EP1453377A1 - Herbicides based on substituted carboxylic acid anilides - Google Patents

Herbicides based on substituted carboxylic acid anilides

Info

Publication number
EP1453377A1
EP1453377A1 EP20020791758 EP02791758A EP1453377A1 EP 1453377 A1 EP1453377 A1 EP 1453377A1 EP 20020791758 EP20020791758 EP 20020791758 EP 02791758 A EP02791758 A EP 02791758A EP 1453377 A1 EP1453377 A1 EP 1453377A1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
chloro
phenyl
chlorine
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.)
Ceased
Application number
EP20020791758
Other languages
German (de)
French (fr)
Inventor
Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
Roland Andree
Karl-Heinz Linker
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
Priority to EP06008155A priority Critical patent/EP1743527A3/en
Publication of EP1453377A1 publication Critical patent/EP1453377A1/en
Ceased 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines

Definitions

  • the invention relates to new herbicidal combinations of active substances, the known substituted carboxylic acid anilides on the one hand and one or more known herbicidally active compound (s) on the other hand and / or optionally a crop plant
  • the substituted carboxylic acid anilides when used together with certain herbicidally active compounds show synergistic effects with regard to the action against weeds and are particularly advantageous as effective combination preparations for the selective control of monocotyledonous and dicotyledonous weeds in crop plants, such as e.g. in cotton, barley, potatoes, corn, rapeseed, rice,
  • Rye soybeans, sunflowers, wheat, sugar cane and sugar beet, but also for controlling monocotyledon and dicotyledon weeds in the semi and non-selective range can be used.
  • the invention therefore relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of (a) at least one substituted carboxylic acid anilide of the general formula (I)
  • n the numbers 0 or 1
  • alkanediyl alkylene
  • alkenediyl each having up to 6 carbon atoms
  • Ar represents optionally substituted aryl with 6 or 10 carbon atoms or for optionally substituted heterocyclyl with up to 9 carbon atoms and 1 to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms,
  • R 1 is alkyl which is optionally substituted by halogen and has 1 to 6 carbon atoms,
  • cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by halogen or C 1 -C 4 alkyl
  • Alkoxy-substituted heterocyclyl with 5 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,
  • R 2 for cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl or alkoxy each optionally substituted by halogen, each with 1 to 4
  • R 3 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen
  • Z represents one of the groupings outlined below
  • R 4 represents hydrogen, amino or optionally halogen-substituted alkyl having 1 to 4 carbon atoms
  • R 5 represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by halogen substituted alkyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the alkyl groups,
  • R 6 represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
  • R 7 represents hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by cyano, halogen or -C 4 -alkoxy, each having 1 to 4 carbon atoms in the alkyl groups, and
  • R 8 represents hydrogen or alkyl, alkoxy, alkylamino, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or - -alkoxy, each having 1 to 4 carbon atoms in the alkyl groups,
  • R 9 represents hydrogen, cyano, halogen or one of the groupings -R ⁇ , -OR 11 , SR 11 , SO-R 11 or SO 2 -R 11 , R 1 represents hydrogen, hydroxy, amino, or one of the groupings -R 11 or -OR 11 , and
  • Chloro-2-methylphenoxy) acetic acid (MCPA), (R) -2- (4-chloro-2-methylphenoxy) propionic acid (Mecoprop-P), 2- (2-benzothiazolyloxy) -N-methyl -N-phenyl-acetamide
  • N, N'-dimethyl-urea (metschizthiazuron), N '- (4-bromophenyl) -N-methoxy-N- methyl urea (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-l, 2,4-triazine-5 ( 4H) -
  • 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-1, 3,5-triazine (Simazine), 2- (2-chloro-4-methylsulfonylbenzoyl)
  • chloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) -phenylsulfonyl] urea (triasulfuron),
  • the invention thus relates to herbicidal combinations of active ingredients which
  • n is preferably the number 0.
  • A preferably represents alkanediyl (alkylene) with 1 to 5 carbon atoms or alkenediyl with 2 to 5 carbon atoms.
  • Ar preferably represents in each case optionally substituted phenyl or naphthyl, or for in each case optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyolyl, pyrazolyl, pyranyl, benzopyranyl, pyridylzyridyl, pyridyl, pyridyl, pyridyl, pyridyl Quinolinyl or
  • R 1 preferably represents alkyl with 1 to 5 carbon atoms optionally substituted by fluorine, chlorine and / or bromine,
  • alkenyl with 2 to 5 carbon atoms optionally substituted by fluorine, chlorine and / or bromine,
  • cycloalkyl with 3 to 6 carbon atoms optionally substituted by fluorine, chlorine and / or bromine or C 1 -C 4 -alkyl,
  • aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 3 carbon atoms in the alkyl part, or
  • nitro, cyano, fluorine, chlorine and / or bromine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-
  • R 2 preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, meth- or ethoxy or n- or i- or optionally substituted by fluorine, chlorine and / or bromine. propoxy.
  • R 3 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
  • R 4 preferably represents hydrogen, amino or methyl, ethyl or n- or i-propyl which is optionally substituted by fluorine, chlorine and / or bromine.
  • R 5 preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl or n- or i-propoxycarbonyl optionally substituted by fluorine, chlorine and / or bromine.
  • R 6 preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl or n- or i-propyl which is optionally substituted by fluorine, chlorine and or bromine.
  • R 7 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-
  • R 8 preferably represents hydrogen or in each case optionally by cyano
  • R 9 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or one of the
  • R 10 preferably represents hydrogen, hydroxy, amino or the grouping -R 11 .
  • R 11 preferably represents alkyl with 1 to 4 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally by Halogen-substituted alkenyl or alkynyl each having 2 to 4 carbon atoms, for cycloalkyl with 3 which is optionally substituted by cyano, fluorine, chlorine, bromine, ethyl, methyl, n- or i-propyl or n-, i-, s- or t-butyl up to 6 carbon atoms, or for phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, CrC-alkyl, C 1 -C -haloalkyl,
  • Ar particularly preferably represents optionally substituted phenyl, or optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, py ⁇ olyl,
  • R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine,
  • phenyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy , Naphthyl, benzyl or phenylethyl, or
  • R 2 particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and or chlorine.
  • R 3 particularly preferably represents hydrogen, cyano, fluorine or chlorine.
  • R particularly preferably represents hydrogen, amino or methyl or ethyl which is optionally substituted by fluorine.
  • R 5 particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, methoxycarbonyl or ethoxycarbonyl which are optionally substituted by fluorine and / or chlorine.
  • R 6 particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
  • R 7 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl, methoxy, ethoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy, n- or i-propoxy , n- or i-Propoxy, methylthio, ethylthio, n- or i-propylthio,, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
  • R 8 particularly preferably represents hydrogen or in each case if appropriate
  • Methyl, ethyl, n- or i-propyl methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, acetyl, propionyl, n- or i-.
  • R 9 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or the grouping -OR 11 or SO 2 -R n .
  • R 10 particularly preferably represents hydrogen or the grouping -R 11 .
  • R .11 particularly preferably represents in each case optionally cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i r propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t butyl, for in each case optionally substituted by fluorine, chlorine and / or bromine ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl cyclopropyl, cyclobutyl , Cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i
  • very particularly preferably represents methylene, ethane-l, l-diyl (ethylidene), ethane-l, 2-diyl (dimethylene), propane-l, l-diyl (propylidene), ethene-l, 2-diyl, propene- 1,2-diyl or propene-2,3-diyl.
  • Ar very particularly preferably represents optionally substituted phenyl
  • R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-, each optionally substituted by fluorine and / or chlorine.
  • R very particularly preferably represents cyano, chlorine, bromine or trifluoromethyl.
  • R 3 very particularly preferably represents hydrogen, fluorine or chlorine.
  • R 4 very particularly preferably represents hydrogen, amino or methyl.
  • R 5 very particularly preferably represents cyano or trifluoromethyl.
  • R 6 very particularly preferably represents hydrogen, chlorine, bromine or methyl.
  • R 7 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
  • R 8 very particularly preferably represents hydrogen or methyl or ethyl which is optionally substituted by fluorine.
  • R 9 very particularly preferably represents hydrogen, chlorine, bromine or the grouping -R ⁇ .
  • R 11 very particularly preferably represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
  • a very particularly preferred group of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grappling designated Z 1 and n, A, Ar, R 1 , R 2 and R 3 are one of the abovementioned Have meanings.
  • Another very particularly preferred category of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grouping designated Z 2 and n, A, Ar, R 1 , R 2 and R 3 are one of the above meanings mentioned.
  • Another very particularly preferred Grappe of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grappling denoted by Z 3 , and n, A, Ar, R 1 , R 2 and R 3 are one of the above have the meanings mentioned.
  • the active substances of Grappe (2) can be assigned to their chemical structure according to the following classes of active substances:
  • 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, 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) - amino] -5-fluoro-benzenecarbothioamide),
  • clodinafop-propargyl cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-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. benfiuralin, ethalfiuralin, oryzalin, pendimethalin
  • trifluralhalin sodium trifluraline, triflurylaline, triflurylaline
  • ureas e.g.
  • imidazolinones e.g. imazamethabenz- methyl, imazamox, imazaquin, imazethapyr
  • isoxazoles e.g. isoxaflutole
  • nicotinanilides
  • Flufenacet Mefenacet
  • phenoxycarboxylic acid derivatives e.g. 2,4-D, dichloroprop-P, MCPA, MCPB, mecoprop
  • pyrazoles e.g. pyrazolates
  • Triazolopyrimidines e.g. Cloransulam-methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam
  • Triketones e.g. Meso-
  • uracile e.g. bromacil
  • a particularly preferred group of compounds of group (2) are the triazolinones, sulfonylureas (in particular iodosulfuron-methyl-sodium), aryloxyphenoxypropionates (in particular fenoxaprop-p-ethyl) and isoxazoles.
  • Imazethapyr iodosulfuron-methyl-sodium, loxynil, isoproturon, isoxaben, isoxa- chlorotole, isoxaflutole, lactofen, linuron, MCPA, mecoprop-P, mefenacet, meso-sulfurone, mesotrione, metamitron, metazachlor, meta-chlorochloron, methabenzachloron Metosulam, Metribuzin, Metsulfuron-methyl, Naproanilide, Neburon, Nicosulfuron, Oxadiargyl, Oxadiazon, Oxaziclomefone, Oxyfluorfen, Pendimethalin,
  • Aclonifen Amicarbazone, Amidosulfuron, Amitrole, Anilofos, Asulam, Benazolin-ethyl, Benfuresate, Bifenox, Bispyribac-sodium, Bromoxynil, Desmedipham, Diclofop-methyl, Diflufenican, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl Fentrazamide, fluazifop-P-butyl, fluazolate, flucarbazone-sodium, Flufenacet, Flurtamone, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Iodosulognion, loxynil, Isoproturon, Isoxachlortole, Isoxaflutole, Lactofen, Linuron, Mefenacet, Mesosulfuron, Oxamethonone, Oxetronuronur
  • the agents according to the invention preferably contain one or two active substances of Grappe (1) and one to three active substances of Grappe (2) and / or optionally one active substance of Grappe (3).
  • the agents according to the invention contain an active ingredient from Grappe (1) and one or two active ingredients from Group (2) and / or optionally an active ingredient from Grappe (3).
  • Examples of combinations according to the invention each consisting of an active ingredient of the Grappe (1) and one or two active ingredients of the Grappe (2) and combinations of one active ingredient of the Grappe (1), one or two active ingredients of the group (2) and a compound of the Grappe ( 3) are listed in Table 2 below.
  • the names of the active compounds of the formula (I) active compounds of the Grappe (1) are in each case taken from Table 1.
  • Table 2 Examples of combinations consisting of an active ingredient from group (1) and one or two active ingredients from Grappe (2) and, where appropriate, an active ingredient from Grappe (3).
  • the herbicidal activity of the active compound combinations according to the invention composed of compounds from groups (1) and (2) listed above is significantly higher than the sum of the effects of the individual active compounds.
  • the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be relative
  • Active ingredient of formula (I) 0.001 to 1000 parts by weight, preferably 0.002 to 500
  • the compounds of group (3) listed above are particularly suitable, the damaging effect of active substances of the formula (I) and its salts, optionally also in combination with one or more of the active ingredients of the grappa (2) mentioned above, on the crop plants almost completely to keep constantly without affecting the herbicidal activity against the weeds.
  • a preferred embodiment is therefore also a mixture comprising a compound of the formula (I) and / or its salts on the one hand and 2,4-D and / or its derivatives on the other hand, optionally in combination with one or more of the active ingredients of group (2 ).
  • Typical derivatives of 2,4-D are e.g. their esters.
  • 3,5-dicarboxylates (mefenpyr-diethyl), (l-methyl-hexyl) - [(5-chloro-8-quinolinyl) oxy] - acetate (cloquintocet-mexyl) and ethyl-l- (2,4-dichlorophenyl) -5- (trichloromethyl) - 1H-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.
  • the advantageous effect of the crop plant tolerance of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active ingredient of the formula (I) or thereof Mixtures with active substances of Grappe (2) 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the compounds (antidots / safeners) which improve crop plant tolerance and are mentioned above (c).
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhiozomes.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • plants and their parts can be treated according to the invention.
  • transgenes are treated.
  • Plants and plant varieties that have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts treated.
  • the term “parts” or “parts of plants” or “plant parts” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects. For example, reduced application rates and / or extensions of the
  • Nutritional value of the harvested products higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetic engineering)
  • plants or plant varieties belong to all plants that received genetic material through genetic modification, which this
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the properties are particularly emphasized of the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes coding for Cry ⁇ A (a), Cry ⁇ A (b ), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • Traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT” gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Brady plants are maize, cotton, soybean and
  • Potato varieties called, which under the trade names YIELD GARD® (e.g., Potato varieties called, which under the trade names YIELD GARD® (e.g., Potato varieties called, which under the trade names YIELD GARD® (e.g., Potato varieties called, which under the trade names YIELD GARD® (e.g., Potato varieties called, which under the trade names YIELD GARD® (e.g., Potato varieties called, which under the trade names YIELD GARD® (e.g.
  • Soybean varieties named under the trade names Roundup Ready® tolerance to glyphosate e.g. corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, e.g. rapeseed
  • IMI® tolerance to imidazolinones
  • STS® tolerance to sulfonylureas e.g. corn ) to be expelled.
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their environment, habitat or location 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 multi-layer coating.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Oryza Panicum, Saccharam, Seeale, Sorghum, Triticale, Triticum, Zea.
  • the active ingredient combinations to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (e.g. wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and with minimum tillage
  • Procedures are used. They are also suitable as burners (killing herbs, for example in potatoes) or as defoliants (for example in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and femst encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
  • Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, 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 stalks;
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lign
  • 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. Further,
  • Additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible. Also a mixture with other known active ingredients, such as fungicides, insecticides,
  • Acaricides, nematicides, bird repellants, growth agents, plant nutrients and soil structure improvers are possible.
  • mineral-based or vegetable-compatible oils for example the commercial preparation "Rako Binol”
  • ammonium salts such as ammonium sulfate or ammonium rhodanide in the formulations as further additives.
  • the new active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring,
  • Spraying, spraying, dusting or sprinkling Spraying, spraying, dusting or sprinkling.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, ie in the pre-emergence and post-emergence processes. They can also be worked into the soil before sowing.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • X % damage by herbicide A (active ingredient of the formula I) at a rate of p kg / ha and
  • Y % damage by herbicide B (active ingredient of the formula II) at q kg / ha application rate
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Test plants are grown under controlled conditions (temperature and light). As soon as the plants have reached a height of 5 to 15 cm, the test substance or the combination of the test substances is sprayed on in such a way that the desired amounts of active compound are applied per unit area.
  • concentration of the spray liquid is chosen so that in 500 liters
  • the planters After spraying, the planters are placed in the greenhouse under constant light and temperature conditions.
  • HORVW Hordeum vulgare (winter barley).
  • TRZAW Triticum aestivum (winter wheat).

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Abstract

The invention relates to novel herbicidal active substance combinations containing known substituted carboxylic acid anilides of formula (I), in which n, A, Ar, R?1, R2, R3¿ and Z have the meanings as cited in the description, one or more known herbicidally active compound(s) and/or optionally containing a compound that improves cultivated plant compatibility. The invention also relates to the use of these active substance combinations for controlling weeds in different useful plant crops and for controlling monocotyl and dicotyl weeds in the semi-selective and non-selective area.

Description

Herbizide auf Basis von substituierten CarbonsäureanilidenHerbicides based on substituted carboxylic acid anilides
Die Erfindung betrifft neue herbizide Wirkstoffkombinationen, die bekannte substituierte Carbonsäureanilide einerseits und eine oder mehrere bekannte herbizid wirk- same Nerbindung(en) andererseits und/oder gegebenenfalls eine die Kulturpflanzen-The invention relates to new herbicidal combinations of active substances, the known substituted carboxylic acid anilides on the one hand and one or more known herbicidally active compound (s) on the other hand and / or optionally a crop plant
Nerträglichkeit verbessernde Verbindung enthalten und deren Verwendung zur Unkrautbekämpfung in verschiedenen Νutzpflanze kulturen sowie zur Bekämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich.Contain intolerance-improving compound and their use for weed control in various crops and for combating monocotyledonous and dicotyledonous weeds in the semi and non-selective range.
Substituierte Carbonsäureanilide sind als wirksame Herbizide bekannt (WO-A-Substituted carboxylic acid anilides are known to be effective herbicides (WO-A-
98/32746, WO-A-00/02867, WO-A-00/75119). Die Wirkung dieser Verbindungen ist bei alleiniger Anwendung dieser Verbindungen jedoch nicht unter allen Bedingungen ganz zufriedenstellend. So können sich gegenüber bestimmten Unkräutern Schwächen bei der Wirkung ergeben, weshalb es wünschenswert ist, solche Wirkungslücken durch die Verwendung eines oder mehrerer geeigneter Wirkstoffe zusammen mit den genannten Verbindungen zu schließen. Ebenso kann durch die Wahl eines geeigneten Mischpartners die herbizide Wirkung auf Grund eines Synergismus deutlich verbessert werden.98/32746, WO-A-00/02867, WO-A-00/75119). However, the action of these compounds is not entirely satisfactory under all conditions when these compounds are used alone. In this way, weaknesses in the action can arise compared to certain weeds, which is why it is desirable to close such gaps in activity by using one or more suitable active ingredients together with the compounds mentioned. Likewise, the choice of a suitable mixing partner can significantly improve the herbicidal action due to a synergism.
Übeπaschenderweise wurde nun gefunden, dass bestimmte Wirkstoffe aus der ReiheSurprisingly, it has now been found that certain active ingredients from the series
,der substituierten Carbonsäureanilide bei gemeinsamer Anwendung mit bestimmten herbizid wirksamen Verbindungen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und besonders vorteilhaft als wirksame Kombinationspräparate zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in Νutz- pflanzenkulturen, wie z.B. in Baumwolle, Gerste, Kartoffeln, Mais, Raps, Reis,, the substituted carboxylic acid anilides when used together with certain herbicidally active compounds show synergistic effects with regard to the action against weeds and are particularly advantageous as effective combination preparations for the selective control of monocotyledonous and dicotyledonous weeds in crop plants, such as e.g. in cotton, barley, potatoes, corn, rapeseed, rice,
Roggen, Soja, Sonnenblumen, Weizen, Zuckeπohr und Zuckerrüben, aber auch zur Bekämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich verwendet werden können.Rye, soybeans, sunflowers, wheat, sugar cane and sugar beet, but also for controlling monocotyledon and dicotyledon weeds in the semi and non-selective range can be used.
Gegenstand der Erfindung sind daher herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus (a) zumindest einem substituierten Carbonsäureanilid der allgemeinen Formel (I)The invention therefore relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of (a) at least one substituted carboxylic acid anilide of the general formula (I)
in welcher in which
n für die Zahlen 0 oder 1 steht,n represents the numbers 0 or 1,
für Alkandiyl (Alkylen) oder Alkendiyl mit jeweils bis zu 6 Kohlenstoffatomen steht,represents alkanediyl (alkylene) or alkenediyl each having up to 6 carbon atoms,
Ar für gegebenenfalls substituiertes Aryl mit 6 oder 10 Kohlenstoffatomen oder für gegebenenfalls substituiertes Heterocyclyl mit bis zu 9 Kohlenstoffatomen und 1 bis 4 Stickstoffatomen und/oder gegebenenfalls 1 oder 2 Sauerstoffoder Schwefelatomen steht,Ar represents optionally substituted aryl with 6 or 10 carbon atoms or for optionally substituted heterocyclyl with up to 9 carbon atoms and 1 to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms,
wobei die jeweils möglichen Substituenten aus folgender Aufzählung zu entnehmen sind:where the possible substituents can be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, C1-C4-Alkyl, CrC -Halogenalkyl, C1-C -Alkoxy, Cι-C4-Halogenalkoxy, Cι-C4-Alkylthio, Cι-C4-Halogenalkylthio, C1-C4-Alkylsulfmyl, CrC4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, Cι-C4-Halogenalkylsulfonyl, CrC -Alkylamino, Di- (Cι-C4-alkyl)-amino, Cι.-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, Ci-C4- Alkylaminocarbonyl, Di-(CrC4-alkyl)-aminocarbonyl, Di-(C1-C -alkyl)~ aminosulfonyl, R1 für gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen,Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 -alkyl, CrC -haloalkyl, C 1 -C -alkoxy, Cι-C 4 -haloalkoxy, Cι-C 4 -alkylthio, Cι-C 4 - haloalkylthio, C 1 -C 4 -Alkylsulfmyl, -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, Cι-C4-haloalkylsulfonyl, CrC alkylamino, di- (Cι-C4 alkyl) amino, Cι. -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, Ci-C 4 -alkylaminocarbonyl, di- (CrC 4 -alkyl) -aminocarbonyl, di- (C 1 -C -alkyl) ~ aminosulfonyl, R 1 is alkyl which is optionally substituted by halogen and has 1 to 6 carbon atoms,
für gegebenenfalls durch Halogen substituiertes Alkenyl mit 2 bis 6 Kohlen- Stoffatomen,for alkenyl with 2 to 6 carbon atoms optionally substituted by halogen,
für gegebenenfalls durch Halogen oder C1-C4-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,for cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by halogen or C 1 -C 4 alkyl,
für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, Cι-C4-Alkyl oderfor each optionally by nitro, cyano, halogen, -CC 4 alkyl or
CrC4- Alkoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgrappe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oderCrC 4 - alkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or
für gegebenenfalls durch Nitro, Cyano, Halogen, - - Alkyl oder C1-C4-for optionally by nitro, cyano, halogen, - - alkyl or C 1 -C 4 -
Alkoxy substituiertes Heterocyclyl mit 5 Kohlenstoffatomen und 1 bis 4 Stickstoffatomen und/oder 1 oder 2 Sauerstoff- oder Schwefelatomen steht,Alkoxy-substituted heterocyclyl with 5 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,
R2 für Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenen- falls durch Halogen substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 4R 2 for cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl or alkoxy each optionally substituted by halogen, each with 1 to 4
Kohlenstoffatomen steht,Carbon atoms,
R3 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl oder Halogen steht, undR 3 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, and
Z für eine der nachstehend skizzierten Gruppierungen steht, Z represents one of the groupings outlined below,
(z1) (Z2) (ϊ) worin(z 1 ) (Z 2 ) (ϊ) where
R4 für Wasserstoff, Amino oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 4 represents hydrogen, amino or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R5 für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Halogen substituiertes Alkyl oder Alkoxycarbonyl mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht,R 5 represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by halogen substituted alkyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the alkyl groups,
R6 für Wasserstoff, Halogen oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 6 represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R7 für Wasserstoff, Cyano, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder -C4- Alkoxy substituiertes Alkyl, Alkoxy, Alkyl- thio, Alkylamino oder Dialkylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht, undR 7 represents hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by cyano, halogen or -C 4 -alkoxy, each having 1 to 4 carbon atoms in the alkyl groups, and
R8 für Wasserstoff oder für jeweils gegebenenfalls durch Cyano, Halogen oder - -Alkoxy substituiertes Alkyl, Alkoxy, Alkylamino, Alkyl- carbonyl oder Alkoxycarbonyl mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht,R 8 represents hydrogen or alkyl, alkoxy, alkylamino, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or - -alkoxy, each having 1 to 4 carbon atoms in the alkyl groups,
R9 für Wasserstoff, Cyano, Halogen oder eine der Gruppierungen -Rπ, -O-R11, S-R11, SO-R11 oder SO2-R11 steht, R1 für Wasserstoff, Hydroxy, Amino, oder eine der Gruppierungen -R11 oder -O-R11 steht, undR 9 represents hydrogen, cyano, halogen or one of the groupings -R π , -OR 11 , SR 11 , SO-R 11 or SO 2 -R 11 , R 1 represents hydrogen, hydroxy, amino, or one of the groupings -R 11 or -OR 11 , and
R11 für gegebenenfalls durch Cyano, Halogen oder C C4- Alkoxy substitu- iertes Alkyl mit 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen, für gegebenenfalls durch Cyano, Halogen oder CrC4-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, -C4- Alkyl,R 11 for alkyl optionally substituted by cyano, halogen or CC 4 - alkoxy having 1 to 6 carbon atoms, for each optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for optionally substituted by cyano, halogen or CrC 4 alkyl substituted cycloalkyl having 3 to 6 carbon atoms, or for each optionally by nitro, cyano, halogen, -C 4 - alkyl,
CrC4-Halogenalkyl, -C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl oder Benzyl steht,-C 4 haloalkyl, -C 4 alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl or benzyl,
(„Wirkstoffe der Gruppe (1)")("Active substances of group (1)")
undand
(b) einer oder mehrerer Verbindung(en) aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(b) one or more compound (s) from a second group of herbicides which contains the active compounds mentioned below:
4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-l- H-l,2,4-triazol-l-carboxamid-Natriumsalz (Flucarbazone-sodium), 2-Chlor-N- (ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4- trifluoπnethyl-phenoxy)-2-nitro-benzoesäure (-Natriumsalz) (Acifluorfen (-sodium)), 2-Chlor-6-nitro-3-phenoxy-benzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -l- Hl, 2,4-triazole-l-carboxamide sodium salt (flucarbazone- sodium), 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)-acetamid (Alachlor), Methyl-4-hydroxy-6,6-dimethyl-2-oxo-3- [ 1 - [(2-prop enyloxy)-imino] -butyl] -3 -cyclohexen- 1 -carboxylat (-Natriumsalz) (All- oxydim (-sodium)), N-Ethyl-N'-i-propyl-6-methylthio-l,3,5-triazin-2,4-diamin (Ametryn), 4-Amino-N-(l , 1 -Dimethyl-ethyl)-4,5-dihydro-3-(l -methyl-ethyl)-5-oxo- lH-l,2,4-triazol-l-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-(2,6-diethyl-phenyl) -acetamide (alachlor), methyl-4-hydroxy-6,6-dimethyl-2-oxo-3- [1 - [(2-prop enyloxy) imino] butyl] - 3 -cyclohexen-1-carboxylate (sodium salt) (all-oxydim (-sodium)), N-ethyl-N'-i-propyl-6-methylthio-l, 3,5-triazine-2,4-diamine ( Ametryn), 4-amino-N- (l, 1-dimethyl-ethyl) -4,5-dihydro-3- (l-methyl-ethyl) -5-oxo-lH-l, 2,4-triazole-l -carboxamide (amicarbazone), N- (4,6-dimethoxy-pyrimidin-2-yl) -
N' -(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), 1H- 1 ,2,4- Triazol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(l-isopropyl)-amino]-2-oxo- ethyl]-0,0-dimethyl-phosphorodithioate (Anilofos), N-(4-Amino-phenyl-sulfonyl)- carbamidsäure-O-methylester (Asulam), 6-Chlor-4-ethylamino-2-isopropylamino- 1,3,5-triazin (Atrazine), 2-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]-5,6,7,8-tetra- hydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-on (Azafenidin), N-(4,6-Dimethoxy-pyri- midin-2-yl)-N'-[l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulfonyl]- harnsto ff (Azimsulfuron), N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4-Chlor-2-oxo-3(2H)-benzthiazolessigsäure (-ethylester) (Benazolin, (-ethyl)), N-Butyl-N-ethyl-2,6-dinitro-4-trifluormethyl-benzenamin (Benfluralin), 2,3-Dihydro-3,3-dimethyl-5-benzofuranyl-ethansulfonat (Benfuresate), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenylmethylsulfonyl)-hamstoff (Bensulfuron-methyl), 3-i-Propyl-lH-2,l,3-benzothiadiazin-4(3H)-on-2,2-dioxid (Bentazone), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thio- bencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyri- midinylphenoxymethyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone),N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H- 1, 2,4- Triazol-3-amine (amitroles), S- [2 - [(4-chlorophenyl) - (l-isopropyl) amino] -2-oxoethyl] -0,0-dimethyl-phosphorodithioate (anilofos), N- (4-aminophenylsulfonyl) carbamic acid O-methyl ester (Asulam), 6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine (Atrazine), 2- [2.4 -Dichlor-5- (2-propynyloxy) phenyl] -5,6,7,8-tetra-hydro-l, 2,4-triazolo- [4,3-a] pyridin-3 (2H) -one (Azafenidin), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- [l-methyl-4- (2-methyl-2H-tetrazol-5-yl) -lH-pyrazole- 5-ylsulfonyl] urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (- ethyl ester) (benazoline, (-ethyl)), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzamine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranyl- ethanesulfonate (benfuresate), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylmethylsulfonyl) urea (bensulfuron-methyl), 3-i-propyl-1H-2 , l, 3-benzothiadiazin-4 (3H) -one-2,2-dioxide (Bentazone), S - [(4-chlorophenyl) - methyl] diethylthiocarbamate (benthiocarb, thiobarbcarb), 2- [2- [4- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) pyridiminylphenoxymethyl] -5-ethyl-phenoxy-propanoic acid methyl ester (benzfendizone),
3 -(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1] -oct-3-en-2-on (Benzobicyclon), 2-[[4-(2,4-Dichlor-3-methyl-benzoyl)-l,3-dimethyl-lH-pyrazol-5- yl]-oxy]-l-(4-methyl-phenyl)-ethanon (Benzofenap), Methyl-5-(2,4-dichlor-phen- oxy)-2-nitro-benzoat (Bifenox), 2,6-Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoe- säure-Natriumsalz (Bispyribac-sodium), 5-Brom-6-methyl-3-(l-methyl-propyl)-2,4-3 - (2-chloro-4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2.1] -oct-3-en-2-one (benzobicyclone), 2 - [[4- (2,4- Dichloro-3-methyl-benzoyl) -l, 3-dimethyl-lH-pyrazol-5-yl] -oxy] -l- (4-methyl-phenyl) -ethanone (benzofenap), 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-
,( 1 H,3H)pyrimidindion (Bromacil), 2-Brom-3 ,3-dimethyl-N-( 1 -methyl- 1 -phenyl- ethyl)-butanamid (Bromobutide), 3 ,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-di- nitro-phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Brom- oxynil), N-Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2- Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)-ben- zoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)] -ethylester (Butafenacil), 4-( 1 -t-, (1 H, 3H) pyrimidinedione (bromacil), 2-bromo-3, 3-dimethyl-N- (1-methyl-1-phenyl-ethyl) -butanamide (bromobutide), 3, 5-dibromo-4-hydroxy -benzaldehyde-O- (2,4-di-nitro-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-l (2H) -pyrimidinyl) -ben - zoic acid [1, 1-dimethyl-2-oxo-2- (2-propenyloxy)] ethyl ester (butafenacil), 4- (1-t-
Butyl)-N-(s-butyl)-2,6-dinitro-anilin (Butralin) 2-(l -Ethoximino-propyl)-3-hydroxy-Butyl) -N- (s-butyl) -2,6-dinitro-aniline (butraline) 2- (l -ethoximino-propyl) -3-hydroxy-
5 - [2,4, 6-trimethyl-3 -(1 -oxo-butyl)-phenyl]-2-cy clohexen- 1 -on (Butroxydim) , S-5 - [2,4,6-trimethyl-3 - (1-oxo-butyl) phenyl] -2-cy clohexen- 1 -one (butroxydim), S-
' Ethyl-bis-(2-methyl-propyl)-thiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-tri- methyl-phenylsulfonyl)-lH-l,2,4-triazol-l-carboxamid (Cafenstrole), (R)-N-Ethyl-2- ' Ethyl-bis- (2-methyl-propyl) -thiocarbamate (butylate), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) -lH-l, 2,4-triazole- l-carboxamide (cafenstrole), (R) -N-ethyl-2-
[(phenylaminocarbonyl)-oxy]-propanamid (Carbetamide), 2-(4-Chlor-2-fluor-5-(2- chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- 1 ,2,4-triazol-3 -on (Carfentrazone-ethyl), 2,4-Dichlor- 1 -(3 -methoxy-4-nitro-phen- oxy)-benzol (Chlomethoxyfen), 5-Amino-4-chlor-2-phenyl-3(2H)-pyriazinon (Chlor- idazon), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl-phenyl- sulfonyl)-harnstoff (Chlorimuron-ethyl), l,3,5-Trichlor-2-(4-nitro-phenoxy)-benzol[(phenylaminocarbonyl) -oxy] propanamide (carbetamide), 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 - 1 - (3-methoxy-4-nitro-phenoxy) benzene (chloromethoxyfen), 5-amino-4-chloro-2-phenyl-3 (2H) -pyriazinone (chloridazazone), N- (4th -Chlor-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) urea (chlorimuron-ethyl), 1,3,5-trichloro-2- (4-nitro-phenoxy )-benzene
(Chlomitrofen), N' -(3 -Chlor-4-methyl-phenyl)-N,N-dimethyl-hamstoff (Chlorotol- uron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-ham- stoff (Chlorsulfuron), 2-Chlor-3-[2-chlor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-iso- indol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl), Exo-l-methyl-4-iso- propyl-2-(2-methyl-phenyl-methoxy)-7-oxabicyclo-[2.2.1]-heptan (Cinmethylin), N-(Chloromitrofen), N '- (3-chloro-4-methylphenyl) -N, N-dimethyl-urea (chlorotol-uron), N- (4-methoxy-6-methyl-l, 3,5-triazine -2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), 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), exo-l-methyl-4-iso-propyl-2- (2- methyl-phenyl-methoxy) -7-oxabicyclo- [2.2.1] -heptane (cinmethylin), N-
(4,6-Dimethoxy-l,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenylsulfonyl)-ham- stoff (Cinosulfuron), 2-[l-[2-(4-Chlor-phenoxy)-propoxyaminobutyl]-5-(tetrahydro- 2H-thiopyran-3-yl)-l ,3-cyclohexandion (Clefoxydim), (E,E)-(+)-2-[l-[[(3-Chlor-2- propenyl)-oxy]-imino]-propyl]-3-hydroxy-2-cyclohexen-l-on (Clethodim), (R)-(2- Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop- propargyl), 2-[(2-Chlor-phenyl)-methyl]-4,4,-dimethyl-3-isoxazolidinone (Clom- azone), 2-(2,4-Dichlor-3-methyl-phenoxy)-N-phenyl-propanamid (Clomeprop), 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), N-[(2-Chlor-phenyl)-methyl]-N'-(l-methyl-l-phenyl-ethyl)-hamstoff (Cumyluron),(4,6-Dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2-methoxyethoxy) phenylsulfonyl) urea (cinosulfuron), 2- [l- [ 2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [l - [[(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), 2 - [(2-chlorophenyl) methyl] -4,4, -dimethyl- 3-isoxazolidinone (Clomazone), 2- (2,4-dichloro-3-methylphenoxy) -N-phenylpropanamide (Clomeprop), 3,6-dichloropyridine-2-carboxylic acid (Clopyralid), methyl -3-chloro-2 - [(5-ethoxy-7-fluoro [l, 2,4] triazolo [l, 5-c] pyrimidin-2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl) , N - [(2-chlorophenyl) methyl] -N '- (l-methyl-l-phenyl-ethyl) urea (cumyluron),
,2-Chlor-4-ethylamino-6-(l -cyano- 1 -methyl-ethylamino)- 1 ,3 ,5 -triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenylsulfonyl)-ham- stoff (Cyclosulfamuron), 2-(l-Ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thio- pyran-3-yl)-2-cyclohexen-l-on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)- phenoxyj-propansäure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure, 2-chloro-4-ethylamino-6- (l-cyano-1-methyl-ethylamino) - 1, 3, 5 -triazine (cyanazines), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 2- (l-ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexene I-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenyl-butanoate (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid
(2,4-D), N-[3-(Phenylaminocarbonyloxy)-phenyl]-carbamidsäure-O-ethylester (Des- medipham), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), 2,6-Dichlor-benzonitril (Dichlobenil), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2- [4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), N-(2,6-Dichlor- ρhenyl)-5-ethoxy-7-fluor-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Diclo- sulam), l,2-Dimethyl-3,5-diphenyl-lH-pyrazolium-methylsulfat (Difenzoquat), N- (2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflu- fenican), 2-[l-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3- carbonsäure (Diflufenzopyr), N'-[3-Chlor-4-(5-t-butyl-oxo-l,3,4-oxadiazol-3(2H)- yl)-phenyl]-N,N-dimethyl-harnstoff (Dimefuron), S-(l-Methyl-l-phenyl-ethyl)-l- piperidin-carbothioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-meth- oxy-ethyl)-acetamid (Dimethachlor), N-(l,2-Dimethyl-propyl)~N'-ethyl-6-methyl- thio-l,3,5-triazin-2,4-diamin (Dimethametryn), (S-) 2-Chlor-N-(2,4-dimethyl-3-thi- enyl)-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 -tri- " azin (Dimexyflam), 6,7-Dihydro-dipyrido[l,2-a:2', -c]pyrazindiium dibromide (Di- quat-dibromide), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethyl-pyridin- 3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor-phenyl)-N,N-dimethyl-hamstoff (Di- uron), N-(4-Methyl-phenyl)-N'-(l-methyl-l-phenyl-ethyl)-hamstoff (Dymron, Daim- uron), S-Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l,2-di- methyl-propyl)-thiocarbamat (Esprocarb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-di- nitro-4-trifluormethyl-benzenamin (Ethalfluralin), Methyl-2-[[[[(4-ethoxy-6-methyl- amino-l,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulfonyl]-benzoate (Ethametsulf- uron-methyl), 2-Ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-methansulfonat (Ethofumesate), (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-(2,4-D), N- [3- (phenylaminocarbonyloxy) phenyl] carbamic acid-O-ethyl ester (desmedipham), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 2,6- Dichlorobenzonitrile (dichlobenil), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] - propanoate (diclofop-methyl), N- (2,6-dichloro-ρhenyl) -5-ethoxy-7-fluoro [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (Diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquate), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (difluorican), 2- [l - [(3,5-difluorophenyl) aminocarbonyl -hydrazono] -ethyl] -pyridine-3-carboxylic acid (diflufenzopyr), N '- [3-chloro-4- (5-t-butyl-oxo-l, 3,4-oxadiazol-3 (2H) - yl) -phenyl] -N, N-dimethyl-urea (dimefuron), S- (l-methyl-l-phenyl-ethyl) -l-piperidine-carbothioate (dimepiperate), 2-chloro-N- (2,6-dimethyl -phenyl) -N- (2-meth-oxy-ethyl) -acetamide (dimethachlor), N- (1,2-dimethyl-propyl) ~ N'-ethyl-6-methyl-thio-l, 3,5- triazine-2,4-diamine (dimethametryn), (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-dimethyl-phenoxy) -ethylamino) - 1, 3,5-tri- " azine (dimexyflam), 6,7-dihydro-dipyrido [1,2-a: 2 ', -c] pyrazinediium dibromide (diquat-dibromide), S, S-dimethyl-2- difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl-urea (diuron), N - (4-methyl -phenyl) -N '- (l-methyl-l-phenyl-ethyl) urea (Dymron, Daimuron), S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- ( 1,2-dimethyl-propyl) -thiocarbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -2,6-di-nitro-4-trifluoromethyl-benzenamine (ethalfluralin), methyl -2 - [[[[(4-ethoxy-6-methylamino-l, 3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] benzoates (ethametsulfuron-methyl ), 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate (ethofumesate), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5 - (2-chloro-4-trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-
,ethoxy-phenoxysulfonyi)-harnstoff (Ethoxysulfuron), N-(2,3-Dichlor-phenyl)-4-eth- oxymethoxy-benzamid (Etobenzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl- oxy)-phenoxy]-ρropanoat (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)-D-alaninat (Flamprop-M-isopropyl), Methyl-N- benzoyl-N-(3-chlor-4-fluor-phenyl)-D-alaninat (Flamprop-M-methyl), N-[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-3-trifluormethyl-2-pyridinsulfonamid (Flazasulfuron), 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)- phenoxyj-propansäure-butylester (Fluazifop-P-butyl), 5-(4-Brom-l-methyl-5-tri- fluormethyl-lH-pyrazol-3-yl)-2-chlor-4-fluor-benzoesäure-i-propylester (Fluazolate), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-Oxy)-acet- amid (Flufenacet), Ethyl-[2-Chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluormethyl- 1 (6H)-pyridazinyl)-phenoxy]-acetate (Flufenpyr), N-(2,6-Difluor-phenyl)-5-methyl- 1 ,2,4-triazolo[l ,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-l,4-benzoxazin-6-yl]-, ethoxy-phenoxysulfonyi) urea (ethoxysulfuron), N- (2,3-dichlorophenyl) -4-eth-oxymethoxy-benzamide (etobenzanide), (R) -ethyl-2- [4- (6-chloro benzoxazol-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) -D-alaninate (Flamprop-M-isopropyl), methyl-N-benzoyl-N - (3-chloro-4-fluorophenyl) -D-alaninate (Flamprop-M-methyl), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- trifluoromethyl-2-pyridinesulfonamide (flazasulfuron), N- (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) - butylphenoxyj-propanoate (fluazifop-P-butyl), 5- (4-bromo-l -methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), ethyl- [2-chloro- 4-fluoro-5- (5-methyl-6-oxo-4-trifluoromethyl-1 (6H) -pyridazinyl) phenoxy] -acetate (flufenpyr), N- (2,6-difluorophenyl) -5-methyl - 1, 2,4-triazolo [l, 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-l, 4-benzoxazin-6-yl] -
4,5,6,7-tetrahydro-lH-isoindol-l,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(l- mefhyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-lH-isoindol-l,3(2H)-dion (Flumipropyn), N,N-Dimethyl-N'-(3-trifluormethyl-phenyl)-hamstoff (Fluomet- uron), 3-Chlor-4-chlormethyl-l-(3-trifluormethyl-phenyl)-2-pyπolidinon (Fluoro- chloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-ethoxy- carbonylmethylester (Fluoroglycofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3-pentafluor-prop- oxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazol-3-carboxamid (Flupoxam), 1-Iso- propyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyri- midyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxy- carbonyl-6-trifluoπnethyl-pyridin-2-yl-sulfonyl)-hamstoff-Natriumsalz (Flupyrsulf- uron-methyl-sodium), 9-Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino- 3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-l-methyl-ethylester, -1- methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl- 4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4-fluor-5-4,5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(l-methyl-2-propynyl) -oxy] - phenyl] -4,5,6,7-tetrahydro-lH-isoindole-1,3, (2H) -dione (flumipropyn), N, N-dimethyl-N '- (3-trifluoromethyl-phenyl) -urea (fluomet- uron), 3-chloro-4-chloromethyl-l- (3-trifluoromethyl-phenyl) -2-pyπolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid- ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1- (4-chloro-3- (2,2,3,3,3-pentafluoro-prop-oxymethyl) phenyl) -5-phenyl-1H-l, 2,4 -triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyri- midyl) benzoate (flupropacil), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxy-carbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (Flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-l-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxy propyl, -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-yliden)-amino- phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl-phenoxy)-N- methylsulfonyl-2-nitro-benzamid (Fomesafen), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)- ammo]-carbonyl]-amino]-sulfonyl]-4-formylamino-N,N-dimethyl-benzamid (Foram- sulfuron), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz), (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 (Fomesafen), 2 - [[[((4,6-Dimethoxy-2-pyrimidinyl) - ammo] carbonyl ] -amino] -sulfonyl] -4-formylamino-N, N-dimethyl-benzamide (foram-sulfuron), 2-amino-4- (hydroxymethylphosphinyl) -butanoic acid (-ammonium salt)
(Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmom'um- salz), (Glyphosate, -isopropylammonium), Methyl-3-chloro-5-[[[[(4,6-dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]- 1 -methyl- lH-pyrazol-4-carboxylate (Halosulfuron-methyl), (R)-2-[4-(3-Chlor-5-trifluormethyl-pyridin-2-yl-oxy)-phen- oxy]-propansäure (-methylester, -2-ethoxy-ethylester, -butylester) (Haloxyfop, - methyl, -P -methyl, -ethoxyethyl, -butyl), 3 -Cyclohexyl-6-dimethylamino-l -methyl- l,3,5-triazin-2,4(lH,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-iso- propyl-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-methoxymethyl-pyri- din-3 -carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH- imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazapic), 2-(4,5-Dihydro-4- methyl-4-(i-propyl)-5-oxo- lH-imidazol-2-yl)-3-pyridincarbonsäure (Imazapyr), 2- (4, 5 -Dihydro-4-methyl-4-isopropyl-5 -oxo- 1 H-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 (Imazo sulfuron), 2-[2-(3-(Glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmom ' salt), (glyphosate, -isopropylammonium), methyl-3-chloro-5 - [[[[(4,6-dimethoxy-2- pyrimidinyl) amino] carbonyl] amino] sulfonyl] -1-methyl-1H-pyrazole-4-carboxylate (halosulfuron-methyl), (R) -2- [4- (3-chloro-5-trifluoromethyl- pyridin-2-yl-oxy) -phen-oxy] -propanoic acid (-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, - methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl -6-dimethylamino-l -methyl- 1,3,5-triazine-2,4 (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazole -2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 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-1H-imidazol-2-yl) -5-methyl-pyridine-3- carboxylic acid (imazapic), 2- (4,5-dihydro-4-methyl-4- (i-propyl) -5-oxo-lH-imidazol-2-yl) -3-pyridinecarboxylic acid (imazapyr), 2- (4th , 5-Dihydro-4-methyl-4-isopropyl-5-oxo-1 H -imidazol-2-yl) -quinolin-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4 -i-propyl-5-oxo-1H-imidazol-2-yl) -5-ethyl-pyridin-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxypyrimidin-2-yl) -N'- (2-chloro-imidazo [l, 2-a] pyridin-3-yl-sulfonyl) urea (Imazo sulfuron), 2- [2- (3-
Chlor-phenyl)-oxiranylmethyl]-2-ethyl-lH-inden-l,3(2H)-dion (Indanofan), N-(4- Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsul- fonyl)-harnstoff-Natriumsalz (Iodosulfiiron-methyl-sodium), 4-Hydroxy-3,5-diiod- benzonitril (loxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-hamstoff (Isoproturon), N-(5-t-Butyl-3-isoxazolyl)-N',N'-dimethylhamstoff (Isouron), N-(3 -(1 -Ethyl- 1- methyl-propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2- methylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5- Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)-methanon (Isoxaflutole), 2- [(2,3 -Dihydro-5 , 8-dimethyl- 1 , 1 ,-dioxidospiro[4H- 1 -benzothio- pyran-4,2'-[l,3]-dioxolan-6-yl)-carbonyl]-l,3-cyclohexan-dion (Ketospiradox), (2-Chlorophenyl) oxiranylmethyl] -2-ethyl-lH-indene-1,3, (2H) -dione (indanofan), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl ) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfiiron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (loxynil), N, N-dimethyl -N '- (4-isopropylphenyl) urea (isoproturon), N- (5-t-butyl-3-isoxazolyl) -N', N'-dimethyl urea (isouron), N- (3 - (1 - Ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlortole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [(2,3-dihydro-5, 8-dimethyl - 1, 1, -dioxidospiro [4H- 1 -benzothio-pyran-4,2 '- [l, 3] -dioxolan-6-yl) -carbonyl] -l, 3-cyclohexanedione (ketospiradox), (2nd -
,Ethoxy-l-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoat, Ethoxy-l-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate
(Lactofen), 3-Cyclohexyl-6,7-dihydro-lH-cyclopentapyrimidin-2,4-(3H,5H)-dion(Lactofen), 3-cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4- (3H, 5H) -dione
(Lenacil), N'-(3,4-dichlor-phenyl)-N-methoxy-N-methyl-hamstoff (Linuron), (4-(Lenacil), N '- (3,4-dichlorophenyl) -N-methoxy-N-methyl-urea (Linuron), (4-
Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (R)-2-(4-Chlor-2-methyl-phenoxy)- propionsäure (Mecoprop-P), 2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamidChloro-2-methylphenoxy) acetic acid (MCPA), (R) -2- (4-chloro-2-methylphenoxy) propionic acid (Mecoprop-P), 2- (2-benzothiazolyloxy) -N-methyl -N-phenyl-acetamide
(Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulf- onyl] -4- [[(methylsulfonyl)-amino]methyl] -b enzoesäure-methylester (Mesosulfuron) , 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-(2,6-dimethyl- phenyl)-N-(lH-pyrazol-l-yl-methyl)-acetamid (Metazachlor), N-(2-Benzthiazolyl)-(Mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4- [[(methylsulfonyl) amino] methyl] -b methyl enzoate (mesosulfuron), 2- (4-methylsulfonyl-2-nitro-benzoyl) -1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-l, 2,4-triazine 5 (4H) -one (metamitron), 2-chloro-N- (2,6-dimethylphenyl) -N- (lH-pyrazol-l-yl-methyl) -acetamide (metazachlor), N- (2- benzothiazolyl) -
N,N'-dimethyl-hamstoff (Methabenzthiazuron), 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-hamstoff (Metoxuron), 4- Amino-6-tert-butyl-3-methylthio-l,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Meth- oxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-hamstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1-carbothioat (Molinate), 2-(2- Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N,N-Diethyl-2-(l -naphthalenyl- oxy)-propanamide (Napropamide), N-Butyl-N'-(3,4-dichlor-phenyl)-N-methyl-harn- stoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarbamoyl-pyri- din-2-yl-sulfonyι)-harnstoff (Nicosulfuron), 4-Chlor-5-methylanuno-2-(3-trifTuor- methyl-phenyl)-3(2H)pyridazinon (Norflurazon), S-(2-Chlor-benzyl)-N,N-diethyl- thiocarbamat (Orbencarb), 4-Dipropylamino-3,5-dinitro-benzensulfonamid (Oryz- alin), 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)-l,3,4-oxadi- azol-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-on (Oxaziclomefone), 2- Chlor-l-(3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl-benzeh (Oxyfluorfen), l,l '-Di- methyl-4,4'-bipyridinium (Paraquat), l-Amino-N-(l-ethyl-propyl)-3,4-dimethy 1-2,6- dinitro-benzol (Pendimethalin), 4-(t-Butyl)-N-(l-ethyl-propyl)-2,6-dinitro-benzen- amin (Pendralin), 2-(2,2-Difluorethoxy)-N-(5,8-dimethoxy[l,2,4]triazolo[l,5-c]pyri- midin-2-yl)-6-trifluormethyl-benzensulfonamid (Penoxsulam), 3-(4-Chlor-5-cyclo- pentyloxy-2-fluor-phenyl)-5-(l-methyl-ethyliden)-2,4-oxazolidin-dion (Pent- oxazone), 2-Chlor-N-(2-ethoxy-ethyl)-N-(2-methyl- 1 -phenyl- 1 -propenyl)-acetamidN, N'-dimethyl-urea (methabenzthiazuron), N '- (4-bromophenyl) -N-methoxy-N- methyl urea (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-l, 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-propanamide (naproanilide), N, N-diethyl-2- (l-naphthalenyl-oxy ) -propanamides (napropamides), N-butyl-N '- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridine-2-yl-sulfonyι) urea (nicosulfuron), 4-chloro-5-methylanuno-2- (3-trifluoromethyl-phenyl) -3 (2H) pyridazinone (Norflurazon), S- (2-chloro-benzyl) -N, N-diethyl-thiocarbamate (Orbencarb), 4-dipropylami no-3,5-dinitro-benzenesulfonamide (oryzaline), 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazole -2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5- (1-methylethoxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazole -2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin-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-1,3-oxazin-4-one (oxaziclomefone), 2- Chloro-l- (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), l, l '-dimethyl-4,4'-bipyridinium (paraquat), l-amino-N- (l-ethyl-propyl) -3,4-dimethyl 1-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (l-ethyl-propyl) -2,6-dinitro- benzene amine (pendralin), 2- (2,2-difluoroethoxy) -N- (5,8-dimethoxy [1,2,4] triazolo [1,5-c] pyrimidine-2-yl) -6 -trifluoromethyl-benzenesulfonamide (penoxsulam), 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5- (l-methylethylidene) -2,4-oxazolidinedione (pentoxazone) , 2-chloro-N- (2-ethoxy-ethyl) -N- (2-methyl-1-phenyl-1-p ropenyl) -acetamide
(Pethoxamid), N-[3-(3-Methyl-phenylaminocarbonyloxy)-phenyl]-carbamidsäure-O- methylester (Phenmedipham), 4-Amino-3,5,6-trichlor-pyridin-2-carbonsäure (Piclo- ram), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2-carboxamid (Pico- linafen), S-[2-(2-Methyl-l-piperidinyl)-2-oxo-ethyl]-O,O-dipropyl-phosphorodithioat (Piperophos), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamid (Pretila- chlor), N-(4,6-Bis-difluormethoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenyl- sιüfonyl)-hamstoff (Primisulfuron-methyl), 1 -Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)- 6-fluor-tetrahydro-l,3-dioxo-lH-pyπolo[l,2-c]imidazol-2(3H)-yl]-phenyl]-methan- sulfonamid (Profluazol), 2- [ 1 - [ [2-(4-Chlor-phenoxy)-propoxy] -imino] -buryl] -3 - hydroxy-5-(tetrahydro-2H-thiopyranyl)-2-cyclohexen-l-on (Profoxydim), N,N'-Bis- i-propyl-6-methylthio-l,3,5-triazin-2,4-diamin (Prometryn), 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)- phenoxyj-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-methyl- ester-Natriumsalz (Propoxycarbazone-sodium), 3,5-Dichlor-N-(l,l-dimethyl-2-prop- inyl)-benzamid (Propyzamide), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Pro- sulfocarb), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)- phenylsulfonyl)-hamstoff (Pro sulfuron) , 1 -(3 -Chlor-4, 5 ,6,7-tetrahydropyrazolo [1,5- a]pyridin-2-yl)-5-(methyl-2-propinylamino)-lH-pyrazol-4-carbonitril (Pyraclonil),(Pethoxamide), N- [3- (3-methylphenylaminocarbonyloxy) phenyl] carbamic acid O-methyl ester (phenmedipham), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (Picloram ), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) pyridine-2-carboxamide (picoline), S- [2- (2-methyl-l-piperidinyl) -2- oxo-ethyl] -O, O-dipropyl phosphorodithioate (Piperophos), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (Pretila-chlorine), N - (4,6-bis-difluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenyl sιüfonyl) urea (Primisulfuron-methyl), 1-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) - 6-fluoro-tetrahydro-l, 3-dioxo-lH-pyπolo [ 1,2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2- [1 - [[2- (4-chlorophenoxy) propoxy] imino] buryl ] -3 - hydroxy-5- (tetrahydro-2H-thiopyranyl) -2-cyclohexen-l-one (profoxydim), N, N'-bis-i-propyl-6-methylthio-l, 3,5-triazine 2,4-diamine (Prometryn), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N- (3,4-dichlorophenyl) propanamide (Propanil), (R) - [2- [[(1-methylethylidene) amino] oxy] ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxyj-propanoate (propaquizafop), 2-chloro-N- (2- ethyl-6-methyl-phenyl) -N - [(1-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] benzoic acid methyl ester sodium salt (propoxycarbazone sodium), 3,5-dichloro-N- (l, l-dimethyl-2-propynyl) benzamide (propyzamide), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-metho xy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (Pro sulfuron), 1 - (3rd -Chlor-4, 5, 6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -lH-pyrazole-4-carbonitrile (pyraclonil),
Ethyl-[2-chlor-5-(4-chlor-5-difluormethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluor- phenoxyj-acetat (Pyraflufen-ethyl), 4-(2,4-Dichlor-benzoyl)- 1 ,3-dimethyl-5-(4- methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(4-ethoxycarbonyl-l-methyl-pyrazol-5-yl-sulfonyl)-hamstoff (Pyrazosulfuron- ethyl), 4-(2,4-Dichlor-benzoyl)-l ,3-dimethyl-5-(phenylcarbonyhnethoxy)-pyrazolEthyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxyj-acetate (pyraflufen-ethyl), 4- (2.4 -Dichlorobenzoyl) - 1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), N- (4,6-dimethoxypyrimidin-2-yl) - N '- (4-ethoxycarbonyl -l-methyl-pyrazol-5-yl-sulfonyl) -urea (pyrazosulfuron-ethyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-5- (phenylcarbonyethylene methoxy) pyrazole
„(Pyrazoxyfen), Diphenylmethanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)- benzoyl]-oxim (Pyriberrzoxim), O[3-(l,l-Dimethyl-ethyl)-phenyl]-(6-methoxy-2- pyridinyl)-methylthiocarbamat (Pyributicarb), 6-Chlor-3-phenyl-4-pyridazinol"(Pyrazoxyfen), diphenylmethanone-O- [2,6-bis- (4,6-dimethoxypyrimidin-2-yl-oxy) benzoyl] oxime (pyriberrzoxime), O [3- (l, l-dimethyl -ethyl) phenyl] - (6-methoxy-2-pyridinyl) methylthiocarbamate (pyributicarb), 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]-(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-Natriumsarz (Pyrithiobac-sodium), 3 ,7-Dichlor- chinolin-8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbonsäure (Quinmerac), 2-Amino-3-chlor-l,4-naphthalindion (Quinoclamine), (R)-2-[4-(6-3-methyl-l (3H) -isobenzofuranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4, Sodium 6-dimethoxy-pyrimidin-2-ylthio) benzoic acid (Pyrithiobac-sodium), 3, 7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac ), 2-amino-3-chloro-l, 4-naphthalenedione (quinoclamine), (R) -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-Ethox- iminobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen- 1 -on (Sethoxydim), 6- Chlor-2,4-bis-ethylamino- 1 ,3 ,5-triazin (Simazine), 2-(2-Chlor-4-methylsulfonyl- benzoyl)-cyclohexan-l,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylaminp- phenyl)-4-difluoπnethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-on (Sulfentra- zone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulf- onylj-benzoate (Sulfometuron-methyl), N-Phosphonomethyl-glycin-trimethyl- sulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imid- azo[l,2-a]pyridin-3-sulfonamid (Sulfosulfuron), N-(5-t-Butyl-l,3,4-thiadiazol-2-yl)-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-1, 3,5-triazine (Simazine), 2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione (Sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamine p - phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (sulfentrazone), methyl 2 - [[[(4,6-dimethyl -2-pyrimidinyl) amino] carbonyl] amino] sulfonylj-benzoate (sulfometuron methyl), N-phosphonomethylglycine trimethyl sulfonium (sulfosate), N- (4,6-dimethoxy pyrimidine) 2-yl) -N '- (2-ethylsulfonyl-imide-azo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), N- (5-t-butyl-l, 3,4-thiadiazol-2 yl) -
N,N'-dimethyl-hamstoff (Tebuthiuron), 2-[l-[(3-Chlor-2-propenyl)-oxy-imino]- propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen- 1 -on (Tepraloxydim), 6-Chlor-4-ethylamino-2-t-butylamino-l ,3,5-triazin (Terbuthylazine), 2-t-Butyl- amino-4-ethylamino-6-methylthio-l,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6-di- methyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluor- methyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluormethyl-pyridin-3- carbonsäure-methylester (Thiazopyr), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)- N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-hamstoff (Thifensulfuron-methyl), S- Phenylmethyl-bis-s-butyl-carbamothioate (Tiocarbazil), 2-(Ethoximino-propyl)-3 - hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-l-on (Tralkoxydim), S-(2,3,3-Tri-N, N'-dimethyl-urea (tebuthiuron), 2- [l - [(3-chloro-2-propenyl) -oxy-imino] - propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4 -yl) -2-cyclohexen- 1 -one (tepraloxydim), 6-chloro-4-ethylamino-2-t-butylamino-l, 3,5-triazine (terbuthylazine), 2-t-butylamino-4- ethylamino-6-methylthio-l, 3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethylphenyl) -N- (3-methoxy-2-thienylmethyl) acetamide (Thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr) , N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) - N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), p - Phenylmethyl-bis-s-butyl-carbamothioate (Tiocarbazil), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-l-one (tralkoxydim) , S- (2,3,3-tri-
,chlor-2-propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl- l,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-hamstoff (Triasulfuron),, chloro-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-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- phenylsulfonyl)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)-pyridin-2-yl-oxy- essigsaure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2-trichlor-ethyl)-oxiran (Tridi- phane), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-etho- xy)-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 (Triflu- sulfuron-methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-(2-trifluor- methyl-phenylsulfonyl)-hamstoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2-pyrimi- dinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino])-2-pyridinsulfon- amid, (vgl. WO-A-92/10660), 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-(ethylsulf- onylamino)-5-fluor-benzolcarbothioamid (HWH4991, vgl. WO-A-95/30661), 2-N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), (3.5 , 6-trichloro-pyridin-2-yl-oxyacetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloro-ethyl) -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) -l, 3.5 -triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Triflu-sulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl ) -N '- (2-trifluoromethylphenylsulfonyl) urea (tritosulfuron), N - [[(4,6-dimethoxy-2-pyrimi- dinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino]) - 2-pyridinesulfonamide, (see WO-A-92/10660), 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- (ethylsulfonylamino) -5-fluoro-benzenecarbothioamide (HWH4991, see WO- A-95/30661), 2-
Chlor-N-[l-(2,6-dichlor-4-difluormethyl-phenyl)-4-nitro-lH-pyrazol-5-yl]-propan- carbonsäureamid (SLA5599, vgl. EP-A-303153), [2-Chlor-3-(4,5-dihydro-3-isox- azolyl)-4-methylsulfonyl-phenyl]-(5-hydrox-l-methyl-lH-pyrazol-4-yl)-methanon (vgl.WO-A-96/26206, WO-A-98/31681), [3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4- methylsulfonyl-phenyl]-(5-hydrox- 1 -methyl- l-H-pyrazol-4-yl)-methanon (vgl. WO-Chloro-N- [l- (2,6-dichloro-4-difluoromethylphenyl) -4-nitro-lH-pyrazol-5-yl] propane carboxamide (SLA5599, see EP-A-303153), [ 2-chloro-3- (4,5-dihydro-3-isoxazolyl) -4-methylsulfonylphenyl] - (5-hydrox-l-methyl-1H-pyrazol-4-yl) -methanone (see WO -A-96/26206, WO-A-98/31681), [3- (4,5-dihydro-3-isoxazolyl) -2-methyl-4-methylsulfonylphenyl] - (5-hydrox-1-methyl - lH-pyrazol-4-yl) methanone (see WO-
A-96/26206, WO-A-98/31681), [3-[2-Chlor-3 [(2,6-dioxo-cyclohexyl)-carbonyl]-6- ethylsulfonyl-phenyl]-5-isoxazolyl]-acetonitril (vgl. WO-A-01/28341), 2-[2-Chlor-4- methylsulfonyl-3-[(2,2,2-trifluor-ethoxy)-methyl]-benzoyl]-l,3-cyclohexandion (vgl. WO-A-01 /28341 ), 2-[[5 ,8-Dimethyl- 1 , 1 -dioxido-4-(2-pyrimidinyloxy)-3 ,4-dihydro- 2H-thiochromen-6-yl]-carbonyl]-l,3-cyclohexandion (vgl. WO-A-01/28341)A-96/26206, WO-A-98/31681), [3- [2-chloro-3 [(2,6-dioxo-cyclohexyl) carbonyl] -6-ethylsulfonylphenyl] -5-isoxazolyl] - acetonitrile (see WO-A-01/28341), 2- [2-chloro-4-methylsulfonyl-3 - [(2,2,2-trifluoroethoxy) methyl] benzoyl] -1, 3-cyclohexanedione (see WO-A-01/28341), 2 - [[5, 8-dimethyl-1, 1 -dioxido-4- (2-pyrimidinyloxy) -3, 4-dihydro-2H-thiochromen-6-yl] -carbonyl] -l, 3-cyclohexanedione (see WO-A-01/28341)
("Wirkstoffe der Gruppe (2)"),("Active substances of group (2)"),
und/oderand or
,(c) gegebenenfalls einer die Kulturpflanzen-Verträglichkeit verbessernden Verbindung aus der folgenden Gruppe von Verbindungen:, (c) if appropriate, a compound which improves crop plant tolerance from the following group of compounds:
4-Dichloracetyl- 1 -oxa-4-aza-spiro [4.5] -decan (AD-67), 1 -Dichloracetyl-hexahydro- 3,3,8a-trimethylpyπolo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), 4-Dichloracetyl-4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyπolo [1,2-a] -pyrimidine-6 (2H ) -on (BAS-145138), 4-dichloroacetyl-
3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor), 4-Carboxy-3,4-dihydro-2H- l-benzopyran-4-essigsäure (CL-304415), 5-Chlor-chinolin-8-oxy-essigsäure-(l- 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 (Daimuron, Dymron), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), l-(2,4-Dichlor-phenyl)-5-trichlormethyl-lH-l,2,4-triazol-3-carbonsäure-ethylester (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-füranyl)-2,2-dimethyl-oxazolidin (Furil- azole, MON-13900), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadi- fen-ethyl), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (+-)-2-(4-Chlor-2- methyl-phenoxy)-propansäure (Mecoprop), Diethyl- 1 -(2,4-dichlorphenyl)-4,5-di- hydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) 2-Dichlormethyl-2- methyl- 1,3-dioxolan (MG-191), 1,8-Naphthalsäureanlιydrid, 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-ox- azolidin (R-29148), N-Cyclopropyl-4-[[(2-methoxy-5-methyl-benzoyl)-amino]-sulf- onyl]-benzamid, N-[[(4-Methoxyacetylamino)-phenyl]-sulfonyl-2-methoxy-benz- amid und N-[[(4-Methylaminocarbonylamino)-phenyl]-sulfonyl-2-methoxy-benz- amid (letztere jeweils bekannt aus WO-A-99/66795), (3-Oxo-isochroman-4-yliden- methoxy)-essigsäure-methylester und (3-Oxo-lH-2-benzothiopyran-4-(3H)-yliden- methoxy)-essigsäure-methylester (letztere jeweils bekannt aus WO-A-98/13361), 1- Ethyl-4-hydroxy-3(lH-tetrazolyl-5-yl-carbonyl)-2(lH)-chinolin (bekannt aus WO-A- 99/00020)3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid (CL-304415), 5-chloro quinoline-8-oxyacetic acid (l-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 (dichloromide), N- (4-methylphenyl) -N '- (1-methyl-1-phenyl- ethyl urea (Daimuron, Dymron), 4,6-dichloro-2-phenyl-pyrimidine (Fenclorim), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole -3-carboxylic acid ethyl ester (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 (furilazoles, MON-13900), ethyl-4,5-dihydro -5,5-diphenyl-3-isoxazole carboxylate (isoxadien-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (+ -) - 2- (4-chloro-2-methyl) -phenoxy) propanoic acid (mecoprop), diethyl 1 - (2,4-dichlorophenyl) -4,5-di-hydro-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-trimethyl-oxazolidine (R-29148) , N- Cyclopropyl-4 - [[(2-methoxy-5-methylbenzoyl) amino] sulfonyl] benzamide, N - [[(4-methoxyacetylamino) phenyl] sulfonyl 2-methoxybenzamide and N - [[(4-methylaminocarbonylamino) phenyl] sulfonyl-2-methoxy-benzamide (the latter is known from WO-A-99/66795), (3-oxo-isochroman-4-ylidene-methoxy) methyl acetate and (3-oxo-1H-2-benzothiopyran-4- (3H) -ylidene-methoxy) -acetic acid methyl ester (the latter is known from WO-A-98/13361), 1-ethyl-4- hydroxy-3 (1H-tetrazolyl-5-yl-carbonyl) -2 (1H) -quinoline (known from WO-A-99/00020)
("Wirkstoffe der Gruppe (3)").("Active substances of group (3)").
Die Erfindung betrifft also herbizide Wirkstoffkombinationen, welcheThe invention thus relates to herbicidal combinations of active ingredients which
entweder aus Wirkstoffen der Gruppen (1) und (2),either from active substances of groups (1) and (2),
oder aus Wirkstoffen der Gruppen (1) und (3),or from active substances of groups (1) and (3),
oder aus Wirkstoffen der Gruppen (1) und (2) und (3) zusammengesetzt sind.or from active substances of groups (1) and (2) and (3) are composed.
Bevorzugte Bedeutungen der oben in Zusammenhang mit der Formel (1) aufgeführten Gruppen werden im Folgenden definiert.Preferred meanings of the groups listed above in connection with the formula (1) are defined below.
n steht bevorzugt für die Zahl 0.n is preferably the number 0.
A steht bevorzugt für Alkandiyl (Alkylen) mit 1 bis 5 Kohlenstoffatomen oder Alkendiyl mit 2 bis 5 Kohlenstoffatomen.A preferably represents alkanediyl (alkylene) with 1 to 5 carbon atoms or alkenediyl with 2 to 5 carbon atoms.
Ar steht bevorzugt für jeweils gegebenenfalls substituiertes Phenyl oder Naphthyl, oder für jeweils gegebenenfalls substituiertes Heterocyclyl aus der Reihe Furyl, Tetrahydrofuryl, Thienyl, Tetrahydrothienyl, Benzofuryl, Di- hydrobenzofuryl, Benzothienyl, Pyπolyl, Pyrazolyl, Pyranyl, Benzopyranyl, Dihydrobenzopyranyl, Tetrahydrobenzopyranyl, Pyridinyl, Chinolinyl oderAr preferably represents in each case optionally substituted phenyl or naphthyl, or for in each case optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyolyl, pyrazolyl, pyranyl, benzopyranyl, pyridylzyridyl, pyridyl, pyridyl, pyridyl, pyridyl Quinolinyl or
Pyrimidinyl,pyrimidinyl,
wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Aufzählung zu entnehmen sind:where the respective possible substituents can preferably be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl,Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,
Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t- Butylthio, Difluormethylthio, Trifluormethylthio, Methylsulfinyl, Ethyl- sulfinyl, n- oder i-Propylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Trifluormethylsulfonyl, Methyl- amino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Di- methylamino, Diethyl-amino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylamino- carbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethyl- aminocarbonyl, Diethylaminocarbonyl, Dimethylaminosulfonyl, Diethyl- aminosulfonyl.Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- Butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, nylamino, n i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i Propylaminocarbonyl, dimethyl aminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl.
R1 steht bevorzugt für gegebenenfalls durch Fluor, Chlor und/oder Brom sub- stituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen,R 1 preferably represents alkyl with 1 to 5 carbon atoms optionally substituted by fluorine, chlorine and / or bromine,
für gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Alkenyl mit 2 bis 5 Kohlenstoffatomen,for alkenyl with 2 to 5 carbon atoms optionally substituted by fluorine, chlorine and / or bromine,
für gegebenenfalls durch Fluor, Chlor und/oder Brom oder Cι-C4- Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,for cycloalkyl with 3 to 6 carbon atoms optionally substituted by fluorine, chlorine and / or bromine or C 1 -C 4 -alkyl,
für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor und/oder Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgrappe und gegebenenfalls 1 bis 3 Kohlenstoffatomen im Alkylteil, oderfor each optionally by nitro, cyano, fluorine, chlorine and / or bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 3 carbon atoms in the alkyl part, or
für gegebenenfalls durch Nitro, Cyano, Fluor, Chlor und/oder Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-for optionally by nitro, cyano, fluorine, chlorine and / or bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-
Propoxy, n-, i-, s- oder t-Butoxy substituiertes Heterocyclyl mit 5 Kohlenstoffatomen und 1 bis 3 Stickstoffatomen und/oder 1 oder 2 Sauerstoff- oder S chwefelatomen.Propoxy, n-, i-, s- or t-butoxy substituted heterocyclyl with 5 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms.
R2 steht bevorzugt für Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy oder n- oder i-Propoxy.R 2 preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, meth- or ethoxy or n- or i- or optionally substituted by fluorine, chlorine and / or bromine. propoxy.
R3 steht bevorzugt für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Fluor,R 3 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,
Chlor oder Brom. R4 steht bevorzugt für Wasserstoff, Amino oder gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl oder n- oder i-Propyl.Chlorine or bromine. R 4 preferably represents hydrogen, amino or methyl, ethyl or n- or i-propyl which is optionally substituted by fluorine, chlorine and / or bromine.
R5 steht bevorzugt für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl, Ethoxycarbonyl oder n- oder i- Propoxycarbonyl.R 5 preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl or n- or i-propoxycarbonyl optionally substituted by fluorine, chlorine and / or bromine.
R6 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor, Chlor und oder Brom substituiertes Methyl, Ethyl oder n- oder i-Propyl.R 6 preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl or n- or i-propyl which is optionally substituted by fluorine, chlorine and or bromine.
R7 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils ge- gebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-R 7 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-
Propoxy, n-, i-, s- oder t-Butoxy substituiertes Alkyl, Alkoxy, Alkylthio,Propoxy, n-, i-, s- or t-butoxy substituted alkyl, alkoxy, alkylthio,
Alkylamino oder Dialkylamino mit jeweils 1 bis 3 Kohlenstoffatomen in denAlkylamino or dialkylamino, each with 1 to 3 carbon atoms in the
Alkylgruppen.Alkyl groups.
R8 steht bevorzugt für Wasserstoff oder jeweils gegebenenfalls durch Cyano,R 8 preferably represents hydrogen or in each case optionally by cyano,
Fluor, Chlor, Brom oder Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t- Butoxy substituiertes Alkyl, Alkoxy, Alkylamino, Alkylcarbonyl oder Alkoxycarbonyl mit jeweils 1 bis 3 Kohlenstoffatomen in den Alkylgruppen.Fluorine, chlorine, bromine or methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted alkyl, alkoxy, alkylamino, alkylcarbonyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl groups.
R9 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder eine derR 9 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or one of the
Gruppierungen -R11, -O-R11, S-R11 oder S02-Rn.Groupings -R 11 , -OR 11 , SR 11 or S0 2 -R n .
R10 steht bevorzugt für Wasserstoff, Hydroxy, Amino oder die Gruppierung -R11. R11 steht bevorzugt für gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 4 Kohlenstoffatomen, für gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Ethyl, Methyl, n- oder i- Propyl oder n-, i-, s- oder t-Butyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, CrC - Alkyl, C1-C -Halogenalkyl, - -Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl oder Benzyl.R 10 preferably represents hydrogen, hydroxy, amino or the grouping -R 11 . R 11 preferably represents alkyl with 1 to 4 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally by Halogen-substituted alkenyl or alkynyl each having 2 to 4 carbon atoms, for cycloalkyl with 3 which is optionally substituted by cyano, fluorine, chlorine, bromine, ethyl, methyl, n- or i-propyl or n-, i-, s- or t-butyl up to 6 carbon atoms, or for phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, CrC-alkyl, C 1 -C -haloalkyl, - -alkoxy or C 1 -C 4 -haloalkoxy.
A steht besonders bevorzugt für Methylen, Ethan-l,l-diyl (Ethyliden), Ethan- 1,2-diyl (Dimethylen), Propan-l,l-diyl (Propyliden), Propan-l,2-diyl, Propan-l,3-diyl (Trimethylen), Ethen-l,2-diyl, Propen- 1,2-diyl oder Propen-A particularly preferably represents methylene, ethane-l, l-diyl (ethylidene), ethane-1,2-diyl (dimethylene), propane-l, l-diyl (propylidene), propane-l, 2-diyl, propane 1,3-diyl (trimethylene), ethene-1,2-diyl, propene-1,2-diyl or propene-
2,3-diyl.2,3-diyl.
Ar steht besonders bevorzugt für gegebenenfalls substituiertes Phenyl, oder für gegebenenfalls substituiertes Heterocyclyl aus der Reihe Furyl, Tetrahydro- furyl, Thienyl, Benzofuryl, Dihydrobenzofuryl, Benzothienyl, Pyπolyl,Ar particularly preferably represents optionally substituted phenyl, or optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyπolyl,
Pyrazolyl, Benzopyranyl, Dihydrobenzopyranyl, Tetrahydrobenzopyranyl,Pyrazolyl, benzopyranyl, dihydrobenzopyranyl, tetrahydrobenzopyranyl,
Pyridinyl oder Pyrimidinyl,Pyridinyl or pyrimidinyl,
wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Auf- Zählung zu entnehmen sind:where the respective possible substituents can preferably be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methyl- thio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio,Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy, trifluoromethoxy, methyl-thio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio,
Methylsulfmyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethyl- sulfonyl, Trifluormethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propyl- a ino, Dimethylamino, Diethyl-amino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylamino- carbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethyl- aminocarbonyl, Diethylaminocarbonyl, Dimethylaminosulfonyl, Diethyl- aminosulfonyl.Methylsulfmyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl sulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propyl-a ino, dimethylamino, diethyl-amino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, Ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl.
R1 steht besonders bevorzugt für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl,R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine,
für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl oder Butenyl,for in each case optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl or butenyl,
für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-for each optionally by fluorine, chlorine, bromine, methyl, ethyl, n- or i-
Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl,Propyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i- Propoxy substituiertes Phenyl, Naphthyl, Benzyl oder Phenylethyl, oderfor phenyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy , Naphthyl, benzyl or phenylethyl, or
. für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Heterocyclyl aus der Reihe Furyl, Thienyl, Pyrazolyl oder Pyridinyl. , for in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy from the series furyl , Thienyl, pyrazolyl or pyridinyl.
R2 steht besonders bevorzugt für Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor und oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy.R 2 particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and or chlorine.
R3 steht besonders bevorzugt für Wasserstoff, Cyano, Fluor oder Chlor. R steht besonders bevorzugt für Wasserstoff, Amino oder jeweils gegebenenfalls durch Fluor substituiertes Methyl oder Ethyl.R 3 particularly preferably represents hydrogen, cyano, fluorine or chlorine. R particularly preferably represents hydrogen, amino or methyl or ethyl which is optionally substituted by fluorine.
R5 steht besonders bevorzugt für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxycarbonyl oder Ethoxycarbonyl.R 5 particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, methoxycarbonyl or ethoxycarbonyl which are optionally substituted by fluorine and / or chlorine.
R6 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl.R 6 particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
R7 steht besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, , Methylamino, Ethylamino, n- oder i-Propylamino, Dimethylamino oder Diethylamino.R 7 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl, methoxy, ethoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy, n- or i-propoxy , n- or i-Propoxy, methylthio, ethylthio, n- or i-propylthio,, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
R8 steht besonders bevorzugt für Wasserstoff oder jeweils gegebenenfalls durchR 8 particularly preferably represents hydrogen or in each case if appropriate
Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertesCyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted
Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methyl- amino, Ethylamino, n- oder i-Propylamino, Acetyl, Propionyl, n- oder i- . Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl.Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, acetyl, propionyl, n- or i-. Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
R9 steht besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder die Gruppierung -O-R11 oder SO2-Rn.R 9 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or the grouping -OR 11 or SO 2 -R n .
R10 steht besonders bevorzugt für Wasserstoff oder die Gruppierung -R11.R 10 particularly preferably represents hydrogen or the grouping -R 11 .
R .11 steht besonders bevorzugt für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder irPropoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, oder für jeweils gegebenenfalls durch Nitro, 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 Phenyl oder Benzyl.R .11 particularly preferably represents in each case optionally cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i r propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t butyl, for in each case optionally substituted by fluorine, chlorine and / or bromine ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl cyclopropyl, cyclobutyl , Cyclopentyl or cyclohexyl, or for each optionally by nitro, 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 phenyl or benzyl.
steht ganz besonders bevorzugt für Methylen, Ethan-l,l-diyl (Ethyliden), Ethan-l,2-diyl (Dimethylen), Propan-l,l-diyl (Propyliden), Ethen-l,2-diyl, Propen- 1,2-diyl oder Propen-2,3-diyl.very particularly preferably represents methylene, ethane-l, l-diyl (ethylidene), ethane-l, 2-diyl (dimethylene), propane-l, l-diyl (propylidene), ethene-l, 2-diyl, propene- 1,2-diyl or propene-2,3-diyl.
Ar steht ganz besonders bevorzugt für gegebenenfalls substituiertes Phenyl,Ar very particularly preferably represents optionally substituted phenyl,
Pyridinyl oder Pyrimidinyl,Pyridinyl or pyrimidinyl,
wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Aufzählung zu entnehmen sind:where the respective possible substituents can preferably be found in the following list:
Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy und Trifluormethoxy.Cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy.
R1 steht ganz besonders bevorzugt für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-, each optionally substituted by fluorine and / or chlorine.
Butyl, für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy substituiertes Phenyl oder Benzyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy substituiertes Heterocyclyl aus der Reihe Furyl, Thienyl,Butyl, for cyclopropyl optionally substituted by fluorine, chlorine or methyl, for each phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, Methoxy or ethoxy substituted heterocyclyl from the series furyl, thienyl,
Pyrazolyl oder Pyridinyl. R steht ganz besonders bevorzugt für Cyano, Chlor, Brom oder Trifluormethyl.Pyrazolyl or pyridinyl. R very particularly preferably represents cyano, chlorine, bromine or trifluoromethyl.
R3 steht ganz besonders bevorzugt für Wasserstoff, Fluor oder Chlor.R 3 very particularly preferably represents hydrogen, fluorine or chlorine.
R4 steht ganz besonders bevorzugt für Wasserstoff, Amino oder Methyl.R 4 very particularly preferably represents hydrogen, amino or methyl.
R5 steht ganz besonders bevorzugt für Cyano oder Trifluormethyl.R 5 very particularly preferably represents cyano or trifluoromethyl.
R6 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Brom oder Methyl.R 6 very particularly preferably represents hydrogen, chlorine, bromine or methyl.
R7 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl.R 7 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
R8 steht ganz besonders bevorzugt für Wasserstoff oder jeweils gegebenenfalls durch Fluor substituiertes Methyl oder Ethyl.R 8 very particularly preferably represents hydrogen or methyl or ethyl which is optionally substituted by fluorine.
R9 steht ganz besonders bevorzugt für Wasserstoff, Chlor, Brom oder die Gruppierung -Rπ.R 9 very particularly preferably represents hydrogen, chlorine, bromine or the grouping -R π .
R11 steht ganz besonders bevorzugt für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl.R 11 very particularly preferably represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
Eine ganz besonders bevorzugte Gruppe der erfindungsgemäßen Wirkstoff- Komponenten der Formel (I) sind diejenigen Verbindungen, bei denen Z für die mit Z1 bezeichnete Grappierung steht, und n, A, Ar, R1, R2 und R3 eine der vorstehend genannten Bedeutungen haben. Eine weitere ganz besonders bevorzugte Grappe der erfindungsgemäßen Wirkstoff- Komponenten der Formel (I) sind diejenigen Verbindungen, bei denen Z für die mit Z2 bezeichnete Gruppierung steht, und n, A, Ar, R1, R2 und R3 eine der vorstehend genannten B edeutungen hab en.A very particularly preferred group of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grappling designated Z 1 and n, A, Ar, R 1 , R 2 and R 3 are one of the abovementioned Have meanings. Another very particularly preferred category of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grouping designated Z 2 and n, A, Ar, R 1 , R 2 and R 3 are one of the above meanings mentioned.
Eine weitere ganz besonders bevorzugte Grappe der erfindungsgemäßen Wirkstoff- Komponenten der Formel (I) sind diejenigen Verbindungen, bei denen Z für die mit Z3 bezeichnete Grappierung steht, und n, A, Ar, R1, R2 und R3 eine der vorstehend genannten Bedeutungen haben.Another very particularly preferred Grappe of the active ingredient components of the formula (I) according to the invention are those compounds in which Z represents the grappling denoted by Z 3 , and n, A, Ar, R 1 , R 2 and R 3 are one of the above have the meanings mentioned.
Beispiele für die als erfmdungsgemäße Wirkstoff-Komponenten ganz besonders bevorzugten Verbindungen der Formel (I) sind in der nachstehenden Tabelle 1 aufgeführt.Examples of the compounds of the formula (I) which are particularly preferred as active ingredient components according to the invention are listed in Table 1 below.
Tabelle 1 : Beispiele für die Verbindungen der Formel (I)Table 1: Examples of the compounds of the formula (I)
31 31
Die Wirkstoffe der Grappe (2) können ihrer chemischen Straktur entsprechend folgenden Wirkstoffklassen zugeordnet werden:The active substances of Grappe (2) can be assigned to their chemical structure according to the following classes of active substances:
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, 4-[4,5- Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-lH-l,2,4-triazol-l-yl]-2-[(ethylsulfonyl)- amino]-5-fluor-benzolcarbothioamid), Aryloxyphenoxypropionate (z.B. Clodinafop- propargyl, Cyhalofop-butyl, Diclofop-methyl, Fenoxaprop-P-ethyl, Fluazifop-P- butyl, Haloxyfop-P-methyl, Quizalofop-P-ethyl), Carbonsäurederivate (z.B. Clopyralid, Dicamba, Fluroxypyr, Picloram, Triclopyr), B enzothiadiazole (z.B. Bent- azon), Chloracetamide (z.B. Acetochlor, Alachlor, Butachlor, (S-) Dimethenamid,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, 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-P-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. Benfiuralin, Ethalfiuralin, Oryzalin, Pendimethalin, Trifluralin), Di- phenylether (z.B. Acifluorfen-sodium, Aclonifen, Bifenox, Fluoroglycofen-ethyl, Fomesafen, Lactofen, Oxyfluorfen), Harnstoffe (z.B. Chlortoluron, Diuron, Isoproturon, Linuron, Metobromuron, Metoxuron), Imidazolinone (z.B. Imazamethabenz- methyl, Imazamox, Imazaquin, Imazethapyr), Isoxazole (z.B. Isoxaflutole), Nicotinanilide (z.B. Diflufenican), Nitrile (z.B. Bromoxynil, loxynil), Organophosphor-Ver- bindungen (z.B. Anilofos, Glufosinate-ammonium, Glyphosate-isopropylammonium, Sulfosate), Oxyacetamide (z.B. Flufenacet, Mefenacet), Phenoxycarbonsäurederivate (z.B. 2,4-D, Dichlorprop-P, MCPA, MCPB, Mecoprop), Pyrazole (z.B. Pyrazolate,Metazachlor, metolachlor, pretilachlor, propachlor, propisochlor), cyclohexanediones (e.g. butroxydim, clefoxydim, cycloxydim, sethoxydim, tralkoxydim), dinitro-aniline (e.g. benfiuralin, ethalfiuralin, oryzalin, pendimethalin), trifluralhalin, sodium trifluraline, triflurylaline, triflurylaline Aclonifen, bifenox, fluoroglycofen-ethyl, fomesafen, lactofen, oxyfluorfen), ureas (e.g. chlortoluron, diuron, isoproturon, linuron, metobromuron, metoxuron), imidazolinones (e.g. imazamethabenz- methyl, imazamox, imazaquin, imazethapyr), isoxazoles (e.g. isoxaflutole), nicotinanilides (e.g. diflufenican), nitriles (e.g. bromoxynil, loxynil), organophosphorus compounds (e.g. anilofos, glufosinate-ammonium, glyphosate, sulfacyl aminopropylammonate) (e.g. Flufenacet, Mefenacet), phenoxycarboxylic acid derivatives (e.g. 2,4-D, dichloroprop-P, MCPA, MCPB, mecoprop), pyrazoles (e.g. pyrazolates,
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, Cinosulfüron, Cyclosulfamuron, Ethoxysulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfüron, Iodosulfiiron-methyl-sodium, Imazo- sulfuron, Metsulfüron-methyl, Nico sulfuron, Oxasulfuron, Primisulfüron-methyl, Prosulfuron, Pyrazosulfuron-ethyl, Rimsulfüron, Sulfometuron-methyl, Sulfosulf- uron, Thifensulfuron-methyl, Triasulfuron, Tribenuron-methyl, Trifloxysulfüron, Tri- flusulfuron-methyl, Tritosulfuron), Tetrazolinone (z.B. Fentrazamide), Thiocarb- amate (z.B. Butylate, Dimepiperate, EPTC, Esprocarb, Molinate, Orbencarb, Pro- sulfocarb, Triallate), Triazine (z.B. Ametryn, Atrazine, 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-Pyrazoxyfen), pyridazinones (for example norflurazon), pyridines (for example dithiopyr, thiazopyr), pyrimidinyl (thio) benzoates (for example bispyribac, pyribenzoxim, pyrithiobac, Pyrimino- bac), sulphonylureas (for example amidosulfuron, azimsulfuron, Bensulfüron-methyl, chlorimuron-ethyl, Chlorsulfuron, Cinosulfüron, Cyclosulfamuron, Ethoxysulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfüron, Iodosulfiiron-methyl-sodium, Imazosulfuron, Metsulfüron-methyl, Nico sulfuron, Oxasulfuron, Primisulfüron-methyl, Prosulfuronuron-Pyraz , Sulfosulfuron, Thifensulfuron-methyl, Triasulfuron, Tribenuron-methyl, Trifloxysulfüron, Triflusulfuron-methyl, Tritosulfuron), Tetrazolinone (eg Fentrazamide), Thiocarbamate (eg Butylate, Dimepiperate, EPTC, Esprocarbcarb, Procin, Molin - sulfocarb, triallates), triazines (e.g. ametryn, atrazines, cyanazines, dimexyflam, simazine, terbuthylazine, terbutryn), triazinones (e.g. hexazinones, metamitron, metribuzin), triazoles (e.g. amitroles), triazolinones (e.g. Amicarbazone, Flucarb-azone-sodium, Propoxycarbazone-sodium) Triazolopyrimidines (e.g. Cloransulam-methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam), Triketones (e.g. Meso-
,trione, Sulcotrione), Uracile (z.B. Bromacil)., trione, sulcotrione), uracile (e.g. bromacil).
Eine besonders bevorzugte Grappe von Verbindungen der Gruppe (2) sind die Triazolinone, Sulfonylharnstoffe (insbesondere Iodsulfuron-methyl-sodium), Aryl- oxyphenoxypropionate (insbesondere Fenoxaprop-p-ethyl) und Isoxazole.A particularly preferred group of compounds of group (2) are the triazolinones, sulfonylureas (in particular iodosulfuron-methyl-sodium), aryloxyphenoxypropionates (in particular fenoxaprop-p-ethyl) and isoxazoles.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe (2) werden weiter besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group (2):
Flucarbazone-sodium, Acetochlor, Aclonifen, Alachlor, Amicarbazone, Amidosulfuron, Amitrole, Anilofos, Asulam, Atrazine, Beflubutamid, Benazolin (-ethyl), Ben- furesate, Bentazone, Bifenox, Bispyribac-sodium, Bromoxynil, Butylate, Carfen- trazone-ethyl, Chlorotoluron, Chlorsulfüron, Cinidon-ethyl, Clodinafop-propargyl, Clopyralid, Cyanazine, 2,4-D, Desmedipham, Dicamba, Dichlorprop-P, Diclofop- methyl, Difenzoquat, Diflufenican, Diflufenzopyr, Dimethenamid, S-Dimethenamid, EPTC, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fen- trazamide, Flamprop-M-isopropyl, Flamprop-M-methyl, Florasulam, Fluazifop-P- butyl, Fluazolate, Flufenacet, Flumetsulam, Fluoroglycofen-ethyl, Flupyrsulfuron- methyl-sodium, Fluroxypyr, -butoxypropyl, -meptyl, Flurtamone, Fluthiacet-methyl, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Halosulfuron-methyl, Haloxy- fop-P -methyl, Imazamethabenz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin,Flucarbazone-sodium, Acetochlor, Aclonifen, Alachlor, Amicarbazone, Amidosulfuron, Amitrole, Anilofos, Asulam, Atrazine, Beflubutamid, Benazolin (-ethyl), Ben- furesate, Bentazone, Bifenox, Bispyribac-sodium, Bromoxynil, Butylate, Carfentrazone-ethyl, Chlorotoluron, Chlorsulfüron, Cinidon-ethyl, Clodinafop-propargyl, Clopyralid, Cyanazine, 2,4-D, Desmedipham, Dicamba, Dichlorprop-P, Diclofop-methyl, difenzoquat, diflufenican, diflufenzopyr, dimethenamid, S-dimethenamid, EPTC, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flampropam-M-methyl, Floras Fluazifop-P-butyl, Fluazolate, Flufenacet, Flumetsulam, Fluoroglycofen-ethyl, Flupyrsulfuron-methyl-sodium, Fluroxypyr, -butoxypropyl, -meptyl, Flurtamone, Fluthiacet-methyl, Foramsulfuron, Glufosinate, Glufosinate-ammonon, Ammonium fop-P -methyl, Imazamethabenz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin,
Imazethapyr, Iodosulfuron-methyl-sodium, loxynil, Isoproturon, Isoxaben, Isoxa- chlortole, Isoxaflutole, Lactofen, Linuron, MCPA, Mecoprop-P, Mefenacet, Meso- sulfuron, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metolachlor, S-Metolachlor, Metosulam, Metribuzin, Metsulfuron-methyl, Naproanilide, Neburon, Nicosulfuron, Oxadiargyl, Oxadiazon, Oxaziclomefone, Oxyfluorfen, Pendimethalin,Imazethapyr, iodosulfuron-methyl-sodium, loxynil, isoproturon, isoxaben, isoxa- chlorotole, isoxaflutole, lactofen, linuron, MCPA, mecoprop-P, mefenacet, meso-sulfurone, mesotrione, metamitron, metazachlor, meta-chlorochloron, methabenzachloron Metosulam, Metribuzin, Metsulfuron-methyl, Naproanilide, Neburon, Nicosulfuron, Oxadiargyl, Oxadiazon, Oxaziclomefone, Oxyfluorfen, Pendimethalin,
Penoxsulam, Phenmedipham, Picolinafen, Primisulfüron-methyl, Profluazol, Pro- panil, Propoxycarbazone-sodium, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen- ethyl, Pyribenzoxim, Pyridafol, Pyridate, Qinclorac; Quinmerac, Rimsulfuron, Sulco- trione, Sulfosate, Sulfosulfüron, Terbuthylazine, Thifensulfuron-methyl, Tralkoxy- dim, Triallate, Triasulfuron, Tribenuron-methyl, Tritosulfüron, 4-(4,5-Dihydro-4-Penoxsulam, Phenmedipham, Picolinafen, Primisulfüron-methyl, Profluazol, Propanil, Propoxycarbazone-sodium, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen-ethyl, Pyribenzoxim, Pyridafol, Pyridate, Qinclorac; Quinmerac, Rimsulfuron, Sulcotrione, Sulfosate, Sulfosulfüron, Terbuthylazine, Thifensulfuron-methyl, Tralkoxydim, Triallate, Triasulfuron, Tribenuron-methyl, Tritosulfüron, 4- (4,5-Dihydro-4-
,methyl-5-oxo-3-trifluormethyl-lH-l,2,4-triazol-l-yl)-2-(ethylsulfonylamino)-5- fluor-benzolcarbothioamid (HWH4991) und 2-Chlor-N-[l-(2,6-dichlor-4-difluor- methyl-phenyl)-4-nitro-lH-pyrazol-5-yl]-propancarbonsäureamid (SLA5599)., methyl-5-oxo-3-trifluoromethyl-lH-l, 2,4-triazol-l-yl) -2- (ethylsulfonylamino) -5- fluoro-benzenecarbothioamide (HWH4991) and 2-chloro-N- [l- (2,6-dichloro-4-difluoromethylphenyl) -4-nitro-1H-pyrazol-5-yl] propane carboxamide (SLA5599).
Insbesondere werden aus den Wirkstoffen der Grappe (2) die folgendenIn particular, the active ingredients of Grappe (2) become the following
Mischungskomponenten hervorgehoben:Mix components highlighted:
Aclonifen, Amicarbazone, Amidosulfuron, Amitrole, Anilofos, Asulam, Benazolin- ethyl, Benfuresate, Bifenox, Bispyribac-sodium, Bromoxynil, Desmedipham, Diclo- fop-methyl, Diflufenican, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fentrazamide, Fluazifop-P-butyl, Fluazolate, Flucarbazone-sodium, Flufenacet, Flurtamone, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Iodo- sulfüron, loxynil, Isoproturon, Isoxachlortole, Isoxaflutole, Lactofen, Linuron, Mefenacet, Mesosulfuron, Metamitron, Methabenzthiazuron, Metribuzin, Neburon, Oxadiargyl, Oxadiazon, Oxaziclomefone, Phenmedipham, Propanil, Propoxycarb- azone-sodium, Pyraclonil, Pyraflufen-ethyl und Sulcotrione.Aclonifen, Amicarbazone, Amidosulfuron, Amitrole, Anilofos, Asulam, Benazolin-ethyl, Benfuresate, Bifenox, Bispyribac-sodium, Bromoxynil, Desmedipham, Diclofop-methyl, Diflufenican, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl Fentrazamide, fluazifop-P-butyl, fluazolate, flucarbazone-sodium, Flufenacet, Flurtamone, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Iodosulfüron, loxynil, Isoproturon, Isoxachlortole, Isoxaflutole, Lactofen, Linuron, Mefenacet, Mesosulfuron, Oxamethonone, Oxetronuronuronuronuronuronuronuron Propoxycarb- azone-sodium, pyraclonil, pyraflufen-ethyl and sulcotrione.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe (3) werden besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group (3):
5-Chlor-chinolin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet-mexyl),5-chloro-quinoline-8-oxy-acetic acid (l-methyl-hexyl ester) (Cloquintocet-mexyl),
Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl) und Diethyl- l-(2,4-dichlor-phenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefen- pyr-diethyl), besonders geeignet zur Verbesserung der Verträglichkeit in Gerste und Weizen sowie in gewissem Umfang auch in Mais und Reis, sowie 4-Dichloracetyl-l- oxa-4-aza-spiro[4.5]-decan (AD-67), l-Dichloracetyl-hexahydro-3,3,8a-trimethyl- pyπolo [ 1 ,2-a] -pyrimidin-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-acetamid (Dichlormid), 3-Dichloracetyl-5-(2-füranyl)-2,2-dimethyl-oxazolidin (Furilazole, MON-13900) und 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148), besonders geeignet zur Verbesserung der Verträglichkeit in Mais. Mefenpyr-diethyl ist alsEthyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl) and diethyl-l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole -3,5-dicarboxylate (mefen-pyr-diethyl), particularly suitable for improving the tolerance in barley and wheat and to a certain extent also in maize and rice, as well as 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5 ] -decane (AD-67), l-dichloroacetyl-hexahydro-3,3,8a-trimethyl-pyπolo [1, 2-a] -pyrimidin-6 (2H) -one (BAS- 145138), 4-dichloroacetyl- 3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), 3-dichloroacetyl-5- (2nd -foranyl) -2,2-dimethyl-oxazolidine (Furilazole, MON-13900) and 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), particularly suitable for improving the tolerance in maize. Mefenpyr-diethyl is considered
,Wirkstoff der Grappe (3) insbesondere von Interesse., Active ingredient of grappa (3) of particular interest.
Vorzugsweise enthalten die erfindungsgemäßen Mittel einen oder zwei Wirkstoffe der Grappe (1) und ein bis drei Wirkstoffe der Grappe (2) und/oder gegebenenfalls einen Wirkstoff der Grappe (3).The agents according to the invention preferably contain one or two active substances of Grappe (1) and one to three active substances of Grappe (2) and / or optionally one active substance of Grappe (3).
Insbesondere enthalten die erfindungsgemäßen Mittel einen Wirkstoff der Grappe (1) und einen oder zwei Wirkstoffe der Gruppe (2) und/oder gegebenenfalls einen Wirkstoff der Grappe (3). Beispiele für erfindungsgemäße Kombinationen aus jeweils einem Wirkstoff der Grappe (1) und ein oder zwei Wirkstoffen der Grappe (2) sowie Kombinationen aus jeweils einem Wirkstoff der Grappe (1), ein oder zwei Wirkstoffen der Gruppe (2) und einer Verbindung der Grappe (3) sind nachstehend in Tabelle 2 aufgeführt. Die Bezeichnung der Wirkstoffe der Formel (I) (Wirkstoffe der Grappe (1)) sind dabei jeweils der Tabelle 1 entnommen. In particular, the agents according to the invention contain an active ingredient from Grappe (1) and one or two active ingredients from Group (2) and / or optionally an active ingredient from Grappe (3). Examples of combinations according to the invention each consisting of an active ingredient of the Grappe (1) and one or two active ingredients of the Grappe (2) and combinations of one active ingredient of the Grappe (1), one or two active ingredients of the group (2) and a compound of the Grappe ( 3) are listed in Table 2 below. The names of the active compounds of the formula (I) (active compounds of the Grappe (1)) are in each case taken from Table 1.
Tabelle 2: Beispiele für Kombinationen bestehend aus einem Wirkstoff der Gruppe (1) und einem oder zwei Wirkstoffen der Grappe (2) sowie gegebenenfalls einem Wirkstoff der Grappe (3).Table 2: Examples of combinations consisting of an active ingredient from group (1) and one or two active ingredients from Grappe (2) and, where appropriate, an active ingredient from Grappe (3).
Es wurde nun übeπaschend gefunden, dass die vorstehend definierten Wirkstoffkombinationen aus den substituierten Carbonsäureaniliden der Formel (I) und den vorstehend angeführten Wirkstoffen der Grappe (2) bei sehr guter Nutzpflanzen-Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in ver- schiedenen Kulturen, vor allem in Baumwolle, Gerste, Kartoffeln, Mais, Raps, Reis, Roggen, Soja, Sonnenblumen, Weizen, Zuckeπohr und Zuckerrüben, insbesondere in Gerste, Mais, Reis und Weizen, 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.It has now surprisingly been found that the combinations of active substances defined above from the substituted carboxanilides of the formula (I) and the active substances of Grappe (2) listed above have a particularly high herbicidal activity and are very herbicidal, and Different crops, especially in cotton, barley, potatoes, corn, rapeseed, rice, rye, soybeans, sunflowers, wheat, sugar cane and sugar beets, especially in barley, corn, rice and wheat, are used for the selective control of monocotyledonous and dicotyledonous weeds can and that they can also be used to control monocotyledon and dicotyledon weeds in the semi and non-selective range.
Übeπaschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirkstoffkombinationen aus Verbindungen der oben aufgeführten Gruppen (1) und (2) deutlich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active compound combinations according to the invention composed of compounds from groups (1) and (2) listed above is significantly 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 bekämpf- bare 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 relativThe 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 relative
,. großen Bereichen variiert werden. Im Allgemeinen entfallen auf 1 Gewichtsteil. large areas can be varied. Generally 1 part by weight
Wirkstoff der Formel (I) 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,002 bis 500Active ingredient of formula (I) 0.001 to 1000 parts by weight, preferably 0.002 to 500
Gewichtsteile und besonders bevorzugt 0,01 bis 100 Gewichtsteile Wirkstoff derParts by weight and particularly preferably 0.01 to 100 parts by weight of active ingredient
Grappe (2).Grappe (2).
Es ist auch als übeπaschend 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 Grappe (2), auf die Kulturpflanzen annähernd voll- ständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen.It is also surprising that from a large number of known safeners or antidotes which are capable of antagonizing the damaging effect of a herbicide on the crop plants, the compounds of group (3) listed above are particularly suitable, the damaging effect of active substances of the formula (I) and its salts, optionally also in combination with one or more of the active ingredients of the grappa (2) mentioned above, on the crop plants almost completely to keep constantly without affecting the herbicidal activity against the weeds.
Übeπaschenderweise wurde zudem gefunden, dass auch die herbizid wirksame Sub- stanz 2,4-Dichlorophenoxy-essigsäure (2,4-D) und ihre Derivate im vorliegenden Fall 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 in the present case can take over the safener task described above.
Eine bevorzugte Ausführangsform 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.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 ). Typical derivatives of 2,4-D are e.g. their esters.
Übeπaschenderweise wurde ebenfalls gefunden, dass auch die herbizid wirksamen Substanzen (4-Chlor-2-methylphenoxy)essigsäure (MCPA) und (+-)-2-(4-Chlor-2- methylphenoxy)propansäure (Mecoprop) im vorliegenden Fall eine Safeneraufgabe übernehmen können. Die genannten Verbindungen sind in den folgenden Patentanmeldungen beschrieben: JP 63 072 605 und GB 00 820 180.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) also act as safeners in the present case can take over. The compounds mentioned are described in the following patent applications: JP 63 072 605 and GB 00 820 180.
Die Verbindungen Diethyl-l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-The compounds diethyl-l- (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.. 3,5-dicarboxylates (mefenpyr-diethyl), (l-methyl-hexyl) - [(5-chloro-8-quinolinyl) oxy] - acetate (cloquintocet-mexyl) and ethyl-l- (2,4-dichlorophenyl) -5- (trichloromethyl) - 1H-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 Kulturpflanzenverträglichkeit der erfindungsgemäßen Wirkstoffkombinationen 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 Grappe (2) 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100 Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile einer der oben unter (c) genannten, die Kulturpflanzen Verträglichkeit verbessernden Verbindungen (Antidots/Safener).The advantageous effect of the crop plant tolerance of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios. 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 ingredient of the formula (I) or thereof Mixtures with active substances of Grappe (2) 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the compounds (antidots / safeners) which improve crop plant tolerance and are mentioned above (c).
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierangsmethoden 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, Fruchtkörper, 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.According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhiozomes. The plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
,. Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfüsion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, transgenes are
Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Bio- und Genotypen sein.Plants and plant varieties that have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive ("synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen desDepending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or extensions of the
Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höhererSpectrum of activity and / or an enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields , higher quality and / or higher
Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechno-The preferred transgenic (genetic engineering)
, logisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen, logically preserved) plants or plant varieties belong to all plants that received genetic material through genetic modification, which this
Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegen- über hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikro- bielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus thuringiensis (z.B. durch die Gene kodierend für CryΙA(a), CryΙA(b), CryΙA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als EigenschaftenGives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted. The properties ("traits") are particularly emphasized of the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes coding for CryΙA (a), CryΙA (b ), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. As properties
("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen.("Traits") are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
,. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und. Examples of "Bt plants" are maize, cotton, soybean and
Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B.Potato varieties called, which under the trade names YIELD GARD® (e.g.
Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard®Maize, cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard®
(Baumwolle), Nucotn® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und(Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and
Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften ("Traits").Soybean varieties named under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. corn ) to be expelled. The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit denThe plants listed can be particularly advantageous according to the invention with the
Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.Compounds of the general formula (I) or the active compound mixtures according to the invention are treated. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lageπaum 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.The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their environment, habitat or location 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 multi-layer coating.
Unter den durch biotechnologische und gentechnologische Methoden oder durch Kombination dieser Methoden erhaltenen Pflanzen werden solche Pflanzen hervorge- hoben, die sog. ALS-, 4-HPPD-, EPSPS- und/oder PPO-Hemmstoffe tolerieren, wieAmong the plants obtained by biotechnological and genetic engineering methods or by a combination of these methods, those plants are emphasized which tolerate so-called ALS, 4-HPPD, EPSPS and / or PPO inhibitors, such as
,. z.B. Acuron-Pflanzen.. e.g. 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, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver,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, Gupopsisia, Euphorbia , 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.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,Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon,
Nicotiana, Phaseolus, Pisum, Solanum, Vicia.Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monokotyle Unkräuter der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchras, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchras, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochlo
Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monokotyle Kulturen der Gattungen: Allium, Ananas, Asparagus, Avena, Hordeum,Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum,
Oryza, Panicum, Saccharam, Seeale, Sorghum, Triticale, Triticum, Zea.Oryza, Panicum, Saccharam, 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) in Plantagenkulturen (z.B. Wein, Obst, Zitrus) sowie in Industrie- und Gleisanlagen, auf Wegen und Plätzen, aber auch zur Stoppelbehandlung und beim Minimum-Tillage-The active ingredient combinations to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (e.g. wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and with 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, Forst, Grünland und Zierpflanzenbau. Die Wirkstoffkombinationen können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Femstverkapselungen in polymeren Stoffen.Procedures are used. They are also suitable as burners (killing herbs, for example in potatoes) or as defoliants (for example in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing. The active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and femst encapsulations in polymeric substances.
Diese Formulierangen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugendenThese formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents
Mitteln.Means.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische 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. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methyl-isobutylketon oder Cyclohexanon, stark polareIf water is used as an extender, e.g. organic solvents can also be 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, 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
,. Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.. 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,e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
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 Tabak- stengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, 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 stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein 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. WeitereAdhesives 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. Further
Additive können mineralische und vegetabile Öle sein.Additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferco- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt,Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
Molybdän und Zink verwendet werden.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 Wirkstoffkombinationen 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 ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
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,The new combinations of active ingredients, as such or in their formulations, can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible. Also a mixture with other known active ingredients, such as fungicides, insecticides,
Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzen- nährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte Anwendungszwecke, 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.Acaricides, nematicides, bird repellants, growth agents, plant nutrients and soil structure improvers are possible. For certain applications, in particular in the post-emergence process, it may also be advantageous to include mineral-based or vegetable-compatible oils (for example the commercial preparation "Rako Binol") or ammonium salts such as ammonium sulfate or ammonium rhodanide in the formulations as further additives.
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,The new active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring,
Spritzen, Sprühen, Stäuben oder Streuen.Spraying, spraying, dusting or sprinkling.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auflaufen der Pflanzen appliziert werden, also im Vorauflauf und Nachauflauf- Ver- fahren. 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, ie in the pre-emergence and post-emergence processes. They can also be worked into the soil before sowing.
Die gute herbizide Wirkung der neuen Wirkstoffkombinationen geht aus den nachfolgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbiziden Wirkung Schwächen aufweisen, zeigen die Kombinationen durchweg eine sehr gute Unkrautwirkung, die über eine einfache Wirkungssummierung hinausgeht.The good herbicidal activity of the new active compound combinations can be seen from the examples below. While the individual active ingredients have weaknesses in the herbicidal action, the combinations consistently show a very good weed action which goes beyond a simple summation of action.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbizide Wirkung der Wirkstoffkombination größer ist als die der einzelnen applizierten Wirkstoffe.Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
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): WennThe expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, SR: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967): If
X = % Schädigung durch Herbizid A (Wirkstoff der Formel I) bei p kg/ha Aufwandmenge undX =% damage by herbicide A (active ingredient of the formula I) at a rate of p kg / ha and
Y = % Schädigung durch Herbizid B (Wirkstoff der Formel II) bei q kg/ha Aufwandmenge undY =% damage by herbicide B (active ingredient of the formula II) at q kg / ha application rate and
die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge,the expected damage to herbicides A and B at p and q kg / ha,
dann istthen
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 zu erwartende Wirkung für eine gegebene Kombination dreier Herbizide kann ebenfalls der oben angegebenen Literatur entnommen werden. The expected effect for a given combination of three herbicides can also be found in the literature given above.
Anwendungsbeispiele:Application examples:
Beispiel AExample A
Post-emergence-Test / GewächshausPost emergence test / greenhouse
Testpflanzen werden unter kontrollierten Bedingungen (Temperatur und Licht) herangezogen. Sobald die Pflanzen eine Wuchshöhe von 5 bis 15 cm eπeicht haben, wird die Testsubstanz bzw. die Kombination der Testsubstanzen in der Weise aufgespritzt, dass die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausge- bracht werden. Die Konzentration der Spritzbrühe wird so gewählt, dass in 500 LiterTest plants are grown under controlled conditions (temperature and light). As soon as the plants have reached a height of 5 to 15 cm, the test substance or the combination of the test substances is sprayed on in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray liquid is chosen so that in 500 liters
Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden.Water / ha the desired amounts of active ingredient are applied.
Nach der Spritzanwendung werden die Pflanzgefäße im Gewächshaus bei konstanten Licht- und Temperaturbedingungen untergebracht.After spraying, the planters are placed in the greenhouse under constant light and temperature conditions.
Nach 5 Tagen (5d) und/oder drei Wochen (21d) wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Nergleich zur Entwicklung der unbehandelten Kontrolle.After 5 days (5d) and / or three weeks (21d), the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
Wirkstoffe, Aufwandmengen, Testpflanzen und Resultate gehen aus den nachfolgenden Tabellen hervor. Soweit nicht anders angegeben, wurden die Versuche bei Anwesenheit von 0,5 % Renex 36 durchgeführt.Active substances, application rates, test plants and results are shown in the tables below. Unless otherwise stated, the tests were carried out in the presence of 0.5% Renex 36.
a.i. steht für „active ingredient" (Wirkstoff). HORVW steht für Hordeum vulgäre (Wintergerste).a.i. stands for "active ingredient". HORVW stands for Hordeum vulgare (winter barley).
TRZAW steht für Triticum aestivum (Winterweizen). Tabelle 3TRZAW stands for Triticum aestivum (winter wheat). Table 3
Tabelle 4Table 4
Tabelle 5Table 5
Tabelle 6 Table 6
Tabelle 9Table 9
Tabelle 10Table 10
Tabelle 11 Table 11
Tabelle 14 Table 14
Tabelle 17 Table 17
Tabelle 21 Table 21
Tabelle 22Table 22
Tabelle 23Table 23
Tabelle 24 Table 24
*) Ohne Zusatz von Renex 36*) Without the addition of Renex 36
Tabelle 25Table 25
Tabelle 27Table 27
Tabelle 29 Table 29
Tabelle 30Table 30

Claims

Patentansprüche claims
1. Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination umfassend1. Composition, characterized by an effective content of an active ingredient combination comprising
(a) zumindest eine Verbindung der allgemeinen Formel (I)(a) at least one compound of the general formula (I)
in welcher in which
n für die Zahlen 0 oder 1 steht,n represents the numbers 0 or 1,
A für Alkandiyl (Alkylen) oder Alkendiyl mit jeweils bis zu 6 Kohlenstoffatomen steht,A represents alkanediyl (alkylene) or alkenediyl each having up to 6 carbon atoms,
Ar für gegebenenfalls substituiertes Aryl mit 6 oder 10 Kohlenstoffatomen oder für gegebenenfalls substituiertes Heterocyclyl mit bis zu 9 Kohlenstoffatomen und 1 bis 4 Stickstoffatomen und/oder gegebenenfalls 1 oder 2 Sauerstoff- oder Schwefelatomen steht,-Ar represents optionally substituted aryl with 6 or 10 carbon atoms or for optionally substituted heterocyclyl with up to 9 carbon atoms and 1 to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms,
wobei die jeweils möglichen Substituenten aus folgender Aufzählung zu entnehmen sind:where the possible substituents can be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, CrC4- Alkyl, CrC4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, d-Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, -C 4 - alkyl, -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, d-
C -Alkylthio, Cι-C -Halogenalkylthio, C1-C4-Alkylsulfinyl, CrC - Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, -Gi-Halogenalkyl- sulfonyl, Cι-C4- Alkylamino, Di-(C1-C -alkyl)-amino, - - Alkylcarbonyl, C1-C4-Alkoxycarbonyl, C1-C -Alkylaminocarbonyl, Di-(C1-C4-alkyl)-aminoarbonyl, Di-^rC^alky^-aminosulfonyl,C -alkylthio, -C-C -haloalkylthio, C 1 -C 4 alkylsulfinyl, CrC - haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, -Gi-haloalkylsulfonyl, Cι-C 4 - alkylamino, di- (C 1 - C -alkyl) -amino, - - Alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) -aminocarbonyl, di- ^ rC ^ alky ^ -aminosulfonyl,
R1 für gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen, für gegebenenfalls durch Halogen substituiertes Alkenyl mit 2 bis 6R 1 for alkyl optionally substituted by halogen with 1 to 6 carbon atoms, for alkenyl optionally substituted with halogen having 2 to 6
Kohlenstoffatomen, für gegebenenfalls durch Halogen oder Ci-C4-Alkyl substituiertesCarbon atoms, optionally substituted by halogen or C 1 -C 4 -alkyl
Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, C1-C4-Alkyl oder d-C -Alkoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgrappe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für gegebenenfalls durch Nitro, Cyano, Halogen, C1-C -Alkyl oder Ci- C -Alkoxy substituiertes Heterocyclyl mit 5 Kohlenstoffat men und 1 bis 4 Stickstoffatomen und/oder 1 oder 2 Sauerstoff- oder Schwefelatomen steht,Cycloalkyl with 3 to 6 carbon atoms, for each aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, optionally substituted by nitro, cyano, halogen, C 1 -C 4 -alkyl or dC -alkoxy, or represents heterocyclyl with 5 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms optionally substituted by nitro, cyano, halogen, C 1 -C alkyl or C 1 -C alkoxy,
R2 für Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils ge- gebenenfalls durch Halogen substituiertes Alkyl oder Alkoxy mit jeweils 1 bis 4 Kohlenstoffatomen steht,R 2 represents cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxy, each optionally substituted by halogen, each having 1 to 4 carbon atoms,
R3 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl oder Halogen steht, undR 3 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, and
für eine der nachstehend skizzierten Gruppierungen steht, represents one of the groupings outlined below,
(z1) (Z2) (z3) wonn(z 1 ) (Z 2 ) (z 3 ) wonn
R4 für Wasserstoff, Amino oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 4 represents hydrogen, amino or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
R für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Halogen substituiertes Alkyl oder Alkoxycarbonyl mit jeweils 1 bis 4 Kohlenstoffatomen in denR for carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by halogen substituted alkyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the
10 Alkylgrappen steht,10 alkyl groups,
R für Wasserstoff, Halogen oder gegebenenfalls durch Halogen substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R represents hydrogen, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen,
15 R für Wasserstoff, Cyano, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder CrC4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgrappen steht, und15 R represents hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by cyano, halogen or CrC 4 alkoxy, each having 1 to 4 carbon atoms in the alkyl groups, and
2020
R für Wasserstoff oder für jeweils gegebenenfalls durch Cyano, Halogen oder C1-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylamino, Alkylcarbonyl oder Alkoxycarbonyl mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen steht,R represents hydrogen or alkyl, alkoxy, alkylamino, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 alkoxy, each having 1 to 4 carbon atoms in the alkyl groups,
25 R9 für Wasserstoff, Cyano, Halogen oder eine der- Gruppierungen -R11, -O-R11, S-R11, SO-R11 oder SO2-Rπ steht,25 R 9 represents hydrogen, cyano, halogen or one of the groupings -R 11 , -OR 11 , SR 11 , SO-R 11 or SO 2 -R π ,
R , 10 für Wasserstoff, Hydroxy, Amino, oder eine der Gruppierungen -R11 oder -O-R11 steht, undR, 10 represents hydrogen, hydroxy, amino, or one of the groupings -R 11 or -OR 11 , and
R11 für gegebenenfalls durch Cyano, Halogen oder d-C - Alkoxy substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen, für gegebenenfalls durch Cyano, Halogen oder Cι-C -Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d- C4-Alkyl, Cι-C4-Halogenalkyl, C1-C4-Alkoxy oder Cι-C4- Halogenalkoxy substituiertes Phenyl oder Benzyl steht,R 11 for optionally substituted by cyano, halogen or dC - alkoxy alkyl having 1 to 6 carbon atoms, for each optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for optionally substituted by cyano, halogen or -CC alkyl -cycloalkyl having 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, d-C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 alkoxy or Cι-C 4 - haloalkoxy-substituted phenyl or benzyl .
(„Wirkstoffe der Grappe (1)")("Active substances of the Grappe (1)")
undand
(b) eine oder mehrere Verbindung(en) aus einer zweiten Grappe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(b) one or more compound (s) from a second group of herbicides, which contains the active compounds mentioned below:
4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulf- onyl]-l-H-l,2,4-triazol-l-carboxamid-Natriumsalz (Flucarbazone-sodium), 2-4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -lHl, 2,4-triazole-l-carboxamide sodium salt (flucarbazone- sodium), 2-
Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure (-Natriumsalz) (Acifluorfen (-sodium)), 2-Chlor-6-nitro-3-phenoxy-benzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid (Alachlor), Methyl-4-hydroxy-6,6-dimethyl-2-oxo-3 - [ 1 - [(2-propenyloxy)-imino ] -butyl] -Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methylphenyl) acetamide (acetochlor), 5- (2-chloro-4-trifluoromethylphenoxy) -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 ), Methyl-4-hydroxy-6,6-dimethyl-2-oxo-3 - [1 - [(2-propenyloxy) imino] butyl] -
3 -cyclohexen-1 -carboxy lat (-Natriumsalz) (AUoxydim (-sodium)), N-Ethyl- N'-i-propyl-6-memyltMo-l,3,5-1riazin-2,4-(hamin (Ametryn), 4-Amino-N- (1,1 -Dimerhyl-ethyl)-4,5-dihydro-3-(l -methyl-ethyl)-5-oxo- 1H- 1 ,2,4-triazol- 1-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N- methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfüron), 1H- 1 ,2,4- Triazol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(l-isopropyl)-amino]-2- oxo-ethyl]-O,O-dimethyl-phosphorodithioate (Anilofos), N-(4-Amino- ρhenyl-sulfonyl)-carbamidsäure-0-methylester (Asulam), 6-Chlor-4-ethyl- amino-2-isopropylamino-l,3,5-triazin (Atrazine), 2-[2,4-Dichlor-5-(2-prop- inyloxy)-ρhenyl]-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'-[l-methyl-4-(2-methyl-3 -cyclohexen-1-carboxy lat (-sodium salt) (AUoxydim (-sodium)), N-ethyl- N'-i-propyl-6-memyltMo-l, 3,5-1riazine-2,4- (hamin (Ametryn), 4-amino-N- (1,1-dimerethyl-ethyl) -4,5-dihydro -3- (l -methyl-ethyl) -5-oxo- 1H- 1, 2,4-triazole-1-carboxamide (amicarbazone), N- (4,6-dimethoxypyrimidin-2-yl) -N ' - (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1, 2,4-triazol-3-amine (amitrole), S- [2 - [(4-chlorophenyl) - ( l-isopropyl) -amino] -2-oxo-ethyl] -O, O-dimethyl-phosphorodithioate (Anilofos), N- (4-amino-ρhenyl-sulfonyl) -carbamic acid-0-methyl ester (Asulam), 6-chlorine -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 ' - [l-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 (-ethylester) (Benazolin, (-ethyl)), N-Bu1yl-N-ethyl-2,6-dinitio-4-trifluormethyl-benzenamin (Benfluralin), 2,3- Dihydro-3,3-dmιethyl-5-benzofüranyl-ethansulfonat (Benfuresate), N-(4,6-2H-tetrazol-5-yl) -lH-pyrazol-5-ylsulfonyl] urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro 2-oxo-3 (2H) -benzthiazole acetic acid (ethyl ester) (benazoline, (-ethyl)), N-Bu1yl-N-ethyl-2,6-dinitio-4-trifluoromethyl-benzenamine (benfluralin), 2,3- Dihydro-3,3-dimethyl-5-benzofüranyl ethanesulfonate (benfuresate), N- (4,6-
Dimethoxy-pyrirm'din-2-yl)-N'-(2-methoxycarbonyl-phenylmethylsulfonyl)- ha nstoff (Bensulfuron-methyl), 3 -i-Propyl- 1H-2, l,3-benzothiadiazin-4(3H)- on-2,2-dioxid (Bentazone), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thiobencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl-l(2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propan- säure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4- phenylthio-bicyclo-[3.2. l]-oct-3-en-2-on (Benzobicyclon), 2-[[4-(2,4-Di- chlor-3 -methyl-benzoyi)- 1 ,3 -dimethyl- 1 H-pyrazol-5-yl] -oxy] - 1 -(4-methyl- phenyl)-ethanon (Benzofenap), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro- benzoat (Bifenox), 2,6-Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Dimethoxy-pyrirm ' din-2-yl) -N' - (2-methoxycarbonyl-phenylmethylsulfonyl) - ha nstoff (bensulfuron-methyl), 3-i-propyl-1H-2, l, 3-benzothiadiazin-4 (3H) - on-2,2-dioxide (bentazone), S - [(4-chlorophenyl) methyl] diethylthiocarbamate (benthiocarb, thiobencarb), 2- [2- [4- (3,6-dihydro-3- methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinylphenoxymethyl] -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), 2 - [[4- (2,4-dichloro-3-methylbenzoyi) - 1, 3-dimethyl-1 H-pyrazol-5-yl] -oxy] - 1 - (4-methylphenyl) ethanone (benzofenap), methyl-5- (2,4-dichlorophenoxy) -2-nitro- benzoate (bifenox), 2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid-
Natriumsalz (Bispyribac-sodium), 5-Brom-6-methyl-3-(l -methyl-propyl)-2,4- (lH,3H)pyrimidindion (Bromacil), 2-Brom-3,3-dimethyl-N-(l-methyl-l- phenyl-ethyl)-butanamid (Bromobutide), 3,5-Dibrom-4-hydroxy-benz- aldehyd-0-(2,4-dinitro-phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4- hydroxy-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- trifluoπnethyl-l(2H)-pyrintidinyl)-benzoesäure-[l,l-dimethyl-2-oxo-2-(2- propenyloxy)]-ethylester (Butafenacil), 4-(l-t-Butyl)-N-(s-butyl)-2,6-dinitro- anilin (Butralin) 2-(l -Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l - oxo-butyl)-ρhenyl]-2-cyclohexen-l-on (Butroxydim), S-Ethyl-bis-(2-methyl- propyl)-thiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl-phenylsulf- onyl)- 1H- 1 ,2,4-triazol- 1 -carboxamid (Cafenstrole), (R)-N-Ethyl-2-[(phenyl- aminocarbonyl)-oxy]-propanamid (Carbetamide), 2-(4-Chlor-2-fluor-5-(2- chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-di- hydro-3H-l,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-l-(3- methoxy-4-nitro-phenoxy)-benzol (Chlomethoxyfen), 5-Amino-4-chlor-2- phenyl-3 (2H)-pyriazinon (Chloridazon), N-(4-Chlor-6-methoxy-pyrimidin-2- yl)-N'-(2-ethoxycarbonyl-phenylsulfonyl)-harnstoff (Clilorimuron-ethyl), 1 ,3,5-Trichlor-2-(4-nitro-phenoxy)-benzol (Chlornitrofen), N'-(3-Chlor-4- methyl-phenyl)-N,N-dimethyl-harnstoff (Chlorotoluron), N-(4-Methoxy-6- methyl- 1 ,3 ,5-triazin-2-yl)-N' -(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulf- uron), 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), Exo-l-methyl-4-iso- propyl-2-(2-methyl-phenyl-methoxy)-7-oxabicyclo-[2.2.1]-heptan (Cin- methylin), N-(4,6-Dimethoxy- 1 ,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)- phenylsulfonyl)-harnstoff (Cinosulfüron), 2-[l-[2-(4-Chlor-phenoxy)- propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclohexandion (Clefoxydim), (E,E)-(+)-2- [ 1 - [[(3 -Chlor-2-propenyl)-oxy] -imino] -propyl] -3 - hydroxy-2-cyclohexen-l-on (Clethodim), (R)-(2-Propinyl)-2-[4-(5-chlor-3- fluor-ρyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 2-[(2- Chlor-phenyl)-methyl]-4,4,-dimethyl-3-isoxazolidinone (Clomazone), 2-(2,4-Sodium salt (bispyribac-sodium), 5-bromo-6-methyl-3- (1-methyl-propyl) -2,4- (1H, 3H) pyrimidinedione (bromoacil), 2-bromo-3,3-dimethyl-N - (l-methyl-l-phenyl-ethyl) -butanamide (bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-0- (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-l (2H) -pyrintidinyl) -benzoic acid- [l, l-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil), 4- (lt-butyl) -N- (s- butyl) -2,6-dinitro-aniline (butraline) 2- (l-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3- (l-oxo-butyl) -phenyl] -2-cyclohexen-l-one (butroxydim), S-ethyl-bis- (2-methylpropyl) thiocarbamate (butylate), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulf- onyl) - 1H- 1, 2,4-triazole-1-carboxamide (cafenstrole), (R) -N-ethyl-2 - [(phenylaminocarbonyl) oxy] propanamide (carbetamide), 2- (4- Chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazole-3 -one (Carfentrazone-ethyl), 2,4-dichloro-1- (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 5-amino-4-chloro-2-phenyl-3 (2H) - pyriazinon (chloridazon), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) urea (clilorimuron-ethyl), 1, 3,5-trichlor-2 - (4-nitro-phenoxy) -benzene (chloronitrofen), N '- (3-chloro-4-methylphenyl) -N, N-dimethyl-urea ff (chlorotoluron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), 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 (cinidone -ethyl), exo-l-methyl-4-isopropyl-2- (2-methylphenyl-methoxy) -7-oxabicyclo- [2.2.1] -heptane (cinemethylin), N- (4, 6-Dimethoxy-1, 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 -Chlor-2-propenyl) -oxy] -imino] -propyl] -3 - hydroxy-2-cyclohexen-l-one (clethodim), (R) - (2-propynyl) -2- [4- (5- chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy-propanoate (Clodinafop-propargyl), 2 - [(2-chloro-phenyl) -methyl] -4,4, -dimethyl-3-isoxazolidinone (Clomazone ), 2- (2,4-
Dichlor-3-methyl-phenoxy)-N-ρhenyl-propanamid (Clomeprop), 3,6-Dichlor- pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5-ethoxy-7-fluor- [ 1 ,2,4]triazolo [ 1 , 5-c]pyrimidin-2-yl-sulfonyl)-amino] -benzoat (Cloransulam- methyl), N-[(2-Chlor-phenyl)-methyl]-N'-(l-methyl-l-phenyl-ethyl)-harn- stoff (Cumyluron), 2-CMor-4-ethylammo-6-(l-cyano-l-methyl-ethylamino)-Dichloro-3-methylphenoxy) -N-ρhenyl-propanamide (Clomeprop), 3,6-dichloropyridine-2-carboxylic acid (Clopyralid), methyl-3-chloro-2 - [(5-ethoxy-7-fluor - [1, 2,4] triazolo [1, 5-c] pyrimidin-2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl), N - [(2-chlorophenyl) methyl] -N '- (l-methyl-l-phenyl-ethyl) urea (cumyluron), 2-CMor-4-ethylammo-6- (l-cyano-l-methyl-ethylamino) -
1,3,5-triazin (Cyanazine), N-(4,6-Dime oxy-pyrimidin-2-yl)-N'-(2-cyclo- propylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(l -Ethox- iιrnnobutyl)-3-hydroxy-5-(tetiahyάio-2H-thiopyran-3-yl)-2-cyclohexen-l-on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propansäure- butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), N-[3- (Phenylaminocarbonyloxy)-phenyl]-carbamidsäure-O-ethylester (Desmedipham), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), 2,6-Dichlor-benzo- nitril (Dichlobenil), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop- P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop- methyl), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Diclosulam), l,2-Dimethyl-3,5-diphenyl-lH-pyr- azolium-methylsulfat (Difenzoquat), N-(2,4-Difluor-phenyl)-2-(3-trifluor- methyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), 2-[l-[(3,5-Difluor- phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3-carbonsäure (Diflufen- zopyr), N'-[3-Chlor-4-(5-t-butyl-oxo-l,3,4-oxadiazol-3(2H)-yl)-ρhenyl]-N,N- dimethyl-harnstoff (Dimefuron), S-(l-Methyl-l-phenyl-ethyl)-l-piperidin- carbothioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-methoxy- ethyl)-acetamid (Dimethachlor), N-(l,2-Dimethyl-propyl)-N'-ethyl-6-methyl- thio-l,3,5-triazin-2,4-diamin (Dimethametryn), (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-(l-methyl-2-(3,5-dimethyl-phenoxy)- ethylamino)-l,3,5-triazin (Dimexyflam), 6,7-Dihydro-dipyrido[l,2-a:2',l '-c]- pyrazindiium dibromide (Diquat-dibromide), S,S-Dimethyl-2-difluormethyl- 4-i-butyl-6-trifluormethyl-pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Di- chlor-phenyl)-N,N-dimethyl-harastoff (Diuron), N-(4-Methyl-phenyl)-N'-(l- methyl- l-phenyl-ethyl)-harnstoff (Dymron, Daimuron), S-Ethyl-dipropylthio- carbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l ,2-dimethyl-propyl)-thio- carbamat (Esprocarb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-dh itro-4-tri- fluormethyl-benzenamin (Ethalfluralin), Methyl-2-[[[[(4-ethoxy-6-methyl- amino-l,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulfonyl]-benzoate (Etha- metsulfuron-methyl), 2-Ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofüranyl- methansulfonat (Ethofumesate), (S)-(2-Ethoxy- 1 -methyl-2-oxoethyl)-2-chlor- 5-(2-chlor-4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimeth- oxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), N-(2,3-Dichlor-phenyl)-4-ethoxymethoxy-benzamid (Etobenzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxa- prop-(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)-D-alaninat (Flamprop-M-isopropyl), Methyl-N- benzoyl-N-(3-chlor-4-fluor-phenyl)-D-alaninat (Flamprop-M-methyl), N- [[(4,6-Dimethoxy-2-pyrirm^inyl)-amino]-carbonyl]-3-trifluormethyl-2-pyri- dinsulfonamid (Flazasulfüron), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-1,3,5-triazine (cyanazines), N- (4,6-dime oxy-pyrimidin-2-yl) -N '- (2-cyclo- propylcarbonyl-phenylsulfonyl) urea (cyclosulfamuron), 2- (l-ethoxy-i-amnobutyl) -3-hydroxy-5- (tetiahyάio-2H-thiopyran-3-yl) -2-cyclohexen-l-one (cycloxydim), ( R) -2- [4- (4-Cyano-2-fluorophenoxy) phenoxy] propanoic acid butyl ester (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D), N- [ 3- (Phenylaminocarbonyloxy) -phenyl] -carbamic acid-O-ethyl ester (Desmedipham), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 2,6-dichloro-benzonitrile (dichlobenil), (R) - 2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2nd , 6-dichlorophenyl) -5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3 , 5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2 - [l - [(3,5-difluorophenyl) aminocarbonylhydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), N '- [3-chloro-4- (5-t -butyl-oxo-l, 3,4-oxadia zol-3 (2H) -yl) -ρhenyl] -N, N-dimethylurea (dimefuron), S- (l-methyl-l-phenyl-ethyl) -l-piperidinecarbothioate (dimepiperate), 2-chlorine -N- (2,6-dimethyl-phenyl) -N- (2-methoxy-ethyl) -acetamide (dimethachlor), N- (1,2-dimethyl-propyl) -N'-ethyl-6-methyl-thio -l, 3,5-triazine-2,4-diamine (dimethametryn), (S-) 2-chloro-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-triazine (dimexyflam), 6,7-dihydro-dipyrido [l, 2-a: 2 ', l' -c] - pyrazinediium dibromide (diquat-dibromide), S, S-dimethyl -2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-di-chlorophenyl) -N, N-dimethyl-hara material (diuron ), N- (4-methyl-phenyl) -N '- (l-methyl-l-phenyl-ethyl) -urea (Dymron, Daimuron), S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thio-carbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -2,6-ie itro-4-tri - fluo rmethyl-benzenamine (ethalfluralin), methyl-2 - [[[[((4-ethoxy-6-methylamino-l, 3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] -benzoates (ethametsulfuron-methyl), 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofüranyl methanesulfonate (ethofumesate), (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), N- (2,3-dichlorophenyl) -4-ethoxymethoxy-benzamide (etobenzanide), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy ] -propanoate (fenoxaprop- (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-fluorophenyl) -D-alaninate (Flamprop-M-isopropyl), methyl-N-benzoyl-N- (3-chloro-4- fluoro-phenyl) -D-alaninate (Flamprop-M-methyl), N- [[(4,6-dimethoxy-2-pyriramininyl) amino] carbonyl] -3-trifluoromethyl-2-pyridinesulfonamide ( Flazasulfüron), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy-
[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Tri- fluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure-butylester (Fluazifop-P- butyl), 5-(4-Brom- 1 -methyl-5-trifluormethyl- lH-pyrazol-3 -yl)-2-chlor-4- fluor-benzoesäure-i-propylester (Fluazolate), N-(4-Fluor-phenyl)-N-i-propyl- 2-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), Ethyl-[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-P-butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid- i-propyl ester (fluazolate), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), ethyl
[2-Chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoπnethyl-l(6H)-pyridazinyl)- phenoxyj-acetate (Flufenpyr), N-(2,6-Difluor-phenyl)-5-methyl- 1 ,2,4-tri- azolo[ 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-l,4- benzoxazin-6-yl]-4,5,6,7-tetrahydro- lH-isoindol- 1 ,3-dion (Flumioxazin), 2- [4-Chlor-2-fluor-5-[(l-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro- lH-isoindol-l,3(2H)-dion (Flumipropyn), N,N-Dimethyl-N'-(3-trifluor- methyl-phenyl)-harnstoff (Fluometuron), 3-Chlor-4-chlormethyl-l-(3-trifluor- methyl-phenyl)-2-pyπolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluor- methyl-phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)- 5-phenyl- 1H- 1 ,2,4-triazol-3 -carboxamid (Flupoxam), 1 -Isopropyl-2-chlor-5- (3,6-dmydro-3-methyl-2,6-dioxo-4-tiifluoπnethyl-l(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6- trifluoπnethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfbron- methyl-sodium), 9-Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino- 3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-l-methyl-ethyl- ester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methyl- amino-2-phenyl-4-(3 -trifluormethyl-phenyl)-3 (2H)-füranon (Flurtamone), 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 (Fome- safen), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]- sulfonyl]-4-foιτnylamino-N,N-dimethyl-benzamid (Foramsulfuron), 2- Amino-4-(hydrox5 ιethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmonium- salz), (Glyphosate, -isopropylammonium), Methyl-3-chloro-5-[[[[(4,6-di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-l-methyl-lH- pyrazol-4-carboxylate (Halosulfüron-methyl), (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-l-methyl-l,3,5-triazin-2,4(lH,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imid- azol-2-yl)-4-methyl-benzoat (hnazamethabenz-methyl), 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)-5-methyl-pyridin-3-carbonsäure (Imazapic), 2-(4,5-Dihydro-4- methyl-4-(i-propyl)-5-oxo-lH-imidazol-2-yl)-3-pyridincarbonsäure (hnaza- pyr), 2-(4,5-Dihydro-4-memyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-chino- lin-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-Di- methoxy-pyrimidin-2-yl)-N'-(2-chlor-imidazo [ 1 ,2-a] -pyridin-3 -yl-sulfonyl)- ha nstoff (Imazosulfüron), 2-[2-(3-Chlor-phenyl)-oxiranylmethyl]-2-ethyl- lH-inden-l,3(2H)-dion (Indanofan), N-(4-Methoxy-6-methyl-l,3,5-triazin-2- yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz[2-chloro-4-fluoro-5- (5-methyl-6-oxo-4-trifluoromethyl-l (6H) pyridazinyl) phenoxyj-acetate (flufenpyr), N- (2,6-difluorophenyl) -5-methyl-1, 2,4-tri-azolo [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-lH-isoindole-1,3-dione (flumioxazin), 2- [4- Chloro-2-fluoro-5 - [(l-methyl-2-propynyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-lH-isoindole-1,3 (2H) -dione (flumipropyn) , N, N-Dimethyl-N '- (3-trifluoromethyl-phenyl) urea (fluometuron), 3-chloro-4-chloromethyl-l- (3-trifluoromethyl-phenyl) -2-pyπolidinone (fluorochloridone ), 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), l- (4-chloro-3- (2,2,3,3,3 -pentafluoropropoxymethyl) phenyl) - 5-phenyl-1H-1, 2,4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5- (3,6-dmydro-3-methyl -2,6-dioxo-4 -tiifluoromethyl-1 (2H) -pyrimidyl) -benzoate (flupropacil), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl- sulfonyl) urea sodium salt (flupyrsulfbrone) 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-ethyl-ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methyl-amino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -foranone (flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-lH, 3H- [l, 3,4] -thiadiazolo- [3,4-a] -pyridazine - 1 -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-foιτnylamino-N, N-dimethyl-benzamide (foramsulfuron), 2-amino-4- (hydrox5 ιethylphosphinyl) -butanoic acid (-ammonium salt) (glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium), methyl-3-chloro-5 - [[[( 4,6-di-methoxy-2-pyrimidinyl) -amino] -carbonyl] -amino] -sulfonyl] -l-methyl-1H-pyrazole-4-carboxylate (halosulfuron-methyl), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy) phenoxy] propanoic acid (methyl ester, -2-ethoxy ethyl ester, butyl ester) (haloxyfop, methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-l-methyl-l, 3,5-triazine-2,4 (lH, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -4-methyl-benzoate (hnazamethabenz-methyl), 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-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (Imazapic), 2- (4,5-dihydro-4-methyl-4- (i-propyl) -5- oxo-lH-imidazol-2-yl) -3-pyridinecarboxylic acid (hnaza- pyr), 2- (4,5-dihydro-4-memyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) - quino-lin-3-carboxylic acid (imazaquine), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxolH-imidazol-2-yl) -5-ethyl-pyridin-3 -carboxylic acid (imazethapyr), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-chloro-imidazo [1, 2-a] -pyridin-3-yl-sulfonyl) - ha nstoff (Imazo sulfüron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3, (2H) -dione (indanofan), N- (4-methoxy-6-methyl- 1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt
(Iodosulfüron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (loxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(5-t-Butyl- 3 -isoxazolyι)-N',N' -dimethylharnstoff (Isouron), N-(3 -( 1 -Ethyl- 1 -methyl- propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2- metlιylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlor- tole), (5 -Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl- phenyl)-methanon (Isoxaflutole), 2-[(2,3-Dihydro-5,8-dimethyl-l,l,-dioxido- spiro[4H-l-benzothiopyran-4,2'-[l,3]-dioxolan-6-yl)-carbonyl]-l,3-cyclo- hexan-dion (Ketospiradox), (2-Ethoxy- 1 -methyl-2-oxo-ethyl)-5-(2-chlor-4- trifluormethyl-phenoxy)-2-nitro-benzoat (Lactofen), 3-Cyclohexyl-6,7-di- hydro-lH-cyclopentapyrimidin-2,4-(3H,5H)-dion (Lenacil), N'-(3,4-dichlor- phenyl)-N-methoxy-N-methyl-harnstoff (Linuron), (4-Chlor-2-methyl-phen- oxy)-essigsäure (MCPA), (R)-2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop-P), 2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulf- onyl]-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-N-(2,6-dimethyl-phenyl)-N-(lH-pyrazol-l-yl-methyl)-acetamid (Metazachlor), N-(2-Benzthiazolyl)-N,N'-dimethyl-harnstoff (Methabenzthiaz- uron), N'-(4-Brom-phenyl)-N-methoxy-N-methylharnstoff (Metobromuron),(Iodosulfüron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (loxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (5-t-butyl-3-isoxazolyι) -N', N '-dimethylurea (isouron), N- ( 3 - (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazole -4-yl) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2 - [(2,3- Dihydro-5,8-dimethyl-l, l, -dioxido- spiro [4H-l-benzothiopyran-4,2 '- [l, 3] -dioxolan-6-yl) -carbonyl] -l, 3-cyclo- hexanedione (ketospiradox), (2-ethoxy-1-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), 3-cyclohexyl- 6,7-di-hydro-lH-cyclopentapyrimidine-2,4- (3H, 5H) -dione (Lenacil), N '- (3,4-dichlorophenyl) -N-methoxy-N-methyl-urea ( Linuron), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (R) -2- (4-chloro-2-methylphenoxy) propionic acid (Mecoprop-P), 2- ( 2-Benzthiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 2 - [[[(4,6-dimethoxy-2-pyrimide inyl) 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- (2nd , 6-dimethyl-phenyl) -N- (1H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N- (2-benzothiazolyl) -N, N'-dimethyl-urea (methabenzthiazuron), N '- (4-bromophenyl) -N-methoxy-N-methylurea (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- 1 ,2,4-triazolo[l ,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-(S) -2-chloro-N- (2-ethyl-6-methylphenyl) -N- (2-methoxy-l-methyl-ethyl) - acetamide (metolachlor, S-metolachlor), N- ( 2,6-dichloro-3-methylphenyl) - 5,7-dimethoxy-1, 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-l, 2,4-triazin-5 (4H) -one (metribuzin) , N- (4-
Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulf- onyl)-harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1-carbo- thioat (Molinate), 2-(2-Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N,N-Diethyl-2-(l-naphthalenyloxy)-propanamide (Napropamide), N-Butyl- N'-(3,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy- pyrimidm-2-yl)-N'-(3-dime ylcarbamoyl-pyrimn-2-yl-sulfonyl)-harnstoff (Nicosulfüron), 4-CMor-5-methylamino-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)-l,3,4- oxadiazol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2-yι)-N'-(2-ox- etan-3 -yl-oxycarbonyl-phenylsulfonyl)-harnstof (Oxasulfuron), 3 -[ 1 -(3 ,5-Di- chlor-phenyl)-l-i-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), 1-Amino-Methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-lH-azepin-1 -carbothioate (Molinate), 2- (2-naphthyloxy) -N-phenyl-propanamide (naproanilide), N, N-diethyl-2- (l-naphthalenyloxy) -propanamide (napropamide), N-butyl-N ' - (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxypyrimidm-2-yl) -N '- (3-dime ylcarbamoyl-pyrimn-2-yl sulfonyl) urea (Nicosulfuron), 4-CMor-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) -pyridazinone (norflurazone), S- (2-chlorobenzyl) -N, N-diethyl-thiocarbamate ( Orbencarb), 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-methylethoxy) phenyl] -5- (t-butyl) -l, 3,4- oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin-2-yι) -N '- (2-ox-etan-3 -yl-oxycarbonyl-phenylsulfonyl) -urea (oxasulfuron ), 3 - [1 - (3,5-di-chlorophenyl) -li-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), 1,1 '-dimethy 1-4,4' -bipyridinium (paraquat), 1- 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), 2-(2,2-Di- fluoremoxy)-N-(5,8-dimemoxy[l,2,4]triazolo[l,5-c]pyrimidin-2-yl)-6-tri- fluormethyl-benzensulfonamid (Penoxsulam), 3-(4-Chlor-5-cyclopentyloxy- 2-fluor-phenyl)-5-(l-methyl-ethyliden)-2,4-oxazolidin-dion (Pentoxazone), 2-N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (1-ethyl-propyl) -2,6-dinitro -benzenamine (pendralin), 2- (2,2-di-fluoroemoxy) -N- (5,8-dimemoxy [1,2,4] triazolo [1,5-c] pyrimidin-2-yl) -6- trifluoromethyl-benzenesulfonamide (penoxsulam), 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5- (l-methyl-ethylidene) -2,4-oxazolidinedione (pentoxazone), 2-
Chlor-N-(2-ethoxy-ethyl)-N-(2-methyl- 1 -phenyl- 1 -propenyl)-acetamid (Peth- oxamid), N-[3-(3-Methyl-phenylaminocarbonyloxy)-phenyl]-carbamidsäure- O-methylester (Phenmedipham), 4-Amino-3,5,6-trichlor-pyridin-2-carbon- säure (Picloram), N-(4-Fluor-phenyl)-6-(3 -trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen), S-[2-(2-Methyl-l-piperidinyl)-2-oxo-ethyl]-O,O- dipropyl-phosphorodithioat (Piperophos), 2-Chlor-N-(2,6-diethyl-phenyl)-N- (2-propoxy-ethyl)-acetamid (Pretilachlor), N-(4,6-Bis-difluormethoxy-pyri- midin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Primisulf- uron-methyl), l-Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)-6-fluor-tetrahydro-l,3- dioxo-lH-pyπolo[l,2-c]imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Pro- fluazol), 2-[l-[[2-(4-Chlor-phenoxy)-propoxy]-imino]-butyl]-3-hydroxy-5- (tetrahydro-2H-thiopyranyl)-2-cyclohexen-l-on (Profoxydim), N,N'-Bis-i- propyl-6-methylthio-l,3,5-triazm-2,4-diamin (Prometryn), 2-Chlor-N-iso- propyl-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- 1H- 1 ,2,4-triazol- 1 -yl)-carbonyl]- aιnino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone- sodium), 3,5-Dichlor-N-(l,l-dimethyl-2-propinyl)-benzamid (Propyzamide), S-Phenylmethyl-N,N-dipropyl-thiocarbamat Prosulfocarb), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)-phenylsulfonyl)-harn- stoff (Prosulfuron), l-(3-Chlor-4,5,6,7-tetrahydropyrazolo[l,5-a]pyridin-2- yl)-5-(methyl-2-propinylamino)- lH-pyrazol-4-carbonitril (Pyraclonil), Ethyl- [2-chlor-5-(4-chlor-5-difluormethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluor- phenoxyj-acetat (Pyraflufen-ethyl), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-5-Chloro-N- (2-ethoxy-ethyl) -N- (2-methyl-1-phenyl-1-propenyl) acetamide (peth-oxamide), N- [3- (3-methyl-phenylaminocarbonyloxy) phenyl] -carbamic acid- O-methyl ester (phenmedipham), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N- (4-fluorophenyl) -6- (3-trifluoromethyl- phenoxy) pyridine-2-carboxamide (picolinafen), S- [2- (2-methyl-1-piperidinyl) -2-oxo-ethyl] -O, O-dipropyl phosphorodithioate (Piperophos), 2-chloro-N - (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bis-difluoromethoxy-pyrimidin-2-yl) -N '- ( 2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), l-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l, 3- dioxo-lH-pyπolo [l, 2-c] imidazole-2 (3H) -yl] -phenyl] methanesulfonamide (pro-fluazole), 2- [l - [[2- (4-chlorophenoxy) propoxy ] -imino] -butyl] -3-hydroxy-5- (tetrahydro-2H-thiopyranyl) -2-cyclohexen-l-one (profoxydim), N, N'-bis-i-propyl-6-methylthio-l, 3,5-triazm-2,4-diamine (Prometryn), 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-1H- 1, 2,4-triazole-1 -yl) -carbonyl] - aιnino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarbazone-sodium), 3,5-dichloro-N- (l, l-dimethyl-2- propynyl) benzamide (propyzamide), S-phenylmethyl-N, N-dipropyl-thiocarbamate prosulfocarb), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- ( 2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (prosulfuron), l- (3-chloro-4,5,6,7-tetrahydropyrazolo [1,5-a] pyridine-2 - yl) -5- (methyl-2-propynylamino) - 1H-pyrazole-4-carbonitrile (pyraclonil), ethyl- [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole -3-yl) -4-fluorophenoxyj-acetate (pyraflufen-ethyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-5-
(4-methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), N-(4,6-Dimethoxy-pyri- midin-2-yl)-N'-(4-ethoxycarbonyl-l-methyl-ρyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-5-( henylcarb- onylmethoxy)-pyrazol (Pyrazoxyfen), Diphenylmethanon-O-[2,6-bis-(4,6-di- methoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxim (Pyribenzoxim), O[3-(l,l-Di- methyl-ethyl)-phenyl]-(6-methoxy-2-pyridinyl)-methylthiocarbamat (Pyri- buticarb), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol), 0-(6-Chlor-3-phenyl- pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl-pyridazin- 4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-ρyrimidinyl)-thio]-3-methyl-l(3H)-iso- benzofüranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoe- säure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimi- din-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor- chinolin-8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbon- säure (Quimnerac), 2-τ mino-3 -chlor- 1,4-naphthalindion (Quinoclamine), (R)-2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, - tetrahydro-2-füranyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4, 6-Dimethoxy-pyrimidin-2-yl)-N'-(3 -ethylsulfonyl-pyridin-2-yl- sulfonyι)-harnstoff (Rimsulfüron), 2-(l-Ethoximinobutyl)-5-(2-ethylthio- propyl)-3-hydroxy-2-cyclohexen-l-on (Sethoxydim), 6-Chlor-2,4-bis-ethyl- amino-l,3,5-triazin (Simazine), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclo- hexan-l,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino- phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- 1 ,2,4-triazol-3-on (Sulfen- trazone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidmyl)-amino]-carbonyl]- amino]-sulfonyl]-benzoate (Sulfometuron-methyl), N-Phosphonomethyl- glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(2-e1iιylsulfonyl-imidazo[l,2-a]pyridin-3-sulfonamid (Sulfosulfüron), N-(4-methylphenylsulfonyloxy) pyrazole (pyrazolates), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1-methyl-ρyrazol-5-yl-sulfonyl ) urea (pyrazosulfuron-ethyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-5- (henylcarbonylmethoxy) pyrazole (pyrazoxyfen), diphenylmethanone-O- [2,6-bis - (4,6-dimethoxypyrimidin-2-yloxy) benzoyl] oxime (pyribenzoxime), O [3- (l, l-dimethylethyl) phenyl] - (6-methoxy -2-pyridinyl) methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), 0- (6-chloro-3-phenylpyridazin-4-yl) -S-octyl- thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-ρyrimidinyl) thio] -3-methyl-l (3H) -iso - methyl benzofüranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimi- din-2-ylthio) -benzoic acid sodium salt (Pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quimnerac), 2-τ mino-3 -chloro-1,4-naphthalenedione (quinoclamine), (R) -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-sulfonyι) urea ( Rimsulfüron), 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-1, 2,4-triazol-3-one (sulfenetrazone), methyl 2 - [[[(4,6-dimethyl- 2-pyrimidmyl) -amino] -carbonyl] - amino] -sulfonyl] -benzoate (sulfometuron-methyl), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (2-e1iιylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), N-
(5-t-Butyl-l,3,4-thiadiazol-2-yl)-N,N,-dimethyl-harnstoff (Tebuthiuron), 2-[l- [(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H- pyran-4-yl)-2-cyclohexen- 1 -on (Tepraloxydim), 6-Chlor-4-ethylamino-2-t- butylamino- 1 ,3 ,5-triazin (Terbuthylazine), 2-t-Butylamino-4-ethylamino-6- methylthio-l,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6-dimethyl-ρhenyl)-N-(3- methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5- dihydro-t azol-2-yl)-4-(2-methyl-propyl)-6-trifluormethyl-pyridin-3-carbon- säure-methylester (Thiazopyr), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)- N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron- methyl), S-Phenylmethyl-bis-s-butyl-carbamothioate (Tiocarbazil), 2-(Ethox- inιino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-l-on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamotbioat (Tri- allate), 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)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)-pyridin-2-yl-oxy-essigsäure (Triclopyr), 2- (3,5-Dichlor-phenyl)-2-(2,2,2-trichlor-ethyl)-oxiran (Tridiphane), N-[[(4,6- Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyri- dinsulfonamid-Natriumsalz (Trifloxysulfüron), l-Amino-2,6-dinitro-N,N-di- propyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamήιo-6-(2,2,2- trifluor-ethoxy)-l,3,5-triazin-2-yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Triflusulfuron-methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5-1ri- azin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), N- [[(4,6-Dimethoxy-2-pyrintidinyl)-ammo]-carbonyl]-3-(N-methyl-N-methyl- sulfbnyl-amino])-2-pyridinsulfonamid, (vgl. WO-A-92/10660), N-[[(4,6-Di- me oxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl- amino)-2-ρyridinsulfonamid, (vgl. WO-A-92/10660), 4-(4,5-Dihydro-4- methyl-5-oxo-3-trifluoιmιemyl-lH-l,2,4-triazol-l-yl)-2-(ethylsulfonylamino)- 5-fluor-benzolcarbothioamid (HWH4991, vgl. WO-A-95/30661), 2-Chlor-N- [l-(2,6-dichlor-4-difluormethyl-phenyl)-4-nitro-lH-pyrazol-5-yl]-propan- carbonsäureamid (SLA5599, vgl. EP-A-303153), [2-Chlor-3-(4,5-dihydro-3- isoxazolyl)-4-methylsulfonyl-phenyl]-(5-hydrox-l-methyl-lH-pyrazol-4-yl)- methanon (vgl.WO-A-96/26206, WO-A-98/31681), [3-(4,5-Dihydro-3-isox- azolyl)-2-methyl-4-methylsulfonyl-phenyl] -(5 -hydrox- 1 -methyl- 1 H-pyrazol- 4-yl)-methanon (vgl.WO-A-96/26206, WO-A-98/31681), [3-[2-Chlor-3[(2,6- dioxo-cyclohexyl)-carbonyl]-6-ethylsulfonyl-phenyl]-5-isoxazolyl]-acetonitril(5-t-Butyl-l, 3,4-thiadiazol-2-yl) -N, N , -dimethyl-urea (tebuthiuron), 2- [l- [(3-chloro-2-propenyl) -oxy- imino] -propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1-one (tepraloxydim), 6-chloro-4-ethylamino-2-t-butylamino-1 , 3, 5-triazine (terbuthylazine), 2-t-butylamino-4-ethylamino-6-methylthio-l, 3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethyl-ρhenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-t azol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) - N '- (2-methoxycarbonyl- thien-3-yl-sulfonyl) -urea (thifensulfuron-methyl), S-phenylmethyl-bis-s-butyl-carbamothioate (tiocarbazil), 2- (ethoxynoxypropyl) -3-hydroxy-5- (2, 4,6-trimethyl-phenyl) -2-cyclohexen-l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) -diisopropylcarbamotbioat (triallate), N- (4-methoxy- 6-methyl-l, 3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (T. riasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3, 5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl), ( 3,5,6-trichloro-pyridin-2-yl-oxyacetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloroethyl) oxirane ( Tridiphanes), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfurone), l-amino-2,6-dinitro-N, N-di-propyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamήιo-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, 3,5-1-riazine- 2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), N- [[(4,6-dimethoxy-2-pyrintidinyl) -ammo] carbonyl] -3- (N-methyl- N-methylsulfonylamino]) - 2-pyridinesulfonamide, (cf. WO-A-92/10660), N - [[(4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonyl- amino) -2-ρyridinsulfonamid, (see WO-A-92/10660), 4- (4,5-dihydro-4-methyl-5-oxo-3-trifluoιmιemyl-lH-l, 2,4-triazole- l-yl) -2- (ethylsulfonylamino) - 5-fluoro-benzenecarbothioamide (HWH4991, see WO-A-95/30661), 2-chloro-N- [l- (2,6-dichloro-4-difluoromethyl- phenyl) -4-nitro-1H-pyrazol-5-yl] propane carboxamide (SLA5599, see EP-A-303153), [2-chloro-3- (4,5-dihydro-3-isoxazolyl) - 4-methylsulfonylphenyl] - (5-hydrox-l-methyl-1H-pyrazol-4-yl) - methanone (see WO-A-96/26206, WO-A-98/31681), [3- ( 4,5-dihydro-3-isoxazolyl) -2-methyl-4-methylsulfonyl-phenyl] - (5-hydrox-1-methyl-1 H-pyrazol-4-yl) -methanone (see WO-A -96/26206, WO-A-98/31681), [3- [2-chloro-3 [(2,6-dioxo-cyclohexyl) carbonyl] -6-ethylsulfonylphenyl] -5-isoxazolyl] acetonitrile
(vgl. WO-A-01/28341), 2-[2-Chlor-4-methylsulfonyl-3-[(2,2,2-trifluor-eth- oxy)-methyl]-benzoyl]-l,3-cyclohexandion (vgl. WO-A-01/28341), 2-[[5,8- Dimethyl- 1 , 1 -dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6- yl]-carbonyl]-l,3-cyclohexandion (vgl. WO-A-01/28341)(cf. WO-A-01/28341), 2- [2-chloro-4-methylsulfonyl-3 - [(2,2,2-trifluoro-ethoxy) methyl] benzoyl] -l, 3- cyclohexanedione (see WO-A-01/28341), 2 - [[5,8-dimethyl-1,1-dioxido-4- (2-pyrimidinyloxy) -3,4-dihydro-2H-thiochromen-6-yl ] -carbonyl] -l, 3-cyclohexanedione (see WO-A-01/28341)
("Wirkstoffe der Gruppe (2)"),("Active substances of group (2)"),
und/oderand or
(c) gegebenenfalls eine die Kulturpflanzen-Nerträglichkeit verbessernde(c) if appropriate, an improvement of the crop plant tolerance
Verbindung aus der folgenden Gruppe von Verbindungen:Connection from the following group of connections:
4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1-Dichloracetyl-hexa- hydro-3,3,8a-trimethylρyπolo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), 4- Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor), 4-4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexa- hydro-3,3,8a-trimethylpyπolo [1,2-a] pyrimidine-6 (2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 4-
Carboxy-3,4-dihydro-2H-l-benzopyran-4-essigsäure (CL-304415), 5-Chlor- chinolin-8-oxy-essigsäure-(l -methyl-hexylester) (Cloquintocet-mexyl), α- (Cyanomethoximino)-phenylacetonitril (Cyometrinil), 2,4-Dichlor-phenoxy- essigsäure (2,4-D), 2,2-Dichlor-Ν-(2-oxo-2-(2-propenylamino)-ethyl)-Ν-(2- propenyl)-acetamid (DKA-24), 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Di- chlormid), N-(4-Methyl-phenyl)-N'-(l -methyl- 1 -phenyl-ethyl)-harnstoff (Daimuron, Dymron), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), l-(2,4- DicMor-phenyl)-5-trichlormethyl-lH-l,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-füranyl)-2,2-dimethyl- oxazolidin (Furilazole, MON-13900), Ethyl-4,5-dihydro-5,5-diphenyl-3-is- oxazolcarboxylat (Isoxadifen-ethyl), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (+-)-2-(4-Chlor-2-methyl-phenoxy)-propansäure (Mecoprop), Di- ethyl-l-(2,4-dichlorphenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarb- oxylat (Mefenpyr-diethyl) 2-Dichlormethyl-2-methyl-l,3-dioxolan (MG-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415), 5-chloro-quinoline-8-oxy-acetic acid (1-methylhexyl ester) (Cloquintocet-mexyl), α- (Cyanomethoximino) phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,2-dichloro-Ν- (2-oxo-2- (2-propenylamino) ethyl) - Ν- (2-propenyl) acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methylphenyl) -N ' - (l-Methyl-1-phenyl-ethyl) urea (Daimuron, Dymron), 4,6-dichloro-2-phenyl-pyrimidine (Fenclorim), 1- (2,4-DicMor-phenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid -ethyl ester (fenchlorazol-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-foranyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl-3 -is-oxazole carboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (+ -) - 2- (4-chloro-2-methylphenoxy) propanoic acid (mecoprop) , Diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxoxide (mefenpyr-diethyl) 2-dichloromethyl-2-methyl-l , 3-dioxolane (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-ox- azolidin (R-29148), N-Cyclopropyl-4-[[(2-methoxy-5-methyl-benzoyl)- amino]-sulfonyl]-benzamid, N-[[(4-Methoxyacetylamino)-phenyl]-sulfonyl-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-trimethyl-oxazolidine (R-29148), N-cyclopropyl-4 - [[(2-methoxy -5-methyl-benzoyl) - amino] sulfonyl] benzamide, N - [[(4-methoxyacetylamino) phenyl] sulfonyl-
2-methoxy-benzamid und N-[[(4-Methylaminocarbonylamino)-phenyl]-sulf- onyl-2-methoxy-benzamid (letztere jeweils bekannt aus WO-A-99/66795), (3- Oxo-isochroman-4-ylidenmethoxy)-essigsäure-methylester und (3-Oxo-lH-2- benzothiopyran-4-(3H)-ylidenmethoxy)-essigsäure-methylester (letztere jeweils bekannt aus WO-A-98/13361), l-Ethyl-4-hydroxy-3(lH-tetrazolyl-5- yl-carbonyl)-2(lH)-chinolin (bekannt aus WO-A-99/00020)2-methoxy-benzamide and N - [[(4-methylaminocarbonylamino) phenyl] sulfonyl-2-methoxy-benzamide (the latter in each case known from WO-A-99/66795), (3-oxo-isochroman-4 -ylidemethoxy) -acetic acid methyl ester and (3-oxo-1H-2-benzothiopyran-4- (3H) -ylidemethoxy) -acetic acid methyl ester (the latter is known from WO-A-98/13361), l-ethyl-4 -hydroxy-3 (1H-tetrazolyl-5-yl-carbonyl) -2 (1H) -quinoline (known from WO-A-99/00020)
("Wirkstoffe der Grappe (3)").("Active substances of the Grappe (3)").
2. Mittel gemäß Ansprach 1, dadurch gekennzeichnet, dass2. Means according spoke 1, characterized in that
n für die Zahl 0 steht,n stands for the number 0,
A für Alkandiyl (Alkylen) mit 1 bis 5 Kohlenstoffatomen oder Alkendiyl mit 2 bis 5 Kohlenstoffatomen steht, Ar für jeweils gegebenenfalls substituiertes Phenyl oder Naphthyl, oder für jeweils gegebenenfalls substituiertes Heterocyclyl aus der Reihe Furyl, Tetrahydrofbryl, Thienyl, Tetrahydrothienyl, Benzofüryl, Di- hydrobenzofuryl, Benzothienyl, Pyπolyl, Pyrazolyl, Pyranyl, Benzo- pyranyl, Dihydrobenzopyranyl, Tetrahydrobenzopyranyl, Pyridinyl, Chinolinyl oder Pyrimidinyl steht,A represents alkanediyl (alkylene) with 1 to 5 carbon atoms or alkenediyl with 2 to 5 carbon atoms, Ar for each optionally substituted phenyl or naphthyl, or for each optionally substituted heterocyclyl from the series furyl, tetrahydrofbryl, thienyl, tetrahydrothienyl, benzofüryl, dihydrobenzofuryl, benzothienyl, pyolyl, pyrazolyl, pyranyl, benzopyranyl, dihydrozopyryl, pyridylbenzyryl, pyridylbenzyrenyl Quinolinyl or pyrimidinyl,
wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Aufzählung zu entnehmen sind:where the respective possible substituents can preferably be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i- Propylthio, n-, i-, s- oder t-Butylthio, Difluormethylthio, Trifluor- methylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i- Propylsulfonyl, Trifluormethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Di- ethyl-amino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl,Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, Methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-but- or t-butyl Dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl,
Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino- carbonyl, Diethylaminocarbonyl, Dimethylaminosulfonyl, Diethyl- aminosulfonyl,Ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl,
R1 für gegebenenfalls durch Fluor, Chlor und oder Brom substituiertes Alkyl mit 1 bis 5 Kohlenstoffatomen, für gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Alkenyl mit 2 bis 5 Kohlenstoffatomen, für gegebenenfalls durch Fluor, Chlor und/oder Brom oder d-C4-R 1 for alkyl with 1 to 5 carbon atoms optionally substituted by fluorine, chlorine and or bromine, for alkenyl with 2 to 5 carbon atoms optionally substituted with fluorine, chlorine and / or bromine, for optionally substituted with fluorine, chlorine and / or bromine or dC 4 -
Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor und oder Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoff- atomen in der Arylgrappe und gegebenenfalls 1 bis 3 Kohlenstoffatomen im Alkylteil, oder für gegebenenfalls durch Nitro, Cyano, Fluor, Chlor und/oder Brom,Alkyl substituted cycloalkyl with 3 to 6 carbon atoms, for each optionally by nitro, cyano, fluorine, chlorine and or bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 3 carbon atoms in the alkyl part, or for optionally by nitro, cyano, fluorine, chlorine and / or Bromine,
Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy,Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,
Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Heterocyclyl mit 5 Kohlenstoffatomen und 1 bis 3 Stickstoffatomen und/oder 1 oder 2 Sauerstoff- oder Schwefelatomen steht,Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted heterocyclyl having 5 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,
R2 für Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substi- tuiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy oder n- oder i-Propoxy steht,R 2 for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each methyl, ethyl, n- or i-propyl, meth- or ethoxy or n- or i- substituted by fluorine, chlorine and / or bromine. Propoxy stands,
R für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor oder Brom steht,R represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine,
für eine der nachstehend skizzierten Gruppierungen steht,represents one of the groupings outlined below,
(Z1) (Z2) R4 für Wasserstoff, Amino oder gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl oder n- oder i-Propyl steht,(Z 1 ) (Z 2 ) R 4 represents hydrogen, amino or methyl, ethyl or n- or i-propyl which is optionally substituted by fluorine, chlorine and / or bromine,
R5 für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl, Ethoxycarbonyl oder n- oder i-Propoxycarbonyl steht,R 5 represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl or n- or i-propoxycarbonyl optionally substituted by fluorine, chlorine and / or bromine,
R6 für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durchR 6 represents hydrogen, fluorine, chlorine, bromine or in each case, if appropriate
Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl oder n- oder i-Propyl steht,Fluorine, chlorine and / or bromine is substituted methyl, ethyl or n- or i-propyl,
R für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils gegebenen- falls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-R represents hydrogen, cyano, fluorine, chlorine, bromine or in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-
Propoxy, n-, i-, s- oder t-Butoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino mit jeweils 1 bis 3 Kohlenstoffatomen in den Alkylgruppen steht,Propoxy, n-, i-, s- or t-butoxy substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 3 carbon atoms in the alkyl groups,
R8 für Wasserstoff oder jeweils gegebenenfalls durch Cyano, Fluor,R 8 represents hydrogen or in each case optionally by cyano, fluorine,
Chlor, Brom oder Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Alkyl, Alkoxy, Alkylamino, Alkylcarbonyl oder Alkoxycarbonyl mit jeweils 1 bis 3 Kohlenstoffatomen in den Alkylgrappen steht,Chlorine, bromine or methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted alkyl, alkoxy, alkylamino, alkylcarbonyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl groups,
R9 für Wasserstoff, Cyano, Fluor, Chlor, Brom oder eine der Gruppierungen -R11, -O-R11, S-R11 oder SO2-Rπ steht,R 9 represents hydrogen, cyano, fluorine, chlorine, bromine or one of the groupings -R 11 , -OR 11 , SR 11 or SO 2 -R π ,
R1 für Wasserstoff, Hydroxy, Amino oder die Gruppierung -R11 steht,R 1 represents hydrogen, hydroxy, amino or the grouping -R 11 ,
und R11 für gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oderand R 11 for alkyl with 1 to 4 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, each optionally substituted by halogen Alkenyl or
Alkinyl mit jeweils 2 bis 4 Kohlenstoffatomen, für gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Ethyl, Methyl, n- oder i-Propyl oder n-, i-, s- oder t-Butyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, d-C4-Alkyl, d-C4-Halogenalkyl, d-C4-Alkoxy oder d-C4- Halogenalkoxy substituiertes Phenyl oder Benzyl steht.Alkynyl each having 2 to 4 carbon atoms, for cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine, ethyl, methyl, n- or i-propyl or n-, i-, s- or t-butyl, or represents phenyl or benzyl which is optionally substituted by nitro, cyano, fluorine, chlorine, bromine, dC 4 -alkyl, dC 4 -haloalkyl, dC 4 -alkoxy or dC 4 - haloalkoxy.
Mittel gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dassAgent according to claim 1 or 2, characterized in that
A für Methylen, Ethan-l,l-diyl (Ethyliden), Ethan-l,2-diyl (Di- methylen), Propan-l,l-diyl (Propyliden), Propan-l,2-diyl, Propan-1,3- diyl (Trimethylen), Ethen-l,2-diyl, Propen- 1,2-diyl oder Propen-2,A for methylene, ethane-l, l-diyl (ethylidene), ethane-l, 2-diyl (dimethyl), propane-l, l-diyl (propylidene), propane-l, 2-diyl, propane-1 , 3-diyl (trimethylene), ethene-1,2-diyl, propene-1,2-diyl or propene-2,
3- diyl steht,3-diyl stands,
Ar für gegebenenfalls substituiertes Phenyl, oder für gegebenenfalls substituiertes Heterocyclyl aus der Reihe Furyl, Tetiahydrofuryl, Thienyl, Benzofüryl, Dihydrobenzofuryl, Benzothienyl, Pyπolyl, Pyrazolyl, Benzopyranyl, Dihydrobenzopyranyl, Tetrahydrobenzopyranyl, Pyri- dinyl oder Pyrimidinyl steht,Ar for optionally substituted phenyl, or for optionally substituted heterocyclyl from the series furyl, tetiahydrofuryl, thienyl, benzofüryl, dihydrobenzofuryl, benzothienyl, pyπolyl, pyrazolyl, benzopyranyl, dihydrobenzopyranyl, tetrahydrobenzopyranyl, pyri- pyridyl, pyri-
wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Aufzählung zu entnehmen sind:where the respective possible substituents can preferably be found in the following list:
Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor,Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine,
Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluor- methyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluor- methylthio, Trifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Tri- fluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Trifluormethyl- sulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, Dimethyl- amino, Diethyl-amino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylamino- carbonyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, Dimethyl- aminosulfonyl, Diethylaminosulfonyl,Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoro- methyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i- Propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl,
R1 für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substitu- iertes Ethenyl, Propenyl oder Butenyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy,R 1 for each optionally substituted by fluorine, chlorine and / or bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine - ized ethenyl, propenyl or butenyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, each optionally by nitro, cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,
Ethoxy, n- oder i-Propoxy substituiertes Phenyl, Naphthyl, Benzyl oder Phenylethyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i- Propoxy substituiertes Heterocyclyl aus der Reihe Furyl, Thienyl,Ethoxy, n- or i-propoxy substituted phenyl, naphthyl, benzyl or phenylethyl, or for each optionally by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy substituted heterocyclyl from the series furyl, thienyl,
Pyrazofyl oder Pyridinyl steht,Pyrazofyl or pyridinyl,
R2 für Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht, R für Wasserstoff, Cyano, Fluor oder Chlor steht,R 2 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, R represents hydrogen, cyano, fluorine or chlorine,
für die nachstehend skizzierte Gruppierung (Z1) steht,stands for the grouping outlined below (Z 1 ),
(z1)(z 1 )
R >4 für Wasserstoff, Amino oder jeweils gegebenenfalls durch Fluor substituiertes Methyl oder Ethyl steht,R> 4 represents hydrogen, amino or in each case optionally substituted by fluorine-substituted methyl or ethyl,
R5 für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxycarbonyl oder Ethoxycarbonyl steht,R 5 represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, methoxycarbonyl or ethoxycarbonyl which are optionally substituted by fluorine and / or chlorine,
R für Wasserstoff, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht,R represents hydrogen, fluorine, chlorine, bromine or in each case methyl or ethyl optionally substituted by fluorine and / or chlorine,
R7 für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertesR 7 represents hydrogen, cyano, fluorine, chlorine, bromine or in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy
Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methyl- thio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-
Propylamino, Dimethylamino oder Diethylamino steht,Propylamino, dimethylamino or diethylamino,
R8 für Wasserstoff oder jeweils gegebenenfalls durch Cyano, Fluor, Chlor,R 8 is hydrogen or in each case optionally by cyano, fluorine, chlorine,
Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i- Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylamino, Ethylamino, n- oder i-Propylamino, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl steht,Methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
R9 für Wasserstoff, Cyano, Fluor, Chlor, Brom oder die Gruppierung -O-R11 oder SO2-Rπ steht,R 9 represents hydrogen, cyano, fluorine, chlorine, bromine or the grouping -OR 11 or SO 2 -R π ,
R10 für Wasserstoff oder die Grappierung -R11 steht, undR 10 represents hydrogen or the Grappung -R 11 , and
R11 für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Ethinyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oderR 11 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, for n-, i-, s- or t-butyl each optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for cyclopropyl, cyclobutyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, Cyclopentyl or
Cyclohexyl, oder für jeweils gegebenenfalls durch Nitro, 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 substitu- iertes Phenyl oder Benzyl steht.Cyclohexyl, or for each optionally by nitro, 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 phenyl or benzyl.
4. Mittel einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass4. Means one of claims 1 to 3, characterized in that
A für Methylen, Ethan-l,l-diyl (Ethyliden), Ethan-l,2-diyl (Di- methylen), Propan-l,l-diyl (Propyliden), Ethen-l,2-diyl, Propen- 1,2- diyl oder Propen-2,3-diyl steht,A for methylene, ethane-l, l-diyl (ethylidene), ethane-l, 2-diyl (dimethyl), propane-l, l-diyl (propylidene), ethene-l, 2-diyl, propene-1 , 2-diyl or propene-2,3-diyl,
Ar für gegebenenfalls substituiertes Phenyl, Pyridinyl oder Pyrimidinyl steht, wobei die jeweils möglichen Substituenten vorzugsweise aus folgender Aufzählung zu entnehmen sind:Ar represents optionally substituted phenyl, pyridinyl or pyrimidinyl, where the respective possible substituents can preferably be found in the following list:
Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy und Trifluormethoxy,Cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy,
R1 für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl, für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl, für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy substituiertes Phenyl oder Benzyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy oder Ethoxy substituiertes Heterocyclyl aus der Reihe Furyl, Thienyl, Pyrazolyl oder Pyridinyl steht,R 1 for each methyl, ethyl, n- or i-propyl, n-, i- or s-butyl optionally substituted by fluorine and / or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine or methyl, for each optionally optionally substituted by fluorine, Chlorine, bromine, methyl, ethyl, methoxy or ethoxy-substituted phenyl or benzyl, or for heterocyclyl from the series furyl, thienyl, pyrazolyl or pyridinyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
R für Cyano, Chlor, Brom oder Trifluormethyl steht,R represents cyano, chlorine, bromine or trifluoromethyl,
R für Wasserstoff, Fluor oder Chlor steht,R represents hydrogen, fluorine or chlorine,
R4 für Wasserstoff, Amino oder Methyl steht,R 4 represents hydrogen, amino or methyl,
R5 für Cyano oder Trifluormethyl steht,R 5 represents cyano or trifluoromethyl,
R6 für Wasserstoff, Chlor, Brom oder Methyl steht,R 6 represents hydrogen, chlorine, bromine or methyl,
R7 für Wasserstoff, Cyano, Fluor, Chlor, Brom oder jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl steht,R 7 represents hydrogen, cyano, fluorine, chlorine, bromine or methyl or ethyl which is optionally substituted by fluorine and / or chlorine,
R für Wasserstoff oder jeweils gegebenenfalls durch Fluor substituiertesR represents hydrogen or in each case optionally substituted by fluorine
Methyl oder Ethyl steht, R9 für Wasserstoff, Chlor, Brom oder die Gruppierung -R11 steht, undIs methyl or ethyl, R 9 represents hydrogen, chlorine, bromine or the grouping -R 11 , and
R11 für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl steht.R 11 stands for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for cyclopropyl optionally substituted by fluorine, chlorine or methyl.
5. Mittel gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gruppe (2) zumindest einen Wirkstoff der folgenden Grappe von Wirkstoffen enthalten:5. Agent according to one of claims 1 to 4, characterized in that it contains as active ingredients of group (2) at least one active ingredient of the following group of active ingredients:
Flucarbazone-sodium, Acetochlor, Aclonifen, Alachlor, Amicarbazone, Amidosulfüron, Amitrole, Anilofos, Asulam, Atrazine, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bentazone, Bifenox, Bispyribac-sodium, Brom- oxynil, Butylate, Carfentrazone-ethyl, Chlorotoluron, Chlorsulfüron, Cinidon- ethyl, Clodinafop-propargyl, Clopyralid, Cyanazine, 2,4-D, Desmedipham, Dicamba, Dichlorprop-P, Diclofop-methyl, Difenzoquat, Diflufenican, Diflu- fenzopyr, Dimethenamid, S-Dimethenamid, EPTC, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fentrazamide, Flamprop-M- isopropyl, Flamprop-M-methyl, Florasulam, Fluazifop-P-butyl, Fluazolate,Flucarbazone-sodium, Acetochlor, Aclonifen, Alachlor, Amicarbazone, Amidosulfüron, Amitrole, Anilofos, Asulam, Atrazine, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bentazone, Bifenox, Bispyribac-sodium, Bromoxynilent, Butrazone, Butylate Chlorotoluron, chlorosulfuron, cinidon-ethyl, clodinafop-propargyl, clopyralid, cyanazine, 2,4-D, desmedipham, dicamba, dichlorprop-P, diclofop-methyl, difenzoquat, diflufenican, diflufenzopyr, dimethenamid, EP-C, Ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, Flamprop-M-isopropyl, Flamprop-M-methyl, florasulam, fluazifop-P-butyl, fluazolate,
Flufenacet, Flumetsulam, Fluoroglycofen-ethyl, Flupyrsulfuron-methyl- sodiu , Fluroxypyr, -butoxypropyl", -meptyl, Flurtamone, Fluthiacet-methyl, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Halosulfüron-methyl, Haloxyfop-P-methyl, Imazamethabenz-methyl, Imazamox, Imazapic, Imaza- pyr, Lnazaquin, hnazethapyr, Iodosulfüron-methyl-sodium, loxynil, Isoproturon, Isoxaben, Isoxachlortole, Isoxaflutole, Lactofen, Linuron, MCPA, Mecoprop-P, Mefenacet, Mesosulfuron, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metolachlor, S-Metolachlor, Metosulam, Metribuzin, Metsulfuron-methyl, Naproanilide, Neburon, Nicosulfuron, Oxadi- argyl, Oxadiazon, Oxaziclomefone, Oxyfluorfen, Pendimethalin, Penox- sulam, Phenmedipham, Picolinafen, Primisulfuron-methyl, Profluazol, Pro- panil, Propoxycarbazone-sodium, Prosulfocarb, Prosulfüron, Pyraclonil, Pyraflufen-ethyl, Pyribenzoxim, Pyridafol, Pyridate, Qinclorac, Quinmerac, Rim- sulfüron, Sulcotrione, Sulfosate, Sulfosulfuron, Terbuthylazine, Thifensulf- uron-methyl, Tralkoxydim, Triallate, Triasulfüron, Tribenuron-methyl, Trito- sulfuron, 4-(4,5-Dihydro-4-methyl-5-oxo-3-trifluormethyl- 1H- 1 ,2,4-triazol- 1 - yl)-2-(ethylsulfonylamino)-5-fluor-benzolcarbothioamid (HWH4991) x d 2- Chlor-N-[l-(2,6-dichlor-4-difluormethyl-phenyl)-4-nitro-lH-pyrazol-5-yl]- propancarbonsäureamid (SLA5599).Flufenacet, Flumetsulam, Fluoroglycofen-ethyl, Flupyrsulfuron-methyl-sodiu, Fluroxypyr, -butoxypropyl " , -meptyl, Flurtamone, Fluthiacet-methyl, Foramsulfuron, Glufosinate, Glufosinate-ammonium, Halosulfüron-methyl, Haloxyzopam , Imazamox, Imazapic, Imazapyr, Lnazaquin, hnazethapyr, Iodosulfüron-methyl-sodium, loxynil, Isoproturon, Isoxaben, Isoxachlortole, Isoxaflutole, Lactofen, Linuron, MCPA, Mecoprop-P, Mefenacet, Mesotrione, Mesotrione , Metolachlor, S-Metolachlor, Metosulam, Metribuzin, Metsulfuron-methyl, Naproanilide, Neburon, Nicosulfuron, Oxadi- argyl, Oxadiazon, Oxaziclomefone, Oxyfluorfen, Pendimethalin, Penox-sulam, Phenmedipham, Picolinafen, Profisulfuronol, Primisulfuron panil, Propoxycarbazone-sodium, Prosulfocarb, Prosulfüron, Pyraclonil, Pyraflufen-ethyl, Pyribenzoxim, Pyridafol, Pyridate, Qinclorac, Quinmerac, Rim-sulfüron, Sulcotrione, Sulfosate, Sulfosulfuron, Terbuthylazine, Thifensulfalkonon, Trifluorosulfuronon, Trifulfonox- Tribenuron-methyl, tritosulfuron, 4- (4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-1H-1, 2,4-triazol-1 - yl) -2- (ethylsulfonylamino) - 5-fluoro-benzenecarbothioamide (HWH4991) xd 2-chloro-N- [l- (2,6-dichloro-4-difluoromethylphenyl) -4-nitro-lH-pyrazol-5-yl] -propane carboxamide (SLA5599).
6. Mittel gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gruppe (2) zumindest einen Wirkstoff der folgenden Gruppe von Wirkstoffen enthalten:6. Composition according to one of claims 1 to 4, characterized in that they contain at least one active ingredient from the following group of active ingredients as active ingredients of group (2):
Aclonifen, Amicarbazone, Amidosulfüron, Amitrole, Anilofos, Asulam, Ben- azolin-ethyl, Benfuresate, Bifenox, Bispyribac-sodium, Bromoxynil, Desmedipham, Diclofop-methyl, Diflufenican, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fentrazamide, Fluazifop-P-butyl, Fluazolate, Flucarbazone-sodium, Flufenacet, Flurtamone, Foramsulfuron, Glufosinate, Glufosinate-ammom'um, Iodosulfuron, loxynil, Isoproturon, Isoxa- chlortole, Isoxaflutole, Lactofen, Linuron, Mefenacet, Mesosulfuron,Aclonifen, Amicarbazone, Amidosulfüron, Amitrole, Anilofos, Asulam, Ben-azolin-ethyl, Benfuresate, Bifenox, Bispyribac-sodium, Bromoxynil, Desmedipham, Diclofop-methyl, Diflufenican, Ethofumesate, Ethoxysulfuron, Fenoxaprop-ethyl Fentrazamide, fluazifop-p-butyl, fluazolate, flucarbazone-sodium, flufenacet, flurtamone, foramsulfuron, glufosinate, glufosinate-ammom ' um, iodosulfuron, loxynil, isoproturon, isoxa- chlortole, isoxaflutacon, mesofeneflutacon, mesofenoflutole, mesofenoflutole, mesofenoflutole, mofen
Metamitron, Methabenzthiazuron, Metribuzin, Neburon, Oxadiargyl, Oxadiazon, Oxaziclomefone, Phenmedipham, Propanil, Propoxycarbazone-sodium, Pyraclonil, Pyraflufen-ethyl und Sulcotrione.Metamitron, Methabenzthiazuron, Metribuzin, Neburon, Oxadiargyl, Oxadiazon, Oxaziclomefone, Phenmedipham, Propanil, Propoxycarbazone-sodium, Pyraclonil, Pyraflufen-ethyl and Sulcotrione.
7. Mittel gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeiclmet, dass sie als Wirkstoffe der Grappe (3) einen Wirkstoff aus der folgenden Grappe von Wirkstoffen enthalten:7. Composition according to one of claims 1 to 6, characterized gekennzeiclmet that they contain as active ingredients of the grappa (3) an active ingredient from the following group of active ingredients:
5-Chlor-chinolin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet- exyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen- ethyl) und 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-DicMoracetyl-hexahydro-3,3,8a-trimethylpyπolo[l,2-a]- pyrimidin-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-acetamid (Dichlormid), 3-Dichloracetyl-5-(2-füranyl)-2,2-dimethyl-oxazolidin (Furil- azole, MON-13900) und 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148).5-chloro-quinoline-8-oxy-acetic acid (l-methyl-hexyl ester) (cloquintocet-exyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl) and diethyl- l- (2,4-dichloro-phenyl) -4,5-dihydro-5-methyl-lH-pyrazol- 3,5-dicarboxylate (mefenpyr-diethyl), 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] - decane (AD-67), l-DicMoracetyl-hexahydro-3,3,8a-trimethylpyπolo [l , 2-a] - pyrimidin-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 (dichloromide), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazoles, MON-13900) and 3-dichloroacetyl-2 , 2,5-trimethyl-oxazolidine (R-29148).
8. Mittel gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gruppe (3) Mefenpyr-diethyl enthalten.8. Composition according to one of claims 1 to 6, characterized in that they contain as active ingredients of group (3) mefenpyr-diethyl.
9. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 8 zur Bekämpfung von unerwünschten Pflanzen.9. Use of an agent according to any one of claims 1 to 8 for controlling unwanted plants.
10. Verfahren zum Bekämpfen von unerwünschten Pflanzen, dadurch gekennzeichnet, dass man ein Mittel gemäß einem der Ansprüche 1 bis 8 auf die Pflanzen und/oder ihren Lebensraum einwirken lässt. 10. A method for controlling unwanted plants, characterized in that an agent according to one of claims 1 to 8 is allowed to act on the plants and / or their habitat.
EP20020791758 2001-12-05 2002-12-02 Herbicides based on substituted carboxylic acid anilides Ceased EP1453377A1 (en)

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US20050090396A1 (en) 2005-04-28
JP2005510577A (en) 2005-04-21
BR0214744A (en) 2004-11-23
EP1743527A2 (en) 2007-01-17
CA2468387A1 (en) 2003-06-12
WO2003047346A1 (en) 2003-06-12
DE10159659A1 (en) 2003-06-26
AU2002358078A1 (en) 2003-06-17
EP1743527A3 (en) 2007-03-21

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