EP1278413A2 - N-aryl-uracile-based herbicides - Google Patents

N-aryl-uracile-based herbicides

Info

Publication number
EP1278413A2
EP1278413A2 EP00989897A EP00989897A EP1278413A2 EP 1278413 A2 EP1278413 A2 EP 1278413A2 EP 00989897 A EP00989897 A EP 00989897A EP 00989897 A EP00989897 A EP 00989897A EP 1278413 A2 EP1278413 A2 EP 1278413A2
Authority
EP
European Patent Office
Prior art keywords
methyl
amino
chloro
ethyl
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00989897A
Other languages
German (de)
French (fr)
Inventor
Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Birgit Krauskopf
Mathias Kremer
Rolf Pontzen
Ingo Wetcholowsky
Roland Andree
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1278413A2 publication Critical patent/EP1278413A2/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Definitions

  • the invention relates to new herbicidal combinations of active ingredients which comprise known N-aryluracils on the one hand and known herbicidally active compounds and / or compounds which improve the tolerance to crop plants on the other and with particularly good success for combating monocotyledonous and dicotyledonous weeds in various crops, but also for Control of monocot and dicot weeds in the semi and non-selective range can be used.
  • N-aryl-uracils are the subject of a number of patent applications (cf. EP-A-408382, EP-A-473551, EP-A-563384, EP-A-648749, US-A-4943309, US Pat. A-5084084, US-A-5127935, US-A-5759957, WO-A-91/00278, WO-A-95/29168, WO-A-95/30661, WO-A-96/35679, WO- A-97/01541, WO-A-98/25909).
  • the known N-aryl-uraciles have a number of gaps in their effectiveness.
  • the invention relates to herbicidal compositions, characterized by comprising an effective content of an active ingredient combination
  • R 1 represents hydrogen, amino or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C] -C 4 -alkoxy,
  • R 2 represents alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen
  • R 3 represents hydrogen, halogen or alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
  • R 4 represents hydrogen, cyano or halogen
  • R 5 represents cyano, thiocarbamoyl or halogen
  • R 6 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, halogen, for each optionally by cyano, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl carbonyl, C1-C4 - Alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C 2 -C 4 -alkynyloxy-carbonyl, Ci -C 4 -alkylamino-carbonyl, di- (-C-C 4 -alkyl) -amino-carbonyl, phenoxy- carbonyl and / or phenylaminocarbonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or
  • R 1 preferably represents hydrogen, amino or, if appropriate, in each case
  • R preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine.
  • R 3 preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine.
  • R 4 preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
  • R 5 preferably represents cyano, thiocarbamoyl, fluorine, chlorine or bromine.
  • R 6 preferably represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, carboxy, hydroxy, methoxy, ethoxy, n- or i- Propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, Methylthio, ethylthio, n- or
  • R 2 particularly preferably represents methyl or ethyl substituted by fluorine and / or chlorine.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine.
  • R 4 particularly preferably represents hydrogen, fluorine or chlorine.
  • R 5 particularly preferably represents cyano, thiocarbamoyl, chlorine or bromine.
  • R 6 particularly preferably represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, carboxy, hydroxy, methoxy, ethoxy, acetyl, Propionyl, methoxycarbonyl and / or ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or
  • Propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n - or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for ethenyl optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl, Propenyl, ethynyl
  • R 1 represents amino
  • R 2 represents trifluoromethyl
  • R, 3 J represents hydrogen, chlorine or methyl
  • R 4 represents fluorine
  • R 5 represents cyano or thiocarbamoyl
  • R 6 for methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N, N-bis-methylsulfonylamino, N, in each case optionally substituted by fluorine and / or chlorine, N-bis-ethyl-sulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-methyl-sulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl- amino, N-propionyl
  • R 1 represents methyl
  • R 2 represents trifluoromethyl
  • R 3 represents hydrogen, chlorine or methyl
  • R 4 represents fluorine
  • R 5 stands for thiocarbamoyl
  • R 1 represents amino or methyl
  • R represents trifluoromethyl
  • R 3 represents hydrogen, chlorine or methyl
  • R 4 represents hydrogen, fluorine or chlorine
  • R 5 represents cyano, thiocarbamoyl or chlorine
  • R 6 for carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, fluorine,
  • 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-n-butoxy-benzonitrile.
  • 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-i-butoxy-benzonitrile.
  • 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-allyloxy-benzonitrile.
  • 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-propargyloxy-benzonitrile.
  • N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo- 4-trifluoromethyl-l (2H) -pyrimidinyl) -4-fluorophenyl] -N-ethylsulfonyl-2-thiophene-car-boxamide is also particularly emphasized as a mixture component of the formula (I) (WO 96/35679) ,
  • the active substances of group 2 can be assigned to their chemical structure according to the following active substance classes: Amides (e.g. Isoxaben, Picolinafen, Propanil), aryl heterocycles (e.g. Azafenidin, Benzfendizone, Butafenacil-allyl, Carfentrazone-ethyl, Cinidon-ethyl, Fluazolate, Flumiclorac-pentyl, Flumioxazin, Flupropacil, Fluthiacet-methyl, Oxi-argol, Oxadiazon, oxadiazon, oxadiazon , Pyraflufen-ethyl, pyridate, pyridafol, sulfentrazone, thidiazimin, 4- [4,5-dihydro-4-methyl-5-oxo- (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethyls
  • clodinafop-propargyl cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop- R-methyl, Quizalofop-P-ethyl), carboxylic acid derivatives (e.g. clopyralid, dicamba, fluroxypyr, picloram, triclopyr), benzothiadiazoles (e.g. bentazone), chloroacetamides (e.g. acetochlor, alachlor, butachlor, (S-) dimethenamid,
  • carboxylic acid derivatives e.g. clopyralid, dicamba, fluroxypyr, picloram, triclopyr
  • benzothiadiazoles e.g. bentazone
  • chloroacetamides e.g. acetochlor, alachlor, butachlor, (S-) dim
  • Metazachlor Metolachlor, Pretilachlor, Propachlor, Propisochlor
  • Cyclohexanediones e.g. Butroxydim, Clefoxydim, Cycloxydim, Sethoxydim, Tralkoxydim
  • Dinitro-aniline e.g. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin
  • Diifphenylin Triflural Aclonifen, Bifenox, Fluoroglycofen-ethyl, Fomesafen, Lactofen, Oxyfluorfen
  • ureas e.g.
  • imidazolinones e.g. imazamethabenz-methyl, imazamox, imazapole), imazapole, eg Isoxaflutole
  • pyrazoles e.g. pyrazolates, pyrazoxyfen
  • pyridazinones e.g. norflurazone
  • pyridines e.g. dithiopyr, thiazopyr
  • pyrimidinyl (thio) benzoates e.g. bispyribac, Pyribenzoxime, pyrithiobac, pyriminobac
  • sulfonylureas e.g.
  • butylates dimepiperates, EPTC, Esprocarb, Molinate, Orbencarb, Prosulfocarb, triallates
  • triazines e.g. ametryn, atrazine, cyanazines, dimexyflam, simazine, terbuthylazine, terbutryn
  • triazinones e.g. hexazinones, metamitron, metribuzin
  • triazoles e.g. amitrole
  • triazolinones e.g.
  • amicarbazone zone sodium, fluc Propoxycarbazone-sodium
  • triazolopyrimidines eg cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam
  • triketones eg mesotrione, sulcotrione
  • uracile eg bromacil
  • Metolachlor S-Metolachlor, Metosulam, Metribuzin, Nicosulfuron, Norflurazon, Pendimethalin, Propoxycarbazone-sodium, Rimsulfuron, Simazin, Sulfometuron-methyl, Sulcotrione, Sulfentrazone, Sulfosate, Terbuthylazine, Thifensulflural-methyl, Trifutylhydro, 4- -4-methyl-5-oxo (3-trifluoromethyl) -IH-l, 2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide.
  • the active substances in Group 2 that are particularly highlighted can be assigned to their chemical structure according to the following classes of active substances:
  • Aryl heterocycles e.g. carfentrazone-ethyl, sulfentrazone, 4- [4,5-dihydro-4-methyl-
  • Sulfosates Sulfosates
  • oxyacetamides e.g. flufenacet
  • pyridazinones e.g. norflurazone
  • Sulfonyl ureas e.g. chlorimuron-ethyl, nicosulfuron, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl
  • tetrazolinones e.g. fentrazamides
  • triazines e.g. metribone
  • triazolopyrimidines e.g. diclosulam, florasulam, metosulam
  • triketones e.g. mesotrione, sulcotrione
  • uracile e.g. bromacil
  • the agents according to the invention can contain one or two active substances from group 1 and one active substance from group 3.
  • the agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally an active substance from group 3.
  • the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
  • each of an active ingredient from group 1 and two active ingredients from group 2 preferably selected from the group of photosynthesis inhibitors on the one hand and the group of acetyl-CoA carboxylase inhibitors on the other hand
  • two Group 2 agents and a Group 3 compound - are listed in Table 1 below.
  • each of an active ingredient of group 1 and one or two active ingredients of group 2 and / or a compound of group 3 are listed in Table 2 below.
  • the active compound combinations defined above from the N-aryl-uracils of the formula (I) and the above-mentioned active compounds from group 2 have a particularly high herbicidal activity and are very good herbicidal activity and in different crops, in particular in Cereals, such as wheat, barley or oats, and corn, can be used to selectively control monocot and dicot weeds and that they can also be used to control monocot and dicot weeds in the semi and non-selective range.
  • Cereals such as wheat, barley or oats, and corn
  • the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • 1 to 1 part by weight of active compound of the formula (I) comprises 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight of active compound of group 2.
  • Cereals are, as well as 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1, 2-a] -pyrimidine-6 (2H) -one (B AS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 2,2-dichloro-N, N -di-2-propenyl-acetamide (dichlormid), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900) and 3-dichloroacetyl-2,2,5 trimethyl-oxazolidine (R-29148), which are particularly suitable for improving the tolerance in maize.
  • AD-67 1-dichloroacet
  • the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate also in combination with one or more of the above-mentioned active ingredients of group 2, to be completely removed from the cultivated plants without impairing the herbicidal activity against the weeds.
  • a preferred embodiment is therefore also a mixture comprising a compound of the formula (I) and / or its salts on the one hand and 2,4-D and / or its derivatives on the other hand, optionally in combination with one or more of the active ingredients of group 2 mentioned above.
  • Typical derivatives of 2,4-D are, for example, their esters.
  • the advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is likewise particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active compound of the formula (I) or mixtures thereof with active compounds of group 2 account for 0.001 to 1000 parts by weight, preferably 0.01 to 100
  • Plants are understood to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by Plant variety rights of protectable or non-protectable plant varieties.
  • Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhiozomes.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multilayer coating.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width)
  • Plantation crops e.g. wine, fruit, citrus
  • plants are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton).
  • defoliants e.g. in cotton
  • They are also suitable for use on fallow land.
  • Other areas of application are tree nurseries,
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,
  • Polyoxyethylene fatty alcohol ethers for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active substances contained in the active substance combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • plant-compatible in the formulations as further additives mineral or vegetable oils (eg the commercial preparation "Rako Binol”) or ammonium salts such as ammonium sulfate or ammonium rhodanide.
  • the new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Herbicides can also be found in the literature cited above.
  • Solvent 2 to 3 parts by weight of acetone or N, N-dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. Formulated products are dissolved in water and then diluted with water to the desired concentration.
  • the solutions of the other mixture components are prepared analogously. Then the separately prepared solutions of the different mixture components are combined, optionally further additives (formulation auxiliaries, additives, etc.) and optionally water are added to produce the desired dilution.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of active ingredient in the spray liquor is chosen so that the desired amount of active ingredient is applied in 500 liters of water per hectare.
  • the tubes with the test plants are kept in the greenhouse until they are rated at a controlled temperature and with controlled lighting.

Abstract

The invention relates to novel herbicidal combinations of active agents which contain known N-aryl-uraciles and known compounds with a herbicidal effect, and compounds which improve compatibility with cultivated plants. The inventive combinations of active agents are particularly effective in combating monocotyledonous and dicotyledonous weeds in different useful plant cultures, but can also be used for combating monocotyledonous and dicotyledonous weeds in the semi-selective and non-selective area.

Description

Herbizide auf Basis von N-Aryl-uracilenHerbicides based on N-aryl-uracils
Die Erfindung betrifft neue herbizide Wirkstoffkombinationen, die bekannte N-Aryl- uracile einerseits und bekannte herbizid wirksame Verbindungen und/oder die Kultuφflanzen- Verträglichkeit verbesserende Verbindungen andererseits umfassen und mit besonders gutem Erfolg zur Bekämpfung von monokotylen und dikotylen Unkräutern in verschiedenen Nutzpflanzenkulturen, aber auch zur Bekämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich verwendet werden können.The invention relates to new herbicidal combinations of active ingredients which comprise known N-aryluracils on the one hand and known herbicidally active compounds and / or compounds which improve the tolerance to crop plants on the other and with particularly good success for combating monocotyledonous and dicotyledonous weeds in various crops, but also for Control of monocot and dicot weeds in the semi and non-selective range can be used.
N-Aryl-uracile sind als herbizid wirksame Stoffe Gegenstand einer Reihe von Patentanmeldungen (vgl. EP-A-408382, EP-A-473551, EP-A-563384, EP-A-648749, US- A-4943309, US-A-5084084, US-A-5127935, US-A-5759957, WO- A-91/00278, WO-A-95/29168, WO-A-95/30661, WO-A-96/35679, WO-A-97/01541, WO-A- 98/25909). Die bekannten N-Aryl-uracile weisen jedoch eine Reihe von Wirkungslücken auf.As herbicidally active substances, N-aryl-uracils are the subject of a number of patent applications (cf. EP-A-408382, EP-A-473551, EP-A-563384, EP-A-648749, US-A-4943309, US Pat. A-5084084, US-A-5127935, US-A-5759957, WO-A-91/00278, WO-A-95/29168, WO-A-95/30661, WO-A-96/35679, WO- A-97/01541, WO-A-98/25909). However, the known N-aryl-uraciles have a number of gaps in their effectiveness.
Eine Reihe von herbiziden Wirkstoffkombinationen auf Basis von N-Aryl-uracilen sind ebenfalls bereits bekannt geworden (vgl. DE-A-4437197, DE-A-19915013, DE- A-19919951, EP-A-714602, WO-A-96/07323, WO-A-96/08151, JP-A-11189506).A number of herbicidal active substance combinations based on N-aryl-uracils have also already been disclosed (cf. DE-A-4437197, DE-A-19915013, DE-A-19919951, EP-A-714602, WO-A-96 / 07323, WO-A-96/08151, JP-A-11189506).
Die Eigenschaften dieser Wirkstoffkombinationen sind jedoch auch nicht in allen Belangen zufriedenstellend.However, the properties of these combinations of active ingredients are also not satisfactory in all respects.
Überraschenderweise wurde nun gefunden, dass eine Reihe von bekannten Wirk- Stoffen aus der Reihe der N-Aryl-uracile bei gemeinsamer Anwendung mit bekannten herbizid wirksamen Verbindungen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in Nutzpflanzenkulturen, wie z.B. in Baumwolle, Getreide, Gras/Weideland, Mais, Rasen („Turf), Reis, Soja, Sonnenblumen und Zuckerrohr, aber auch zur Be- kämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich verwendet werden können.Surprisingly, it has now been found that a number of known active compounds from the N-aryl-uracil series, when used together with known herbicidally active compounds, show synergistic effects with regard to the action against weeds and are particularly advantageous as broadly active combination preparations for the selective control of monocotyledons and dicotyledon weeds in crops such as cotton, cereals, grass / pasture, maize, lawn ("turf"), rice, soybeans, sunflowers and sugar cane, but also for Control of monocot and dicot weeds in the semi and non-selective area can be used.
Gegenstand der Erfindung sind herbizide Mittel, gekennzeichnet durch einen wirk- samen Gehalt an einer Wirkstoffkombination umfassendThe invention relates to herbicidal compositions, characterized by comprising an effective content of an active ingredient combination
(a) zumindest ein N-Aryl-uracil der Formel (I)(a) at least one N-aryl-uracil of the formula (I)
in welcher in which
R1 für Wasserstoff, Amino oder gegebenenfalls durch Cyano, Halogen oder C]-C4-Alkoxy substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen steht,R 1 represents hydrogen, amino or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C] -C 4 -alkoxy,
R2 für gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 5 Kohlen- Stoffatomen steht,R 2 represents alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
R3 für Wasserstoff, Halogen oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen steht,R 3 represents hydrogen, halogen or alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
R4 für Wasserstoff, Cyano oder Halogen steht,R 4 represents hydrogen, cyano or halogen,
R5 für Cyano, Thiocarbamoyl oder Halogen steht, undR 5 represents cyano, thiocarbamoyl or halogen, and
R6 für Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy, Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Halogen, für jeweils gegebenenfalls durch Cyano, Hydroxy, Cι -C4-Alkoxy, Cι-C4-Alkyl-carbonyl, C1-C4- Alkoxy-carbonyl, C2-C4-Alkenyloxy-carbonyl, C2-C4-Alkinyloxy-carbonyl, Ci -C4-Alkylamino-carbonyl, Di-(Cι -C4-alkyl)-amino-carbonyl, Phenoxy- carbonyl und/oder Phenylaminocarbonyl substituiertes Alkyl, Alkoxy, Alkyl- thio, Alkylsulfmyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxycarbonyl oder Alkylamino mit jeweils bis zu 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Carboxy, Halogen und/oder Cι-C4-Alkoxy-carbonyl substituiertes Alkenyl, Alkinyl, Alkenyloxy oder Alkinyloxy mit jeweils bis zu 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen oder C]-C4- Alkoxy substituiertes Alkylcarbonylamino, Alkoxycarbonylamino, Alkyl- sulfonylamino, N,N-Bis-alkylsulfonyl-amino oder N-Alkylcarbonyl-N-alkyl- sulfonyl-amino mit jeweils bis zu 6 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Cyano oder Halogen, oder durch Cι -C4-Alkyl, Cι-C4-Alkoxy oder Cι-C4-Alkoxy-carbonyl (welche jeweils gegebenenfalls durch Cι-C4-Alkoxy-carbonyl, C3-C4-Alkenyloxy-carbonyl oder C3-C4-Alkinyloxy-carbonyl substituiert sind) substituiertes Phenyloxy,R 6 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, halogen, for each optionally by cyano, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl carbonyl, C1-C4 - Alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C 2 -C 4 -alkynyloxy-carbonyl, Ci -C 4 -alkylamino-carbonyl, di- (-C-C 4 -alkyl) -amino-carbonyl, phenoxy- carbonyl and / or phenylaminocarbonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino each having up to 6 carbon atoms, each optionally substituted by cyano, carboxy, halogen and / or C 1 -C 4 alkoxycarbonyl Alkenyl, alkynyl, alkenyloxy or alkynyloxy each having up to 6 carbon atoms, each for alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, N, N-bis-alkylsulfonylamino or N-alkylcarbonyl- optionally substituted by halogen or C] -C 4 -alkoxy N-alkyl-sulfonyl-amino, each with up to 6 carbon atoms in the alkyl groups, or for each optionally by cyano or halogen, or by -C -C4-alkyl, -C-C4-alkoxy or -C-C 4 -alkoxy-carbonyl (which each optionally by -C-C 4 alkoxy car bonyl, C 3 -C 4 -alkenoxy-carbonyl or C 3 -C 4 -alkynyloxy-carbonyl are substituted) substituted phenyloxy,
Naphthyloxy, N-Phenylcarbonyl-N-alkylsulfonyl-amino, N-Pyridylcarbonyl- N-alkylsulfonyl-amino, N-Furylcarbonyl-N-alkylsulfonyl-amino oder N- Thienylcarbonyl-N-alkylsulfonyl-amino mit jeweils bis zu 6 Kohlenstoffatomen in den Alkylgruppen steht,Naphthyloxy, N-phenylcarbonyl-N-alkylsulfonyl-amino, N-pyridylcarbonyl-N-alkylsulfonyl-amino, N-furylcarbonyl-N-alkylsulfonyl-amino or N-thienylcarbonyl-N-alkylsulfonyl-amino, each with up to 6 carbon atoms in the alkyl groups stands,
(„Wirkstoffe der Gruppe 1")("Active substances of group 1")
undand
(b) zumindest eine Verbindung aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(b) at least one compound from a second group of herbicides which contains the active compounds mentioned below:
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methylphenyl) acetamide (acetochlor), 5-
(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-Natriumsalz (Acifluorfen- sodium), 2-Chlor-6-nitro-3-phenoxy-benzenamin (Aclonifen), 2-Chlor-N-(methoxy- methyl)-N-(2,6-diethyl-phenyl)-acetamid (Alachlor), N-Ethyl-N'-i-propyl-6-methyl- thio-l,3,5-triazin-2,4-diamin (Ametryn), 4-Amino-N-(l,l-Dimethyl-ethyl)-4,5-di- hydro-3-( 1 -methyl-ethyl)-5-oxo- 1 H- 1 ,2,4-triazol- 1 -carboxamid (Amicarbazone), N- (4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harn- stoff (Amidosulfuron), lH-l,2,4-Triazol-3-amin (Amitrole), 6-Chlor-4-ethylamino-2- isopropylamino-l,3,5-triazin (Atrazin), 2-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]-(2-Chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid sodium salt (Acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxy-benzene amine (Aclonifen), 2-chloro-N- (methoxy - methyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor), N-ethyl-N'-i-propyl-6-methyl- thio-l, 3,5-triazine-2,4-diamine (ametryn), 4-amino-N- (l, l-dimethyl-ethyl) -4,5-di-hydro-3- (1-methyl- ethyl) -5-oxo-1 H-1, 2,4-triazole-1-carboxamide (amicarbazone), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N -methylsulfonyl-sulfamoyl) urea (amidosulfuron), lH-l, 2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-l, 3,5-triazine ( Atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -
5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-ρyridin-3(2H)-on (Azafenidin), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N' -[ 1 -methyl-4-(2-methyl-2H-tetrazol-5 -yl)- 1 H-pyrazol-5 - ylsulfonylj-harnstoff (Azimsulfuron), N-Benzyl-2-(4-fluor-3-trifluormethyl- phenoxy)-butanamid (Beflubutamid), 4-Chlor-2-oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4-trifluormethyl-benzenamin (Benflurahn),5,6,7,8-tetrahydro-l, 2,4-triazolo- [4,3-a] -pyridin-3 (2H) -one (azafenidin), N- (4,6-dimethoxypyrimidine -2-yl) -N '- [1 -methyl-4- (2-methyl-2H-tetrazol-5-yl) - 1 H-pyrazol-5 - ylsulfonylj-urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethylphenoxy) butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl-N-ethyl-2,6-dinitro-4 trifluoromethylbenzamine (benflurahn),
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenylmethylsulfonyl)- harnstoff (Bensulfuron), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- l(2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propansäure-methylester (Benz- fendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct- 3-en-2-on (Benzobicyclon), Ethyl N-benzoyl-N-(3,4-dichlor-phenyl)-DL-alaninatN- (4,6-Dimethoxypyrimidin-2-yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuron), 2- [2- [4- (3,6-dihydro-3-methyl -2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinylphenoxymethyl] -5-ethyl-phenoxy-propanoic acid, methyl ester (benzendendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4- phenylthio-bicyclo- [3.2.1] oct-3-en-2-one (benzobicyclone), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate
(Benzoylprop-ethyl), 3-i-Propyl-lH-2,l,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 2,6-Bis-(4,6-dimethoxy- pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyribac-sodium), 5-Brom-6- methyl-3-(l-methyl-propyl)-2,4(lH,3H)pyrimidindion (Bromacil), 2-Brom-3,3-di- methyl-N-(l-methyl-l-phenyl-ethyl)-butanamid (Bromobutide), 3,5-Dibrom-4-hy- droxy-benzaldehyd-O-(2,4-dinitro-phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4-hy- droxy-benzonitril (Bromoxynil), N-Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)- acetamid (Butachlor), 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidinyl)-benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxo- butyl)-phenyl]-2-cyclohexen-l-on (Butroxydim), S-Ethyl-bis-(2-methyl-propyl)-thio- carbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl-phenylsulfonyl)-lH-l,2,4- triazol-1 -carboxamid (Cafenstrole), 2-[l-[(3-Chlor-2-propenyl)-oxy-imino]-propyl]- 3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen- 1 -on (Caloxydim, Tepraloxy- dim), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluor- methyl-5-methyl-2,4-dihydro-3H- 1 ,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4- Dichlor-l-(3-methoxy-4-nitro-phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5- dichlor-benzoesäure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2- ethoxycarbonyl-phenylsulfonyl)-harnsto f (Chlorimuron-ethyl), 1 ,3,5-Trichlor-2-(4- nitro-phenoxy)-benzol (Chlornitrofen), N-(4-Methoxy-6-methyl- 1 ,3,5-triazin-2-yl)- N'-(2-chlor-phenylsulfonyl)-hamstoff (Chlorsulfuron), N'-(3-Chlor-4-methyl- phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(l ,3,4,5,6,7- hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon- ethyl), N-(4,6-Dimethoxy-l,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenyl- sulfonyl)-harnstoff (Cinosulfuron), 2-[l-[2-(4-Chlor-phenoxy)-propoxyaminobutyl]- 5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclohexandion (Clefoxydim), (E,E)-(+)-2-[l-(Benzoylprop-ethyl), 3-i-propyl-lH-2, l, 3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) -2-nitro- benzoate (bifenox), 2,6-bis (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzoic acid sodium salt (bispyribac-sodium), 5-bromo-6-methyl-3- (l-methyl -propyl) -2,4 (lH, 3H) pyrimidinedione (bromacil), 2-bromo-3,3-dimethyl-N- (l-methyl-l-phenyl-ethyl) -butanamide (bromobutide), 3, 5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) -oxime (bromofenoxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl- 2-chloro-N- (2,6-diethyl-phenyl) acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 ( 2H) -pyrimidinyl) -benzoic acid- [1, 1 -dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (l-ethoximinopropyl) -3-hydroxy-5 - [2,4,6-trimethyl-3- (l-oxobutyl) phenyl] -2-cyclohexen-l-one (butroxydim), S-ethyl-bis- (2-methyl-propyl) -thio- carbamate (butylates), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) -lH-l, 2,4-triazole-1-carboxamide (cafenstrole), 2- [l - [(3-chloro-2-propenyl) -oxy-imino] propyl] - 3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1 -one ( Caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro -3H- 1, 2,4-triazol-3-one (Carfentrazone-ethyl), 2,4- Dichloro-l- (3-methoxy-4-nitro-phenoxy) benzene (chloromethoxyfen), 3-amino-2,5-dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidine-2 -yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) urea (chlorimuron-ethyl), 1, 3,5-trichloro-2- (4-nitro-phenoxy) -benzene (chloronitrofen), N- (4th -Methoxy-6-methyl-1, 3,5-triazin-2-yl) - N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N-dimethyl-urea (chlorotoluron), 2-chloro-3- [2-chloro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindole- 2-yl) -phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), N- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2- methoxy-ethoxy) -phenyl-sulfonyl) -urea (Cinosulfuron), 2- [l- [2- (4-chlorophenoxy) -propoxyaminobutyl] - 5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclohexanedione (Clefoxydim), (E, E) - (+) - 2- [l-
[[(3-Chlor-2-propenyl)-oxy]-imino]-propyl]-3-hydroxy-2-cyclohexen-l-on (Cletho- dim), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3- chloro-2-[(5-ethoxy-7-fluor[l,2,4]triazolo[l,5-c]pyrimidin-2-yl-sulfonyl)-amino]- benzoat (Cloransulam-methyl), 2-Chlor-4-ethylamino-6-(l -cyano- 1 -methyl-ethyl- amino)-l,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-cyclo- propylcarbonyl-phenylsulfonyl)-harnsto f (Cyclosulfamuron), 2-(l-Ethoximino- butyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen- 1 -on (Cycloxy- dim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propansäure-butylester (Cy- halofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy- benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichloφrop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), N-(2,6- Dichlor-phenyl)-5-ethoxy-7-fluor-[ 1 ,2,4]-triazolo-[ 1 ,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 1 ,2-Dimethyl-3,5-diphenyl-lH-pyrazolium-methylsulfat (Difenzo- quat), N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid[[(3-chloro-2-propenyl) oxy] imino] propyl] -3-hydroxy-2-cyclohexen-l-one (clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxypropanoate (clodinafop-propargyl), 3,6-dichloropyridine-2-carboxylic acid (clopyralid), methyl-3-chloro -2 - [(5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) -amino] benzoate (chlorosulam-methyl), 2-chloro 4-ethylamino-6- (l-cyano-1-methyl-ethyl-amino) -l, 3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N'- (2-cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 2- (l-ethoximino-butyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexene-1 - on (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propanoic acid butyl ester (cyhalofop butyl), 2,4-dichlorophenoxyacetic acid ( 2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (Dichloφrop-P), methyl-2- [ 4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro- [1 , 2,4] -triazolo- [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-lH-pyrazolium methyl sulfate (difenzoquate), N- (2,4-difluoro-phenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide
(Diflufenican), 2-[l-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]- pyridin-3 -carbonsäure (Diflufenzopyr), S-( 1 -Methyl- 1 -phenyl-ethyl)- 1 -piperidin- carbothioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-methoxy-ethyl)- acetamid (Dimethachlor), (S-) 2-Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-l- methyl-ethyl)-acetamid (S-) (Dimethenamid), 2-Amino-4-(l-fluor-l-methyl-ethyl)-6-(Diflufenican), 2- [l - [(3,5-difluorophenyl) aminocarbonylhydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl- ethyl) - 1-piperidine carbothioate (dimepiperate), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (2-methoxy-ethyl) - acetamide (dimethachlor), (S-) 2-chlorine -N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (l-fluoro-l -methyl-ethyl) -6-
(l-methyl-2-(3,5-dimethyl-phenoxy)-ethylamino)-l,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl- 1 ,3-diamino-benzol (Dinitramine), 6,7- Dihydro-dipyrido[l,2-a:2', -c]pyrazindiium (Diquat), S,S-Dimethyl-2-difluor- methyl-4-i-butyl-6-trifluormethyl-pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Di- chlor-phenyl)-N,N-dimethyl-harnstoff (Diuron), 2-[2-(3-Chlor-phenyl)-oxiranyl- methyl]-2-ethyl-lH-inden-l,3(2H)-dion (Epropodan), S-Ethyl-dipropylthiocarbamat(l-methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -l, 3,5-triazine (dimexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', -c] pyrazinediium (diquat ), S, S-Dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-di-chlorophenyl) - N, N-dimethylurea (diuron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-lH-indene-1,3, (2H) -dione (epropodane), p ethyl-dipropylthiocarbamate
(EPTC), S-(Phenylmethyl)-N-ethyl-N-( 1 ,2-dimethyl-propyl)-thiocarbamat (Espro- carb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzenamin (Ethalfluralin), (S)-(2-Ethoxy- 1 -methyl-2-oxoethyl)-2-chlor-5 -(2-chlor-4-trifluor- methyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), (R)-Ethyl-2-[4-(6-chlor-benz- oxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)- N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazol-l-carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluor-phenyl)-DL-alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluor-phenyl)-L-alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)-DL-alaninat (Flamprop-methyl), N-(EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethylpropyl) thiocarbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -2 , 6-dinitro-4-trifluoromethyl-benzenamine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5 - (2-chloro-4-trifluoromethyl-phenoxy ) -benzoate (ethoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethoxy-phenoxysulfonyl) -urea (ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro-benz-oxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop- (P) -ethyl), 4- (2-chlorophenyl) - N-cyclohexyl-N-ethyl-4, 5-dihydro-5-oxo-lH-tetrazole-l-carboxamide (fentrazamide), isopropyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -DL-alaninate (flamprop-isopropyl), isopropyl- N-benzoyl-N- (3-chloro-4-fluorophenyl) -L-alaninate (Flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) -DL -alaninate (Flamprop-methyl), N-
(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfon- amid (Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propan- säure-butylester (Fluazifop, -butyl, -P-butyl), 5-(4-Brom-l-methyl-5-trifluormethyl- lH-pyrazol-3-yl)-2-chlor-4-fluor-benzoesäure-i-propylester (Fluazolate), 4,5-Di- hydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-l-H-(2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), (R) -2- [4- (5-Trifluoromethyl-pyridin-2-yl-oxy) phenoxy] propanoic acid butyl ester (fluazifop, butyl, P-butyl), 5- (4-bromo-l-methyl -5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), 4,5-di-hydro-3-methoxy-4-methyl-5-oxo N - [(2-trifluoromethoxy-phenyl) sulfonyl] -lH-
1 ,2,4-triazol- 1 -carboxamid-Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)- N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N- (2,6-Difluor-phenyl)-5-methyl- 1 ,2,4-triazolo[ 1 ,5-a]-pyrimidin-2-sulfonamid (Flumet- sulam), Pentyl-[2-chlor-4-fluor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2- yl)-phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4-dihydro-3-oxo-4-(2- propinyl)-2H-l,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-lH-isoindol-l,3-dion (Flumi- oxazin), 2-[4-Chlor-2-fluor-5-[(l-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetra- hydro-lH-isoindol-l,3(2H)-dion (Flumipropyn), 3-Chlor-4-chlormethyl-l-(3-trifluor- methyl-phenyl)-2-pyrrolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluormethyl- phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), 1-1, 2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N- (4-fluorophenyl) - Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2- yl-oxy) -acetamide (Flufenacet), N- (2,6-difluorophenyl) -5-methyl-1, 2,4-triazolo [1, 5-a] pyrimidine-2-sulfonamide (Flumet-sulam ), Pentyl- [2-chloro-4-fluoro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenoxy] acetate ( Flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-l, 4-benzoxazin-6-yl] -4,5,6,7 tetrahydro-lH-isoindole-1,3-dione (flumoxoxazine), 2- [4-chloro-2-fluoro-5 - [(l-methyl-2-propynyl) -oxy] -phenyl] -4, 5,6,7-tetra-hydro-lH-isoindole-l, 3 (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl-l- (3-trifluoromethyl-phenyl) -2-pyrrolidinone ( Fluorochloridones), 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1-
(4-Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazol- 3 -carboxamid (Flupoxam), 1 -Isopropyl-2-chlor-5 -(3 ,6-dihydro-3 -methyl-2,6-dioxo- 4-trifluormethyl- 1 (2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)- harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 9-Hydroxy-9H-fluoren-9- carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure(4-chloro-3- (2,2,3,3,3-pentafluoro-propoxymethyl) -phenyl) -5-phenyl-lH-l, 2,4-triazol- 3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5 - (3, 6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidyl) -benzoate (flupropacil) , N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 9 -Hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid
(-2-butoxy-l-methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flur- tamone), Methyl-[(2-chlor-4-fluor-5-(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadiazolo- [3,4-a]-pyridazin- 1 -yliden)-amino-phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2- Chlor-4-trifluormethyl-phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fomesafen),(-2-butoxy-l-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H ) -furanon (Flur- tamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-lH, 3H- [l, 3,4] thiadiazolo- [3,4-a ] -pyridazin-1-ylidene) -amino-phenyl] -thio-acetate (Fluthiacet-methyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) -N-methylsulfonyl-2-nitro-benzamide (Fomesafen),
2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formyl- amino-N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4-(hydroxymethylphos- phinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphono- methyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure2 - [[[[(4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N-dimethyl-benzamide (foramsulfuron), 2-amino -4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammonium salt), (glyphosate, isopropylammonium), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy) phenoxy] propanoic acid
(-methylester, -2-ethoxy-ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-Cyclohexyl-6-dimethylamino- 1 -methyl-1 ,3,5-triazin-2,4- (lH,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH- imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Im- azamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5- methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Di- hydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-chlor-imidazo[ 1 ,2-a]- pyridin-3-yl-sulfonyl)-harnstoff (Imazosulfuron), N-(4-Methoxy-6-methyl-l ,3,5- triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Di- methyl-N' -(4-isopropyl-phenyl)-harnstoff (Isopro turon), N-(3 -( 1 -Ethyl- 1 -methyl- propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methyl- sulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5-Cyclo- propyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)-methanon (Isoxa- flutole), 2-[2-[4-[3,5-Dichlor-2-pyridinyl)-oxy]-phenoxy]-l-oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Ethoxy-l-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl- phenoxy)-2-nitro-benzoat (Lactofen), N'-(3,4-dichlor-phenyl)-N-methoxy-N-methyl- harnstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2- methyl-phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N-methyl-N- phenyl-acetamid (Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]- amino]sulfonyl]-4-[[(methylsulfonyl)amino]methyl]-benzoesäure-methylester (Mesosulfuron), 2-(4-Methylsulfonyl-2-nitro-benzoyl)-l ,3-cyclohexandion (Meso- trione), 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-(-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-1-methyl-1, 3,5- triazin-2,4- (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4 -methyl benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid ( Imazamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquin), 2- (4,5-di-hydro- 4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxy-pyrimidin-2-yl ) -N '- (2-chloro-imidazo [1, 2-a] - pyridin-3-yl-sulfonyl) urea (imazosulfuron), N- (4-methoxy-6-methyl-l, 3,5- triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-d iodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isopropyl), N- (3 - (1-ethyl-1-methyl-propyl) -isoxazole -5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonylphenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5th cyclo- propyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [2- [4- [3,5-dichloro-2-pyridinyl) -oxy] -phenoxy] -l-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-l-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro- benzoate (lactofen), N '- (3,4-dichlorophenyl) -N-methoxy-N-methylurea (Linuron), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mefenacet), 2 - [[[[(4,6-dimethoxy -2-pyrimidinyl) amino] carbonyl] - amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 2- (4-methylsulfonyl-2-nitro-benzoyl) -l, 3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one (metamitron), 2-chloro
N-(2,6-dimethyl-phenyl)-N-(lH-pyrazol- 1 -yl-methyl)-acetamid (Metazachlor), N'-(4- (3,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy)-phenyl)-N- methoxy-N-methyl-harnstoff (Metobenzuron), N'-(4-Brom-phenyl)-N-methoxy-N- methylharnstoff (Metobromuron), (S)-2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-(2- methoxy-l-methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N-(2,6-Dichlor-3- methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Meto- sulam), N'-(3-Chlor-4-methoxy-phenyl)-N,N-dimethyl-harnstoff (Metoxuron), 4- Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Meth- oxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1-carbothioat (Molinate), 2-(2-N- (2,6-dimethyl-phenyl) -N- (1H-pyrazole-1-yl-methyl) -acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2, 4,4-trimethyl-2H-l-benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl-urea (metobenzuron), N '- (4-bromo-phenyl) -N-methoxy- N-methylurea (metobromuron), (S) -2-chloro-N- (2-ethyl-6-methyl-phenyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (metolachlor, S -Metolachlor), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam ), N '- (3-chloro-4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazine 5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (metsulfuron -methyl), S-ethyl-hexahydro-lH-azepine-1-carbothioate (Molinate), 2- (2-
Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N-Butyl-N'-(3 ,4-dichlor- phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-di- methylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfuron), 4-Chlor-5-methyl- amino-2-(3-trifluormethyl-phenyl)-3(2H)pyridazinon (Norflurazon), S-(2-Chlor- benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4-Dipropylamino-3,5-dinitro- benzensulfonamid (Oryzalin), 3-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)- l,3,4-oxadiazol-2(3H)-on (Oxadiargyl), 3-[2,4-Dichlor-5-(l-methyl-ethoxy)-phenyl]- 5-(t-butyl)- 1 ,3 ,4-oxadiazol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2-yl)- N'-(2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl)-harnstoff (Oxasulfuron), 3-[l -(3,5- Dichlor-phenyl)-l-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-l,3-oxazin-4-onNaphthyloxy) -N-phenyl-propanamide (naproanilide), N-butyl-N '- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxy-pyrimidine-2 -yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 ( 2H) pyridazinone (norflurazone), S- (2-chlorobenzyl) -N, N-diethylthiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitrobenzenesulfonamide (Oryzalin), 3- [2,4- Dichloro-5- (2-propynyloxy) phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5- (l-methyl-ethoxy) phenyl] - 5- (t-butyl) - 1,3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidine-2- yl) - N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [l - (3,5-dichlorophenyl) -li-propyl] -2,3-dihydro -6-methyl-5-phenyl-4H-l, 3-oxazin-4-on
(Oxaziclomefone), 2-Chlor- 1 -(3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl-benzen (Oxyfluorfen), 1,1 '-Dimethy 1-4,4 '-bipyridinium (Paraquat), l-Amino-N-(l-ethyl- propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t-Butyl)-N-( 1 -ethyl- propyl)-2,6-dinitro-benzenamin (Pendralin), 4-Amino-3,5,6-trichlor-pyridin-2- carbonsäure (Picloram), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acet- amid (Pretilachlor), N-(4,6-Bis-difluormethoxy-pyrimidin-2-yl)-N'-(2-methoxy- carbonyl-phenylsulfonyl)-harnstoff (Primisulfuron-methyl), 1 -Chlor-N-[2-chlor-4- fluor-5-[(6S,7aR)-6-fluor-tetrahydro-l,3-dioxo-lH-pyrrolo[l,2-c]imidazol-2(3H)-yl]- phenyl]-methansulfonamid (Profluazol), 2-Chlor-N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor-phenyl)-propanamid (Propanil), (R)-[2-[[(l-Methyl- ethyliden)-amino]-oxy]-ethyl]-2-[4-(6-chlor-2-chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[(l-methyl-ethoxy)- methylj-acetamid (Propisochlor), 2-[[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH- l,2,4-triazol-l-yl)-carbonyl]-amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone-sodium), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Prosulfo- carb), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)- phenylsulfonyl)-harnstoff (Prosulfüron), Ethyl-[2-Chlor-5-(4-chlor-5-difluor- methoxy- 1 -methyl- 1 H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 1 - (3-Chlor-4,5,6,7-tetrahydro-pyrazolo[l,5-a]pyridin-2-yl)-5-(methyl-2-propinyl- amino)- lH-pyrazol-4-carbonitril (Pyrazogyl), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-(Oxaziclomefone), 2-chloro-1 - (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (Oxyfluorfen), 1,1 '-dimethy 1-4,4' -bipyridinium (paraquat), l-amino-N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene ( Pendimethalin), 4- (t-butyl) -N- (1-ethyl-propyl) -2,6-dinitro-benzenamine (pendralin), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid ( Picloram), N- (4-fluoro-phenyl) -6- (3-trifluoromethyl-phenoxy) -pyridine-2-carboxamide (picolinafen), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bis-difluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxy-carbonyl-phenylsulfonyl) -urea (primisulfuron- methyl), 1-Chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l, 3-dioxo-lH-pyrrolo [l, 2-c] imidazole -2 (3H) -yl] - phenyl] methanesulfonamide (profluazole), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N- (3,4-dichlorophenyl) propanamide (propanil) , (R) - [2 - [[(l-methylethylidene) amino] oxy] ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(l-methyl-ethoxy) - methylj-acetamide (propisochlor), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) carbonyl] amino] sulfonyl] benzoic acid - methyl ester sodium salt (Propoxycarbazone-sodium), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarbam), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) - N '- (2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (prosulfuron), ethyl- [2-chloro-5- (4-chloro-5-difluoro-methoxy-1-methyl- 1 H-pyrazol-3-yl) -4-fluoro-phenoxy] acetate (pyraflufen-ethyl), 1 - (3-chloro-4,5,6,7-tetrahydro-pyrazolo [1,5-a] pyridine -2-yl) -5- (methyl-2-propynylamino) - 1H-pyrazole-4-carbonitrile (pyrazogyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-
5-(4-methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)- 1,3- dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(4-ethoxycarbonyl-l-methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenylmethanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2- yl-oxy)-benzoyl]-oxim (Pyribenzoxim), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol),5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4- (2,4-dichlorobenzoyl) - 1,3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxyfen), N- (4.6 -Dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-l-methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenylmethanone-O- [2,6-bis- ( 4,6-dimethoxypyrimidin-2-yloxy) benzoyl] oxime (pyribenzoxime), 6-chloro-3-phenyl-4-pyridazinol (pyridafol),
O-(6-Chlor-3-phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3- phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl- 1 (3H)-isobenzofuranon (Pyriflalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoe- säure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-yl- thio)-benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor-chinolin-8-carbon- säure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbonsäure (Quinmerac), 2-[4-(6- Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, -tetrahydro-2-furanyl- methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin- 2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfuron), 2-(l-Ethox- iminobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen- 1 -on (Sethoxydim), 6- Chlor-2,4-bis-ethylamino-l,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonyl- benzoyl)-cyclohexan- 1 ,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino- phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-on (Sulfentra- zone), Methyl 2-[[[[(4,6-dimethyl-2-p)τimidinyl)amino]carbonyl]amino]sulfonyl]- benzoat (Sulfometuron-methyl), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[l,2-a]- pyridin-3-sulfonamid (Sulfosulfuron), 6-Chlor-4-ethylamino-2-tert-butylamino- 1,3,5-triazin (Terbuthylazine), 2-tert-Butylamino-4-ethylamino-6-methylthio- 1,3,5- triazin (Terbutryn), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl- methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2- methyl-propyl)-6-trifluormethyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-O- (6-chloro-3-phenyl-pyridazin-4-yl) -S-octyl-thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7 - [(4, 6-Dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H) -isobenzofuranone (pyriflalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester ( Pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-yl-thio) -benzoic acid sodium salt (Pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid ( Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6- Chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester, tetrahydro-2-furanyl methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy- pyrimidin-2-yl) -N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfuron), 2- (l-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy -2-cyclohexen- 1 -one (sethoxydim), 6-chloro-2,4-bis-ethylamino-l, 3,5-triazine (simazine), 2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane - 1,3-dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylaminophenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazole- 3-one (sulfentrazone), methyl 2 - [[[[(4,6-dimethyl-2-p) τimidinyl) amino] carbonyl] amino] sulfonyl] benzoate (sulfometuron-methyl), N-phosphonomethylglycine -trimethylsulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethylsulfonyl-imidazo [l, 2-a] - pyridine-3-sulfonamide (sulfosulfuron), 6- Chloro-4-ethylamino-2-tert-butylamino-1,3,5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2 -Chlor-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazole-2 -yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6-
(6,7-Dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,l-c]-l,2,4-thiadiazol-3-ylidenamino)-7- fluor-4-(2-propinyl)-2H- 1 ,4-benzoxazin-3(4H)-on (Thidiazimin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl- phenyl)-2-cyclohexen-l-on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopro- pylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2- chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6- methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnsto f (Tri- benuron-methyl), (3,5,6-Trichlor)-pyridin-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Di- chlor-phenyl)-2-(2,2,2-trichlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid- Natriumsalz (Trifloxysulfuron), 1 -Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl- benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfuron-methyl), N-(4- Methoxy-6-trifluormethoxy- 1 ,3 ,5 -triazin-2-yl)-N' -(2-trifluormethyl-pheny lsulfonyl)- harnstoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3- (N-methyl-N-methylsulfonyl-amino)-2-pyridinsulfonamid (vgl. WO-A-92/ 10660), 4- [4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-lH-l,2,4-triazol-l-yl]-2-[(ethyl- sulfonyl)amino]-5-fluor-benzencarbothioamid (vgl. WO-A-95/30661)(6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2, lc] -l, 2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) -2H - 1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylthiene -3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-l-one (tralkoxydim ), S- (2,3,3-trichloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tri-benuron-methyl), (3,5,6-trichloro) -pyridin-2-yl-oxyacetic acid (triclopyr), 2- (3,5- Dichlorophenyl) -2- (2,2,2-trichloroethyl) oxirane (tridiphane), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), 1-amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoroethoxy) -1, 3,5-triazin-2-yl] -N '- (2-methoxycarbonylphenylsulfonyl) urea (triflusulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), N - [[(4,6- dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino) -2-pyridinesulfonamide (see WO-A-92/10660), 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) - lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide (cf. WO-A-95/30661)
("Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
und/oderand or
(c) eine die Kultuφflanzen-Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:(c) a compound which improves crop plant tolerance from the following group of compounds:
4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1 -Dichloracetyl-hexahydro- 3,3,8a-trimethylpyrrolo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), 4-Dichloracetyl- 3,4-dihydro-3-methyl-2H- 1 ,4-benzoxazin (Benoxacor), 5-Chlor-chinoxalin-8-oxy- essigsäure-(l-methyl-hexylester) (Cloquintocet-mexyl), α-(Cyanomethoximino)- phenylacetonitril (Cyometrinil), 2,4-Dichloφhenoxy-essigsäure (2,4-D), 2,2-Dichlor- N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamid (DKA-24), 2,2-Di- chlor-N,N-di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-( 1 -methyl- l-phenyl-ethyl)-harnstoff (Dymron), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), 1- (2,4-Dichlor-phenyl)-5-trichlormethyl-lH-l,2,4-triazol-3-carbonsäure-ethylester4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] -pyrimidine-6 (2H ) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor), 5-chloro-quinoxaline-8-oxyacetic acid- (l-methyl -hexyl ester) (Cloquintocet-mexyl), α- (cyanomethoximino) - phenylacetonitrile (Cyometrinil), 2,4-dichloφhenoxy-acetic acid (2,4-D), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2,2-di-chloro-N, N-di-2-propenyl-acetamide (dichlormid), N- ( 4-methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron), 4,6-dichloro-2-phenyl-pyrimidine (Fenclorim), 1- (2,4-dichloro phenyl) -5-trichloromethyl-lH-l, 2,4-triazol-3-carboxylic acid ethyl ester
(Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure-phenylmethyl- ester (Flurazole), 4-Chlor-N-(l ,3-dioxolan-2-yl-methoxy)-α-trifluor-acetophenon- oxim (Fluxofenim), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furil- azole, MON- 13900), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxa- difen-ethyl), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (+-)-2-(4-Chlor-2- methylphenoxy)propansäure (Mecoprop), Diethyl- 1 -(2,4-dichloφhenyl)-4,5-dihydro- 5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) 2-Dichlormethyl-2- methyl-l,3-dioxolan (MG-191), 1,8-Naphthalsäureanhydrid, α-(l,3-Dioxolan-2-yl- methoximino)-phenylacetonitril (Oxabetrinil), 2,2-Dichlor-N-(l ,3-dioxolan-2-yl- methyl)-N-(2-propenyl)-acetamid (PPG- 1292), 3-Dichloracetyl-2,2,5-trimethyl- oxazolidin (R-29148), N-Cyclopropyl-4-[[(2-methoxy-5-methyl-benzoyl)-amino]- sulfonylj-benzamid (WO-A-99/66795), N-[[(4-Methoxyacetylamino)-phenyl]- sulfonyl-2-methoxy-benzamid (WO-A-99/66795) und N-[[(4-Methylaminocarbonyl- amino)-phenyl]-sulfonyl-2-methoxy-benzamid (WO-A-99/66795)(Fenchlorazol-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (Flurazole), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -α-trifluoro -acetophenone-oxime (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furil-azoles, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl -3-isoxazole carboxylate (isoxydif-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (+ -) - 2- (4-chloro-2-methylphenoxy) propanoic acid (mecoprop), Diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) 2-dichloromethyl-2-methyl-1,3-dioxolane ( MG-191), 1,8-naphthalic anhydride, α- (1,3-dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-yl - methyl) -N- (2-propenyl) acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), N-cyclopropyl-4 - [[(2-methoxy -5-methyl-benzoyl) amino] - sulfonylj-benzamide (WO-A-99/66795), N - [[(4-methoxyacetylamino) phenyl] - sulfonyl-2-methoxy-benzamide (WO-A-99/66795) and N - [[(4- Methylaminocarbonylamino) phenyl] sulfonyl-2-methoxybenzamide (WO-A-99/66795)
("Wirkstoffe der Gruppe 3").("Active substances of group 3").
Bevorzugte Bedeutungen der in der vorstehend gezeigten Formel (I) aufgeführten Reste werden im folgenden erläutert.Preferred meanings of the radicals listed in the formula (I) shown above are explained below.
R1 steht bevorzugt für Wasserstoff, Amino oder jeweils gegebenenfalls durchR 1 preferably represents hydrogen, amino or, if appropriate, in each case
Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl.Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl.
R steht bevorzugt für jeweils gegebenenfalls durch Fluor und/oder Chlor sub- stituiertes Methyl, Ethyl, n- oder i-Propyl.R preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine.
R3 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i- Propyl.R 3 preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine.
R4 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor oder Brom.R 4 preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R5 steht bevorzugt für Cyano, Thiocarbamoyl, Fluor, Chlor oder Brom.R 5 preferably represents cyano, thiocarbamoyl, fluorine, chlorine or bromine.
R6 steht bevorzugt für Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy, Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy, Hydroxy, Methoxy, Ethoxy, n- oder i-Propoxy, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy- carbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Allyloxycarbonyl oder Propargyloxycarbonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i- oder s-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i- oder s-Butylthio, Methyl- sulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxy- carbonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i- oder s- Butylamino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor,R 6 preferably represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, carboxy, hydroxy, methoxy, ethoxy, n- or i- Propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, Methylthio, ethylthio, n- or i-propylthio, n-, i- or s-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i -Propoxy-carbonyl, methylamino, ethylamino, n- or i-propylamino, n-, i- or s-butylamino, for each optionally by cyano, carboxy, fluorine, chlorine,
Brom, Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl, Butinyl, Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Acetyl- amino, Propionylamino, n- oder i-Butyroylamino, Methoxycarbonylamino,Bromine, methoxycarbonyl and / or ethoxycarbonyl substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, each for acetyl optionally substituted by fluorine and / or chlorine, methoxy, ethoxy, n- or i-propoxy - amino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino,
Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methylsulfonyl- amino, Ethylsulfonylamino, n- oder i-Propylsulfonylamino, n-, i-, s- oder t- Butylsulfonylamino, N,N-Bis-methylsulfonyl-amino, N,N-Bis-ethylsulfonyl- amino, N-Ethylsulfonyl-N-methylsulfonyl-amino, N-Methylsulfonyl-N-n- propylsulfonyl-amino, N-Methylsulfonyl-N-i-propylsulfonyl-amino, N-Ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N-bis -ethylsulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-
Acetyl-N-methylsulfonyl-amino, N-Propionyl-N-methylsulfonyl-amino, N-n- Butyroyl-N-methylsulfonyl-amino, N-i-Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl-amino, N-t-Butyroyl-N-methylsulfonyl- amino, N-(2,2-Dimethyl-propanoyl)-N-ethylsulfonyl-amino, N-(2-Methyl- propanoyl)-N-ethylsulfonyl-amino, N-Acetyl-N-ethylsulfonyl-amino, N-Acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, Nt- Butyroyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methyl-propanoyl) -N-ethylsulfonyl-amino, N-acetyl-N-ethylsulfonyl- amino, N-
Propionyl-N-ethylsulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i- Butyroyl-N-ethylsulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl-amino, N-t- Butyroyl-N-ethylsulfonyl-amino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes N-Phenylcarbonyl-N-methylsulfonyl- amino, N-Phenylcarbonyl-N-ethylsulfonyl-amino, N-Thienylcarbonyl-N- methylsulfonyl-amino oder N-Thienylcarbonyl-N-ethylsulfonyl-amino.Propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni- butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt-butyroyl-N-ethylsulfonyl-amino, or for each optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or Trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino.
steht besonders bevorzugt für Wasserstoff, Amino, Methyl oder Ethyl. R2 steht besonders bevorzugt für jeweils durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl.particularly preferably represents hydrogen, amino, methyl or ethyl. R 2 particularly preferably represents methyl or ethyl substituted by fluorine and / or chlorine.
R3 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl.R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine.
R4 steht besonders bevorzugt für Wasserstoff, Fluor oder Chlor.R 4 particularly preferably represents hydrogen, fluorine or chlorine.
R5 steht besonders bevorzugt für Cyano, Thiocarbamoyl, Chlor oder Brom.R 5 particularly preferably represents cyano, thiocarbamoyl, chlorine or bromine.
R6 steht besonders bevorzugt für Nitro, Cyano, Carboxy, Carbamoyl, Thio- carbamoyl, Hydroxy, Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy, Hydroxy, Methoxy, Ethoxy, Acetyl, Propionyl, Methoxycarbonyl und/oder Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Allyloxycarbonyl oderR 6 particularly preferably represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, carboxy, hydroxy, methoxy, ethoxy, acetyl, Propionyl, methoxycarbonyl and / or ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or
Propargyloxycarbonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propyl- thio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i- Propoxycarbonyl, Methylamino, Ethylamino, n- oder i-Propylamino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor, Brom, Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl, Ethinyl, Propinyl, Propenyloxy oder Propinyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor, Methoxy oder Ethoxy substituiertes Acetylamino, Propionylamino, Methoxycarbonylamino, Ethoxycarbonylamino, Methyl- sulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonylamino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl-amino, N,N-Bis-ethyl- sulfonyl-amino, N-Ethylsulfonyl-N-methylsulfonyl-amino, N-Methyl- sulfonyl-N-n-propylsulfonyl-amino, N-Methylsulfonyl-N-i-propylsulfonyl- amino, N-Acetyl-N-methylsulfonyl-amino, N-Propionyl-N-methylsulfonyl- amino, N-(2,2-Dimethyl-propanoyl)-N-ethylsulfonyl-amino, N-(2-Methyl- propanoyl)-N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i-Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Acetyl-N-ethylsulfonyl- amino, N-Propionyl-N-ethylsulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl- amino, N-i-Butyroyl-N-ethylsulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl- amino, N-t-Butyroyl-N-ethylsulfonyl-amino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifiuormethoxy substituiertes N-Phenyl- carbonyl-N-methylsulfonyl-amino, N-Phenylcarbonyl-N-ethylsulfonyl- amino, N-Thienylcarbonyl-N-methylsulfonyl-amino oder N-Thienylcarbonyl-Propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n - or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for ethenyl optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl, Propenyl, ethynyl, propynyl, propenyloxy or propynyloxy, for each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i- , s- or t-butylsulfonylamino, N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl- amino, N-methylsulfonyl-Ni-propy Isulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methyl- propanoyl) -N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, Nt-butyroyl-N-methylsulfonyl-amino, N -Acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt -Butyroyl-N-ethylsulfonyl-amino, or for N-phenylcarbonyl-N-methylsulfonyl-amino, N- which are each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy Phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-
N-ethylsulfonyl-amino.N-ethylsulfonyl-amino.
Ganz besonders bevorzugte Komponenten der erfindungsgemässen Wirkstoffkombinationen sind Verbindungen der Formel (I), in welcherVery particularly preferred components of the active compound combinations according to the invention are compounds of the formula (I) in which
R1 für Amino steht,R 1 represents amino,
R2 für Trifluormethyl steht,R 2 represents trifluoromethyl,
R , 3J für Wasserstoff, Chlor oder Methyl steht,R, 3 J represents hydrogen, chlorine or methyl,
R4 für Fluor steht,R 4 represents fluorine,
R5 für Cyano oder Thiocarbamoyl steht, undR 5 represents cyano or thiocarbamoyl, and
R6 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl- sulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonylamino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl-amino, N,N-Bis-ethyl- sulfonyl-amino, N-Ethylsulfonyl-N-methylsulfonyl-amino, N-Methyl- sulfonyl-N-n-propylsulfonyl-amino, N-Methylsulfonyl-N-i-propylsulfonyl- amino, N-Acetyl-N-methylsulfonyl-amino, N-Propionyl-N-methylsulfonyl- amino, N-(2,2-Dimethyl-propanoyl)-N-ethylsulfonyl-amino, N-(2-Methyl- propanoyl)-N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i-Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Methoxyacetyl-N-methyl- sulfonylamino, N-Acetyl-N-ethylsulfonyl-amino, N-Propionyl-N-ethyl- sulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i-Butyroyl-N-ethyl- sulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl-amino, N-t-Butyroyl-N-ethyl- sulfonyl-amino, N-Methoxyacetyl-N-ethylsulfonylamino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluor- methyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes N-Phenylcarbonyl-N-methylsulfonyl-amino, N-Phenylcarbonyl-N- ethylsulfonyl-amino, N-Thienylcarbonyl-N-methylsulfonyl-amino oder N- Thienylcarbonyl-N-ethylsulfonyl-amino steht.R 6 for methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N, N-bis-methylsulfonylamino, N, in each case optionally substituted by fluorine and / or chlorine, N-bis-ethyl-sulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-methyl-sulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl- amino, N-propionyl-N-methylsulfonyl amino, N- (2,2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methyl-propanoyl) -N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl- N-methylsulfonylamino, Ns-butyroyl-N-methylsulfonylamino, Nt-butyroyl-N-methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N-propionyl- N-ethyl-sulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethyl-sulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt-butyroyl-N-ethylsulfonyl- amino, N-methoxyacetyl-N-ethylsulfonylamino, or for N-phenylcarbonyl-N-methylsulfonylamino, N optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy -Phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino.
Ganz besonders bevorzugte Komponenten der erfindungsgemässen Wirkstoffkombinationen sind weiter Verbindungen der Formel (I), in welcherVery particularly preferred components of the active compound combinations according to the invention are further compounds of the formula (I) in which
R1 für Methyl steht,R 1 represents methyl,
R2 für Trifluormethyl steht,R 2 represents trifluoromethyl,
R3 für Wasserstoff, Chlor oder Methyl steht,R 3 represents hydrogen, chlorine or methyl,
R4 für Fluor steht,R 4 represents fluorine,
R , 5 für Thiocarbamoyl steht, undR 5 stands for thiocarbamoyl, and
R >6 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl- sulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonylamino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl-amino, N,N-Bis-ethyl- sulfonyl-amino, N-Ethylsulfonyl-N-methylsulfonyl-amino, N-Methyl- sulfonyl-N-n-propylsulfonyl-amino, N-Methylsulfonyl-N-i-propylsulfonyl- amino, N-Acetyl-N-methylsulfonyl-amino, N-Propionyl-N-methylsulfonyl- amino, N-(2,2-Dimethyl-propanoyl)-N-ethylsulfonyl-amino, N-(2-Methyl- propanoyl)-N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i-Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Methoxyacetyl-N-methyl- sulfonylamino, N-Acetyl-N-ethylsulfonyl-amino, N-Propionyl-N-ethyl- sulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i-Butyroyl-N-ethyl- sulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl-amino, N-t-Butyroyl-N-ethyl- sulfonyl-amino, N-Methoxyacetyl-N-ethylsulfonylamino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes N-Phenylcarbonyl-N-methylsul fonyl-amino, N-Phenylcarbonyl-N- ethylsulfonyl-amino, N-Thienylcarbonyl-N-methylsulfonyl-amino oder N- Thienylcarbonyl-N-ethylsulfonyl-amino steht.R> 6 for methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, each optionally substituted by fluorine and / or chlorine , N-bis-ethyl-sulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-methyl sulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) - N-ethylsulfonyl-amino, N- (2-methyl-propanoyl) -N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl- amino, Nt-butyroyl-N-methylsulfonyl-amino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N- ethylsulfonylamino, Ni-butyroyl-N-ethylsulfonylamino, Ns-butyroyl-N-ethylsulfonylamino, Nt-butyroyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, or for each, if appropriate N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N- substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy methylsulfonyl-amino or N-thienylcarbonyl-N-ethyl Isulfonyl-amino.
Ganz besonders bevorzugte Komponenten der erfindungsgemässen Wirkstoffkombinationen sind weiter Verbindungen der Formel (I), in welcherVery particularly preferred components of the active compound combinations according to the invention are further compounds of the formula (I) in which
R1 für Amino oder Methyl steht,R 1 represents amino or methyl,
R für Trifluormethyl steht,R represents trifluoromethyl,
R3 für Wasserstoff, Chlor oder Methyl steht,R 3 represents hydrogen, chlorine or methyl,
R4 für Wasserstoff, Fluor oder Chlor steht,R 4 represents hydrogen, fluorine or chlorine,
R5 für Cyano, Thiocarbamoyl oder Chlor steht, undR 5 represents cyano, thiocarbamoyl or chlorine, and
R6 für Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy, Mercapto, Amino, Fluor,R 6 for carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, fluorine,
Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy, Hydroxy, Methoxy, Ethoxy, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Allyloxycarbonyl oder Propargyloxycarbonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i- Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethyl- sulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyl, Propionyl, n- oder i-Chlorine, bromine, for each optionally by cyano, carboxy, hydroxy, Methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-
Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylamino, Ethylamino, n- oder i-Propylamino, N-(2,2-Dimethyl- propanoyl)-N-ethylsulfonyl-amino, N-(2-Methyl-propanoyl)-N-ethylsulfonyl- amino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor, Brom, Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl,Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, N- (2,2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methyl-propanoyl ) -N-ethylsulfonylamino, for in each case optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl, ethenyl, propenyl,
Ethinyl, Propinyl, Propenyloxy oder Propinyloxy steht.Ethynyl, propynyl, propenyloxy or propynyloxy.
Als Beispiele für die als erfindungsgemässe Mischungspartner zu verwendendenAs examples of those to be used as mixing partners according to the invention
Verbindungen der Formel (I) seien genannt: 5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2- methoxy-benzonitril.Compounds of formula (I) may be mentioned: 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-methoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2- ethoxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-ethoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-n- propoxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-n-propoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-i- propoxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-i-propoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-n- butoxy-benzonitril. 5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-i- butoxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-n-butoxy-benzonitrile. 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-i-butoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-s- butoxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-s-butoxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2- allyloxy-benzonitril. 5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2- propargyloxy-benzonitril.5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-allyloxy-benzonitrile. 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-propargyloxy-benzonitrile.
5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-
[(l-methyl-2-propinyl)-oxy]-benzonitril. 2-Chlor-5 -(3 ,6-dihydro-3 -methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidinyl)- benzoesäure-methylester.[(L-methyl-2-propynyl) oxy] benzonitrile. 2-Chloro-5 - (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) - methyl benzoate.
2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)- benzoesäure-ethylester.2-Chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) pyrimidinyl) ethyl benzoate.
2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)- benzoesäure-n-propylester.2-Chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) pyrimidinyl) benzoic acid n-propyl ester.
2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)- benzoesäure-i-propylester.2-Chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) pyrimidinyl) benzoic acid i-propyl ester.
2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)- benzoesäure-[l,l-dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester. 2-(Methylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluormethyl-3,6-di- hydro-l(2H)-pyrimidinyl]-benzencarbothioamid.2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) - benzoic acid- [l, l-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester. 2- (Methylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl] benzene carbothioamide.
2-(Ethylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro- l(2H)-pyrimidinyl]-benzencarbothioamid.2- (ethylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydrol (2H) pyrimidinyl] benzene carbothioamide.
2-(n-Propylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluormethyl-3,6-di- hydro-l(2H)-pyrimidinyl]-benzencarbothioamid.2- (n-propylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl] benzene carbothioamide.
2-(i-Propylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluormethyl-3,6-di- hydro- 1 (2H)-pyrimidinyl]-benzencarbothioamid.2- (i-Propylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl] -benzenecarbothioamide.
2-(n-Butylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluormethyl-3,6-di- hydro- 1 (2H)-pyrimidinyl]-benzencarbothioamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(acetyl)- 1 -methansulfonamid.2- (n-butylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl] -benzenecarbothioamide. N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (acetyl) - 1-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(methylsulfonyl)- 1 -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (methylsulfonyl) - 1-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(ethylsulfonyl)-l -methansulfonamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenylJ-N-(ethylsulfonyl)- 1 -ethansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (ethylsulfonyl) -l-methanesulfonamide. N- [2-Cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenylJ-N- (ethylsulfonyl) - 1 -ethanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(n-propylsulfonyl)- 1 -methansulfonamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(i-propylsulfonyl)- 1 -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (n- propylsulfonyl) -1-methanesulfonamide. N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (i- propylsulfonyl) -1-methanesulfonamide.
N-[2-Cyano-4-fluor-5 -(3 -methyl-2,6-dioxo-4-trifluormethyl-3 ,6-dihydro- 1 (2H)- pyrimidinyl)-phenyl]-N-(acetyl)- 1 -methansulfonamid.N- [2-cyano-4-fluoro-5 - (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) phenyl] -N- (acetyl) - 1-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl] -N-(acetyl)- 1 -ethansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (acetyl) - 1 -ethanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(propanoyl)-l -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (propanoyl) -l-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(propanoyl)- 1 -ethansulfonamid. N-[2-Cyano-4-fluor-5 -(3 -methyl-2,6-dioxo-4-trifluormethyl-3 ,6-dihydro- 1 (2H)- pyrimidinyl)-phenyl]-N-(2-methyl-propanoyl)-l -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (propanoyl) - 1 -ethanesulfonamide. N- [2-cyano-4-fluoro-5 - (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) phenyl] -N- (2- methyl-propanoyl) -l-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(2-methyl-propanoyl)- 1 -ethansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (2- methyl-propanoyl) -1-ethanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(butanoyl)-l -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (butanoyl) -l-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl] -N-(butanoy 1)- 1 -ethansulfonamid.N- [2-Cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (butanoy 1 ) - 1 -ethanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(2-methyl-butanoyl)-l-methansulfonamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro- 1 (2H)- pyrimidinyl)-phenyl]-N-(2-methyl-butanoyl)- 1 -ethansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (2- methyl-butanoyl) -L-methanesulfonamide. N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) pyrimidinyl) phenyl] -N- (2- methyl-butanoyl) -1-ethanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(2,2-dimethyl-propanoyl)-l-methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (2, 2-dimethyl-propanoyl) -l-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(2,2-dimethyl-propanoyl)-l -ethansulfonamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(methoxyacetyl)- 1 -methansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (2, 2-dimethyl-propanoyl) -l-ethanesulfonamide. N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (methoxyacetyl) - 1-methanesulfonamide.
N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(methoxyacetyl)- 1 -ethansulfonamid. N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)- pyrimidinyl)-phenyl]-N-(4-methoxy-benzoyl)-ethansulfonamid.N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (methoxyacetyl) - 1 -ethanesulfonamide. N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- (4- methoxy-benzoyl) -ethanesulfonamide.
N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-cyano-N- [5- (3-Amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-cyano-
4-fluoro-phenyl]-N-benzoyl- 1 -methansulfonamid.4-fluoro-phenyl] -N-benzoyl-1-methanesulfonamide.
N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-cyano- 4-fluoro-phenyl]-N-benzoyl- 1 -ethansulfonamid.N- [5- (3-Amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) -2-cyano- 4-fluoro-phenyl] -N-benzoyl-1 -ethanesulfonamide.
N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-cyano-N- [5- (3-Amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-cyano-
4-fluoro-phenyl]-N-(4-methoxy-benzoyl)- 1 -methansulfonamid.4-fluoro-phenyl] -N- (4-methoxy-benzoyl) -1-methanesulfonamide.
N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-cyano-N- [5- (3-Amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-cyano-
4-fluoro-phenyl]-N-(2-thienyl-carbonyl)- 1 -methansulfonamid. N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-2-cyano-4-fluoro-phenyl] -N- (2-thienyl-carbonyl) -1-methanesulfonamide. N- [5- (3-Amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-cyano-
4-fluoro-phenyl]-N-(2-thienyl-carbonyl)-l -ethansulfonamid.4-fluoro-phenyl] -N- (2-thienyl-carbonyl) -l -ethanesulfonamide.
Die Verbindung 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)- pyrimidinyl)-benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (I- 1 ) - CAS-Reg.Nr.: 134605-64-4 - wird als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 91/00278).The compound 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoic acid- [1, 1-dimethyl-2-oxo 2- (2-propenyloxy)] - ethyl ester (I- 1) - CAS Reg.Nr .: 134605-64-4 - is particularly emphasized as a mixture component of formula (I) (WO 91/00278).
Die Verbindung 5-Fluor-4-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro- 1 (2H)- pyrimidinyl)-2-[(l-methyl-2-propinyl)-oxy]-benzonitril (1-2) - CAS-Reg.Nr.: 186605-50-5 - wird ebenfalls als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 97/01541).The compound 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) - pyrimidinyl) -2 - [(l-methyl-2-propynyl) - oxy] -benzonitrile (1-2) - CAS Reg.Nr .: 186605-50-5 - is also particularly emphasized as a mixture component of formula (I) (WO 97/01541).
Die Verbindung N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-di- hydro-l(2H)-pyrimidinyl)-phenyl]-N-(2,2-dimethyl-propanoyl)-l-ethansulfonamid (1-3) - nach Chem. Abstracts auch als N-[2-Cyano-5-(3,6-dihydro-3-methyl-2,6-di- oxo-4-trifluormethyl-l(2H)-pyrimidinyl)-4-fluor-phenyl]-N-ethylsulfonyl-2,2-di- methyl-propanamid zu bezeichnen (CAS-Reg.-Nr.: 232262-67-8) - wird ebenfalls als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 95/29168).The compound N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-di-hydro-l (2H) pyrimidinyl) phenyl] -N - (2,2-dimethyl-propanoyl) -l-ethanesulfonamide (1-3) - according to Chem. Abstracts also as N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6- di-oxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -4-fluorophenyl] -N-ethylsulfonyl-2,2-di- To designate methyl propanamide (CAS Reg.No .: 232262-67-8) - is also particularly emphasized as a mixture component of the formula (I) (WO 95/29168).
Die Verbindung N-[2-Cyano-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6- dihydro-l(2H)-pyrimidinyl)-phenyl]-N-(4-methoxy-benzoyl)-ethansulfonamid (1-4) - nach Chem. Abstracts auch als N-[2-Cyano-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl-l(2H)-pyrimidinyl)-4-fluor-phenyl]-N-ethylsulfonyl-4-methoxy-benz- amid zu bezeichnen (CAS-Reg.-Nr.: 184293-08-1) - wird ebenfalls als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 96/35679).The compound N- [2-cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) pyrimidinyl) phenyl] -N- ( 4-methoxy-benzoyl) -ethanesulfonamide (1-4) - according to Chem. Abstracts also as N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-tri- To designate fluoromethyl-1 (2H) -pyrimidinyl) -4-fluoro-phenyl] -N-ethylsulfonyl-4-methoxy-benzamide (CAS Reg.No .: 184293-08-1) - is also used as a mixture component of formula (I) particularly emphasized (WO 96/35679).
Die Verbindung N-[5-(3-Amino-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyri- midinyl)-2-cyano-4-fluoro-phenyl]-N-(2-thienyl-carbonyl)- 1 -ethansulfonamid (1-5) - nach Chem. Abstracts auch als N-[2-Cyano-5-(3,6-dihydro-3-methyl-2,6-dioxo-4- trifluormethyl-l(2H)-pyrimidinyl)-4-fluor-phenyl]-N-ethylsulfonyl-2-thiophen-car- boxamid zu bezeichnen - wird ebenfalls als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 96/35679).The compound N- [5- (3-amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-cyano-4-fluoro-phenyl] -N - (2-thienyl-carbonyl) - 1 -ethanesulfonamide (1-5) - according to Chem. Abstracts also as N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo- 4-trifluoromethyl-l (2H) -pyrimidinyl) -4-fluorophenyl] -N-ethylsulfonyl-2-thiophene-car-boxamide is also particularly emphasized as a mixture component of the formula (I) (WO 96/35679) ,
Die Verbindung 2-(Ethylsulfonylamino)-5-fluor-4-[3-methyl-2,6-dioxo-4-trifluor- methyl-3,6-dihydro-l(2H)-pyrimidinyl]-benzencarbothioamid (1-6) - nach Chem. Abstracts auch als 4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyri- midinyl)-2-ethylsulfonylamino-5-fluor-benzencarbothioamid zu bezeichnen (CAS- Reg.-Nr.: 173980-09-1) - wird ebenfalls als Mischungskomponente der Formel (I) besonders hervorgehoben (WO 95/30661).The compound 2- (ethylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl] -benzenecarbothioamide (1-6 ) - According to Chem. Abstracts also as 4- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -2-ethylsulfonylamino-5-fluorobenzenecarbothioamide to designate (CAS Reg.No .: 173980-09-1) - is also emphasized as a mixture component of formula (I) (WO 95/30661).
Die Verbindungen der Formel (I) sind in den oben zu den N-Aryl-uracilen angegebenen Patentanmeldungen bzw. Patentschriften beschrieben.The compounds of the formula (I) are described in the patent applications or patents given above for the N-aryluracils.
Die Wirkstoffe der Gruppe 2 können ihrer chemischen Struktur entsprechend folgenden Wirkstoffklassen zugeordnet werden: Amide (z.B. Isoxaben, Picolinafen, Propanil), Arylheterocyclen (z.B. Azafenidin, Benzfendizone, Butafenacil-allyl, Carfentrazone-ethyl, Cinidon-ethyl, Fluazolate, Flumiclorac-pentyl, Flumioxazin, Flupropacil, Fluthiacet-methyl, Oxadiazon, Oxadi- argyl, Profluazol, Pyraflufen-ethyl, Pyridate, Pyridafol, Sulfentrazone, Thidiazimin, 4-[4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-lH-l,2,4-triazol-l-yl]-2-[(ethyl- sulfonyl)amino]-5-fluor-benzolcarbothioamid), Aryloxyphenoxypropionate (z.B. Clodinafop-propargyl, Cyhalofop-butyl, Diclofop-methyl, Fenoxaprop-P-ethyl, Flu- azifop-P-butyl, Haloxyfop-R-methyl, Quizalofop-P-ethyl), Carbonsäurederivate (z.B. Clopyralid, Dicamba, Fluroxypyr, Picloram, Triclopyr), Benzothiadiazole (z.B. Bent- azon), Chloracetamide (z.B. Acetochlor, Alachlor, Butachlor, (S-) Dimethenamid,The active substances of group 2 can be assigned to their chemical structure according to the following active substance classes: Amides (e.g. Isoxaben, Picolinafen, Propanil), aryl heterocycles (e.g. Azafenidin, Benzfendizone, Butafenacil-allyl, Carfentrazone-ethyl, Cinidon-ethyl, Fluazolate, Flumiclorac-pentyl, Flumioxazin, Flupropacil, Fluthiacet-methyl, Oxi-argol, Oxadiazon, oxadiazon, oxadiazon , Pyraflufen-ethyl, pyridate, pyridafol, sulfentrazone, thidiazimin, 4- [4,5-dihydro-4-methyl-5-oxo- (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide), aryloxyphenoxypropionates (e.g. clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop- R-methyl, Quizalofop-P-ethyl), carboxylic acid derivatives (e.g. clopyralid, dicamba, fluroxypyr, picloram, triclopyr), benzothiadiazoles (e.g. bentazone), chloroacetamides (e.g. acetochlor, alachlor, butachlor, (S-) dimethenamid,
Metazachlor, Metolachlor, Pretilachlor, Propachlor, Propisochlor), Cyclohexandione (z.B. Butroxydim, Clefoxydim, Cycloxydim, Sethoxydim, Tralkoxydim), Dinitro- aniline (z.B. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Trifluralin), Di- phenylether (z.B. Acifluorfen-sodium, Aclonifen, Bifenox, Fluoroglycofen-ethyl, Fomesafen, Lactofen, Oxyfluorfen), Harnstoffe (z.B. Chlortoluron, Diuron, Isoprot- uron, Linuron, Metobromuron, Metoxuron), Imidazolinone (z.B. Imazamethabenz- methyl, Imazamox, Imazaquin, Imazethapyr), Isoxazole (z.B. Isoxaflutole), Nicotinanilide (z.B. Diflufenican), Nitrile (z.B. Bromoxynil, Ioxynil), Organophosphor- Verbindungen (z.B. Glufosinate-ammonium, Glyphosate-isopropylammonium, Sulfosate), Oxyacetamide (z.B. Flufenacet, Mefenacet), PhenoxycarbonsäurederivateMetazachlor, Metolachlor, Pretilachlor, Propachlor, Propisochlor), Cyclohexanediones (e.g. Butroxydim, Clefoxydim, Cycloxydim, Sethoxydim, Tralkoxydim), Dinitro-aniline (e.g. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin), Diifphenylin, Triflural Aclonifen, Bifenox, Fluoroglycofen-ethyl, Fomesafen, Lactofen, Oxyfluorfen), ureas (e.g. chlortoluron, diuron, isoproturon, linuron, metobromuron, metoxuron), imidazolinones (e.g. imazamethabenz-methyl, imazamox, imazapole), imazapole, eg Isoxaflutole), nicotinanilides (e.g. diflufenican), nitriles (e.g. bromoxynil, ioxynil), organophosphorus compounds (e.g. glufosinate-ammonium, glyphosate-isopropylammonium, sulfosate), oxyacetamides (e.g. flufenacet, mefenacetate), phenoxycarboxylic acid derivatives
(z.B. 2,4-D, Dichloφrop-P, MCPA, MCPB, Mecoprop), Pyrazole (z.B. Pyrazolate, Pyrazoxyfen), Pyridazinone (z.B. Norflurazon), Pyridine (z.B. Dithiopyr, Thiazopyr), Pyrimidinyl(thio)benzoate (z.B. Bispyribac, Pyribenzoxim, Pyrithiobac, Pyrimino- bac), Sulfonylharnstoffe (z.B. Amidosulfuron, Azimsulfuron, Bensulfüron-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Cyclosulfamuron, Ethoxysulfüron,(e.g. 2,4-D, Dichloφrop-P, MCPA, MCPB, Mecoprop), pyrazoles (e.g. pyrazolates, pyrazoxyfen), pyridazinones (e.g. norflurazone), pyridines (e.g. dithiopyr, thiazopyr), pyrimidinyl (thio) benzoates (e.g. bispyribac, Pyribenzoxime, pyrithiobac, pyriminobac), sulfonylureas (e.g. amidosulfuron, azimsulfuron, bensulfüron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfüron,
Flupyrsulfuron-methyl-sodium, Foramsulfuron, Iodosulfuron-methyl-sodium, Imazo- sulfuron, Metsulfuron-methyl, Nicosulfuron, Oxasulfuron, Primisulfuron-methyl, Prosulfuron, Pyrazosulfuron-ethyl, Rimsulfuron, Sulfometuron-methyl, Sulfo- sulfuron, Thifensulfuron-methyl, Triasulfuron, Tribenuron-methyl, Trifloxysulfuron, Triflusulfuron-methyl, Tritosulfuron), Tetrazolinone (z.B. Fentrazamide), Thio- carbamate (z.B. Butylate, Dimepiperate, EPTC, Esprocarb, Molinate, Orbencarb, Prosulfocarb, Triallate), Triazine (z.B. Ametryn, Atrazin, Cyanazine, Dimexyflam, Simazin, Terbuthylazine, Terbutryn), Triazinone (z.B. Hexazinone, Metamitron, Metribuzin), Triazole (z.B. Amitrole), Triazolinone (z.B. Amicarbazone, Flucarb- azone-sodium, Propoxycarbazone-sodium), Triazolopyrimidine (z.B. Cloransulam- methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam), Triketone (z.B. Meso- trione, Sulcotrione), Uracile (z.B. Bromacil).Flupyrsulfuron-methyl-sodium, foramsulfuron, iodosulfuron-methyl-sodium, imazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, Triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron), tetrazolinones (e.g. fentrazamides), thiocarbamates (e.g. butylates, dimepiperates, EPTC, Esprocarb, Molinate, Orbencarb, Prosulfocarb, triallates), triazines (e.g. ametryn, atrazine, cyanazines, dimexyflam, simazine, terbuthylazine, terbutryn), triazinones (e.g. hexazinones, metamitron, metribuzin), triazoles (e.g. amitrole), triazolinones (e.g. amicarbazone zone, sodium, fluc Propoxycarbazone-sodium), triazolopyrimidines (eg cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam), triketones (eg mesotrione, sulcotrione), uracile (eg bromacil).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 2 werden besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group 2:
Acetochlor, Alachlor, Amicarbazone, Amitrole, Atrazin, Bromacil, Carfentrazone- ethyl, Chlorimuron-ethyl, Clodinafop-propargyl, Cyanazine, Diclosulam, Dimethen- amid, S-Dimethenamid, Diuron, EPTC, Fenoxaprop-P-ethyl, Fentrazamide, Flucarb- azone-sodium, Flufenacet, Flumetsulam, Glufosinate-ammonium, Glyphosate-iso- propylammonium, Imazamox, Imazaquin, Imazethapyr, Isoxaflutole, Mesotrione,Acetochlor, alachlor, amicarbazone, amitrole, atrazine, bromacil, carfentrazone-ethyl, chlorimuron-ethyl, clodinafop-propargyl, cyanazine, diclosulam, dimethenamide, S-dimethenamid, diuron, EPTC, fenoxaprop-P-ethyl, fentrazamide, flentrazamide azone-sodium, flufenacet, flumetsulam, glufosinate-ammonium, glyphosate-isopropylammonium, imazamox, imazaquin, imazethapyr, isoxaflutole, mesotrione,
Metolachlor, S-Metolachlor, Metosulam, Metribuzin, Nicosulfuron, Norflurazon, Pendimethalin, Propoxycarbazone-sodium, Rimsulfuron, Simazin, Sulfometuron- methyl, Sulcotrione, Sulfentrazone, Sulfosate, Terbuthylazine, Thifensulfuron- methyl, Trifluralin, 4-[4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-lH-l,2,4- triazol- 1 -yl]-2-[(ethylsulfonyl)amino]-5-fluor-benzolcarbothioamid.Metolachlor, S-Metolachlor, Metosulam, Metribuzin, Nicosulfuron, Norflurazon, Pendimethalin, Propoxycarbazone-sodium, Rimsulfuron, Simazin, Sulfometuron-methyl, Sulcotrione, Sulfentrazone, Sulfosate, Terbuthylazine, Thifensulflural-methyl, Trifutylhydro, 4- -4-methyl-5-oxo (3-trifluoromethyl) -IH-l, 2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide.
Die besonders hervorgehobenen Wirkstoffe der Gruppe 2 können ihrer chemischen Struktur entsprechend folgenden Wirkstoffklassen zugeordnet werden:The active substances in Group 2 that are particularly highlighted can be assigned to their chemical structure according to the following classes of active substances:
Arylheterocyclen (z.B. Carfentrazone-ethyl, Sulfentrazone, 4-[4,5-Dihydro-4-methyl-Aryl heterocycles (e.g. carfentrazone-ethyl, sulfentrazone, 4- [4,5-dihydro-4-methyl-
5-oxo-(3-trifluormethyl)- 1 H- 1 ,2,4-triazol- 1 -yl]-2-[(ethylsulfonyl)amino]-5-fluor- benzolcarbothioamid), Chloracetamide (z.B. Acetochlor, Alachlor, Dimethenamid, S-Dimethenamid, Metolachlor, S-Metolachlor), Dinitroaniline (z.B. Pendimethalin, Trifluralin), Harnstoffe (z.B. Diuron), Imidazolinone (z.B. Imazamox, Imazaquin, Imazethapyr), Organophosphor-Verbindungen (z.B. Glufosinate, Glyphosate,5-oxo (3-trifluoromethyl) -1 H-1, 2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide), chloroacetamides (e.g. acetochlor, alachlor, dimethenamide , S-dimethenamid, metolachlor, S-metolachlor), dinitroanilines (e.g. pendimethalin, trifluralin), ureas (e.g. diuron), imidazolinones (e.g. imazamox, imazaquin, imazethapyr), organophosphorus compounds (e.g. glufosinate, glyphosate,
Sulfosate), Oxyacetamide (z.B. Flufenacet), Pyridazinone (z.B. Norflurazon), Sulfonylhamstoffe (z.B. Chlorimuron-ethyl, Nicosulfuron, Rimsulfuron, Sulfometuron-methyl, Thifensulfuron-methyl), Tetrazolinone (z.B. Fentrazamide), Triazine (z.B. Atrazin, Cyanazine, Simazin, Terbuthylazine), Triazinone (z.B. Metribuzin), Triazolinone (z.B. Amicarbazone, Flucarbazone-sodium, Propoxycarbazone- sodium), Triazolopyrimidine (z.B. Diclosulam, Florasulam, Metosulam), Triketone (z.B. Mesotrione, Sulcotrione), Uracile (z.B. Bromacil).Sulfosates), oxyacetamides (e.g. flufenacet), pyridazinones (e.g. norflurazone), Sulfonyl ureas (e.g. chlorimuron-ethyl, nicosulfuron, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl), tetrazolinones (e.g. fentrazamides), triazines (e.g. metribone), tricarbiazine -sodium, propoxycarbazone- sodium), triazolopyrimidines (e.g. diclosulam, florasulam, metosulam), triketones (e.g. mesotrione, sulcotrione), uracile (e.g. bromacil).
Die erfindungsgemäßen Mittel können einen oder zwei Wirkstoffe der Gruppe 1 und einen Wirkstoff der Gruppe 3 enthalten.The agents according to the invention can contain one or two active substances from group 1 and one active substance from group 3.
Vorzugsweise enthalten die erfindungsgemäßen Mittel einen oder zwei Wirkstoffe der Gruppe 1, ein bis drei Wirkstoffe der Gruppe 2 und gegebenenfalls einen Wirkstoff der Gruppe 3.The agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally an active substance from group 3.
Insbesondere enthalten die erfindungsgemäßen Mittel einen Wirkstoff der Gruppe 1, einen oder zwei Wirkstoffe der Gruppe 2 und gegebenenfalls einen Wirkstoff der Gruppe 3.In particular, the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
Beispiele für erfindungsgemässe Kombinationen aus jeweils einem Wirkstoff der Gruppe 1 und zwei Wirkstoffen der Gruppe 2 (vorzugsweise ausgewählt aus der Gruppe der Photosynthese-Inhibitoren einerseits und der Gruppe der Acetyl-CoA- Carboxylase-Inhibitoren andererseits) - bzw. aus jeweils einem Wirkstoff der Gruppe 1, zwei Wirkstoffen der Gruppe 2 und einer Verbindung der Gruppe 3 - sind in nachstehenden Tabelle 1 aufgeführt.Examples of combinations according to the invention each of an active ingredient from group 1 and two active ingredients from group 2 (preferably selected from the group of photosynthesis inhibitors on the one hand and the group of acetyl-CoA carboxylase inhibitors on the other hand) - or from one active ingredient of the group in each case 1, two Group 2 agents and a Group 3 compound - are listed in Table 1 below.
Tabelle 1:Table 1:
Weitere Beispiele für erfindungsgemäße Kombinationen aus jeweils einem Wirkstoff der Gruppe 1 und einem oder zwei Wirkstoffen der Gruppe 2 und/oder einer Verbindung der Gruppe 3 sind in der nachstehenden Tabelle 2 aufgeführt.Further examples of combinations according to the invention, each of an active ingredient of group 1 and one or two active ingredients of group 2 and / or a compound of group 3, are listed in Table 2 below.
Tabelle 2:Table 2:
Es wurde nun überraschend gefunden, dass die vorstehend definierten Wirkstoffkombinationen aus den N-Aryl-uracilen der Formel (I) und den vorstehend angeführten Wirkstoffen der Gruppe 2 bei sehr guter Nutzpflanzen- Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Getreide, wie z.B. Weizen, Gerste oder Hafer, und Mais, zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern verwendet werden können und dass sie auch zur Bekämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich verwendet werden können. Besonders ausgeprägt ist dieser Effekt bei Getreide. Ebenso ist der Effekt bei Mais be- sonders ausgeprägt. It has now surprisingly been found that the active compound combinations defined above from the N-aryl-uracils of the formula (I) and the above-mentioned active compounds from group 2 have a particularly high herbicidal activity and are very good herbicidal activity and in different crops, in particular in Cereals, such as wheat, barley or oats, and corn, can be used to selectively control monocot and dicot weeds and that they can also be used to control monocot and dicot weeds in the semi and non-selective range. This effect is particularly pronounced with cereals. The effect is also particularly pronounced with maize.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirk- stoffkombinationen aus Verbindungen der oben aufgeführten Gruppen 1 und 2 erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active compound combinations according to the invention from compounds of groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungsergänzung. Die neuen Wirkstoffkombinationen sind in vielen Kulturen gut verträglich, wobei die neuen Wirkstoffkombinationen auch sonst schwer bekämpfbare Unkräuter gut bekämpfen. Die neuen Wirkstoffkombinationen stellen somit eine wertvolle Bereicherung der Herbizide dar.There is therefore an unforeseeable synergistic effect and not just an addition. The new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control. The new active ingredient combinations thus represent a valuable addition to the herbicides.
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) 0,01 bis 1000 Gewichtsteile, vorzugsweise 0,02 bis 500 Gewichtsteile und besonders bevorzugt 0,05 bis 100 Gewichtsteile Wirkstoff der Gruppe 2.The synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 to 1 part by weight of active compound of the formula (I) comprises 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight of active compound of group 2.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden besonders hervorgehoben: 5-Chlor-chinoxalin-8-oxy-essigsäure-( 1 -methyl-hexylester) (Cloquintocet-mexyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl) und Diethyl- 1 -(2,4-dichlor-phenyl)-4,5-dihydro-5-methyl- 1 H-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl), die besonders geeignet zur Verbesserung der Verträglichkeit inThe following are particularly emphasized as mixture components from the active ingredients of group 3: 5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifene-ethyl) and diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1 H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), which is particularly suitable for improving the tolerance in
Getreide sind, sowie 4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1-Di- chloracetyl-hexahydro-3,3,8a-trimethylpyrrolo[ 1 ,2-a]-pyrimidin-6(2H)-on (B AS- 145138), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l ,4-benzoxazin (Benoxacor), 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid), 3-Dichloracetyl-5-(2-fura- nyl)-2,2-dimethyl-oxazolidin (Furilazole, MON- 13900) und 3-Dichloracetyl-2,2,5- trimethyl-oxazolidin (R-29148), die besonders geeignet zur Verbesserung der Verträglichkeit in Mais sind.Cereals are, as well as 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1, 2-a] -pyrimidine-6 (2H) -one (B AS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 2,2-dichloro-N, N -di-2-propenyl-acetamide (dichlormid), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900) and 3-dichloroacetyl-2,2,5 trimethyl-oxazolidine (R-29148), which are particularly suitable for improving the tolerance in maize.
Es ist als überraschend anzusehen, dass aus einer Vielzahl von bekannten Safenern oder Antidots, die befähigt sind, die schädigende Wirkung eines Herbizids auf die Kulturpflanzen zu antagonisieren, gerade die oben aufgeführten Verbindungen der Gruppe 3 geeignet sind, die schädigende Wirkung von Wirkstoffen der Formel (I) und deren Salzen, gegebenenfalls auch in Kombination mit einem oder mehreren der oben angeführten Wirkstoffe der Gruppe 2, auf die Kultuφflanzen annähernd vollständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen.It is surprising that from a large number of known safeners or antidots which are capable of antagonizing the harmful effect of a herbicide on the crop plants, the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate also in combination with one or more of the above-mentioned active ingredients of group 2, to be completely removed from the cultivated plants without impairing the herbicidal activity against the weeds.
Überraschenderweise wurde zudem gefunden, dass auch die herbizid wirksame Substanz 2,4-Dichlorophenoxy-essigsäure (2,4-D) und ihre Derivate die oben beschriebene Safeneraufgabe übernehmen können.Surprisingly, it was also found that the herbicidally active substance 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives can also take over the safener task described above.
Eine bevorzugte Ausführungsform ist daher auch eine Mischung enthaltend eine Verbindung der Formel (I) und/oder deren Salze einerseits und 2,4-D und/oder dessen Derivate andererseits, gegebenenfalls in Kombination mit einem oder mehreren der oben angeführten Wirkstoffe der Gruppe 2. Typische Derivate von 2,4-D sind z.B. deren Ester. Überraschenderweise wurde ebenfalls gefunden, dass auch die herbizid wirksamen Substanzen (4-Chlor-2-methylphenoxy)essigsäure (MCPA) und (+-)-2-(4-Chlor-2- methylphenoxy)propansäure (Mecoprop) eine Safeneraufgabe übernehmen können. Die genannten Verbindungen sind in den folgenden Patentanmeldungen beschrieben:A preferred embodiment is therefore also a mixture comprising a compound of the formula (I) and / or its salts on the one hand and 2,4-D and / or its derivatives on the other hand, optionally in combination with one or more of the active ingredients of group 2 mentioned above. Typical derivatives of 2,4-D are, for example, their esters. Surprisingly, it was also found that the herbicidally active substances (4-chloro-2-methylphenoxy) acetic acid (MCPA) and (+ -) - 2- (4-chloro-2-methylphenoxy) propanoic acid (mecoprop) can also take over a safener task. The compounds mentioned are described in the following patent applications:
JP 63 072 605 und GB 00 820 180.JP 63 072 605 and GB 00 820 180.
Die Verbindungen Diethyl- 1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- lH-pyrazole- 3,5-dicarboxylate (Mefenpyr-diethyl), (l-Methyl-hexyl)-[(5-chloro-8-quinolinyl)oxy]- acetate (Cloquintocet-mexyl) und Ethyl- l-(2,4-dichlorophenyl)-5-(trichloromethyl)- lH-l,2,4-triazole-3-carboxylate (Fenchlorazole-ethyl) sind in den folgenden Patentanmeldungen beschrieben: DE-A-39 39 503, EP- A-191 736 bzw. DE-A-35 25 205. 2,4-D ist ein bekanntes Herbizid.The compounds diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), (l-methyl-hexyl) - [(5 -chloro-8-quinolinyl) oxy] - acetate (Cloquintocet-mexyl) and ethyl l- (2,4-dichlorophenyl) -5- (trichloromethyl) - lH-l, 2,4-triazole-3-carboxylate (fenchlorazole -ethyl) are described in the following patent applications: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a known herbicide.
Der vorteilhafte Effekt der Kultuφflanzenverträglichkeit der erfindungsgemäßen Wirk- stoffkombinationen ist bei bestimmten Konzentrationsverhältnissen ebenfalls besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) oder dessen Mischungen mit Wirkstoffen der Gruppe 2 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100The advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is likewise particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I) or mixtures thereof with active compounds of group 2 account for 0.001 to 1000 parts by weight, preferably 0.01 to 100
Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile einer der oben unter (c) genannten, die Kultuφflanzen Verträglichkeit verbessernden Verbindungen (Anti- dots/Safener).Parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the compounds mentioned above under (c) which improves the tolerance of the crop plants (antidots / safener).
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. UnterAccording to the invention, all plants and parts of plants can be treated. Under
Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kultuφflanzen (einschließlich natürlich vorkommender Kultuφflanzen). Kultuφflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Pflanzenteile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtköφer, Früchte und Samen sowie Wurzeln, Knollen und Rhiozome aufgeführt werden. Zu den Pflanzenteilen gehört auch vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.Plants are understood to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by Plant variety rights of protectable or non-protectable plant varieties. Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhiozomes. The plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirk- Stoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oderThe treatment of the plants and plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or
Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen weiterhin durch ein- oder mehrschichtiges Umhüllen.Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multilayer coating.
Unter den durch biotechnologische und gentechnologische Methoden oder durchAmong those through biotechnological and genetic engineering methods or through
Kombination dieser Methoden erhaltenen Pflanzen werden solche Pflanzen hervorgehoben, die sog. ALS-, 4-HPPD-, EPSP- und/oder PPO-Hemmstoffe tolerieren, wie z.B. Acuron-Pflanzen.Combinations of these methods obtained plants are highlighted plants that tolerate so-called ALS, 4-HPPD, EPSP and / or PPO inhibitors, such as Acuron plants.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden:The active compounds according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dikotyle Kulturen der Gattungen: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippex, Rotal Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monokotyle Unkräuter der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus,Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sciφus, Setaria, Sorghum.Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Lumochloemum, Lolochochumem, Lolochochumum, Lolochochumem, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sciφus, Setaria, Sorghum.
Monokotyle Kulturen der Gattungen: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
Die Verwendung der erfindungsgemäßen Wirkstoffkombinationen ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.However, the use of the active compound combinations according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
Die erfindungsgemäß zu verwendenden Wirkstoffkombinationen können sowohl in konventionellen Anbauverfahren (Reihenkulturen mit geeigneter Reihenweite) inThe active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width)
Plantagenkulturen (z.B. Wein, Obst, Zitrus) sowie in Industrie- und Gleisanlagen, auf Wegen und Plätzen, aber auch zur Stoppelbehandlung und beim Minimum-Tillage- Verfahren eingesetzt werden. Sie eignen sich weiterhin als Abbrenner (Krautabtötung z.B. in Kartoffeln) oder als Defoliantien (z.B. in Baumwolle). Ferner sind sind sie für den Einsatz auf Bracheflächen geeignet. Weitere Einsatzgebiete sind Baumschulen,Plantation crops (e.g. wine, fruit, citrus) as well as in industrial and track systems, on paths and squares, but also for stubble treatment and the minimum tillage process. They are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries,
Forst, Grünland und Zieφflanzenbau.Forest, grassland and zieφflanzenbau.
Die Wirkstoffkombinationen können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäube- mittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festenThese formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.Carriers, where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organischeIf water is used as an extender, e.g. also organic
Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaph- thaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdöl fraktionen, mineralische und pflanzlicheSolvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methyl-isobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage:The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester,e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,
Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffkombinationen werden im allgemeinen in Form von Fertigformulierungen zur Anwendung gebracht. Die in den Wirkstoff- kombinationen enthaltenen Wirkstoffe können aber auch in Einzelformulierungen bei der Anwendung gemischt, d.h. in Form von Tankmischungen zur Anwendung gebracht werden.The active compound combinations according to the invention are generally used in the form of finished formulations. The active substances contained in the active substance combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischungen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte An- wendungszwecke, insbesondere im Nachauflauf- Verfahren, kann es ferner vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle (z.B. das Handelspräparat "Rako Binol" ) oder Ammoniumsalze wie z.B. Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen.The new combinations of active ingredients, as such or in their formulations, can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible. For certain applications, in particular in the post-emergence process, it can furthermore be advantageous to include plant-compatible in the formulations as further additives mineral or vegetable oils (eg the commercial preparation "Rako Binol") or ammonium salts such as ammonium sulfate or ammonium rhodanide.
Die neuen Wirkstoffkombinationen können als solche, in Form ihrer Formulierungen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Stäuben oder Streuen.The new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auflaufen der Pflanzen appliziert werden, also im Vorauflauf und Nachauflauf- Verfahren. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
Die gute herbizide Wirkung der neuen Wirkstoffkombinationen geht aus den nach- folgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbizidenThe good herbicidal activity of the new active compound combinations can be seen from the examples below. While the individual active ingredients in the herbicidal
Wirkung Schwächen aufweisen, zeigen die Kombinationen durchweg eine sehr gute Unkrautwirkung, die über eine einfache Wirkungssummierung hinausgeht.Effects have weaknesses, the combinations consistently show a very good weed effect that goes beyond a simple summation of effects.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbizide Wirkung der Wirkstoffkombination größer ist als die der einzelnen appliziertenA herbicide always has a synergistic effect if the herbicidal action of the active ingredient combination is greater than that of the individual agents applied
Wirkstoffe.Agents.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl. COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Seiten 20 - 22, 1967):The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, S.R .: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
WennIf
X = % Schädigung durch Herbizid A (Wirkstoff der Formel I) bei p kg/ha Aufwandmenge und Y = % Schädigung durch Herbizid B (Wirkstoff der Formel II) bei q kg/haX =% damage by herbicide A (active ingredient of the formula I) at a rate of p kg / ha and Y =% damage by herbicide B (active ingredient of the formula II) at q kg / ha
Aufwandmenge undApplication rate and
die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge, dann istthe expected damage to herbicides A and B at p and q kg / ha, then
E = X + Y - (X * Y/100).E = X + Y - (X * Y / 100).
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt.If the actual damage is greater than calculated, the effect of the combination is super-additive, that is, it shows a synergistic effect.
Die theorethisch zu erwartende Wirkung für eine gegebene Kombination dreierThe theoretically expected effect for a given combination of three
Herbizide kann ebenfalls der oben angegebenen Literatur entnommen werden. Herbicides can also be found in the literature cited above.
Anwendungsbeispiele:Application examples:
Beispiel AExample A
Pre-emergence-TestPre-emergence test
Lösungsmittel: 2 bis 3 Gewichtsteile Aceton oder N,N-Dimethyl-formamid Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherSolvent: 2 to 3 parts by weight of acetone or N, N-dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Formulierte Produkte werden in Wasser gelöst und dann mit Wasser auf die gewünschte Konzentration verdünnt.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. Formulated products are dissolved in water and then diluted with water to the desired concentration.
Die Lösungen der weiteren Mischungskomponenten (Wirkstoffe oder Safener) werden analog hergestellt. Dann werden die getrennt hergestellten Lösungen der verschiedenen Mischungkomponenten vereinigt, gegebenenfalls weitere Zusatzstoffe (Formulierungshilfsmittel, Additive etc.) und gegebenenfalls noch Wasser zur Her- Stellung der gewünschten Verdünnung dazu gegeben.The solutions of the other mixture components (active ingredients or safeners) are prepared analogously. Then the separately prepared solutions of the different mixture components are combined, optionally further additives (formulation auxiliaries, additives, etc.) and optionally water are added to produce the desired dilution.
Samen der Testpflanzen werden in normalen Boden ausgesät. Nach 24 Stunden wird der Boden so mit der Wirkstoffzubereitung besprüht, daß die jeweils gewünschte Wirkstoffmenge pro Flächeneinheit ausgebracht wird. Die Wirkstoffkonzentration in der Spritzbrühe wird so gewählt, daß in 500 Liter Wasser pro Hektar die jeweils gewünschte Wirkstoffmenge ausgebracht wird. Die Gefäße mit den Testpflanzen werden im Gewächshaus bis zur Bonitierung bei kontrollierter Temperatur und bei kontrollierter Beleuchtung gehalten.Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of active ingredient in the spray liquor is chosen so that the desired amount of active ingredient is applied in 500 liters of water per hectare. The tubes with the test plants are kept in the greenhouse until they are rated at a controlled temperature and with controlled lighting.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. Es bedeuten: 0 % = keine Wirkung / kein Schaden (wie unbehandelte Kontrolle) 100 % = totale VernichtungAfter three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means: 0% = no effect / no damage (like untreated control) 100% = total destruction
In diesem Test zeigen beispielsweise Kombinationen der Verbindung (1-3) mit den Verbindungen 4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67) und 2-Chlor-4- trifluormethyl-thiazol-5-carbonsäure-phenylmethylester (Flurazole) erheblich bessere Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Mais als die Verbindung (1-3) allein (vgl. Tabelle AI).In this test, for example, combinations of the compound (1-3) with the compounds 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67) and 2-chloro-4-trifluoromethyl-thiazole- 5-carboxylic acid phenylmethyl ester (Flurazole) considerably better compatibility with cultivated plants, such as Corn as the compound (1-3) alone (see Table AI).
Tabelle AI: Pre-emergence-Test in MaisTable AI: Pre-emergence test in maize
Alle Varianten wurden mit 0,1% Renex-36 in der Spritzbrühe behandelt. In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-6) mit der Verbindung Diethyl-l-(2,4-dichloφhenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-di- carboxylat (Mefenpyr-diethyl) erheblich bessere Verträglichkeit gegenüber Kulturpflanzen, wie z.B. Gerste und Weizen, als die Verbindung (1-6) allein (vgl. Tabelle A2).All variants were treated with 0.1% Renex-36 in the spray mixture. In this test, combinations of the compound (1-6) with the compound diethyl-1- (2,4-dichloφhenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-di-carboxylate ( Mefenpyr-diethyl) significantly better tolerance to crops, such as barley and wheat, than the compound (1-6) alone (see Table A2).
Tabelle A2: Post-emergence-Test in Gerste und WeizenTable A2: Post emergence test in barley and wheat
Alle Varianten wurden mit 0,1% Renex-36 in der Spritzbrühe behandelt.All variants were treated with 0.1% Renex-36 in the spray mixture.
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-6) mit den Verbindungen 5-Chlor-chinoxalin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet-mexyl) und 1 -(2,4-Dichlor-phenyl)-5-trichlormethyl- 1 H- 1 ,2,4-triazol-3-carbon- säure-ethylester (Fenchlorazol-ethyl) erheblich bessere Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Gerste und Weizen, als die Verbindung (1-6) allein (vgl. Tabelle A3). Tabelle A3: Post-emergence-Test in Gerste und WeizenIn this test, combinations of the compound (1-6) with the compounds 5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (Cloquintocet-mexyl) and 1 - (2,4-dichloro- phenyl) -5-trichloromethyl-1 H-1, 2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl) considerably better tolerance to cultivated plants, such as barley and wheat, than the compound (1-6) alone (see Table A3). Table A3: Post emergence test in barley and wheat
Alle Varianten wurden mit 0,1% Renex-36 in der Spritzbrühe behandelt.All variants were treated with 0.1% Renex-36 in the spray mixture.
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-6) mit der Verbindung 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid) erheblich bessere Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Gerste und Weizen, als die Verbindung (1-6) allein (vgl. Tabelle A4).In this test, combinations of the compound (1-6) with the compound 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide) also show considerably better Compatibility with cultivated plants, such as barley and wheat, as the compound (1-6) alone (see Table A4).
Tabelle A4: Post-emergence-Test in Gerste und WeizenTable A4: Post emergence test in barley and wheat
Alle Varianten wurden mit 0,1 % Renex-36 in der Spritzbrühe behandelt.All variants were treated with 0.1% Renex-36 in the spray mixture.
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-6) mit der Ver- bindung 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim) erheblich bessere Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Gerste und Weizen, als die Verbindung (1-6) allein (vgl. Tabelle A5). In this test, combinations of the compound (1-6) with the compound 4,6-dichloro-2-phenyl-pyrimidine (fenclorim) also show considerably better tolerance to cultivated plants, such as barley and wheat, than the compound (1- 6) alone (see Table A5).
Tabelle A5: Post-emergence-Test in Gerste und WeizenTable A5: Post emergence test in barley and wheat
Alle Varianten wurden mit 0,1 % Renex-36 in der Spritzbrühe behandelt.All variants were treated with 0.1% Renex-36 in the spray mixture.
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-6) mit der Verbindung 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor) erheblich bessere Verträglichkeit gegenüber Kultuφflanzen, wie z.B. Gerste und Weizen, als die Verbindung (1-6) allein (vgl. Tabelle A6).In this test, combinations of the compound (1-6) with the compound 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor) also show considerably better compatibility with cultivated plants, such as e.g. Barley and wheat as the compound (1-6) alone (see Table A6).
Tabelle A6: Post-emergence-Test in Gerste und WeizenTable A6: Post emergence test in barley and wheat
Alle Varianten wurden mit 0,1 % Renex-36 in der Spritzbrühe behandelt. In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen 2,4-D und Glyphosate-isopropylammonium erhebliche synergistische Wirksamkeit (vgl. Tabelle A7).All variants were treated with 0.1% Renex-36 in the spray mixture. In this test, combinations of the compound (1-3) with the compounds 2,4-D and glyphosate-isopropylammonium also show considerable synergistic activity (cf. Table A7).
Tabelle A7: Post-emergence-Test (in Klammern: nach Colby errechnete Werte)Table A7: Post emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Sulfentrazone erhebliche synergistische Wirksamkeit (vgl. Tabelle A8). Tabelle A8: Post-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound sulfentrazone also show considerable synergistic activity (cf. Table A8). Table A8: Post emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Imazamox erhebliche synergistische Wirksamkeit (vgl. Tabelle A9). In this test, combinations of the compound (1-3) with the compound imazamox also show considerable synergistic activity (cf. Table A9).
Tabelle A9: Post-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A9: Post emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Acetochlor erhebliche synergistische Wirksamkeit (vgl. Tabelle AlO). In this test, combinations of the compound (1-3) with the compound acetochlor also show considerable synergistic activity (cf. Table AlO).
Tabelle AlO: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table AlO: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Metolachlor erhebliche synergistische Wirksamkeit (vgl. Tabelle Al l). Tabelle All: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound metolachlor also show considerable synergistic activity (cf. Table A1). Table All: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Isoxaflutole erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 2). In this test, combinations of the compound (1-3) with the compound isoxaflutole also show considerable synergistic activity (cf. Table AI 2).
Tabelle A12: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A12: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Flufenacet erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 3). In this test, combinations of the compound (1-3) with the compound flufenacet also show considerable synergistic activity (cf. Table AI 3).
Tabelle A13: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A13: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Metribuzin erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 4). Tabelle A14: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound metribuzin also show considerable synergistic activity (cf. Table AI 4). Table A14: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Amicarbazone erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 5). In this test, combinations of the compound (1-3) with the compound amicarbazone also show considerable synergistic activity (cf. Table AI 5).
Tabelle A15: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A15: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Sulcotrione erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 6). In this test, combinations of the compound (1-3) with the compound sulcotrione continue to show considerable synergistic activity (cf. Table AI 6).
Tabelle A16: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A16: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen Flufenacet und Amicarbazone erhebliche synergistische Wirksamkeit (vgl. Tabelle A17). Tabelle A17: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compounds flufenacet and amicarbazone also show considerable synergistic activity (cf. Table A17). Table A17: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen Flufenacet und Metribuzin erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 8). Tabelle A18: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compounds flufenacet and metribuzin also show considerable synergistic activity (cf. Table AI 8). Table A18: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen Flufenacet und Amicarbazone erhebliche synergistische Wirksamkeit (vgl. Tabelle AI 9). In this test, combinations of the compound (1-3) with the compounds flufenacet and amicarbazone also show considerable synergistic activity (cf. Table AI 9).
Tabelle A19: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A19: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Acetochlor erhebliche synergistische Wirksamkeit (vgl. Tabelle A20). In this test, combinations of the compound (1-3) with the compound acetochlor also show considerable synergistic activity (cf. Table A20).
Tabelle A20: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A20: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Flufenacet erhebliche synergistische Wirksamkeit (vgl. Tabelle A21). Tabelle A21: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound flufenacet also show considerable synergistic activity (cf. Table A21). Table A21: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Amicarbazone erhebliche synergistische Wirksamkeit (vgl. Tabelle A22). Tabelle A22: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound amicarbazone also show considerable synergistic activity (cf. Table A22). Table A22: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen Flufenacet und Metribuzin erhebliche synergistische Wirksamkeit (vgl. Tabelle A23). In this test, combinations of the compound (1-3) with the compounds flufenacet and metribuzin also show considerable synergistic activity (cf. Table A23).
Tabelle A23: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A23: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Trifluralin erhebliche synergistische Wirksamkeit (vgl. Tabelle A24). In this test, combinations of the compound (1-3) with the compound trifluralin also show considerable synergistic activity (cf. Table A24).
Tabelle A24: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A24: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Atrazin erhebliche synergistische Wirksamkeit (vgl. Tabelle A25). Tabelle A25: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound atrazine also show considerable synergistic activity (cf. Table A25). Table A25: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit den Verbindungen Isoxaflutole und Metribuzin erhebliche synergistische Wirksamkeit (vgl. Tabelle A26).In this test, combinations of compound (1-3) with the compounds isoxaflutole and metribuzin also show considerable synergistic activity (cf. Table A26).
Tabelle A26: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)Table A26: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test zeigen weiterhin Kombinationen der Verbindung (1-3) mit der Verbindung Foramsulfuron erhebliche synergistische Wirksamkeit (vgl. Tabelle A27). Tabelle A27: Pre-emergence-Test (in Klammem: nach Colby errechnete Werte)In this test, combinations of the compound (1-3) with the compound foramsulfuron also show considerable synergistic activity (cf. Table A27). Table A27: Pre-emergence test (in brackets: values calculated according to Colby)
In diesem Test kann weiterhin gezeigt werden, dass gerade Verbindungen der Gruppe 3 geeignet sind, die schädigende Wirkung von Wirkstoffen der Formel (I) bei Kultuφflanzen zu antagonisieren (Tab. A28-A32). This test can also show that compounds of group 3 are particularly suitable for antagonizing the damaging effect of active compounds of the formula (I) on cultivated plants (Table A28-A32).
Tabelle A28: Pre-emergence-Test in MaisTable A28: Pre-emergence test in maize
Tabelle A29: Pre-emergence-Test in MaisTable A29: Pre-emergence test in maize
Tabelle A30: Pre-emergence-Test in Mais Table A30: Pre-emergence test in maize
Tabelle A31: Pre-emergence-Test in MaisTable A31: Pre-emergence test in maize
Tabelle A32: Pre-emergence-Test in MaisTable A32: Pre-emergence test in maize

Claims

Patentansprüche claims
1. Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination umfassend1. Herbicidal agents, characterized by comprising an effective content of an active ingredient combination
(a) zumindest ein N-Aryl-uracil der Formel (I)(a) at least one N-aryl-uracil of the formula (I)
in welcher in which
R für Wasserstoff, Amino oder gegebenenfalls durch Cyano, Halogen oder Cι-C4-Alkoxy substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen steht,R represents hydrogen, amino or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,
R für gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen steht,R represents alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
R für Wasserstoff, Halogen oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen steht,R represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 5 carbon atoms,
R für Wasserstoff, Cyano oder Halogen steht,R represents hydrogen, cyano or halogen,
R für Cyano, Thiocarbamoyl oder Halogen steht, undR represents cyano, thiocarbamoyl or halogen, and
R für Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy,R for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy,
Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Halogen, für jeweils gegebenenfalls durch Cyano, Hydroxy, Cι -C_ι-Alkoxy, C1 -C4- Alkyl-carbonyl, Cι -C4-Alkoxy-carbonyl, C2-C4-Alkenyloxy- carbonyl, C2-C4-Alkinyloxy-carbonyl, Ct-C4-Alkylamino-carbonyl, Di-(Cι-C4-alkyl)-amino-carbonyl, Phenoxycarbonyl und/oder Phenyl- aminocarbonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxycarbonyl oder Alkylamino mit jeweils bis zu 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Carboxy, Halogen und/oder Cι -C4-Alkoxy-carbonyl substituiertes Alkenyl, Alkinyl, Alkenyloxy oder Alkinyloxy mit jeweils bis zu 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen oder Cj-C4- Alkoxy substituiertes Alkylcarbonylamino, Alkoxy- carbonylamino, Alkylsulfonylamino, N,N-Bis-alkylsulfonyl-amino oder N-Alkylcarbonyl-N-alkylsulfonyl-amino mit jeweils bis zu 6 Kohlenstoffatomen in den Alkylgruppen, oder für jeweils gegebenenfalls durch Cyano oder Halogen, oder durch C1 -C4- Alkyl, C1 -C4- Alkoxy oder Cι-C4-Alkoxy-carbonyl (welche jeweils gegebenenfalls durch -CrAlkoxy-carbonyl, C3-C4-Alkenyloxy-carbonyl oder C3-C4-Alkinyloxy-carbonyl substituiert sind) substituiertes Phenyloxy, Naphthyloxy, N-Phenylcarbonyl-N-alkylsulfonyl-amino, N-Pyridyl- carbonyl-N-alkylsulfonyl-amino, N-Furylcarbonyl-N-alkylsulfonyl- amino oder N-Thienylcarbonyl-N-alkylsulfonyl-amino mit jeweils bis zu 6 Kohlenstoffatomen in den Alkylgruppen steht,Mercapto, amino, hydroxyamino, aminosulfonyl, halogen, for each optionally by cyano, hydroxy, C 1 -C 4 -alkoxy, C1 -C4- Alkyl-carbonyl, -C4-alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C 2 -C 4 -alkynyloxy-carbonyl, C t -C 4 -alkylamino-carbonyl, di- (-C-C 4 - alkyl) aminocarbonyl, phenoxycarbonyl and / or phenylaminocarbonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino each having up to 6 carbon atoms, each optionally with cyano, carboxy, halogen and / or Cι -C4-alkoxy-carbonyl-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy each having up to 6 carbon atoms, each for alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, N, N-bis-alkylsulfonyl- optionally substituted by halogen or Cj-C 4 -alkoxy amino or N-alkylcarbonyl-N-alkylsulfonylamino, each with up to 6 carbon atoms in the alkyl groups, or for each optionally by cyano or halogen, or by C1-C4-alkyl, C1-C4-alkoxy or C 1 -C 4 -alkoxy -carbonyl (which each optionally d substituted by -Cralkoxycarbonyl, C 3 -C 4 alkenyloxycarbonyl or C 3 -C 4 alkynyloxycarbonyl) substituted phenyloxy, naphthyloxy, N-phenylcarbonyl-N-alkylsulfonylamino, N-pyridylcarbonyl-N alkylsulfonylamino, N-furylcarbonyl-N-alkylsulfonylamino or N-thienylcarbonyl-N-alkylsulfonylamino, each having up to 6 carbon atoms in the alkyl groups,
(„Wirkstoffe der Gmppe 1")("Active substances of group 1")
undand
(b) zumindest eine Verbindung aus einer zweiten Gmppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(b) at least one compound from a second group of herbicides which contains the active compounds mentioned below:
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-Natrium- salz (Acifluorfen-sodium), 2-Chlor-6-nitro-3-phenoxy-benzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid (Alachlor), N-Ethyl-N'-i-propyl-6-methylthio-l,3,5-triazin-2,4-diamin (Ametryn), 4- Amino-N-( 1 , 1 -Dimethyl-ethyl)-4,5 -dihydro-3 -( 1 -methyl-ethyl)-5-oxo- 1 H- 1,2,4-triazol-l -carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-hamstoff (Amidosulfuron), 1H-1 ,2,4-Triazol-3-amin (Amitrole), 6-Chlor-4-ethylamino-2-isopropyl- amino-l,3,5-triazin (Atrazin), 2-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]- 5,6,7, 8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-on (Azafenidin), N- (4,6-Dimethoxy-pyrimidin-2-yl)-N'-[ 1 -methyl-4-(2-methyl-2H-tetrazol-5-yl)- lH-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfuron), N-Benzyl-2-(4-fluor-3- trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4-Chlor-2-oxo-3(2H)- benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4-trifluor- methyl-benzenamin (Benflurahn), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- methoxycarbonyl-phenylmethylsulfonyl)-hamstoff (Bensulfuron), 2-[2-[4-2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid sodium - salt (Acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxy-benzenamine (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor) , N-ethyl-N'-i-propyl-6-methylthio-l, 3,5-triazine-2,4-diamine (ametryn), 4-amino-N- (1, 1-dimethyl-ethyl) -4 , 5-dihydro-3 - (1-methyl-ethyl) -5-oxo-1 H- 1,2,4-triazole-l-carboxamide (amicarbazone), N- (4,6-dimethoxy-pyrimidine-2- yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1, 2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2- isopropylamino-l, 3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] - 5,6,7, 8-tetrahydro-l, 2,4 -triazolo- [4,3-a] pyridin-3 (2H) -one (azafenidin), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [1 -methyl-4- ( 2-methyl-2H-tetrazol-5-yl) - 1H-pyrazol-5-ylsulfonyl] urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzenamine (benflurahn), N- (4, 6-Dimethoxypyrimidin-2-yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuron), 2- [2- [4-
(3 ,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidinyl- phenoxymethyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en- 2-on (Benzobicyclon), Ethyl N-benzoyl-N-(3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl- 1 H-2, 1 ,3-benzothiadiazin-4(3H)-on(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl-phenoxymethyl] -5-ethyl-phenoxy-propanoic acid methyl ester (benzfendizone), 3- (2-chloro -4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2.1] -oct-3-en-2-one (benzobicyclone), ethyl N-benzoyl-N- (3,4-dichlorophenyl) - DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1 H-2, 1, 3-benzothiadiazin-4 (3H) -one
(Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 2,6- Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyri- bac-sodium), 5-Brom-6-methyl-3-(l-methyl-propyl)-2,4(lH,3H)pyrimidin- dion (Bromacil), 2-Brom-3 ,3-dimethyl-N-( 1 -methyl- 1 -phenyl-ethyl)-butan- amid (Bromobutide), 3,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-dinitro- phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Brom- oxynil), N-Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Buta- chlor), 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)- pyrimidinyl)-benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(Bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), 2,6-bis (4,6-dimethoxypyrimidin-2-yl-oxy) benzoic acid Sodium salt (bispyribac-sodium), 5-bromo-6-methyl-3- (l-methyl-propyl) -2.4 (1H, 3H) pyrimidinedione (bromoacil), 2-bromo-3, 3 -dimethyl-N- (1-methyl-1-phenyl-ethyl) -butane amide (bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) -oxime ( Bromofenoxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2,6-diethyl-phenyl) -acetamide (buta-chloro), 2-chloro -5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoic acid- [1, 1 -dimethyl-2-oxo-2- (2- propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (l-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3-
( 1 -oxo-butyl)-pheny l]-2-cyclohexen- 1 -on (Butroxydim), S-Ethyl-bis-(2- methyl-propyl)-thiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl- phenylsulfonyl)-lH-l,2,4-triazol-l -carboxamid (Cafenstrole), 2-[l-[(3-Chlor- 2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2- cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor- 2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-l-(3-methoxy-4-nitro- phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl- phenylsulfonyl)-hamstoff (Chlorimuron-ethyl), 1 ,3,5-Trichlor-2-(4-nitro- phenoxy)-benzol (Chlomitrofen), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-(1-oxo-butyl) phenyl] -2-cyclohexen- 1 -one (butroxydim), S-ethyl-bis- (2- methyl-propyl) -thiocarbamate (butylates), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) -lH-l, 2,4-triazole-l-carboxamide (cafenstrole), 2- [ l - [(3-chloro-2-propenyl) oxyimino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1-one (caloxydim, tepraloxydim ), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2. 4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-l- (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 3-amino-2,5-dichloro-benzoic acid ( Chloramben), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonylphenylsulfonyl) urea (chlorimuron-ethyl), 1, 3,5-trichloro-2- ( 4-nitrophenoxy) benzene (chloromitrofen), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -
N'-(2-chlor-phenylsulfonyl)-hamstoff(Chlorsulfuron), N'-(3-Chlor-4-methyl- phenyl)-N,N-dimethyl-hamstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5- (l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure- ethylester (Cinidon-ethyl), N-(4,6-Dimethoxy-l ,3,5-triazin-2-yl)-N'-(2-(2- methoxy-ethoxy)-phenylsulfonyl)-harnstoff (Cinosulfuron), 2-[l-[2-(4-Chlor- phenoxy)-propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclo- hexandion (Clefoxydim), (E,E)-(+)-2-[ 1 -[[(3-Chlor-2-propenyl)-oxy]-imino]- propyl]-3-hydroxy-2-cyclohexen- 1 -on (Clethodim), (R)-(2-Propinyl)-2-[4-(5- chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5-eth- oxy-7-fluor[l,2,4]triazolo[l,5-c]pyrimidin-2-yl-sulfonyl)-amino]-benzoat (Cloransulam-methyl), 2-Chlor-4-ethylamino-6-( 1 -cyano- 1 -methyl-ethyl- amino)-l,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- cyclopropylcarbonyl-phenylsulfonyl)-hamstoff (Cyclosulfamuron), 2-( 1 - Ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlorotoluron), 2-chloro-3- [2 -chloro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid, ethyl ester (cinidon-ethyl), N - (4,6-Dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2-methoxy-ethoxy) phenylsulfonyl) urea (cinosulfuron), 2- [l- [2 - (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [ 1 - [[(3-chloro-2-propenyl) -oxy] imino] - propyl] -3-hydroxy-2-cyclohexen-1-one (clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoro-pyridin-2-yl-oxy) phenoxypropanoate (clodinafop-propargyl), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralide), methyl-3-chloro -2 - [(5-eth-oxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl), 2- Chloro-4-ethylamino-6- (1-cyano-1-methyl-ethyl-amino) -l, 3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonyl-phenylsulfony l) -urea (cyclosulfamuron), 2- (1 - ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexene
1 -on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propan- säure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phen- oxy)-propansäure (Dichloφrop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phen- oxy]-propanoat (Diclofop-methyl), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor-1 -one (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propanoic acid butyl ester (cyhalofop butyl), 2,4-dichlorophenoxyacetic acid ( 2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (Dichloφrop-P), methyl-2 - [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro-
[ 1 ,2,4]-triazolo-[ 1 ,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 1 ,2-Dimethyl- 3,5-diphenyl- 1 H-pyrazolium-methylsulfat (Difenzoquat), N-(2,4-Difluor- phenyl)-2-(3 -trifluormethyLphenoxy)-pyridin-3 -carboxamid (Diflufenican), 2-[l-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3- carbonsäure (Diflufenzopyr), S-( 1 -Methyl- 1 -phenyl-ethyl)- 1 -piperidin-carbo- thioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-methoxy- ethyl)-acetamid (Dimethachlor), (S-) 2-Chlor-N-(2,4-dimethyl-3-thienyl)-N- (2-methoxy-l-methyl-ethyl)-acetamid (S-) (Dimethenamid), 2-Amino-4-(l- fluor- 1 -methyl-ethyl)-6-( 1 -methyl-2-(3 ,5 -dimethyl-phenoxy)-ethylamino)- 1,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl-l,3- diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[l,2-a:2', -c]pyrazin- diium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethyl- pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor-phenyl)-N,N-di- methyl-hamstoff (Diuron), 2-[2-(3-Chlor-phenyl)-oxiranylmethyl]-2-ethyl- lH-inden-l,3(2H)-dion (Epropodan), S-Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l ,2-dimethyl-propyl)-thiocarbamat (Espro- carb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzen- amin (Ethalfluralin), (S)-(2-Ethoxy- 1 -methyl-2-oxoethyl)-2-chlor-5-(2-chlor- 4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy-pyri- midin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), (R)- Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-[1,2,4] triazolo- [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl 3,5-diphenyl-1 H-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [l- [(3,5-difluorophenyl) amino carbonyl hydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl-ethyl) -1-piperidine-carbo- thioate (dimepiperate), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (2-methoxy-ethyl) -acetamide (dimethachlor), (S-) 2-chloro-N- (2,4 -dimethyl-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (l-fluoro-1-methyl-ethyl) -6 - (1-methyl-2- (3,5-dimethylphenoxy) ethylamino) - 1,3,5-triazine (dimexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-l, 3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', -c] pyrazine-diium (diquat), S, S-dimethyl-2-difluoromethyl-4-i- butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl urea (diuron), 2- [2- (3rd -Chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3, (2H) -dione (epropodane), S-Et hyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Espro-carb), N-ethyl-N- (2-methyl-2-propenyl ) -2,6-dinitro-4-trifluoromethyl-benzene-amine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4- trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (ethoxysulfuron), (R) - ethyl 2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop-
(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH- tetrazol- 1 -carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3 -chlor-4- fluor-phenyl)-DL-alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3- chlor-4-fluor-phenyl)-L-alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl- N-(3-chlor-4-fluor-phenoxy)-DL-alaninat (Flamprop-methyl), N-(2,6-Difluor- phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propan- säure-butylester (Fluazifop, -butyl, -P-butyl), 5-(4-Brom-l-methyl-5-trifluor- methyl-lH-pyrazol-3-yl)-2-chlor-4-fluor-benzoesäure-i-propylester (Fluazo- late), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy- phenyl)-sulfonyl] - 1 -H- 1 ,2,4-triazol- 1 -carboxamid-Natriumsalz (Flu- carbazone-sodium), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl- 1 ,3,4- thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(2,6-Difluor-phenyl)-5-methyl- 1 ,2,4-triazolo[ 1 ,5-a]-pyrimidin-2-sulfonamid (Flumetsulam), Pentyl-[2-chlor- 4-fluor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenoxy]- acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4-dihydro-3-oxo-4-(2-propinyl)-2H-(P) -ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N- benzoyl-N- (3-chloro-4-fluoro-phenyl) -DL-alaninate (Flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -L-alaninate (Flamprop -isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) -DL-alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8-fluorine -5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), (R) -2- [4- (5-trifluoromethyl-pyridine-2- yl-oxy) -phenoxy] -propanoic acid butyl ester (fluazifop, -butyl, -P-butyl), 5- (4-bromo-l-methyl-5-trifluoromethyl-lH-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl ] - 1 -H- 1, 2,4-triazole-1-carboxamide sodium salt (flu- carbazone-sodium), N- (4-fluorophenyl) -Ni-propyl-2- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide (Flufenacet), N- (2 , 6-difluorophenyl) -5-methyl-1, 2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), pentyl- [2-chloro-4-fluoro-5- ( l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4- dihydro-3-oxo-4- (2-propynyl) -2H-
1 ,4-benzoxazin-6-yl] -4,5 ,6,7-tetrahydro- 1 H-isoindol- 1 ,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(l-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro- 1 H-isoindol- l,3(2H)-dion (Flumipropyn), 3-Chlor-4-chlormethyl-l-(3-tri- fluormethyl-phenyl)-2-pyrrolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluor- methyl-phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluorogly- cofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5- phenyl-lH-l,2,4-triazol-3-carboxamid (Flupoxam), l-Isopropyl-2-chlor-5- (3 ,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6- trifluormethyl-pyridin-2-yl-sulfonyl)-hamstoff-Natriumsalz (Flupyrsulfuron- methyl-sodium), 9-Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino- 3 ,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl-ethyl- ester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methyl- amino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4-fluor-5-(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadiazolo-[3,4- a]-pyridazin-l -yliden)-amino-phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2- Chlor-4-trifluormethyl-phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fome- safen), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]- sulfonyl]-4-formylamino-N,N-dimethyl-benzamid (Foramsulfüron), 2- Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glu- fosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluor- methyl-pyridin-2-yl-oxy)-phenoxy]-propansäure (-methylester, -2-ethoxy- ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3 -Cyclohexyl-6-dimethylamino- 1 -methyl- 1 ,3 ,5 -triazin-2,4( 1 H,3H)-dion1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1 H-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [( l-methyl-2-propynyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-1 H-isoindole-1,3, (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl- 1- (3-trifluoromethyl-phenyl) -2-pyrrolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1- (4-chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-l, 2,4-triazole-3-carboxamide (flupoxam), l -Isopropyl-2-chloro-5- (3, 6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidyl) -benzoate (flupropacil), N- (4,6- Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluoren-9 -carboxylic acid (flurenol), (4-amino-3, 5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl- heptyl ester) (fluroxypyr, butoxypropyl, meptyl), 5-methylamino-2- phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (Flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-lH, 3H- [l, 3,4] -thiadiazolo- [3,4-a] -pyridazin-l-ylidene -amino-phenyl] -thio-acetate (Fluthiacet-methyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) - N-methylsulfonyl-2-nitro-benzamide (Fom- safen), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N , N-dimethyl-benzamide (foramsulfüron), 2-amino-4- (hydroxymethylphosphinyl) -butanoic acid (-ammonium salt) (glucosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium ), (R) -2- [4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenoxy] propanoic acid (methyl ester, -2-ethoxy ethyl ester, butyl ester) ( Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-1-methyl-1, 3, 5 -triazine-2,4 (1 H, 3H) -dione
(Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imid- azol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-lHr-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol- 2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro- 4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5- ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(2-chlor-imidazo[l,2-a]-pyridin-3-yl-sulfonyl)-hamstoff (Imazosulf- uron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxy- carbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl- sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl-N'-(4-iso- propyl-phenyl)-hamstoff (Isoproturon), N-(3-( 1 -Ethyl- 1 -methyl-propyl)- isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methyl- sulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5 -Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)- methanon (Isoxaflutole), 2-[2-[4-[3,5-Dichlor-2-pyridinyl)-oxy]-phenoxy]-l- oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Ethoxy-l-methyl-2-oxo-ethyl)-5- (2-chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoat (Lactofen), N' -(3 ,4-di- chlor-phenyl)-N-methoxy-N-methyl-hamstoff (Linuron), (4-Chlor-2-methyl- phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure(Hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imide- azol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lHr-imidazol-2-yl) -5- methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (Imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquine), 2- (4,5- Dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxy-pyrimidin-2 yl) -N '- (2-chloro-imidazo [1,2-a] -pyridin-3-yl-sulfonyl) urea (imazosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfuron methyl sodium), 4-hydroxy-3,5-diiodobenzonitrile (Ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3- (1-ethyl-1-methylpropyl) isoxazol-5-yl ) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonylphenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (Isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) methanone (isoxaflutole), 2- [2- [4- [3,5-dichloro-2- pyridinyl) -oxy] -phenoxy] -l-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-l-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3, 4-di-chlorophenyl) -N-methoxy-N-methyl-urea (Linuron), (4-chloro-2-methylphenoxy) - acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid
(Mecoprop), 2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefen- acet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]- 4-[[(methylsulfonyl)amino]methyl]-benzoesäure-methylester (Mesosulmron), 2-(4-Methylsulfonyl-2-nitro-benzoyl)- 1 ,3-cyclohexandion (Mesotrione), 4- Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(Mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefen-acet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] - 4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulmron), 2- (4-methylsulfonyl-2-nitro-benzoyl) - 1, 3-cyclohexanedione (mesotrione), 4-amino-3 -methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one (metamitron), 2-chloro-N-
(2,6-dimethyl-phenyl)-N-( 1 H-pyrazol- 1 -yl-methyl)-acetamid (Metazachlor), N'-(4-(3 ,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H- 1 -benzopyran-7-yl-oxy)- phenyl)-N-methoxy-N-methyl-hamstoff (Metobenzuron), N'-(4-Brom- phenyl)-N-methoxy-N-methylhamstoff (Metobromuron), (S)-2-Chlor-N-(2- ethyl-6-methyl-phenyl)-N-(2 -methoxy- 1 -methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- 1 ,2,4-triazolo[ 1 ,5-a]-pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4- methoxy-phenyl)-N,N-dimethyl-harnstoff (Metoxuron), 4-Amino-6-tert- butyl-3-methylthio-l,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-hamstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1-carbothioat (Moli- nate), 2-(2-Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N-Butyl-N'- (3,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyri- midin-2-yl)-N'-(3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl)-hamstoff (Nicosulfuron), 4-Chlor-5-methylamino-2-(3-trifluormethyl-phenyl)-3(2H)pyrid- azinon (Norflurazon), S-(2-Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orben- carb), 4-Dipropylamino-3,5-dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Di- chlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-on (Oxa- diargyl), 3-[2,4-Dichlor-5-(l-methyl-ethoxy)-phenyl]-5-(t-butyl)-l,3,4-oxadi- azol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2-yl)-N'-(2-oxetan- 3-yl-oxycarbonyl-phenylsulfonyl)-hamstoff (Oxasulfuron), 3-[l-(3,5-Dichlor- phenyl)- 1 -i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H- 1 ,3-oxazin-4-on (Oxaziclomefone), 2-Chlor- 1 -(3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl- benzen (Oxyfluorfen), l, -Dimethyl-4,4'-bipyridinium (Paraquat), 1-Amino- N-( 1 -ethyl-propyl)-3 ,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t- Butyl)-N-(l-ethyl-propyl)-2,6-dinitro-benzenamin (Pendralin), 4-Amino-(2,6-dimethyl-phenyl) -N- (1 H-pyrazole-1-yl-methyl) -acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2,4 , 4-trimethyl-2H-1-benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl-urea (metobenzuron), N '- (4-bromophenyl) -N-methoxy-N -methyl urea (metobromuron), (S) -2-chloro-N- (2-ethyl-6-methylphenyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (metolachlor, S- Metolachlor), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy- 1, 2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4-methoxyphenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-l, 2,4-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-l, 3,5-triazine -2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-1H-azepine-1-carbothioate (molate), 2- (2-naphthyloxy) -N-phenyl-propanamide (naproanilide), N-butyl-N'- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxy-pyrimidine-2 -yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) pyrid- azinone (norflurazone), S- (2-chloro-benzyl) -N, N-diethyl-thiocarbamate (orben-carb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (oryzalin), 3- [2,4- Dichloro-5- (2-propynyloxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4- Dichloro-5- (l-methyl-ethoxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6- dimethyl-p yrimidin-2-yl) -N '- (2-oxetan- 3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [l- (3,5-dichlorophenyl) - 1-i-propyl] -2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1 - (3-ethoxy-4-nitro-phenoxy) -4- trifluoromethylbenzene (oxyfluorfen), l, -dimethyl-4,4'-bipyridinium (paraquat), 1-amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2,6-dinitro-benzene ( Pendimethalin), 4- (t-butyl) -N- (l-ethyl-propyl) -2,6-dinitrobenzenamine (pendralin), 4-amino-
3,5,6-trichlor-pyridin-2-carbonsäure (Picloram), N-(4-Fluor-phenyl)-6-(3-tri- fluormethyl-phenoxy)-pyridin-2-carboxamid (Picolinafen), 2-Chlor-N-(2,6- diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamid (Pretilachlor), N-(4,6-Bis-di- fluormethoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-ham- stoff (Primisulfüron-methyl), l-Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)-6-fluor- tetrahydro-l,3-dioxo-lH-pyrrolo[l,2-c]imidazol-2(3H)-yl]-phenyl]-methan- sulfonamid (Profluazol), 2-Chlor-N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor-phenyl)-propanamid (Propanil), (R)-[2-[[(l-Methyl- ethyliden)-amino]-oxy]-ethyl]-2-[4-(6-chlor-2-chinoxalinyloxy)-phenoxy]- propanoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[(l- methyl-ethoxy)-methyl]-acetamid (Propisochlor), 2-[[[(4,5-Dihydro-4- methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]-amino]-sulfonyl]- benzoesäure-methylester-Natriumsalz (Propoxycarbazone-sodium), S-Phenyl- methyl-N,N-dipropyl-thiocarbamat (Prosulfocarb), N-(4-Methoxy-6-methyl- l,3,5-triazin-2-yl)-N,-(2-(3,3,3-trifluor-propyl)-phenylsulfonyl)-hamstoff (Prosulfuron), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy- 1 -methyl- 1 H-pyr- azol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 1 -(3-Chlor-4,5,6,7- tetrahydro-pyrazolo[l,5-a]pyridin-2-yl)-5-(methyl-2-propinylamino)-lH-pyr- azol-4-carbonitril (Pyrazogyl), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-5-(4- methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)- l,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl-l-methyl-pyrazol-5-yl- sulfönyl)-hamstoff (Pyrazosulfuron-ethyl), Diphenylmethanon-O-[2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxim (Pyribenzoxim), 6-Chlor- 3-phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3-phenyl-pyridazin-4-yl)-S- octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N- (4-fluorophenyl) -6- (3-trifluoromethyl-phenoxy) pyridine-2-carboxamide (picolinafen), 2- Chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bis-di-fluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfüron-methyl), l-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l , 3-dioxo-lH-pyrrolo [l, 2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor ), N- (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(l-methylethylidene) amino] oxy] ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] - propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methyl-phenyl) -N - [(l-methyl-ethoxy) -methyl] - acetamide (propisochlor), 2 - [[[(4,5-dihydro-4- methyl-5-oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) -carbonyl] -amino] -sulfonyl] - methyl benzoate-sodium salt (propoxycarbazone-sodium), S-phenyl-methyl -N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N , - (2- (3,3,3-trifluoro -propyl) -phenylsulfonyl) -urea (prosulfuron), ethyl- [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1 H-pyr-azol-3-yl) -4-fluorine phenoxy] acetate (pyraflufen-ethyl), 1 - (3-chloro-4,5,6,7-tetrahydro-pyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino ) -lH-pyr-azole-4-carbonitrile (pyrazogyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-5- (4-methyl-phenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2,4-dichlorobenzoyl) - 1,3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4th -ethoxycarbonyl-l-methyl-pyrazol-5-yl-sulfonyl) -urea (pyrazosulfuron-ethyl), diphenylmethanone-O- [2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) - benzoyl] oxime (pyribenzoxime), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O - (6-chloro-3-phenyl-pyridazin-4-yl) -S- octyl-thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7-
[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl-l(3H)-isobenzofuranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-ylthio)- benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor-chinolin-8- carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbonsäure (Quin- merac), 2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, -tetrahydro-2-furanyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl- sulfonyl)-hamstoff (Rimsulfuron), 2-(l-Ethoximinobutyl)-5-(2-ethylthio- propyl)-3-hydroxy-2-cyclohexen-l-on (Sethoxydim), 6-Chlor-2,4-bis-ethyl- amino-1 ,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclo- hexan-l,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino-phe- nyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-on (Sulfentrazone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sul- fonyl]-benzoat (Sulfometuron-methyl), N-Phosphonomethyl-glycin-tri- methylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethyl- sulfonyl-imidazo[ 1 ,2-a]pyridin-3-sulfonamid (Sulfosulfuron), 6-Chlor-4- ethylamino-2-tert-butylamino-l,3,5-triazin (Terbuthylazine), 2-tert-Butyl- amino-4-ethylamino-6-methylthio- 1 ,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6- dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluor- methyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6- dimethyl-3H,5H-pyrrolo[2,l-c]-l,2,4-thiadiazol-3-ylidenamino)-7-fluor-4-(2- propinyl)-2H- 1 ,4-benzoxazin-3(4H)-on (Thidiazimin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-ham- stoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-tri- methyl-phenyl)-2-cyclohexen-l-on (Tralkoxydim), S-(2,3,3-Trichlor-2- propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl- l,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-hamstoff (Triasulf- uron), N-Methyl-N-(4-methoxy-6-methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxy- carbonyl-phenylsulfonyl)-hamstoff (Tribenuron-methyl), (3,5,6-Trichlor)- pyridin-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2-tri- chlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]- carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Tri- floxysulfuron), l-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-hamstoff (Triflusulfuron- methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-(2-trifluor- methyl-phenylsulfonyl)-hamstoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino)-2- pyridinsulfonamid, 4-[4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-l H- l,2,4-triazol-l-yl]-2-[(ethylsulfonyl)amino]-5-fluor-benzencarbothioamid[(4,6-Dimethoxy-2-pyrimidinyl) thio] -3-methyl-l (3H) -isobenzofuranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid- methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) - benzoic acid sodium salt (pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid (quinchlorac) , 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester, tetrahydro-2-furanyl- methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl ) -urea (rimsulfuron), 2- (l-ethoximinobutyl) -5- (2-ethylthio-propyl) -3-hydroxy-2-cyclohexen-l-one (sethoxydim), 6-chloro-2,4-bis- ethylamino-1, 3,5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione), 2- (2,4-dichloro -5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (sulfentrazone), methyl 2 - [[[(4 , 6-dimethyl-2-pyrimidinyl) amino no] carbonyl] amino] sulfonyl] benzoate (sulfometuron-methyl), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl) -N'- (2-ethyl- sulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-l, 3,5-triazine (terbuthylazine), 2-tert-butyl amino-4-ethylamino-6-methylthio-1, 3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid, methyl ester ( Thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2, lc] -l, 2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2 - propynyl) -2H- 1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- ( 2-methoxycarbonyl-thien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-tri-methyl-phenyl) - 2-cyclohexen-l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-triazine -2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-met hyl-1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) pyridin-2-yl -oxy-acetic acid (triclopyr), 2- (3,5-dichlorophenyl) -2- (2,2,2-trichloroethyl) oxirane (tridiphane), N - [[(4,6- Dimethoxy-2-pyrimidinyl) amino] - carbonyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), l-amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -l, 3,5-triazin-2-yl] -N'- (2-methoxycarbonyl-phenylsulfonyl) urea (triflusulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl ) urea (tritosulfuron), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino) -2-pyridinesulfonamide, 4- [ 4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -l H-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide
("Wirkstoffe der Gmppe 2"),("Active substances of group 2"),
und/oder (c) eine die Kultuφflanzen- Verträglichkeit verbessernde Verbindung aus der folgenden Gmppe von Verbindungen:and or (c) a compound which improves the tolerance to cultivated plants from the following group of compounds:
4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1-Dichloracetyl-hexa- hydro-3,3,8a-trimethylpyrrolo[l,2-a]-ρyrimidin-6(2H)-on (BAS-145138), 4- Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor), 5- Chlor-chinoxalin-8-oxy-essigsäure-( 1 -methyl-hexylester) (Cloquintocet- mexyl), α-(Cyanomethoximino)-phenylacetonitril (Cyometrinil), 2,4-Dichlor- phenoxy-essigsäure (2,4-D), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)- ethyl)-N-(2-propenyl)-acetamid (DKA-24), 2,2-Dichlor-N,N-di-2-propenyl- acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-( 1 -methyl- 1 -phenyl-ethyl)- hamstoff (Dymron), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), l-(2,4-Di- chlor-phenyl)-5 -trichlormethyl- 1 H- 1 ,2,4-triazol-3 -carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure-phenyl- methylester (Flurazole), 4-Chlor-N-(l ,3-dioxolan-2-yl-methoxy)-α-trifluor- acetophenonoxim (Fluxofenim), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl- oxazolidin (Furilazole, MON-13900), Ethyl-4,5-dihydro-5,5-diphenyl-3- isoxazolcarboxylat (Isoxadifen-ethyl), (4-Chlor-2-methyl-phenoxy)essigsäure (MCPA), (+-)-2-(4-Chlor-2-methylphenoxy)propansäure (Mecoprop), Di- ethyl-l-(2,4-dichloφhenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-di- carboxylat (Mefenpyr-diethyl) 2-Dichlormethyl-2 -methyl- 1,3-dioxolan (MG- 191), 1 ,8-Naphthalsäureanhydrid, α-( 1 ,3-Dioxolan-2-yl-methoximino)- phenylacetonitril (Oxabetrinil), 2,2-Dichlor-N-(l ,3-dioxolan-2-yl-methyl)-N- (2-ρroρenyl)-acetamid (PPG- 1292), 3-Dichloracetyl-2,2,5-trimethyl- oxazo lidin (R-29148), N-Cyclopropyl-4-[[(2-methoxy-5-methyl-benzoyl)- amino]-sulfonyl]-benzamid, N-[[(4-Methoxyacetylamino)-phenyl]-sulfonyl- 2-methoxy-benzamid und N-[[(4-Methylaminocarbonylamino)-phenyl]- sulfonyl-2-methoxy-benzamid4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexa- hydro-3,3,8a-trimethylpyrrolo [1,2-a] -pyrimidine-6 (2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 5-chloro-quinoxalin-8-oxyacetic acid- (1st -methyl-hexyl ester) (Cloquintocet-mexyl), α- (cyanomethoximino) -phenylacetonitrile (Cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,2-dichloro-N- (2- oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichlormid), N - (4-methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) - urea (Dymron), 4,6-dichloro-2-phenyl-pyrimidine (Fenclorim), l- (2,4 -Dichlorophenyl) -5-trichloromethyl-1 H-1, 2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenyl- methyl ester (flurazole), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2,2- dimethyl-oxazolidine (furilazole, MON- 13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), (4-chloro-2-methyl-phenoxy) acetic acid (MCPA), (+ -) - 2- ( 4-chloro-2-methylphenoxy) propanoic acid (mecoprop), diethyl l- (2,4-dichloφhenyl) -4,5-dihydro-5-methyl-lH-pyrazole-3,5-di-carboxylate (mefenpyr -diethyl) 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1, 8-naphthalic anhydride, α- (1, 3-dioxolan-2-yl-methoximino) - phenylacetonitrile (oxabetrinil), 2 , 2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-ρroρenyl) -acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyl-oxazoidin (R-29148), N-cyclopropyl-4 - [[(2-methoxy-5-methyl-benzoyl) amino] sulfonyl] benzamide, N - [[(4-methoxyacetylamino) phenyl] sulfonyl 2 -methoxy-benzamide and N - [[(4-methylaminocarbonylamino) phenyl] sulfonyl-2-methoxy-benzamide
("Wirkstoffe der Gmppe 3"). Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 1 Verbindungen der Formel (I) enthalten, in welcher("Active substances of group 3"). Herbicidal agents according to Claim 1, characterized in that they contain compounds of the formula (I) as active ingredients of group 1, in which
R1 für Wasserstoff, Amino oder jeweils gegebenenfalls durch Cyano,R 1 represents hydrogen, amino or in each case optionally by cyano,
Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl steht,Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl,
R2 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl steht,R 2 represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine,
R3 für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl steht,R 3 represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,
R4 für Wasserstoff, Cyano, Fluor, Chlor oder Brom steht,R 4 represents hydrogen, cyano, fluorine, chlorine or bromine,
R ,5 für Cyano, Thiocarbamoyl, Fluor, Chlor oder Brom steht, undR 5 represents cyano, thiocarbamoyl, fluorine, chlorine or bromine, and
R >6 für Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy,R> 6 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy,
Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy, Hydroxy, Methoxy, Ethoxy, n- oder i-Propoxy, Acetyl, Propionyl, n- oder i- Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxy- carbonyl, Allyloxycarbonyl oder Propargyloxycarbonyl substituiertesMercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each for optionally by cyano, carboxy, hydroxy, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-Propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted
Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i- oder s-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i- oder s-Butylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl,Methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i Propylthio, n-, i- or s-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
Methylamino, Ethylamino, n- oder i-Propylamino, n-, i- oder s-Butyl- amino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor, Brom, Methoxycarbonyl und oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl, Butinyl, Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Acetylamino, Propionylamino, n- oder i- Butyroylamino, Methoxycarbonylamino, Ethoxycarbonylamino, n- oder i-Propoxycarbonylamino, Methylsulfonylamino, Ethylsulfonyl- amino, n- oder i-Propylsulfonylamino, n-, i-, s- oder t-Butylsulfonyl- amino, N,N-Bis-methylsulfonyl-amino, N,N-Bis-ethylsulfonyl-amino,Methylamino, ethylamino, n- or i-propylamino, n-, i- or s-butyl- amino, for each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and or ethoxycarbonyl or ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine and / or chlorine , Methoxy, ethoxy, n- or i-propoxy substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino,
N-Ethylsulfonyl-N-methylsulfonyl-amino, N-Methylsulfonyl-N-n- propylsulfonyl-amino, N-Methylsulfonyl-N-i-propylsulfonyl-amino, N-Acetyl-N-methylsulfonyl-amino, N-Propionyl-N-methylsulfonyl- amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i-Butyroyl-N- methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl-amino, N-t-N-ethylsulfonyl-N-methylsulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, Nt-
Butyroyl-N-methylsulfonyl-amino, N-(2,2-Dimethyl-propanoyl)-N- ethylsulfonyl-amino, N-(2-Methylpropanoyl)-N-ethylsulfonyl-amino, N-Acetyl-N-ethylsulfonyl-amino, N-Propionyl-N-ethylsulfonyl- amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i-Butyroyl-N-ethyl- sulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl-amino, N-t-Butyroyl-Butyroyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methylpropanoyl) -N-ethylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt-butyroyl-
N-ethylsulfonyl-amino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluor- methoxy oder Trifluormethoxy substituiertes N-Phenylcarbonyl-N- methylsulfonyl-amino, N-Phenylcarbonyl-N-ethylsulfonyl-amino, N-N-ethylsulfonyl-amino, or for each optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n - or i-propoxy, difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl-N-ethylsulfonyl-amino, N-
Thienylcarbonyl-N-methylsulfonyl-amino oder N-Thienylcarbonyl-N- ethylsulfonyl-amino steht.Thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino is.
3. Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 1 Verbindungen der Formel (I) enthalten, in welcher R1 für Wasserstoff, Amino, Methyl oder Ethyl steht,3. Herbicidal compositions according to Anspmch 1, characterized in that they contain compounds of the formula (I) as active ingredients of group 1, in which R 1 represents hydrogen, amino, methyl or ethyl,
R2 für jeweils durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht,R 2 represents methyl or ethyl substituted by fluorine and / or chlorine,
R3 für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht,R 3 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
R4 für Wasserstoff, Fluor oder Chlor steht,R 4 represents hydrogen, fluorine or chlorine,
R5 für Cyano, Thiocarbamoyl, Chlor oder Brom steht, undR 5 represents cyano, thiocarbamoyl, chlorine or bromine, and
R6 für Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy, Mercapto, Amino, Hydroxyamino, Aminosulfonyl, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy, Hydroxy,R 6 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally with cyano, carboxy, hydroxy,
Methoxy, Ethoxy, Acetyl, Propionyl, Methoxycarbonyl und/oder Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Allyloxycarbonyl oder Propargyloxycarbonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfmyl, Ethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylamino, Ethyl- amino, n- oder i-Propylamino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor, Brom, Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl, Ethinyl, Propinyl,Methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl and / or ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-Propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i Propylamino, for ethenyl, propenyl, ethynyl, propynyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl,
Propenyloxy oder Propinyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor, Methoxy oder Ethoxy substituiertes Acetylamino, Propionylamino, Methoxycarbonylamino, Ethoxycarbonylamino, Methylsulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonyl- amino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl- amino, N,N-Bis-ethylsulfonyl-amino, N-Ethylsulfonyl-N-methyl- sulfonyl-amino, N-Methylsulfonyl-N-n-propylsulfonyl-amino, N- Methylsulfonyl-N-i-propylsulfonyl-amino, N-Acetyl-N-methyl- sulfonyl-amino, N-Propionyl-N-methylsulfonyl-amino, N-(2,2- Dimethyl-propanoyl)-N-ethylsulfonyl-amino, N-(2-Methylpropanoyl)- N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i-Propenyloxy or propynyloxy, for each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t- Butylsulfonylamino, N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-ethylsulfonyl-N-methyl- sulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N- (2nd , 2-dimethyl-propanoyl) -N-ethylsulfonyl-amino, N- (2-methylpropanoyl) - N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-
Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Acetyl-N-ethyl- sulfonyl-amino, N-Propionyl-N-ethylsulfonyl-amino, N-n-Butyroyl- N-ethylsulfonyl-amino, N-i-Butyroyl-N-ethylsulfonyl-amino, N-s- Butyroyl-N-ethylsulfonyl-amino, N-t-Butyroyl-N-ethylsulfonyl- amino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluor- methoxy oder Trifluormethoxy substituiertes N-Phenylcarbonyl-N- methylsulfonyl-amino, N-Phenylcarbonyl-N-ethylsulfonyl-amino, N- Thienylcarbonyl-N-methylsulfonyl-amino oder N-Thienylcarbonyl-N- ethylsulfonyl-amino steht.Butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, Nt-butyroyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt-butyroyl-N-ethylsulfonyl-amino, or for each optionally by cyano, fluorine, chlorine , Bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N -Thienylcarbonyl-N-ethylsulfonyl-amino is.
4. Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 1 Verbindungen der Formel (I) enthalten, in welcher4. Herbicidal compositions according to Anspmch 1, characterized in that they contain compounds of the formula (I) in which
R1 für Amino steht,R 1 represents amino,
R2 für Trifluormethyl steht,R 2 represents trifluoromethyl,
R3 für Wasserstoff, Chlor oder Methyl steht,R 3 represents hydrogen, chlorine or methyl,
R4 für Fluor steht,R 4 represents fluorine,
R für Cyano oder Thiocarbamoyl steht, und R6 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertesR represents cyano or thiocarbamoyl, and R 6 for each optionally substituted by fluorine and / or chlorine
Methylsulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonyl- amino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl- amino, N,N-Bis-ethylsulfonyl-amino, N-Ethylsulfonyl-N-methyl- sulfonyl-amino, N-Methylsulfonyl-N-n-propylsulfonyl-amino, N-Methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl- N-methyl-sulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl-amino, N-
Methylsulfonyl-N-i-propylsulfonyl-amino, N-Acetyl-N-methyl- sulfonyl-amino, N-Propionyl-N-methylsulfonyl-amino, N-(2,2- Dimethyl-propanoyl)- 1 -ethylsulfonyl-amino, N-(2-Methylpropanoyl)- N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i- Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Methoxyacetyl-N- methylsulfonylamino, N-Acetyl-N-ethylsulfonyl-amino, N-Propionyl- N-ethylsulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i- Butyroyl-N-ethylsulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl- amino, N-t-Butyroyl-N-ethylsulfonyl-amino, N-Methoxyacetyl-N- ethylsulfonylamino, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes N-Phenyl- carbonyl-N-methylsulfonyl-amino, N-Phenylcarbonyl-N-ethylsulfo- nyl-amino, N-Thienylcarbonyl-N-methylsulfonyl-amino oder N-Methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methyl-sulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) -1-ethylsulfonyl-amino, N- (2-methylpropanoyl) - N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni- butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, Nt-butyroyl-N-methylsulfonyl- amino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni- butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonylamino, Nt-butyroyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, or for each optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy , Difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-
Thienylcarbonyl-N-ethylsulfonyl-amino steht.Thienylcarbonyl-N-ethylsulfonyl-amino is.
5. Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 1 Verbindungen der Formel (I) enthalten, in welcher5. Herbicidal compositions according to Anspmch 1, characterized in that they contain compounds of the formula (I) as active ingredients of group 1, in which
R1 für Methyl steht,R 1 represents methyl,
R2 für Trifluormethyl steht,R 2 represents trifluoromethyl,
R3 für Wasserstoff, Chlor oder Methyl steht, R4 für Fluor steht,R 3 represents hydrogen, chlorine or methyl, R 4 represents fluorine,
R5 für Thiocarbamoyl steht, undR 5 represents thiocarbamoyl, and
R6 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertesR 6 for each optionally substituted by fluorine and / or chlorine
Methylsulfonylamino, Ethylsulfonylamino, n- oder i-Propylsulfonyl- amino, n-, i-, s- oder t-Butylsulfonylamino, N,N-Bis-methylsulfonyl- amino, N,N-Bis-ethylsulfonyl-amino, N-Ethylsulfonyl-N-methyl- sulfonyl-amino, N-Methylsulfonyl-N-n-propylsulfonyl-amino, N- Methylsulfonyl-N-i-propylsulfonyl-amino, N-Acetyl-N-methyl- sulfonyl-amino, N-Propionyl-N-methylsulfonyl-amino, N-(2,2- Dimethyl-propanoyl)- 1 -ethylsulfonyl-amino, N-(2-Methylpropanoyl)- N-ethylsulfonyl-amino, N-n-Butyroyl-N-methylsulfonyl-amino, N-i- Butyroyl-N-methylsulfonyl-amino, N-s-Butyroyl-N-methylsulfonyl- amino, N-t-Butyroyl-N-methylsulfonyl-amino, N-Methoxyacetyl-N- methylsulfonylamino, N-Acetyl-N-ethylsulfonyl-amino, N-Propionyl- N-ethylsulfonyl-amino, N-n-Butyroyl-N-ethylsulfonyl-amino, N-i- Butyroyl-N-ethylsulfonyl-amino, N-s-Butyroyl-N-ethylsulfonyl- amino, N-t-Butyroyl-N-ethylsulfonyl-amino, N-Methoxyacetyl-N- ethylsulfonylamino, oder für jeweils gegebenenfalls durch Cyano,Methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl- N-methylsulfonyl-amino, N-methylsulfonyl-Nn-propylsulfonyl-amino, N-methylsulfonyl-Ni-propylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N- (2,2-dimethyl-propanoyl) -1-ethylsulfonyl-amino, N- (2-methylpropanoyl) -N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl- amino, Ns-butyroyl-N-methylsulfonylamino, Nt-butyroyl-N-methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N-propionyl-N-ethylsulfonylamino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni- butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, Nt-butyroyl-N-ethylsulfonyl-amino, N-methoxyacetyl-N-ethylsulfonylamino, or for in each case optionally by cyano,
Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes N-Phenyl- carbonyl-N-methylsulfonyl-amino, N-Phenylcarbonyl-N-ethyl- sulfonyl-amino, N-Thienylcarbonyl-N-methylsulfonyl-amino oder N- Thienylcarbonyl-N-ethylsulfonyl-amino steht.Fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N- methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino.
6. Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gruppe 1 Verbindungen der Formel (I) enthalten, in welcher6. Herbicidal compositions according to claim 1, characterized in that they contain compounds of the formula (I) as active ingredients in group 1, in which
R1 für Amino oder Methyl steht, R2 für Trifluormethyl steht,R 1 represents amino or methyl, R 2 represents trifluoromethyl,
R3 für Wasserstoff, Chlor oder Methyl steht,R 3 represents hydrogen, chlorine or methyl,
R4 für Wasserstoff, Fluor oder Chlor steht,R 4 represents hydrogen, fluorine or chlorine,
R5 für Cyano, Thiocarbamoyl oder Chlor steht, undR 5 represents cyano, thiocarbamoyl or chlorine, and
R6 für Carboxy, Carbamoyl, Thiocarbamoyl, Hydroxy, Mercapto, Amino, Fluor, Chlor, Brom, für jeweils gegebenenfalls durch Cyano, Carboxy,R 6 for carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, fluorine, chlorine, bromine, for each optionally by cyano, carboxy,
Hydroxy, Methoxy, Ethoxy, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Allyloxycarbonyl oder Propargyloxycarbonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylamino, Ethyl- amino, n- oder i-Propylamino, N-(2,2-Dimethyl-propanoyl)-N-ethyl- sulfonyl-amino, N-(2-Methylpropanoyl)-N-ethylsulfonylamino, für jeweils gegebenenfalls durch Cyano, Carboxy, Fluor, Chlor, Brom,Hydroxy, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl or propargyloxycarbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i -Propylamino, N- (2,2-dimethyl-propanoyl) -N-ethyl-sulfonyl-amino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, each optionally with cyano, carboxy, fluorine, chlorine, bromine,
Methoxycarbonyl und/oder Ethoxycarbonyl substituiertes Ethenyl, Propenyl, Ethinyl, Propinyl, Propenyloxy oder Propinyloxy steht.Methoxycarbonyl and / or ethoxycarbonyl substituted ethenyl, propenyl, ethynyl, propynyl, propenyloxy or propynyloxy.
7. Herbizide Mittel gemäß Anspmch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 1 mindestens eine der folgenden Verbindungen enthalten:7. Herbicidal compositions according to claim 1, characterized in that they contain at least one of the following compounds as active ingredients in group 1:
2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidi- nyl)-benzoesäure-[l,l-dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester, 5- Fluor-4-(3 -methyl-2,6-dioxo-4-trifluormethyl-3 ,6-dihydro- 1 (2H)-pyrimidi- nyl)-2-[(l-methyl-2-propinyl)-oxy]-benzonitril, N-[2-Cyano-4-fluor-5-(3- methyl-2,6-dioxo-4-trifluormethyl-3 ,6-dihydro- 1 (2H)-pyrimidinyl)-phenyl]- N-(2,2-dimethyl-propanoyl)- 1 -ethansulfonamid, N-[2-Cyano-4-fluor-5-(3- methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydro-l(2H)-pyrimidinyl)-phenyl]- N-(4-methoxy-benzoyl)-ethansulfonamid, N-[5-(3-Amino-2,6-dioxo-4-tri- fluormethyl-3,6-dihydro- 1 (2H)-pyrimidinyl)-2-cyano-4-fluoro-phenyl]-N-(2- thienyl-carbonyl)- 1 -ethansulfonamid, 2-(Ethylsulfonylamino)-5-fluor-4-[3- methyl-2,6-dioxo-4-trifluormethyl-3 ,6-dihydro- 1 (2H)-pyrimidinyl]-benzen- carbothioamid.2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoic acid- [l, l-dimethyl-2-oxo 2- (2-propenyloxy)] - ethyl ester, 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3, 6-dihydro-1 (2H) -pyrimidinyl) -2- [(l-methyl-2-propynyl) oxy] benzonitrile, N- [2-cyano-4-fluoro-5- (3- methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -phenyl] - N- (2,2-dimethyl-propanoyl) -1-ethanesulfonamide, N- [2- Cyano-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -phenyl] - N- (4-methoxy-benzoyl) - ethanesulfonamide, N- [5- (3-amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) pyrimidinyl) -2-cyano-4-fluoro-phenyl] -N - (2-thienyl-carbonyl) -1-ethanesulfonamide, 2- (ethylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl] -benzene-carbothioamide.
8. Herbizide Mittel gemäß einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gmppe 2 zumindest eine Verbindung aus der folgenden Gmppe von Verbindungen enthalten:8. Herbicidal compositions according to one of claims 1 to 7, characterized in that they contain at least one compound from the following group of compounds as active ingredients of group 2:
Acetochlor, Alachlor, Amicarbazone, Amitrole, Atrazin, Bromacil, Carfen- trazone-ethyl, Chlorimuron-ethyl, Clodinafop-propargyl, Cyanazine, Diclosulam, Dimethenamid, S-Dimethenamid, Diuron, EPTC, Fenoxaprop-P-ethyl, Fentrazamide, Flucarbazone-sodium, Flufenacet, Flumetsulam, Glufosinate- ammonium, Glyphosate-isopropylammonium, Imazamox, Imazaquin, Imazethapyr, Isoxaflutole, Mesotrione, Metolachlor, S-Metolachlor, Metribuzin, Nicosulfuron, Norflurazon, Pendimethalin, Propoxycarbazone-sodium, Rimsulfuron, Simazin, Sulfometuron-methyl, Sulcotrione, Sulfentrazone, Sulfosate, Terbuthylazine, Thifensulfuron-methyl, Trifluralin, 4-[4,5-Dihydro-4- methyl-5-oxo-(3-trifluormethyl)- 1 H- 1 ,2,4-triazol- 1 -yl]-2-[(ethylsulfonyl)- amino]-5-fluor-benzolcarbothioamid.Acetochlor, alachlor, amicarbazone, amitrole, atrazine, bromacil, carfentrazone-ethyl, chlorimuron-ethyl, clodinafop-propargyl, cyanazine, diclosulam, dimethenamid, S-dimethenamid, diuron, EPTC, fenoxaprop-P-ethyl, fentazone-amide, flucarbazamide sodium, flufenacet, flumetsulam, glufosinate-ammonium, glyphosate-isopropylammonium, imazamox, imazaquin, imazethapyr, isoxaflutole, mesotrione, metolachlor, s-metolachlor, metribuzin, nicosulfuron, norflurazon, rimimazulfonone, pendimetulfone sodium, pendimetulfone sodium, Sulcotrione, sulfentrazone, sulfosate, terbuthylazine, thifensulfuron-methyl, trifluralin, 4- [4,5-dihydro-4-methyl-5-oxo- (3-trifluoromethyl) - 1 H- 1, 2,4-triazole-1 - yl] -2 - [(ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide.
9. Herbizide Mittel gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass sie als Wirkstoff der Gmppe 3 zumindest eine der Verbindungen aus der folgenden Gmppe von Verbindungen enthalten:9. Herbicidal compositions according to one of claims 1 to 8, characterized in that they contain at least one of the compounds from the following group of compounds as active ingredient of group 3:
5-Chlor-chinoxalin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet- mexyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen- ethyl), Diethyl-l-(2,4-dichlor-phenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5- dicarboxylat (Mefenpyr-diethyl), 4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]- decan (AD-67), l-Dichloracetyl-hexahydro-3,3,8a-trimethylpyrrolo[l,2-a]- ρyrimidin-6(2H)-on (BAS- 145138), 4-Dichloracetyl-3,4-dihydro-3-methyl- 2H-l,4-benzoxazin (Benoxacor), 2,2-Dichlor-N,N-di-2-propenyl-acetamid5-chloro-quinoxaline-8-oxyacetic acid (l-methyl-hexyl ester) (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifene ethyl), diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 4-dichloroacetyl-l-oxa- 4-aza-spiro [4.5] - decane (AD-67), l-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] - ρyrimidin-6 (2H) -one (BAS- 145138) , 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 2,2-dichloro-N, N-di-2-propenyl-acetamide
(Dichlormid), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furilazole, MON-13900) und 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R- 29148).(Dichlormid), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (Furilazole, MON-13900) and 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148).
10. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 9 zur Bekämpfung von unerwünschten Pflanzen.10. Use of an agent according to any one of claims 1 to 9 for controlling unwanted plants.
11. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekennzeichnet, dass man Mittel gemäß einem der Ansprüche 1 bis 9 auf die uner- wünschten Pflanzen und/oder ihren Lebensraum einwirken lässt.11. A method for controlling unwanted plants, characterized in that agents according to one of claims 1 to 9 are allowed to act on the undesired plants and / or their habitat.
12. Verfahren zur Herstellung eines herbiziden Mittels, dadurch gekennzeichnet, dass man ein Mittel gemäß einem der Ansprüche 1 bis 9 mit oberflächenaktiven Mitteln und/oder Streckmitteln vermischt. 12. A process for the preparation of a herbicidal composition, characterized in that a composition according to one of claims 1 to 9 is mixed with surface-active compositions and / or extenders.
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BR0016120A (en) 2002-08-27
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US20040171488A1 (en) 2004-09-02
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