyl;
  • X is O or S
  • Y is O or S
  • R 1 is hydrogen or d-C ⁇ -alkyl
  • R 2 is hydrogen, Nhb, Ci-C6-alkyl or Cs-C ⁇ -alkynyl;
  • R 3 is hydrogen or halogen
  • R 4 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl,
  • X is O or S.
  • benzoxazinone compounds of formula I and especially those of the formulae 1.2, 1.3 and 1.4 can be prepared by various routes, for example by the following processes:
  • the isocyanates IV are reacted with the ureas III, preferably in the presence of an activated carbonyl source such as carbonyldiimidazole, phosgene, diphosgene, triphosgene and chloroformic ester.
  • an activated carbonyl source such as carbonyldiimidazole, phosgene, diphosgene, triphosgene and chloroformic ester.
  • the cyclization is preferably carried out without isolation of the intermediate V.
  • the isocyanates IV in turn can be obtained from the corresponding amines Vl:
  • Alkylation of compounds of formula I where R 4 is hydrogen in a manner known per se leads to compounds of formula I, wherein R 4 is Ci-C ⁇ -alkyl, d-C ⁇ -haloalkyl, C3-C6- cycloalkyl, Cs-C ⁇ -alkenyl, Cs-C ⁇ -haloalkenyl, Cs-C ⁇ -alkynyl, Cs-C ⁇ -haloalkynyl or C3-C6- cycloalkyl-Ci-C ⁇ -alkyl.
  • the alkylation is carried out in a manner known per se, for example, using an alkylating reagent, e.g. a halide R 4 -Hal, in the presence of a base, in a solvent.
  • Processes A), B) and C) are preferably carried out in the presence of a suitable reaction auxiliary.
  • Suitable reactants are, in general, the customary inorganic or organic bases and acid acceptors. These preferably include the acetates, amides, carbonates, hydrogen- carbonates, hydrides, hydroxides and alkoxides of alkali metals and alkaline earth metals, i.e., for example, sodium acetate, potassium acetate, calcium acetate, lithium amide, sodium amide, potassium amide, calcium amide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium n-butoxide, sodium isobutoxide, sodium sec-butoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, potassium
  • Processes A), B) and C) are usually carried out in the presence of an inert diluent, suitable diluents generally being the usual organic solvents.
  • suitable diluents generally being the usual organic solvents.
  • suitable diluents generally being the usual organic solvents.
  • suitable diluents generally being the usual organic solvents.
  • These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, benzene, toluene, the xylenes, chlorobenzenes, dichlorobenzenes, cyclohexane, methylcyclohexane, dichloro- methane, trichloromethane, tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl
  • reaction temperatures can be varied within a substantial range, such as from 0 to 200 0 C.
  • the processes are preferably carried out at from 10 to 15O 0 C, in particular at from 2O 0 C to the boiling point of the reaction mixture in question.
  • the starting materials are employed in approximately equimolar amounts. However, it is also possible to use an excess of each of the reactants, up to
  • Processes A), B) and C) are expediently carried out under atmospheric pressure or under the inherent pressure of the reaction mixture in question. However, the processes may also be carried out under elevated or reduced pressure, in general at from 0.1 to 10 bar.
  • reaction mixtures in question are worked up by methods known per se, for example by diluting the reaction solution with water and subsequently isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent, and working up the organic phase to give the product.
  • the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ).
  • These are compounds which inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetyl CoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides).
  • ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
  • compositions contain at least one ALS inhibitor (herbicide b2).
  • the herbicidal activity of these compounds is based on the inhibition of acetolactate synthase und thus on the inhibiton of the branched chain aminoacid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • compositions contain at least one inhibitor of photosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the inhibition of the photosystem Il in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSII inhibitors are preferred.
  • compositions contain at least one inhibitor of protoporphyrinogen-IX-oxidase (herbicide b4).
  • the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
  • These inhibitors belong to the group E of the HRAC classification system.
  • the compositions contain at least one bleacher-herbicide (herbicide b5).
  • the herbicidal activity of these compounds is based on the inhibition of the carotinoid biosynthesis.
  • These include compounds which inhibit carotinoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds which inhibit the 4-hydroxyphenyl- pyruvat-dioxygenase (HPPD inhibitors, group F2 of HRAC classification) and compounds which inhibit carotinoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
  • compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase und thus on the inhibition of the aminoacid biosynthesis in plants.
  • These inhibitors belong to the group G of the HRAC classification system.
  • compositions contain at least one glutamin synthetase inhibitor (herbicide b7).
  • the herbicidal activity of these compounds is based on the inhibition of glutamin synthetase und thus on the inhibition of the aminoacid biosynthesis in plants.
  • These inhibitors belong to the group H of the HRAC classification system.
  • compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • the herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthetase. These inhibitors belong to the group I of the HRAC classification system.
  • the compositions contain at least one mitose inhibitor (herbicide b9).
  • the herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization and thus on the mitosis inhibition.
  • These inhibitors belong to the groups K1 and K2 of the HRAC classification system.
  • compounds of the group K1 in particular dinitroanilines, are preferred.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • the herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants.
  • These inhibitors belong to the group K3 of the HRAC classification system.
  • compositions contain at least one cellulose biosynthesis inhibitor (herbicide b1 1).
  • the herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants.
  • These inhibitors belong to the group L of the HRAC classification system.
  • compositions contain at least one decoupler herbicide (herbicide b12).
  • the herbicidal activity of these compounds is based on the disruption of the cell membrane.
  • These inhibitors belong to the group M of the HRAC classification system.
  • the compositions contain at least one auxin herbicide (herbicide b13).
  • auxin herbicide include compounds which act like auxins, i.e. plant hormones, and inhibit the growth of the plants. These compounds belong to the group O of the HRAC classification system.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor hereinicide b14
  • the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b2, b3, b4, b5, b6, b9 and b10.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b4, b6 and b10.
  • herbicides B which can be used in combination with the benzoxazinone compounds of the formula I according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,
  • flucetosulfuron flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,
  • inhibitors of the photosystem II e.g. triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazin, simazin, simetryn, terbumeton,
  • triazine herbicides including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazin, simazin, simetryn, terbumeton,
  • aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridatre, pyrida
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide; b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone,
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)- pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone and bicyclopyrone, bleacher, unknown target: aclonifen, amitrole, clomazone and flumeturon; b6) from the group of the EPSP synthase inhibitors:
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium; b8) from the group of the DHP synthase inhibitors:
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin,
  • phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos
  • benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam
  • compounds of group K2 chlorpropham, propham and carbetamide, among these, compounds of group K1 , in particular dinitroanilines are preferred
  • chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide and napropamide, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos and isoxazoline compounds of the formula Il which are different from pyroxasulfone,
  • R 11 , R 12 , R 13 , R 14 , W, Z and n have the following meanings:
  • R 11 , R 12 , R 13 , R 14 independently of one another hydrogen, halogen or C T
  • W phenyl or monocyclic 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclyl containing, in addition to carbon ring members one, two or three same or different heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein phenyl and heterocyclyl are uns- ubstituted or carry 1 , 2 or 3 substituents Rw selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; preferably phenyl or 5- or 6-membered aromatic heterocyclyl (hetaryl) which contains, in addition to carbon ring members, one, two or three nitrogen atoms as ring members, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2 or 3 substituents Rw ;
  • n zero or one
  • R H 1 R 12 _ R iS 1 R 14 independently of one another are H, F, Cl or methyl; Z is oxygen;
  • n 0 or 1 ;
  • W is phenyl, pyrazolyl or 1 ,2,3-triazolyl, wherein the three last- mentioned radicals are unsubstituted or carry one, two or three substituents Rw, especially one of the following radicals
  • R 15 is halogen, Ci-C4-alkyl or Ci-C4-haloalkyl
  • R 16 is Ci-C 4 -alkyl
  • R 17 is halogen, Ci-C4-alkoxy or Ci-C4-haloalkoxy
  • R 18 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl or Ci-C4-haloalkoxy;
  • n 0, 1 , 2 or 3;
  • # denotes the point of attachment to the group CR 13 R 14 ;
  • R 11 is hydrogen
  • R 12 is fluorine
  • R 13 is hydrogen or fluorine
  • R 14 is hydrogen or fluorine
  • W is one of the radicals of the formulae W 1 , W 2 , W 3 or W 4
  • n is zero or 1 , in particular 1 ;
  • the isoxazoline compounds of the formula Il are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11 ) from the group of the cellulose biosynthesis inhibitors:
  • Preferred herbicides B which can be used in combination with the benzoxazinone compounds of the formula I according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thio
  • acifluorfen-sodium bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen-ethyl, saflufenacil, sulfentrazone, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4- dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31- 6; S-3100), N-ethyl-3-
  • glufosinate from the group of the DHP synthase inhibitors: asulam; b9) from the group of the mitose inhibitors:
  • acetochlor alachlor, anilofos, butachlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, pretilachlor, fenoxasulfone, ipfencarbazone, thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above; b11 ) from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, isoxaben and 1-Cyclohexyl-5-pentafluorphenyloxy-1 4 -[1 ,2,4,6]thiatriazin-3-ylamine; b13) from the group of the auxin herbicide
  • aminopyralid and its salts such as aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr-meptyl, MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, and aminocyclopyrachlor and its salts and esters; b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr- sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, dalapon, difenzoquat, difenzoqua
  • herbicides B which can be used in combination with the benzoxazinone compounds of the formula I according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate; b2) from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium,
  • b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate- isopropylammonium and glyphosate-trimesium (sulfosate); b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium; b9) from the group of the mitose inhibitors: pendimethalin and trifluralin; b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone and ipfencarbazone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 ,
  • Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil,
  • cyprosulfamide dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07- 3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4).
  • Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro-
  • Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)- 1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4).
  • Also particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)- 1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and naphthalic anhydride.
  • the active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of
  • the assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action. If the herbicides B and/or the safener C are capable of forming geometrical isomers, for example E/Z isomers, both the pure isomers and mixtures thereof may be used in the compositions according to the invention. If the herbicides B and/or the safener C have one of more centers of chirality and are thus present as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof may be used in the compositions according to the invention.
  • herbicides B and/or the safener C have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4- alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethyl- ammonium, 2-(2-hydroxyeth-1-oxy)
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt or else in the form of an agriculturally acceptable derivative in the compositions according to the invention, for example as amides, such as mono- and di-Ci-C ⁇ -alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters and also as thioesters, for example as Ci-Cio-alkylthio esters.
  • Preferred mono- and di-Ci-C6- alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl) or isooctyl (2-ethylhexyl) esters.
  • Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the methoxyethyl, ethoxyethyl or butoxyethyl ester.
  • An example of a straight-chain or branched Ci-Cio- alkylthio ester is the ethylthio ester.
  • the composition comprises as herbicidal active compound B or component B, at least one, preferebly exactly one herbicide B.
  • the composition comprises as herbicidal active compound B or component B, at least two, preferebly exactly two herbicides B different from each other.
  • the composition comprises as herbicidal active compound B or component B, at least three, preferebly exactly three herbicides B different from each other.
  • the composition comprises as safening component C at least one, preferebly exactly one safener C.
  • the composition comprises as component B, at least one, preferebly exactly one herbicide B, and at lest one, preferebly exactly one, safener C.
  • the composition comprises as component B, preferebly exactly two herbicides B different from each other, and at lest one, preferebly exactly one, safener C.
  • the composition comprises as component B, at least three, preferebly exactly three herbicides B different from each other, and at lest one, preferebly exactly one, safener C.
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of formula I, preferably of formula 1.1 , and as component B, at least one, preferebly exactly one, herbicide B.
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of formula I, preferably of formula 1.1 , and as component B, at least two, preferebly exactly two, herbicides B different from each other.
  • the composition comprises as component A at least one, preferebly exactly one, benzoxazinone compound of formula I, preferably of formula 1.1 , and as component B, at least three, preferebly exactly three herbicides, B different from each other.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , and at least one, preferebly exactly one, herbicide B.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , and at least two, preferebly exactly two, herbicides B different from each other.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , and at least three, preferebly exactly three, herbicides B different from each other.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , and at least one, preferebly exactly one, safener C.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , at least two, preferebly exactly two herbicides B different from each other, and at least one, preferebly exactly one, safener C.
  • the composition comprises as only active components at least one, preferebly exactly one,
  • benzoxazinone compound of formula I preferably of formula 1.1 , at least three, preferebly exactly three herbicides B different from each other, and at least one, preferebly exactly one, safener C.
  • a first preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b1 ), in particular selected from the group consisting of clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate.
  • a benzoxazinone compound of the formula I especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from
  • a second preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl- sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron,
  • metazosulfuron metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, pyrazosulfuron- ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl and tritosulfuron.
  • a third preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat- dichloride, propanil, terbutryn and terbuthylazine.
  • a benzoxazinone compound of the formula I especially an active compound from the group consisting 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, diuron,
  • a fourth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of flumioxazin, oxyfluorfen, saflufenacil, sulfentrazone and ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292- 31-6; S-3100).
  • a fifth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of clomazone, diflufenican, flurochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, topramezone, bicyclopyrone, amitrole and flumeturon.
  • a sixth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate- isopropylammonium and glyphosate-trimesium (sulfosate).
  • a seventh preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-P and glufosinate-ammonium.
  • An eighth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
  • a ninth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S- metolachlor and fenoxasulfone.
  • compositions comprising in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, Il .8 and II.9, as defined above.
  • a tenth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b11 ), in particular isoxaben.
  • compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluroxypyr-meptyl, quinclorac, quinmerac and aminocyclopyrachlor and its salts and esters.
  • a benzoxazinone compound of the formula I especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b13),
  • a twelfth preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr and diflufenzopyr-sodium.
  • a 14th preferred embodiment of the invention relates to compositions according to the invention comprising, in addition to a benzoxazinone compound of the formula I, especially an active compound from the group consisting of 1.1.1 , 1.2.1 , 1.2.2, 1.3.1 , 1.3.2 and 1.4.1 , at least one and especially exactly one herbicidally active compound from the safeners C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4).
  • a benzoxazinone compound of the formula I especially
  • ternary compositions which correspond to the binary compositions of embodiments 1 to 14 and additionally comprise a safener C, in particular selected from the group consisting of benoxacor, cloquintocet,
  • cyprosulfamide dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4).
  • binary compositions includes compositions comprising one or more, for example 1 , 2 or 3, active compounds of the formula I and either one or more, for example 1 , 2 or 3, herbicides B or one or more safeners.
  • ternary compositions includes compositions comprising one or more, for example 1 , 2 or 3, active compounds of the formula I, one or more, for example 1 , 2 or 3, herbicides B and one or more, for example 1 , 2 or 3, safeners C.
  • the weight ratio of the active compounds A: B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75: 1.
  • the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • the relative proportions by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
  • the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
  • the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250
  • herbicides B are the herbicides B as defined above; in particular the herbicides B.1 - B.139 listed below in table B:
  • Herbicide B Herbicide B
  • safeners C which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.1 1 listed below in table C:
  • weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
  • compositions mentioned below are particularly preferred.
  • benzoxazinone compound as defined and and the substance(s) as defined in the respective row of table 1 ;
  • compositions 1.1 to 1.1668 comprising the benzoxazinone compound 1.1.1 and the substance(s) as defined in the respective row of table 1 :
  • Table 1 compositions 1.1 to 1.1668:
  • Composition 1.777 for example comprises the benzoxazinone 1.1.1 , flurochloridone (B.82) and fenclorim (C.5) (see table 1 , entry 1.777; as well as table B, entry B.82 and table C, entry C.5).
  • Composition 2.777 for example comprises the benzoxazinone 1.2.1 (see the definition for compositions 2.1 to 2.1668 below), flurochloridone (B.82) and fenclorim (C.5) (see table 1 , entry 1.777; as well as table B, entry B.82 and table C, entry C.5).
  • Composition 7.777 for example comprises clodinafop (B2) (see the definition for compositions 7.1 to 7.1668 below), and the benzoxazinone 1.1.1 , flurochloridone (B.82) and fenclorim (C.5) (see table 1 , entry 1.777; as well as table B, entry B.82 and table C, entry C.5).
  • compositions 2.1. to 2.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they comprise as the active compound A the benzoxazinone compound 1.2.1.
  • compositions 3.1. to 3.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they comprise as the active compound A the benzoxazinone compound 1.2.2.
  • compositions 4.1. to 4.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they comprise as the active compound A the benzoxazinone compound 1.3.1.
  • compositions 5.1. to 5.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they comprise as the active compound A the benzoxazinone compound 1.3.2.
  • compositions 6.1. to 6.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they comprise as the active compound A the benzoxazinone compound 1.4.1.
  • compositions 7.1. to 7.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.2 as further herbicide B.
  • compositions 8.1. to 8.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.7 as further herbicide B.
  • compositions 9.1. to 9.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.29 as further herbicide B.
  • compositions 10.1. to 10.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.30 as further herbicide B.
  • compositions 11.1. to 11.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.31 as further herbicide B.
  • compositions 12.1. to 12.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.32 as further herbicide B.
  • compositions 13.1. to 13.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.33 as further herbicide B.
  • compositions 14.1. to 14.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.40 as further herbicide B.
  • compositions 15.1. to 15.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.44 as further herbicide B.
  • compositions 16.1. to 16.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.45 as further herbicide B.
  • compositions 17.1. to 17.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.52 as further herbicide B.
  • compositions 18.1. to 18.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.53 as further herbicide B.
  • compositions 19.1. to 19.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.54 as further herbicide B.
  • compositions 20.1. to 20.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.55 as further herbicide B.
  • compositions 21.1. to 21.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.56 as further herbicide B.
  • compositions 22.1. to 22.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.57 as further herbicide B.
  • compositions 23.1. to 23.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.65 as further herbicide B.
  • compositions 24.1. to 24.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.66 as further herbicide B.
  • compositions 25.1. to 25.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.69 as further herbicide B.
  • compositions 26.1. to 26.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.72 as further herbicide B.
  • compositions 27.1. to 27.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.73 as further herbicide B.
  • compositions 28.1. to 28.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.76 as further herbicide B.
  • compositions 29.1. to 29.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.77 as further herbicide B.
  • compositions 30.1. to 30.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.79 as further herbicide B.
  • compositions 31.1. to 31.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.80 as further herbicide B.
  • compositions 32.1. to 32.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.83 as further herbicide B.
  • compositions 33.1. to 33.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.83 and B.54 as further herbicides B.
  • compositions 34.1. to 34.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.83 and B.60 as further herbicides B.
  • compositions 35.1. to 35.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.83 and B.66 as further herbicides B.
  • compositions 36.1. to 36.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 84 as further herbicide B.
  • compositions 37.1. to 37.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 84 and B.54 as further herbicides B.
  • compositions 38.1. to 38.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 84 and B.60 as further herbicides B.
  • compositions 39.1. to 39.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 84 and B.66 as further herbicides B.
  • compositions 40.1. to 40.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.86 as further herbicide B.
  • compositions 41.1. to 41.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 87 as further herbicide B.
  • compositions 42.1. to 42.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 87 and B.54 as further herbicides B.
  • compositions 43.1. to 43.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 87 and B.60 as further herbicides B.
  • compositions 44.1. to 44.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B. 87 and B.66 as further herbicides B.
  • compositions 45.1. to 45.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.89 as further herbicide B.
  • compositions 46.1. to 46.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.90 as further herbicide B.
  • compositions 47.1. to 47.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.90 and B.54 as further herbicides B.
  • compositions 48.1. to 48.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.90 and B.60 as further herbicides B.
  • compositions 49.1. to 49.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.90 and B.66 as further herbicides B.
  • compositions 50.1. to 50.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 as further herbicide B.
  • compositions 51.1. to 51.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.54 as further herbicides B.
  • compositions 52.1. to 52.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.76 as further herbicides B.
  • compositions 53.1. to 53.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.83 as further herbicides B.
  • compositions 54.1. to 54.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.102 as further herbicides B.
  • compositions 55.1. to 55.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.84 as further herbicides B.
  • compositions 56.1. to 56.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.87 as further herbicides B.
  • compositions 57.1. to 57.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.94 and B.90 as further herbicides B.
  • compositions 58.1. to 58.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.97 as further herbicide B.
  • compositions 59.1. to 59.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.100 as further herbicide B.
  • compositions 60.1. to 60.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.102 as further herbicide B.
  • compositions 61.1. to 61.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.105 as further herbicide B.
  • compositions 62.1. to 62.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.106 as further herbicide B.
  • compositions 63.1. to 63.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.107 as further herbicide B.
  • compositions 64.1. to 64.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.109 as further herbicide B.
  • compositions 65.1. to 65.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.1 11 as further herbicide B.
  • compositions 66.1. to 66.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.1 15 as further herbicide B.
  • compositions 67.1. to 67.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.1 17 as further herbicide B.
  • compositions 68.1. to 68.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.1 18 as further herbicide B.
  • compositions 69.1. to 69.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.120 as further herbicide B.
  • compositions 70.1. to 70.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.121 as further herbicide B.
  • compositions 71.1. to 71.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.1 12 as further herbicide B.
  • compositions 72.1. to 72.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise B.128 as further herbicide B.
  • compositions 73.1. to 73.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide.
  • compositions 74.1. to 74.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.54 as further herbicide B.
  • compositions 75.1. to 75.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.60 as further herbicide B.
  • compositions 76.1. to 76.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.66 as further herbicide B.
  • compositions 77.1. to 77.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.76 as further herbicide B.
  • compositions 78.1. to 78.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.83 as further herbicide B.
  • compositions 79.1. to 79.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.84 as further herbicide B.
  • compositions 80.1. to 80.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.87 as further herbicide B.
  • compositions 81.1. to 81.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.90 as further herbicide B.
  • compositions 82.1. to 82.1668 which differ from the corresponding compositions 1.1 to 1.1668 only in that they additionally comprise pyroxasulfone as further herbicide and B.94 as further herbicide B.
  • compositions 83.1 to 83.11 comprising as active compound A) the benzoxazinone compound 1.1 and as further compound the substance as defined in the respective row of table C:
  • compositions 83a.1 to 83a.11 comprising as active compound A) the benzoxazinone compound 1.1.1. and as further compound the substance as defined in the respective row of table Ca:
  • compositions 84. 1. to 84.1 1 which differ from the corresponding compositions 83.1 to 83.1 1 only in that they comprise as the active compound A the benzoxazinone compound 1.2.1.
  • compositions 85. 1. to 85.1 1 which differ from the corresponding compositions 83.1 to 83.1 1 only in that they comprise as the active compound A the benzoxazinone compound 1.2.2.
  • compositions 86. 1. to 86.1 1 which differ from the corresponding compositions 83.1 to 83.11 only in that they comprise as the active compound A the benzoxazinone compound 1.3.1.
  • compositions 87. 1. to 87.1 1 which differ from the corresponding compositions 83.1 to 83.11 only in that they comprise as the active compound A the benzoxazinone compound 1.3.2.
  • compositions 88.1. to 88.11 which differ from the corresponding compositions 83.1 to 83.11 only in that they comprise as the active compound A the benzoxazinone compound 1.4.1.
  • compositions 84a.1. to 84a.11 which differ from the corresponding compositions 83a.1 to 83a.1 1 only in that they comprise as the active compound A the benzoxazinone compound 1.2.1.
  • compositions 85a.1. to 85a.11 which differ from the corresponding compositions 83a.1 to 83a.1 1 only in that they comprise as the active compound A the benzoxazinone compound 1.2.2.
  • compositions 86a.1. to 86a.11 which differ from the corresponding compositions 83a.1 to 83a.11 only in that they comprise as the active compound A the benzoxazinone compound 1.3.1.
  • compositions 87a.1. to 87a.11 which differ from the corresponding compositions 83a.1 to 83a.11 only in that they comprise as the active compound A the benzoxazinone compound 1.3.2.
  • compositions 88a.1. to 88a.11 which differ from the corresponding compositions 83a.1 to 83a.11 only in that they comprise as the active compound A the benzoxazinone compound 1.4.1.
  • compositions 89a.1. to 89a.11 which differ from the corresponding compositions 83a.1 to 83a.11 only in that they additionally comprise pyroxasulfone as further herbicide.
  • the compounds of formulae 1.2, 1.3 and 1.4 and the compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition.
  • the compounds of formulae 1.2, 1.3 and 1.4 and compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the compounds of formulae I.2, 1.3 and 1.4 and the compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants.
  • suitable crops are the following:
  • Preferred crops are: Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum
  • compositions according to the invention may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.
  • compositions according to the invention can also be used in crops which tolerate insects or fungal attack as the result of breeding, including genetic engineering methods.
  • the compounds of formulae 1.2, 1.3 and I.4 and the compositions according to the invention can also be used in genetically modified plants.
  • genetically modified plants is to be understood as plants, which genetic material has been modified by the use of recombinant DNA techniques in a way that under natural circumstances it cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post- transtional modification of protein(s), oligo- or polypeptides e. g.
  • HPPD hydroxyphenyl pyruvate dioxygenase
  • acetolactate synthase (ALS) inhibitors such as sulfonyl ureas (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO
  • ALS acetolactate synthase
  • EPSPS enolpyruvylshikimate-3- phosphate synthase
  • GS glutamine synthetase
  • EP-A 242 236, EP- A 242 246) or oxynil herbicides see e. g. US 5,559,024.
  • Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to mutagenesis, e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to
  • imidazolinones e. g. imazamox.
  • Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glypho-sate and glufosinate, some of which are commercially available under the trade names RoundupReady ® (glyphosate-tolerant, Monsanto, U.S.A.) and LibertyLink ® (glufosinate-tolerant, Bayer CropScience, Germany).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry ⁇ c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • delta-endotoxins e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry ⁇ c
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; aggluti-nins;
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases.
  • RIP ribosome-inactivating proteins
  • RIP ribosome-inactivating proteins
  • steroid metabolism enzymes such as 3-
  • these insecticidal proteins or toxins are to be under-stood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are dis-closed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.
  • insects e.g. in the published literature.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coelop-tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nema-toda).
  • Genetically modified plants capable to synthesize one or more insecticidal pro-teins are, e.
  • Phosphinothricin-N-Acetyltransferase [PAT] Phosphinothricin-N-Acetyltransferase
  • NuCOTN ® 33B cotton cultivars
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars produ-cing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to in-crease the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins examples include the so-called " pathogenesis-related proteins" (PR proteins, see, e.g. EP-A 392 225), plant disease resistance genes (e. g. potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lyso-zym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lyso-zym e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions for the desiccation and/or defoliation of plants processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
  • the compounds of formulae 1.2, 1.3 and I.4 and the compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • the compounds of formulae 1.2, 1.3 and 1.4 and the compositions according to the invention or the crop protection compositions comprising them or formulated therefrom can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, broadcasting or watering or treatment of the seed or mixing with the seed.
  • the use forms depend on the intended purpose; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the crop protection compositions comprise a herbicidally effective amount of the compound of formulae 1.2, 1.3 and 1.4 or the composition according to the invention, i.e. at least one compound I or at least one compound I or an agriculturally useful salt of I and at least one further active compound, selected from herbicides B and the abovementioned safeners C, and also auxiliaries customary for formulating crop protection agents.
  • auxiliaries customary for the formulation of crop protection agents are inert auxilaries, solid or liquid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and, for seed formulations, adhesives.
  • surfactants such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers
  • organic and inorganic thickeners such as bactericides, antifreeze agents, antifoams, optionally colorants and, for seed formulations, adhesives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion
  • thickeners are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from RT. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides can be added for stabilizing the aqueous herbicidal formulations.
  • bactericides examples include bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I.
  • Solvent Red 1 and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Suitable inert auxiliaries are in particular liquid or solid carriers.
  • liquid carriers are: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N- methylpyrrolidone, and water.
  • Solid carriers are for example mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and
  • Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g.
  • methylcellulose methylcellulose
  • hydrophobically modified starches polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF AG, Sokalan types), polyalkoxylates, polyvinylamine (BASF AG, Lupamine types), polyethyleneimine (BASF AG, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of the formula I, specially I. a and l.b,, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • a wetting agent e.g., tackifier, dispersant or emulsifier
  • concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
  • concentrations of the active compounds in the ready-to-use preparations can be varied within wide ranges.
  • the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound.
  • the active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • compositions of the invention can for example be formulated as follows:
  • active compound 10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
  • active compound 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyrrolidone.
  • the active compound content is 20% by weight
  • dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight. Dilution with water gives an emulsion.
  • the formulation has an active compound content of 15% by weight.
  • dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • the formulation has an active compound content of 25% by weight.
  • active compound 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
  • the active compound content in the formulation is 20% by weight.
  • active compound 50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water- soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
  • the formulation has an active compound content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
  • the active compound content of the formulation is 75% by weight.
  • active compound 0.5 parts by weight are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.
  • the components A and B and/or C can be present formulated jointly or separately in suspended, emulsified or dissolved form.
  • the use forms depend entirely on the intended applications.
  • a first embodiment of the invention relates to compositions in the form of a crop protection composition formulated as a 1 -component composition comprising the at least one active compound of the formula I or the at least one active compound of the formula I (active compound A) and at least one further active compound selected from the herbicides B and the safeners C and also a solid or liquid carrier and, if appropriate, one or more surfactants.
  • a second embodiment of the invention relates to compositions in the form of a crop protection composition formulated as a 2-component composition
  • a first formulation comprising the at least one active compound A, a solid or liquid carrier and, if appropriate, one or more surfactants
  • a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and, if appropriate, one or more surfactants.
  • the active compound A and the at least one further active compound B and/or C can be applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants.
  • the order of the application of the active compounds A, B and/or C is of minor importance. The only thing that is important is that the at least one active compound A and the at least one further active compound B and/or C are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled.
  • the required application rate of pure active compound composition i.e. A and B and, if appropriate, C without formulation auxiliaries depends on the composition of the plant stand, on the development stage of the plants, on the climatic conditions at the site of use and on the application technique.
  • the application rate of A and B and, if appropriate, C is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
  • the required application rates of compounds I are generally in the range of from
  • the required application rates of compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
  • the required application rates of compounds C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
  • the compounds of formulae 1.2, 1.3 and I.4 and the compositions according to the imvention are applied to the plants mainly by spraying the leaves.
  • the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 I/ha (for example from 300 to 400 I/ha).
  • the herbicidal compositions may also be applied by the low- volume or the ultra-low-volume method, or in the form of microgranules.
  • the compounds of formulae 1.2, 1.3 and I.4 or the herbicidal compositions according to the present invention can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds A and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • the compounds of formulae 1.2, 1.3 and 1.4 or the composition according to the invention can be applied by treating seed.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting
  • compositions prepared therefrom can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the rates of application of the active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
  • the compounds I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
  • N-chloro-succinimide (213 mg, 1.594 mmol) was added portion-wise.
  • the mixture was stirred at -78 0 C for 2h and subsequently poured as such (-78 0 C) into a saturated aqueous solution of NH 4 CI. Extraction with EtOAc, drying with Na2SO 4 and concentration afforded 510 mg of the title compound.
  • the culture containers used were plastic pots containing loamy sand with
  • the active compounds suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
  • test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly, and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C and 20 - 35°C, respectively.
  • the test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.
  • Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth. Good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
  • test period extended over 20 and 21 days, respectively. During this time, the plants were tended, and their reaction to the treatment with active compound was monitored.
  • X percent activity using active compound A at an application rate a
  • E expected activity (in %) by A + B at application rates a + b.
  • topramezone (group b5): herbicide B.90
  • dimethenamid-P group b10
  • flufenacet (group b10): herbicide B. 107
  • the plants used in the greenhouse experiments were of the following species:
  • a.s. means active substance, based on 100 % active ingredient.
  • Use example 1 Synergistic herbicidal action of the mixture 1.1.76 applied by the pre- emergence method
  • the compound 1.2.1 showed very good pre-emergence action against the unwanted plants Amaranthus retroflexus, Apera spica-venti, Lamium purpureum, Setaria verticillata, Solanum nigrum and Veronica persica.
  • compound I.2.2 applied by the pre-emergence method, effected, at application rates of 100 g/ha, very good control of the harmful plants Amaranthus retroflexus, Apera spica-venti, Lamium purpureum, Setaria verticillata, Solanum nigrum and Veronica persica.
  • Use example 4 Synergistic herbicidal action of the mixture 1.54 (mixture of 1.1.1 +
  • Use example 5 Synergistic herbicidal action of the mixture 1.54 (mixture of 1.1.1 +
  • example 10 Synergistic herbicidal action of the mixture 1.100 (mixture of 1.1.1 + B.100) applied by the pre-emergence method
  • e example 14 Synergistic herbicidal action of the mixture 28.95 (mixture of 1.1.1 + B.76 + B.95) applied by the post-emergence method
  • e example 15 Synergistic herbicidal action of mixture of 1.1.1 and pyroxasulfone applied by the pre-emergence method
  • e example 16 Synergistic herbicidal action of the mixture of 1.1.1 and pyroxasulfone applied by the post-emergence method
  • e example 17 Synergistic herbicidal action of the mixture of 1.1.1 , pyroxasulfone and

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Abstract

La présente invention concerne une composition herbicide comprenant : A) au moins un composé benzoxazinone de formule I, dans laquelle les variables sont définies comme indiqué dans la spécification ; et au moins un autre composé actif choisi parmi B) des herbicides de classe b1) à b15) tels que définis dans la spécification, et C) des phytoprotecteurs.
PCT/EP2010/061718 2009-08-14 2010-08-12 Composition herbicide active comprenant des benzoxazinones Ceased WO2011018486A2 (fr)

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