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WO2003000058A1 - Selective herbicides based on pyrimidine derivatives - Google Patents

Selective herbicides based on pyrimidine derivatives Download PDF

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Publication number
WO2003000058A1
WO2003000058A1 PCT/EP2002/006314 EP0206314W WO03000058A1 WO 2003000058 A1 WO2003000058 A1 WO 2003000058A1 EP 0206314 W EP0206314 W EP 0206314W WO 03000058 A1 WO03000058 A1 WO 03000058A1
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WIPO (PCT)
Prior art keywords
methyl
chloro
ethyl
phenyl
urea
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PCT/EP2002/006314
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German (de)
French (fr)
Inventor
Dieter Feucht
Mathias Kremer
Helmut FÜRSCH
Arndt Wellmann
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
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Bayer Cropscience Ag
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Publication of WO2003000058A1 publication Critical patent/WO2003000058A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the invention relates to new herbicidal, synergistic active ingredient combinations consisting of at least three mixing partners which consist of known pyrimidine derivatives on the one hand and known, herbicidally active compounds and, if appropriate, safeners on the other hand and can be used with particularly good success for selective weed control in different crops.
  • Pyrimidine derivatives are the subject of a number of broad-spectrum herbicides
  • Patent applications see US 4,906,285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4427 437.
  • the known pyrimidine derivatives have a number of activity gaps.
  • the compatibility of these compounds with crop plants is also not entirely satisfactory under all conditions.
  • the phenoxypyrimidine derivatives together with other, preferably two further, known herbicidally active compounds when used together, if appropriate with the compounds (safeners / antidots) which improve crop tolerance and are described below, are particularly advantageous as broadly active combination preparations for selective use Control of weeds in crops such as cereals, such as wheat, barley, rye and rice, but can also be used in maize.
  • the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
  • R is hydrogen, -CH 2 CH 2 S (O) n R 1 (where Rj is C r C 4 alkyl and n is 0.1 or 2) or
  • R 2 for hydrogen, halogen, cyano, phenyl, C j -Cs-alkyl, C1-C4- alkoxy, C ⁇ -C4-alkylthio, C ⁇ -C -alkoxycarbonyl, mono- or di-C i -C4- alkylaminocarbonyl, phenyl- C j -C4-Alkylaminocarb- onyl, where the phenyl group may optionally be substituted by halogen, -CC C2-alkyl or C C2-alkoxy, furylmethylaminocarb- onyl or phenyl, and
  • R3 represents in each case optionally substituted by halogen, cyano, nitro, C j - C4 substituted alkyl, C C4-alkoxy or allyloxy phenyl, optionally substituted by C ⁇ - alky !, phenoxy, benzyloxy or acetoxy-substituted amino, for -C-C4-alkylthio or for the grouping -COR 4 , where R 4 is C j - C4-alkyl, benzyloxy or benzylamino,
  • A represents chlorine or methoxy
  • D and E which may be the same or different, represent hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxy substituted by halogen,
  • N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), 1 - chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l, 3-dioxo-lH-pyrrolo [l, 2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N - (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(l-methylethylidene) amino] oxy] ethyl] -2-
  • phenylcarbothiamide- 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1, 2,4-triazole - 1 -yl] -2- [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and 2-chloro-N- [1 - [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2; SLA5599).
  • R preferably represents hydrogen or
  • R 2 preferably represents hydrogen, chlorine, cyano, phenyl, C Cg-alkyl, methoxy,
  • R 3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR4, in which
  • R4 represents methoxy, ethoxy, methyl, benzyloxy or benzylamino
  • A preferably represents chlorine or methoxy
  • R 2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
  • R3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
  • D and E are particularly preferably methoxy.
  • R 2 very particularly preferably represents phenyl.
  • R 3 very particularly preferably represents phenyl.
  • Preferred mixture components from the active ingredients in group 3 are one or more compounds from a group of herbicides which contain the active ingredients mentioned below:
  • N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) - 2-cyclohexen- 1 -one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3.5 -triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3) , 5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl),
  • Herbicides from the class of the sulfonylureas, triazolopyrimidines, are used in particular as mixture components from the active ingredients of group 3.
  • Imidazolinones ureas, triazinediones, triketones, triazolinones, benzonitriles, Phenoxypropionic acid derivatives, dichlo ⁇ henoxyacid derivatives, carboxamides, oxyacetamides and other herbicidal active ingredients, which are listed in detail below:
  • bromoxynil 3,5-dibromo-4-hydroxy-benzonitrile
  • ioxynil 4-hydroxy-3,5-diiodobenzonitrile
  • N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium),
  • N-phosphonomethyl-glycine trimethyl sulfonium (sulfosate).
  • the active substance combinations defined above from the phenoxypyrimidine derivatives of the formula (I) and the active substance from group 2 in combination with active substances from group 3, if appropriate in combinations with active substances from group 4, with very good crop plant tolerance have particularly high herbicidal activity and in various crops such as. B. in soy, potatoes, corn or rice and especially in Cereals such as barley, rye, triticale and especially wheat can be used for selective weed control.
  • the herbicidal activity of the active substance combinations according to the invention composed of compounds from groups 1, 2 and 3 listed above is considerably higher than the sum of the effects of the individual active substances.
  • 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 selective herbicides.
  • active substances of group 4 in combination with one or more of the one or more Listed active ingredients of group 2 and group 3 with very good crop tolerance, have a particularly high herbicidal activity and can be used in various crops, in particular in cereals, especially wheat, but also in soybeans, potatoes, corn and rice for selective weed control.
  • 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, in combination with one or more of the active ingredients or of the group mentioned above 2 and 3.
  • Typical derivatives of 2,4-D are their esters.
  • a preferred embodiment is also a mixture comprising a compound of formula (I) and / or its salts on the one hand and MCPA on the other hand in combination with the above-mentioned active ingredient of group 2 and one or more compounds of group 3.
  • Safeners or antidots which are capable of antagonizing the damaging effect of a herbicide on the cultivated plants, are particularly suitable for the group 4 compounds listed above, the damaging effect of compounds of the formula (I) and their salts in combination with one or more of the or the above-mentioned active ingredients of groups 2 and 3, to almost completely cancel the cultivated plants without impairing the herbicidal activity against the weeds.
  • the active substance combinations according to the invention can e.g. can be used in the following plants:
  • Brassica, lactuca, cucumis, cuburbita Brassica, lactuca, cucumis, cuburbita.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including 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 parts and organs of plants, such as shoots, leaves, flowers and roots, examples being used
  • Roots are listed.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • plants and their parts can be treated according to the invention.
  • transgenes are also preferred.
  • 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 certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”).
  • 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, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products , Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton,
  • Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton and rapeseed are particularly emphasized.
  • the properties (“traits”) that are particularly emphasized are the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CrylA), Cry ⁇ A ( c), CryllA, CrylHA, CryIIIB2, Cry9c, Cry2Ab, CrySBb 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 through systemic acquired resistance (SAR),
  • Plant plants are maize varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • YIELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® Cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide Tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rape), IMI® (tolerance to imidazolinones) and ST
  • Plants (conventionally bred to herbicide tolerance) should also be mentioned the varieties sold under the name Clearfield® (e.g. 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").
  • Clearfield® e.g. maize
  • 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 varied within relatively large ranges. Generally 1 part by weight
  • Active ingredient of the formula (I) in each case 0.001 to 1000 parts by weight, preferably 0.005 to 200 parts by weight in each case and particularly preferably in each case 0.01 to 100 parts by weight of active ingredient of groups 2 and 3.
  • 1 to 1 part by weight of group 1 each contains 0.1 to 1 part by weight of active substances in groups 2 and 3.
  • the advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the 1 to 1 part by weight of active compound of the formula (I), its salts or mixtures thereof with active compounds of groups 2 and 3 Above under (d), the crop plants tolerability-improving compounds (antidots / safeners).
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. 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.
  • 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,
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, including the safing active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active substances contained in the active substance combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. 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. For certain applications, particularly in the post-emergence process, it may also be advantageous to include plant-compatible mineral or vegetable oils or 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 scattering.
  • 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 process. 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.
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • the required amounts of the formulations were mixed with one another and optionally other substances were added, and then diluted with water to the desired concentration.
  • the amount of formulation in the solutions to be tested corresponds to the desired application rates per hectare. preemergence
  • Seeds of the test plants are sown in normal soil. After 24 hours, the desired amount of active substance is sprayed onto the soil surface as a formulation.
  • the concentration of the active substances in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
  • Test plants are grown under controlled temperature and light conditions. Spraying with the test solution takes place when the plants have reached a height of 5 to 15 cm.
  • the concentration of the active substance in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
  • the evaluation takes place about three weeks after the application.
  • the herbicidal activity is assessed visually in comparison to the untreated control. Mean it

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Abstract

The invention relates to novel herbicide and synergistic combinations of active ingredients consisting of known pyrimidine derivatives, at least two other known herbicidally active compounds, and optionally additional safeners. Said combinations are especially successful when used for selective weed control in different useful plant cultures.

Description

Selektive Herbizide auf Basis von Pyrimidin-DerivatenSelective herbicides based on pyrimidine derivatives
Die Erfindung betrifft neue herbizide, synergistische Wirkstoffkombinationen be- stehend aus zumindest drei Mischpartnern, die aus bekannten Pyrimidin-Derivaten einerseits und bekannten, herbizid wirksamen Verbindungen sowie gegebenenfalls Safenern andererseits bestehen und mit besonders gutem Erfolg zur selektiven Unkrautbekämpfung in verschiedenen Nutzpflanzenkulturen verwendet werden können.The invention relates to new herbicidal, synergistic active ingredient combinations consisting of at least three mixing partners which consist of known pyrimidine derivatives on the one hand and known, herbicidally active compounds and, if appropriate, safeners on the other hand and can be used with particularly good success for selective weed control in different crops.
Pyrimidin-Derivate sind als breit wirksame Herbizide Gegenstand einer Reihe vonPyrimidine derivatives are the subject of a number of broad-spectrum herbicides
Patentanmeldungen (vgl. US 4 906 285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4427 437). Die bekannten Pyrimidin-Derivate weisen jedoch eine Reihe von Wirkungslücken auf. Die Verträglichkeit dieser Verbindungen gegenüber Kulturpflanzen ist ebenfalls nicht unter allen Bedingungen ganz zufriedenstellend.Patent applications (see US 4,906,285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4427 437). However, the known pyrimidine derivatives have a number of activity gaps. The compatibility of these compounds with crop plants is also not entirely satisfactory under all conditions.
Überraschenderweise wurde nun gefunden, dass eine Reihe von bekannten Wirkstoffen aus der Reihe der Phenoxypyrimidin-Derivate bei gemeinsamer Anwendung mit bekannten herbizid wirksamen Verbindungen aus verschiedenen Stoffklassen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und be- sonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in verschiedenen Nutzpflanzenkulturen wie z. B. in Soja, Kartoffeln, Mais oder Reis und insbesondere in Getreide, wie z.B. Gerste, Roggen, Triticale und besonders Weizen, verwendet werden können.Surprisingly, it has now been found that a number of known active compounds from the series of the phenoxypyrimidine derivatives, when used together with known herbicidally active compounds from different classes of substances, have extremely synergistic effects with regard to the action against weeds and are particularly advantageous as broadly active combination preparations for selective control of weeds in various crops such as B. in soybeans, potatoes, corn or rice and especially in cereals such as e.g. Barley, rye, triticale and especially wheat can be used.
Überraschenderweise wurde ebenfalls gefunden, dass die Phenoxypyrimidin-Derivate zusammen mit anderen, bevorzugt zwei weiteren bekannten herbizid wirksamen Verbindungen bei gemeinsamer Anwendung, gegebenenfalls mit den im Weiteren beschriebenen, die Kultu flanzenverträglichkeit verbessernden Verbindungen (Safenern/Antidots) besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in Nutzpflanzenkulturen wie Getreide, so z.B. Weizen, Gerste, Roggen und Reis, aber auch in Mais verwendet werden können. Gegenstand der Erfindung sind selektiv-herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination umfassendSurprisingly, it has also been found that the phenoxypyrimidine derivatives, together with other, preferably two further, known herbicidally active compounds when used together, if appropriate with the compounds (safeners / antidots) which improve crop tolerance and are described below, are particularly advantageous as broadly active combination preparations for selective use Control of weeds in crops such as cereals, such as wheat, barley, rye and rice, but can also be used in maize. The invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
(a) zumindest ein Phenoxypyrimidin-Derivat der allgemeinen Formel (I)(a) at least one phenoxypyrimidine derivative of the general formula (I)
Figure imgf000003_0001
Figure imgf000003_0001
in welcherin which
R für Wasserstoff, -CH2CH2S(O)nR1 (wobei Rj für CrC4-Alkyl und n für 0,1 oder 2 steht) oderR is hydrogen, -CH 2 CH 2 S (O) n R 1 (where Rj is C r C 4 alkyl and n is 0.1 or 2) or
/ 3 / 3rd
-N=C steht,-N = C stands,
\\
R,R
wobeiin which
R2 für Wasserstoff, Halogen, Cyano, Phenyl, Cj-Cs-Alkyl, C1-C4- Alkoxy, Cι-C4-Alkylthio, Cι-C -Alkoxycarbonyl, Mono- oder Di-C i -C4- Alkylaminocarbonyl, Phenyl-C j -C4-Alkylaminocarb- onyl steht, wobei die Phenylgruppe gegebenenfalls durch Halogen, Cι-C2-Alkyl oder C C2-Alkoxy, Furylmethylaminocarb- onyl oder Phenyl substituiert sein kann, undR 2 for hydrogen, halogen, cyano, phenyl, C j -Cs-alkyl, C1-C4- alkoxy, Cι-C4-alkylthio, Cι-C -alkoxycarbonyl, mono- or di-C i -C4- alkylaminocarbonyl, phenyl- C j -C4-Alkylaminocarb- onyl, where the phenyl group may optionally be substituted by halogen, -CC C2-alkyl or C C2-alkoxy, furylmethylaminocarb- onyl or phenyl, and
R3 für jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Cj- C4-Alkyl, C C4-Alkoxy oder Allyloxy substituiertes Phenyl, für gegebenenfalls durch C^^-Alky!, Phenoxy, Benzyloxy oder Acetoxy substituiertes Amino, für Cι-C4-Alkylthio oder für die Gruppierung -COR4 steht, wobei R4 für
Figure imgf000004_0001
Cj- C4-Alkyl, Benzyloxy oder Benzylamino steht,R3 represents in each case optionally substituted by halogen, cyano, nitro, C j - C4 substituted alkyl, C C4-alkoxy or allyloxy phenyl, optionally substituted by C ^^ - alky !, phenoxy, benzyloxy or acetoxy-substituted amino, for -C-C4-alkylthio or for the grouping -COR 4 , where R 4 is
Figure imgf000004_0001
C j - C4-alkyl, benzyloxy or benzylamino,
A für Chlor oder Methoxy steht undA represents chlorine or methoxy and
D und E, die gleich oder unterschiedlich sein können, für Wasserstoff, Halogen, Cj-Cg-Alkyl, Ci-Cg-Alkoxy oder durch Halogen substituiertes Ci-Cg- Alkoxy stehen,D and E, which may be the same or different, represent hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxy substituted by halogen,
und/oder einem Salz einer Verbindung der Formel (I) („Wirkstoffe der Gruppe 1"),and / or a salt of a compound of the formula (I) (“active compounds of group 1”),
undand
zumindest eine Verbindung aus einer weiteren Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:at least one compound from a further group of herbicides which contains the active compounds mentioned below:
Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone- sodium) der FormelMethyl 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-l, 2,4-triazol-l-yl) carbonyl] amino] sulfonyl] benzoic acid, sodium Salt (Propoxycarbazone- sodium) of the formula
Figure imgf000004_0002
Figure imgf000004_0002
und 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)phenyl] sulfonyl]-lH-l,2,4-triazol-l-carboxamid, Natrium-Salz (Flucarbazone-sodium) der Formeland 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [[2- (trifluoromethoxy) phenyl] sulfonyl] -lH-l, 2,4-triazole-l-carboxamide, sodium salt ( Flucarbazone-sodium) of the formula
Figure imgf000005_0001
(„Wirkstoffe der Gruppe 2"), sowie
Figure imgf000005_0001
("Active substances of group 2"), as well
einer oder mehrerer Verbindungen aus einer weiteren Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:one or more compounds from a further group of herbicides which contains the active compounds mentioned below:
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Aceto- chlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-Natrium- salz (Acifluorfen-sodium), 2-Chlor-6-nitro-3-phenoxy-benzenamin (Acloni- fen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid (Ala- chlor), N-Ethyl-N'-i-propyl-6-methylthio-l,3,5-triazin-2,4-diamin (Ametryn), 4- Amino-N-( 1 , 1 -Dimethyl-ethyl)-4,5-dihydro-3 -( 1 -methyl-ethyl)-5-oxo- 1 H- 1 ,2,4-triazol- 1 -carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), lH-l,2,4-Triazol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(l-isopropyl)- amino]-2-oxo-ethyl]-O,O-dimethyl-phosphorodithioate (Anilofos), 6-Chlor-4- ethylamino-2-isopropylamino-l ,3,5-triazin (Atrazin), 2-[2,4-Dichlor-5-(2- propinyloxy)-phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)- on (Azafenidin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-[l-methyl-4-(2- methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfüron),2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (aceto-chloro), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid -Sodium salt (Acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxy-benzenamine (Acloni- fen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide (ala-chloro), N-ethyl-N'-i-propyl-6-methylthio-l, 3,5-triazine-2,4-diamine (ametryn), 4-amino-N- (1, 1 -Dimethyl-ethyl) -4,5-dihydro-3 - (1-methyl-ethyl) -5-oxo- 1 H-1, 2,4-triazole-1-carboxamide (amicarbazone), N- (4,6 -Dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), lH-l, 2,4-triazol-3-amine (amitrole), S- [ 2 - [(4-chlorophenyl) - (l-isopropyl) - amino] -2-oxo-ethyl] -O, O-dimethyl-phosphorodithioate (Anilofos), 6-chloro-4-ethylamino-2-isopropylamino- l, 3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-l, 2,4-triazolo- [ 4,3-a] pyridin-3 (2H) - one (azafenidin), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [l-methyl-4- (2-methyl- 2H-tetrazol-5-yl) -lH-pyrazolo l-5-ylsulfonyl] urea (azimsulfüron),
N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4- Chlor-2-oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-But l-N-ethyl-2,6- dinitro-4-trifluormethyl-benzenamin (Benfluralin), 2,3-Dihydro-3,3-dimethyl- yl)-N'-(2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuron- methyl), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thiobencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- l(2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propansäure-methylesterN-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-but IN-ethyl-2, 6- dinitro-4-trifluoromethylbenzamine (benfluralin), 2,3-dihydro-3,3-dimethyl- yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuronmethyl), 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-phenoxypropanoic acid methyl ester
(Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bi- cyclo-[3.2.1]-oct-3-en-2-on (Benzobicyclon), 2-[[4-(2,4-Dichlor-3-methyl- benzoyl)- 1 ,3-dimethyl- 1 H-pyrazol-5-yl]-oxy]- 1 -(4-methyl-phenyl)-ethanon (Benzofenap), Ethyl N-benzoyl-N-(3 ,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-lH-2,l,3-benzothiadiazin-4(3H)-on(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-methylbenzoyl) - 1, 3-dimethyl-1H-pyrazol-5-yl] -oxy] - 1 - (4-methylphenyl) ethanone (benzofenap), ethyl N-benzoyl-N- (3, 4-dichlorophenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2, 1, 3-benzothiadiazin-4 (3H) -one
(Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 5- Brom-6-methyl-3-(l-methyl-propyl)-2,4(lH,3H)pyrimidindion (Bromacil), 2- Brom-3,3-dimethyl-N-(l -methyl- 1 -phenyl-ethyl)-butanamid (Bromobutide), 3,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-dinitro-phenyl)-oxim (Bromofen- oxim), 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-trifluormethyl- 1 (2H)-pyrimidinyl)-benzoesäure-[ 1 , 1 -di- methyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-( 1 -Ethox- imino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxo-butyl)-phenyl]-2-cyclo- hexen- 1-on (Butroxydim), S-Ethyl-bis-(2-methyl-propyl)-thiocarbamat (Buty- late), N,N-Diethyl-3 -(2,4,6-trimethyl-phenylsulfonyl)- 1 H- 1 ,2,4-triazol- 1 - carboxamid (Cafenstrole), 2-[l-[(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3- hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen- 1 -on (Caloxydim,(Bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), 5-bromo-6-methyl-3- (l-methyl-propyl) -2.4 (1H , 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-dinitro-phenyl) oxime (bromine oxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2,6-diethyl- phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid- [1, 1 - dimethyl-2-oxo-2- (2-propenyloxy)] ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl -3- (l-oxobutyl) phenyl] -2-cyclohexen-1-one (butroxydim), S-ethyl-bis- (2-methyl-propyl) thiocarbamate (butyl latex), N, N-Diethyl-3 - (2,4,6-trimethyl-phenylsulfonyl) -1 H-1, 2,4-triazole-1-carboxamide (cafenstrole), 2- [l - [(3-chloro-2-propenyl ) -oxy-imino] -propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen- 1 -one (caloxydim,
Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)- phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-l ,2,4-triazol-3-on (Carfen- trazone-ethyl), 2,4-Dichlor- 1 -(3-methoxy-4-nitro-phenoxy)-benzol (Chlo- methoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6- methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl-phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), 1 ,3,5-Trichlor-2-(4-nitro-phenoxy)-benzol (Chlornitro- fen), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)- harnstoff (Chlorsulfuron), N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harn- stoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo- 2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl), Exo- 1 - methyl-4-isopropyl-2-(2-methyl-phenyl-methoxy)-7-oxabicyclo-[2.2.1]- heptan (Cinmethylin), N-(4,6-Dimethoxy-l ,3,5-triazin-2-yl)-N'-(2-(2-meth- oxy-ethoxy)-phenylsulfonyl)-harnstoff (Cinosulfüron), 2-[l-[2-(4-Chlor- phenoxy)-propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclo- hexandion (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-(2,4-Dichlor-3-methyl-phenoxy)-N-phenyl-propanamid (Clomeprop), 3,6-Tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2 , 4-triazol-3-one (Carfentrazone-ethyl), 2,4-dichloro-1 - (3-methoxy-4-nitro-phenoxy) -benzene (chloro-methoxyfen), 3-amino-2,5 -dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) -urea (chlorimuron-ethyl), 1, 3.5- Trichloro-2- (4-nitro-phenoxy) -benzene (chloronitrene), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-chloro -phenylsulfonyl) urea (chlorosulfuron), N '- (3-chloro-4-methylphenyl) -N, N-dimethyl-urea- substance (chlorotoluron), 2-chloro-3- [2-chloro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenyl] Ethyl 2-propanoate (cinidon-ethyl), exo-1-methyl-4-isopropyl-2- (2-methylphenyl-methoxy) -7-oxabicyclo [2.2.1] heptane (cinmethylin), N - (4,6-Dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2-methoxy-ethoxy) phenylsulfonyl) urea (cinosulfurone), 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- (2,4-dichloro-3-methylphenoxy) -N -phenyl-propanamide (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 (Cloransu- lam-methyl), N- [(2-Chlor-phenyl)-methyl] -N' -( 1 -methyl- 1 -phenyl-ethyl)- harnstoff (Cumyluron), 2-Chlor-4-ethylamino-6-( 1 -cyano- 1 -methyl-ethyl- amino)-l,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- cyclopropylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(l - Ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen- 1 -on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fiuor-phenoxy)-phenoxy]-propan- säure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phen- oxy)-propansäure (Dichloφrop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phen- oxy]-propanoat (Diclofop-methyl), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor- [l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 1,2-Dimethyl- 3,5-diphenyl-lH-pyrazolium-methylsulfat (Difenzoquat), N-(2,4-Difluor- phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican),Dichloropyridine-2-carboxylic acid (clopyralide), methyl-3-chloro-2 - [(5-ethoxy-7-fluoro [1, 2,4] triazolo [1, 5-c] pyrimidin-2-yl-sulfonyl ) -amino] -benzoate (chlorosulfam-methyl), N- [(2-chlorophenyl) -methyl] -N '- (1-methyl-1-phenyl-ethyl) - urea (cumyluron), 2- Chloro-4-ethylamino-6- (1-cyano-1-methyl-ethyl-amino) -l, 3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-Cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 2- (l - ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one (cycloxydim ), (R) -2- [4- (4-Cyano-2-fluorophenoxy) phenoxy] propanoic acid butyl ester (Cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D ), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (Dichloφrop-P), methyl-2- [4- ( 2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro [1,2,4] triazolo - [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazo lithium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican),
2-[l-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3-car- bonsäure (Diflufenzopyr), S-(l -Methyl- 1-phenyl-ethyl)- 1-piperi din-carbo- thioat (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-2- [l - [(3,5-difluorophenyl) amino carbonyl hydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (l methyl 1-phenylethyl) - 1-piperi din-carbothioate (dimepiperate), 2-chloro-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)-acetamid (S-) (Dimethenamid), 2- Amino-4-( 1 -fluor- 1 -methyl-ethyl)-6-( 1 -methyl-2-(3 ,5-dimethyl-phenoxy)- ethylamino)-l,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-tri- fluormethyl- 1 ,3-diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[ 1 ,2- a:2',l '-c]pyrazindiium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6- trifluormethyl-pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor- phenyl)-N,N-dimethyl-harnsto f (Diuron), N-(4-Methyl-phenyl)-N'-( 1 - methyl- l-phenyl-ethyl)-harnstoff (Dymron, Daimuron), 2-[2-(3-Chlor- phenyl)-oxiranylmethyl]-2-ethyl- 1 H-inden- 1 ,3 (2H)-dion (Epropodan), S- Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l ,2-di- methyl-propyl)-thiocarbamat (Esprocarb), N-Ethyl-N-(2-methyl-2-propenyl)-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (S-) (dimethenamid), 2- Amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) -l, 3,5-triazine (dimexyflam), N3 , N3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', l' -c] pyrazinediium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N , N-dimethyl-urea (diuron), N- (4-methylphenyl) -N '- (1 - methyl-l-phenyl-ethyl) urea (Dymron, Daimuron), 2- [2- (3rd -Chlor- phenyl) -oxiranylmethyl] -2-ethyl-1 H-indene-1, 3 (2H) -dione (epropodane), S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N - (1,2-dimethyl-propyl) thiocarbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -
2,6-dinitro-4-trifluormethyl-benzenamin (Ethalfluralin), (S)-(2-Ethoxy- 1 - methyl-2-oxoethyl)-2-chlor-5-(2-chlor-4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfo- nyl)-harnstoff (Ethoxysulfuron), N-(2,3-Dichlor-phenyl)-4-ethoxymethoxy- benzamid (Etobenzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phen- oxy]-propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N- ethyl-4,5-dihydro-5-oxo- lH-tetrazol- 1 -carboxamid (Fentrazamide), Iso- propyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flamprop-iso- propyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L-alaninat (Flam- prop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)-DL- alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy- [1 ,2,4]-triazolo-[l ,5-c]-pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Tri- fluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure-butylester (Fluazifop, -butyl, -P-butyl), 5-(4-Brom- 1 -methyl-5-trifluormethyl- 1 H-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), N-(2,6-Difluor-phenyl)-5-methyl-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfon- amid (Flumetsulam), Pentyl-[2-chlor-4-fluor-5-(l ,3,4,5,6,7-hexahydro-l ,3-di- oxo-2H-isoindol-2-yl)-phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4- dihydro-3-oxo-4-(2-propinyl)-2H-l,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro- lH-isoindol-l,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(l-methyl-2-pro- pinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-lH-isoindol-l,3(2H)-dion (Flumipro- pyn), 3-Chlor-4-chlormethyl- 1 -(3-trifluormethyl-phenyl)-2-pyrrolidinon2,6-dinitro-4-trifluoromethyl-benzenamine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -benzoate (ethoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethoxy-phenoxysulfonyl) -urea (ethoxysulfuron), N- (2,3-dichlorophenyl) ) -4-ethoxymethoxy-benzamide (etobenzanide), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phen-oxy] propanoate (fenoxaprop- (P) -ethyl ), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-1-carboxamide (fentrazamide), isopropyl-N-benzoyl-N - (3-chloro-4-fluro-phenyl) -DL-alaninate (flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (flam- prop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) -DL- alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8- fluoro-5-methoxy- [1,2,4] -triazolo- [1,5-c] pyrimidine-2-sulfonamide (florasulam), (R) -2- [4- (5-trifluoromethyl-pyridine -2-yl-oxy) -phenoxy] -propanoic acid butyl ester (fluazifop, -butyl, -P-butyl), 5- (4-bromo-1-methyl-5-tri i-propyl fluoromethyl- 1 H -pyrazol-3-yl) -2-chloro-4-fluoro-benzoate (fluazolates), N- (4-fluorophenyl) -nipropyl-2- (5-trifluoromethyl- l, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (2,6-difluorophenyl) -5-methyl-l, 2,4-triazolo [l, 5-a] -pyrimidine-2-sulfone-amide (flumetsulam), pentyl- [2-chloro-4-fluoro-5- (l, 3,4,5,6,7-hexahydro-l, 3-di-oxo-2H- isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-l, 4-benzoxazin- 6-yl] -4,5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(l-methyl-2-pro - pinyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-lH-isoindole-1,3, (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl-1 - (3- trifluoromethyl-phenyl) -2-pyrrolidinone
(Fluorochloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoe- säure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), 1 -(4-Chlor-3- (2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazol-3- carboxamid (Flupoxam), 1 -Isopropyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-di- oxo-4-trifluormethyl-l(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2- yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfüron-methyl-sodium), 9-Hy- droxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fTuor- pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 -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-(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-trifluor- methyl-phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fomesafen), 2- [[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4- formylamino-N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4-(hy- droxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammo- nium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Gly- phosate, -isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluormethyl-pyridin-2- yl-oxy)-phenoxy]-propansäure (-methylester, -2-ethoxy-ethylester, -butyl- ester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-Cyclohexyl-6- dimethylamino- 1 -methyl- 1 ,3,5-triazin-2,4( 1 H,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4- methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-lH-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imaza- methapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5- methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imaza- quin), 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[ 1 ,2-a]-pyridin-3-yl-sulfonyl)-harnstoff (Imazosulfuron), N- (4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl- phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 4- Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl-N'-(4-isopropyl- phenyl)-harnstoff (Isoproturon), N-(3-(l-Ethyl-l-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 (Isoxa- flutole), 2-[2-[4-[3,5-Dichlor-2-pyridinyl)-oxy]-phenoxy]-l-oxo-propyl]-is- oxazolidin (Isoxapyrifop), (2-Ethoxy- 1 -methyl-2-oxo-ethyl)-5-(2-chlor-4-tri- fluormethyl-phenoxy)-2-nitro-benzoat (Lactofen), N' -(3 ,4-dichlor-phenyl)-N- methoxy-N-methyl-hamstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essig- säure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2- (2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6-(Fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1 - (4-chloro-3- (2,2,3,3 , 3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-l, 2,4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5- (3,6-dihydro-3 -methyl-2,6-di-oxo-4-trifluoromethyl-l (2H) -pyrimidyl) -benzoate (flupropacil), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- ( 3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfüron-methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino- 3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5 -Methylamino-2-phenyl- 4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (Flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-lH, 3H- [l, 3,4] thiadiazolo- [3,4-a] pyridazin-l-ylidene) aminophenyl] thioacetate (Fluthiacet-methyl), 5- (2-chloro-4- trifluoromethyl-phenoxy) -N-methylsulfonyl -2-nitro-benzamide (fomesafen), 2- [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N-dimethyl- benzamide (foramsulfuron), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammmonium salt), (glyphosate, isopropylammonium) , (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-1-methyl-1, 3,5-triazine-2,4 (1 H, 3H) -dione (hexazinones) , Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4.5 Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro- 4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl -5-oxo-lH-imidazole -2-yl) -quinolin-3-carboxylic acid (imaza- quin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-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) urea (imazosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfuron -methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3- (l -Ethyl-l-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl ) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [2- [4- [3.5 -Dichlor-2-pyridinyl) -oxy] -phenoxy] -l-oxo-propyl] -is-oxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2-oxo-ethyl) -5- (2-chloro -4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3,4-dichlorophenyl) -N-methoxy-N-methyl-urea (linuron), (4-chloro 2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methy l-phenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mefenacet), 2 - [[[[(4,6-
Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methyl- sulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 2-(4- Methylsulfonyl-2-nitro-benzoyl)-l,3-cyclohexandion (Mesotrione), 4-Amino- 3-methyl-6-phenyl-l ,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(2,6-di- methyl-phenyl)-N-(lH-pyrazol-l-yl-methyl)-acetamid (Metazachlor), N'-(4-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 2- (4-methylsulfonyl-2- nitro-benzoyl) -l, 3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one (metamitron), 2-chloro-N- (2,6-dimethylphenyl) -N- (1H-pyrazol-1-ylmethyl) acetamide (metazachlor), N '- (4-
(3,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy)- phenyl)-N-methoxy-N-methyl-harastoff (Metobenzuron), N'-(4-Brom- phenyl)-N-methoxy-N-methylharnstoff (Metobromuron), (S)-2-Chlor-N-(2- ethyl-6-methyl-phenyl)-N-(2-methoxy- 1 -methyl-ethyl)-acet-amid (Metola- chlor, S-Metolachlor), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- l,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-Methoxy-6- methyl- 1 ,3 ,5 -triazin-2-yl)-N' -(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1-carbothioat (Moli- nate), 2-(2-Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N-Butyl-N'- (3 ,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyri- midin-2-yl)-N'-(3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nico- sulfuron), 4-Chlor-5-methylamino-2-(3-trifluormethyl-phenyl)-3(2H)pyrid- azinon (Norflurazon), S-(2-Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orben- carb), 4-Dipropylamino-3,5-dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Di- chlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-on (Oxa- diargyl), 3-[2,4-Dichlor-5-(l-methyl-ethoxy)-phenyl]-5-(t-butyl)-l,3,4-oxadi- azol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2-yl)-N'-(2-oxetan- 3-yl-oxycarbonyl-phenylsulfonyl)-harnstoff (Oxasulfuron), 3-[l-(3,5-Dichlor- phenyl)- 1 -i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H- 1 ,3-oxazin-4-on (Ox- aziclomefone), 2-Chlor- 1 -(3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl- benzen (Oxyfluorfen), l, -Dimethyl-4,4'-bipyridinium (Paraquat), 1-Amino- N-( 1 -ethyl-propyl)-3 ,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t- Butyl)-N-(1 -ethyl-propyl)-2,6-dinitro-benzenamin (Pendralin), 3-(4-Chlor-5- cyclopentyloxy-2-fluor-phenyl)-5-(l -methyl-ethyliden)-2,4-oxazolidin-dion(3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy) phenyl) -N-methoxy-N-methyl-hara (metobenzuron), N ' - (4-Bromophenyl) -N-methoxy-N-methylurea (metobromuron), (S) -2-chloro-N- (2-ethyl-6-methylphenyl) -N- (2-methoxy-1 -methyl-ethyl) -acet-amide (metol chlorine, 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-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-lH-azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N-phenyl-propanamide (naproanilide) , N-butyl-N'- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl -sulfonyl) -urea (nico-sulfurone), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) pyrid-azinone (norflurazone), S- (2-chloro-benzyl) - N, N-diethyl-thiocarbamate (orben-carb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (oryzalin), 3- [2,4-di-chloro-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-yl) -N '- (2- oxetan- 3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [l- (3,5-dichlorophenyl) -1-i-propyl] -2,3-dihydro-6-methyl-5- phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1 - (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), 1,3-dimethyl -4,4'-bipyridinium (paraquat), 1-amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl) - N- (1-ethyl-prop yl) -2,6-dinitro-benzenamine (pendralin), 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5- (l-methylethylidene) -2,4-oxazolidinedione
(Pentoxazone), 4-Amino-3,5,6-trichlor-pyridin-2-carbonsäure (Picloram), 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-phos- phorodithioat (Piperophos), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxy- ethyl)-acetamid (Pretilachlor), N-(4,6-Bis-difluormethoxy-pyrimidin-2-yl)-(Pentoxazone), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) pyridine-2-carboxamide (Pico-linafen), S- [2- (2-methyl-l-piperidinyl) -2-oxo-ethyl] -O, O-dipropylphosphorodithioate (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)-harnstoff (Primisulfuron-methyl), 1 - Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)-6-fluor-tetrahydro-l,3-dioxo-lH- pyrrolo[l ,2-c]imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Profluazol), 2- Chlor-N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor-phenyl)- propanamid (Propanil), (R)-[2-[[(l-Methyl-ethyliden)-amino]-oxy]-ethyl]-2-N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), 1 - chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l, 3-dioxo-lH-pyrrolo [l, 2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N - (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(l-methylethylidene) amino] oxy] ethyl] -2-
[4-(6-chlor-2-chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2- Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[(l-methyl-ethoxy)-methyl]-acetamid (Propisochlor), 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)-harnstoff (Prosulfüron), Ethyl-[2-Chlor-5-(4-chlor-5-difluor- methoxy- 1 -methyl- 1 H-pyrazol-3 -yl)-4-fluor-phenoxy] -acetat (Pyraflufen- ethyl), l-(3-Chlor-4,5,6,7-tetrahydro-pyrazolo[l,5-a]pyridin-2-yl)-5-(methyl- 2-propinylamino)-lH-pyrazol-4-carbonitril (Pyraclonil, Pyrazogyl), 4-(2,4- Dichlor-benzoyl)- 1 ,3-dimethyl-5-(4-methyl-phenylsulfonyloxy)-pyrazol (Pyr- azolate), 4-(2,4-Dichlor-benzoyl)- 1 ,3-dimethyl-5-(phenylcarbonylmethoxy)- pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxy- carbonyl- 1 -methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenylmethanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]- oxim (Pyribenzoxim), O[3-(l,l-Dimethyl-ethyl)-phenyl]-(6-methoxy-2-pyri- dinyl)-methylthiocarbamat (Pyributicarb), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3-phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyri- date), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyri- midinyl)-thio]-3-methyl-l(3H)-isobenzofüranon (Pyriftalid), 2-(4,6-Di- methoxy-pyrimidin-2-yl-oxy)-benzoesäure-methylester (Pyriminobac- methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-ylthio)-benzoesäure- Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor-chinolin-8-carbonsäure (Quin- chlorac), 7-Chlor-3-methyl-chinolin-8-carbonsäure (Quinmerac), 2-[4-(6- Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, -tetrahydro-2- furanyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfuron), 2-(l-Ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2- cyclohexen- 1 -on (Sethoxydim), 6-Chlor-2,4-bis-ethylamino- 1 ,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion[4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(l-methyl-ethoxy) - methyl] -acetamide (propisochlor), 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), ethyl- [2-chloro-5- (4-chloro-5-difluoro-methoxy-1-methyl-1 H- pyrazol-3 -yl) -4-fluorophenoxy] acetate (pyraflufen- ethyl), 1- (3-chloro-4,5,6,7-tetrahydro-pyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -IH-pyrazole-4 -carbonitrile (pyraclonil, pyrazogyl), 4- (2,4-dichlorobenzoyl) - 1,3-dimethyl-5- (4-methylphenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2,4- Dichlorobenzoyl) - 1,3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1 - methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenylmethanone-O- [2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoyl] - oxime ( Pyribenzoxime), O [3- (l, l-dimethylethyl) phenyl] - (6-methoxy-2-pyridinyl) methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol ), O- (6-chloro-3-phenyl-pyridazin-4-yl) -S-octyl-thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7- [(4,6-Dimethoxy-2-pyrimidinyl) thio] -3-methyl-l (3H) -isobenzofüranon (pyriftalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy ) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy- pyrimidin-2-ylthio) benzoic acid sodium salt (Pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester, -tetrahydro-2-furanyl methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N - (4,6-dimethoxypyrimidin-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-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione
(Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino-phenyl)-4-difluor- methyl-5-methyl-2,4-dihydro-3H-l ,2,4-triazol-3-on (Sulfentrazone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]- benzoate (Sulfometuron-methyl), N-Phosphonomethyl-glycin-trimethyl- sulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethyl- sulfonyl-imidazo[l,2-a]pyridin-3-sulfonamid (Sulfosulfuron), 6-Chlor-4- ethylamino-2-tert-butylamino-l,3,5-triazin (Terbuthylazine), 2-tert-Butyl- amino-4-ethylamino-6-methylthio-l,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6- dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluor- methyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6- dimethyl-3H,5H-pyrrolo[2, 1 -c]- 1 ,2,4-thiadiazol-3-ylidenamino)-7-fluor-4-(2- propinyl)-2H- 1 ,4-benzoxazin-3(4H)-on (Thidiazimin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harn- stoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-tri- methyl-phenyl)-2-cyclohexen-l-on (Tralkoxydim), S-(2,3,3-Trichlor-2- propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl- l,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulf- uron), N-Methyl-N-(4-methoxy-6-methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxy- carbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)- pyridin-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2-tri- chlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]- carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Tri- floxysulfuron), 1 - Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol(Sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one ( Sulfentrazone), methyl 2 - [[[((4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoates (sulfometuron methyl), N-phosphonomethylglycine trimethyl sulfonium (Sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro -4-ethylamino-2-tert-butylamino-l, 3,5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-l, 3,5-triazine (terbutryn), 2 -Chlor-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6- ( 6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2, 1-c] - 1, 2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) - 2H- 1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl- thien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-tri-methyl-phenyl) -2-cyclohexene l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl ) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1, 3,5-triazine-2 -yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) - pyridin-2-yl-oxyacetic acid (triclopyr), 2- ( 3,5-dichlorophenyl) -2- (2,2,2-trichloroethyl) oxirane (tridiphane), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl ] -3- (2,2,2-tr ifluoro-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-trifluor-ethoxy)-l,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfüron- methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-(2-trifluor- methyl-phenylsulfonyl)-harnstoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino])-2- pyridinsulfonamid, (vgl. WO-A-92/10660), 4-[4,5-Dihydro-4-methyl-5-oxo- (3-trifluormethyl)-lH-l,2,4-triazol-l-yl]-2-[(ethylsulfonyl)amino]-5-fluor- benzencarbothioamid (vgl. WO-A-95/30661), Phenylcarbothiamid-,4-[4,5- dihydro-4-methyl-5-oxo-3-(trifluormethyl)- 1H- 1 ,2,4-triazol- 1 -yl]-2- [(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991) und 2-Chloro-N-[ 1 -[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro- 1 H- pyrazol-5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599).(Trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoroethoxy) -l, 3,5-triazin-2-yl] -N '- (2-methoxycarbonylphenylsulfonyl) urea (Triflusulfüron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), N- [[(4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino]) - 2-pyridinesulfonamide, (see WO-A-92/10660) , 4- [4,5-Dihydro-4-methyl-5-oxo (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5- fluorobenzenecarbothioamide (cf. WO-A-95/30661), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1, 2,4-triazole - 1 -yl] -2- [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and 2-chloro-N- [1 - [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2; SLA5599).
("Wirkstoffe der Gruppe 3"),("Active substances of group 3"),
sowie gegebenenfalls zusätzlich (d) zumindest eine die Kulturpflanzen- Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:as well as, if necessary, additionally (d) at least one compound which improves crop plant tolerance from the following group of compounds:
α-(l,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), α-(Cya- nomethoximino)-phenylacetonitril (Cyometrinil), 4-Chlor-N-(l ,3-dioxolan-2- yl-methoxy)-α-trifluor-acetophenonoxim (Fluxofenim), 4,6-Dichlor-2-phenyl- pyrimidin (Fenclorim), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l ,4-benz- oxazin (Benoxacor), 5-Chlor-chinoxalin-8-oxy-essigsäure-(l -methyl-hexyl- ester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-α- (1,3-Dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinil), α- (cyano-methoximino) -phenylacetonitrile (cyometrinil), 4-chloro-N- (1,3-dioxolan-2-yl -methoxy) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benz- oxazin (Benoxacor), 5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N-
(2-propenyl)-acetamid (DKA-24), 1,8-Naphthalsäureanhydrid, l-(2,4-Di- chlor-phenyl)-5-trichlormethyl-lH-l,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure-phenyl- methylester (Flurazole), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazoli- din (Furilazole, MON-13900), 4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan(2-propenyl) acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-di-chlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid -ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid-phenyl-methyl ester (Flurazole), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazoline-din (Furilazole, MON-13900), 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] decane
(AD-67), 2-Dichlormethyl-2-methyl-l,3-dioxolan (MG-191), 2,2-Dichlor-N- (1 ,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamid (PPG- 1292), 2,2-Di- chlor-N,N-di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-(l - methyl- l-phenyl-ethyl)-harnstoff (Dymron), 1-Dichloracetyl-hexahydro- 3,3,8a-trimethylpyπOlo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), N-(2-(AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- ( 2-propenyl) acetamide (PPG-1292), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methylphenyl) -N '- (l - methyl-1-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyπOlo [1,2-a] -pyrimidin-6 (2H) -one (BAS-145138), N- (2-
Methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl- 4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), (4-Chlor- 2-methylphenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methylphenoxy)-pro- pionsäure (Mecoprop), Diethyl-1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichloro- phenoxyessigsäure (2,4-D) und dessen DerivateMethoxy-benzoyl) -4- (methylaminocarbonylamino) benzenesulfonamide, ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA) , 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5- dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and their derivatives
("Wirkstoffe der Gruppe 4").("Active substances of group 4").
Bevorzugte Substituenten der in der vorstehend gezeigten Formel (I) aufgeführtenPreferred substituents of those shown in formula (I) shown above
Reste werden im folgenden erläutert. R steht bevorzugt für Wasserstoff oderLeftovers are explained below. R preferably represents hydrogen or
Figure imgf000015_0001
wobei
Figure imgf000015_0001
in which
R2 bevorzugt für Wasserstoff, Chlor, Cyano, Phenyl, C Cg-Alkyl, Methoxy,R 2 preferably represents hydrogen, chlorine, cyano, phenyl, C Cg-alkyl, methoxy,
Methylthio, Cι-C2-Alkoxycarbonyl, Propylaminocarbonyl, Dimethylamino- carbonyl, Benzylaminocarbonyl (wobei die Benzylgruppe gegebenenfalls durch Chloro, Methyl oder Methoxy substituiert ist), 2'-Phenylethylaminocarbonyl oder Furylmethylaminocarbonyl steht, undMethylthio, -C-C2-alkoxycarbonyl, propylaminocarbonyl, dimethylamino-carbonyl, benzylaminocarbonyl (where the benzyl group is optionally substituted by chloro, methyl or methoxy), 2'-phenylethylaminocarbonyl or furylmethylaminocarbonyl, and
R3 bevorzugt für gegebenenfalls durch Chlor, Fluor, Cyano, Nitro, Methyl, Methoxy, Ethoxy, Butoxy, Allyloxy, Methylthio, Dimethylamino, Phenoxy, Benzyloxy oder Acetoxy substituiertes Phenyl oder für -COR4 steht, worinR 3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR4, in which
R4 für Methoxy, Ethoxy, Methyl, Benzyloxy oder Benzylamino steht,R4 represents methoxy, ethoxy, methyl, benzyloxy or benzylamino,
A bevorzugt für Chlor oder Methoxy steht undA preferably represents chlorine or methoxy and
D und E, die gleich oder unterschiedlich sein können, bevorzugt für Wasserstoff,D and E, which can be the same or different, preferably for hydrogen,
Methoxy oder Ethoxy stehen.Methoxy or ethoxy are available.
R2 steht besonders bevorzugt für Wasserstoff, Methyl, Methylthio, Cyano, Methoxycarbonyl oder Phenyl.R 2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
R3 steht besonders bevorzugt für gegebenenfalls durch Methyl oder Methoxy substituiertes Phenyl.R3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
A steht besonders bevorzugt für Methoxy. D und E stehen besonders bevorzugt für Methoxy.A particularly preferably represents methoxy. D and E are particularly preferably methoxy.
R2 steht ganz besonders bevorzugt für Phenyl.R 2 very particularly preferably represents phenyl.
R3 steht ganz besonders bevorzugt für Phenyl.R 3 very particularly preferably represents phenyl.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden eine oder mehrere Verbindungen aus einer Gruppe von Herbiziden bevorzugt, welche die nachstehend genannten Wirkstoffe enthält:Preferred mixture components from the active ingredients in group 3 are one or more compounds from a group of herbicides which contain the active ingredients mentioned below:
4-Amino-N-(l , l-Dimethyl-ethyl)-4,5-dihydro-3-(l -methyl-ethyl)-5-oxo-lH- 1 ,2,4-tri- azol- 1 -carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N- methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), N-Benzyl-2-(4- fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 3-i-Propyl-lH-2,l,3- benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro- benzoat (Bifenox), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 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), N-(4-Methoxy-6-methyl- 1,3,5- triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N'-(3-Chlor-4- methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5- (l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethyl- ester (Cinidon-ethyl), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phen- oxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clopyr- alid), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure4-amino-N- (l, l-dimethyl-ethyl) -4,5-dihydro-3- (l-methyl-ethyl) -5-oxo-lH- 1, 2,4-tri-azole-1 - carboxamide (amicarbazone), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N-benzyl-2- (4- fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 3-i-propyl-1H-2, 1, 3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichloro -phenoxy) -2-nitro-benzoate (bifenox), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl- ethyl) phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (carfentrazone-ethyl), N- (4-methoxy-6- methyl-1,3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N- dimethyl urea (chlorotoluron), 2-chloro-3- [2-chloro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) - phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) -phen oxy-propanoate (Clodinafop-propargy l), 3,6-dichloropyridine-2-carboxylic acid (clopyralide), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid
(Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2-[4- (2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), 1 ,2-Dimethyl-3,5-di- phenyl-lH-pyrazolium-methylsulfat (Difenzoquat), N-(2,4-Difluor-phenyl)-2-(3-tri- fluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfüron), (R)-(Dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop -methyl), 1,2-dimethyl-3,5-di-phenyl-1H-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (Diflufenican), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (2-ethoxy-phenoxysulfonyl) -urea (Ethoxysulfüron), (R) -
Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)- ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazol-l- carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL- alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L- alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)- DL-alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[ 1,2,4]- triazolo-[ 1 ,5-c]-pyrimidin-2-sulfonamid (Florasulam), 5-(4-Brom- 1 -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), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure- ethoxycarbonylmethylester (Fluoroglycofen-ethyl), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-hamstoff- Natriumsalz (Flupyrsulfuron-methyl-sodium), (4-Amino-3,5-dichlor-6-fluor-pyridin- 2-yl-oxy)-essigsäure (-2-butoxy-l-methyl-ethylester, -1-methyl-heptylester) (Flur- oxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluormethyl- phenyl)-3(2H)-furanon (Flurtamone), 2-Amino-4-(hydroxymethylphosphinyl)-butan- säure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), Methyl-2-(4,5-di- hydro-4-methyl-4-isopropyl-5-oxo- 1 H-imidazol-2-yl)-4-methyl-benzoat (Imaza- methabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)- 5 -methyl-pyridin-3 -carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imaza- mox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-chinolin-3- carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2- yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4-Methoxy-6-methyl-l ,3,5- triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-NatriumsalzEthyl 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-fluro-phenyl) -DL- alaninate (Flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop-isopropyl-L ), Methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) - DL-alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy - [1,2,4] - triazolo- [1,5-c] pyrimidine-2-sulfonamide (Florasulam), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazole-3 -yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazole- 2-yl-oxy) -acetamide (flufenacet), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), N- (4,6-dimethoxy- pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), (4-amino-3,5-dichloro- 6-fluoro-pyridin-2-yl-oxy) acetic acid (-2-butox yl-methyl-ethyl ester, -1-methyl-heptyl ester) (corridor oxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone ( Flurtamone), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammmonium salt), (glyphosate, isopropylammonium), methyl 2- ( 4,5-di-hydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) - 5-methyl-pyridin-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4 -isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl- 5-oxo-lH-imidazol-2-yl) -quinolin-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2 - yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2 methoxycarbonyl-phenylsulfonyl) urea sodium salt
(Iodosulfuron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Di- methyl-N' -(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3 -( 1 -Ethyl- 1 -methyl- propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methyl- sulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5-Cyclo- propyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)-methanon (Isoxa- flutole), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl- phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl- acetamid (Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]- amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 4-Amino-3-methyl-6-phenyl-l ,2,4-triazin-5(4H)-on (Metamitron), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2- sulfonamid (Metosulam), 4-Amino-6-tert-butyl-3-methylthio-l ,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- phenylsulfonyl)-harnstoff (Metsulfuron-methyl), 1 -Amino-N-( 1 -ethyl-propyl)-3,4-di- methyl-2,6-dinitro-benzol (Pendimethalin), N-(4-Fluor-phenyl)-6-(3-trifluormethyl- phenoxy)-pyridin-2-carboxamid (Picolinafen), N-(3,4-Dichlor-phenyl)-propanamid(Iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- ( 3 - (1-Ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methyl-sulfonyl-phenyl) - (5-cyclopropyl -isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), (4-chlorine -2-methyl-phenoxy) acetic acid (MCPA), 2- (4-chloro-2-methyl- phenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenylacetamide (mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] - carbonyl] - amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 4-amino-3-methyl-6-phenyl-l, 2,4-triazine-5 (4H) -one (metamitron), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2- sulfonamide (metosulam), 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-methoxycarbonylphenylsulfonyl) urea (metsulfuron-methyl), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl -2,6-dinitrobenzene (pendimethalin), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) pyridine-2-carboxamide (picolinafen), N- (3,4-dichloro- phenyl) propanamide
(Propanil), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy- 1 -methyl- 1 H-pyrazol-3-yl)- 4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 2-(2-Chlor-4-methylsulfonyl-benzoyl)- cyclohexan- 1 ,3-dion (Sulcotrione), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[l,2-a]- pyridin-3 -sulfonamid (Sulfosulfuron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-(Propanil), ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1 H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), 2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl ) -N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridin-3-sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl ) -
N' -(2-methoxycarbonyl-thien-3 -yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2- (Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen- 1 -on (Tral- koxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamothioat (Triallate), N-(4- Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-harn- Stoff (Triasulfüron), N-Methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2- methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), 1 - Amino-2,6-di- nitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-(4-Methoxy-6-trifluor- methoxy-l,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-hamstoff (Tritosul- furon), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-lH- l,2,4-triazol-l-yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1,N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) - 2-cyclohexen- 1 -one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3.5 -triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3) , 5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), 1-amino-2,6-di-nitro-N, N-dipropyl-4-trifluoromethyl- benzene (trifluralin), N- (4-methoxy-6-trifluoro-methoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosul-furon), phenylcarbothiamide -, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -lH-l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] -5 -fluoro- (CAS number 173980-17-1,
H WH4991 ) und (2-Chloro-N-[ 1 -[2,6-dichloro-4-(difluoromethyl)ρhenyl]-4-nitro- 1 H- pyrazol-5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599).H WH4991) and (2-chloro-N- [1 - [2,6-dichloro-4- (difluoromethyl) ρhenyl] -4-nitro- 1 H-pyrazol-5-yl] propane carboxamide (CAS number 121750- 17-2; SLA5599).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden in be- sonderem Maße Herbizide der Klasse der Sulfonylharnstoffe, Triazolopyrimidine,Herbicides from the class of the sulfonylureas, triazolopyrimidines, are used in particular as mixture components from the active ingredients of group 3.
Imidazolinone, Harnstoffe, Triazindione, Triketone, Triazolinone, Benzonitrile, Phenoxypropionsäurederivate, Dichloφhenoxysäurederivate, Carboxamide, Oxy- acetamide sowie weitere herbizide Wirkstoffe hervorgehoben, die nachstehend im einzelnen aufgeführt werden:Imidazolinones, ureas, triazinediones, triketones, triazolinones, benzonitriles, Phenoxypropionic acid derivatives, dichloφhenoxyacid derivatives, carboxamides, oxyacetamides and other herbicidal active ingredients, which are listed in detail below:
a) Sulfonylharnstoffe:a) Sulfonylureas:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamo- yl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-l ,3,5-triazin-2-yl)- N' -(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfüron), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfo- nyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), N-(4-Methoxy- 6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)- harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 2-[[[[(4,6-Dimethoxy- 2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)- amino]methyl]-benzoesäure-methylester (Mesosulfuron), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfo- nyl-imidazo[ 1 ,2-a]pyridin-3-sulfonamid (Sulfosulfuron), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harn- Stoff (Thifensulfuron-methyl), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-N- (4,6-Dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-l , 3,5-triazin-2-yl) - N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N- (4,6-dimethoxypyrimidin-2-yl) -N' - (3- methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl ) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl ] -amino] -sulfonyl] -4 - [[(methylsulfonyl) - amino] methyl] -benzoic acid methyl ester (mesosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl ) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N- (4,6-dimethoxypyrimidin-2-yl) -N' - (2-ethylsulfonyl-imidazo [1, 2-a] pyridin-3-sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl -sulfonyl) urea substance (thifensulfuron-methyl), N- (4-methox y-6-methyl-l, 3,5-triazin-2-yl) -N'
[2-(2-chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4- methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfo- nyl)-harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5- triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff(Tritosulfuron),[2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N'- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl ) urea (tritosulfuron),
b) Triazolopyrimidine:b) Triazolopyrimidines:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin- 2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Metosulam), c) Imidazolinone:N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam), c) Imidazolinones:
Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4- methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo- 1 H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazametha- pyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-meth- oxymethyl-pyridin-3 -carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5- Dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridin-3- carbonsäure (Imazethapyr),Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1 H -imidazol-2-yl) -5-methylpyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro- 4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -5-meth-oxymethyl-pyridin-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4 -isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo 1H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr),
d) Harnstoffe:d) ureas:
N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), N,N- Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon),N '- (3-chloro-4-methyl-phenyl) -N, N-dimethyl-urea (chlorotoluron), N, N-dimethyl-N' - (4-isopropyl-phenyl) -urea (isoproturon),
e) Triazindione:e) Triazinediones:
4- Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metribuzin),4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (metribuzin),
f) Triketone:f) Triketones:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion (Sulcotrione),2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione),
g) Triazolinone:g) triazolinones:
2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluor- methyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-on (Carfentrazone-ethyl), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-lH- 1 ,2,4-triazol-l -yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer2- (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), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -IH-1, 2,4-triazole-l -yl] -2 - [(ethylsulfonyl) amino] -5-fluoro- (CAS number
173980-17-1, HWH4991), h) Benzonitrile:173980-17-1, HWH4991), h) Benzonitrile:
3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 4-Hydroxy-3,5-diiod- benzonitril (Ioxynil),3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil),
i) Phenoxypropionsäurederivate:i) Phenoxypropionic acid derivatives:
(R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propa- noat (Diclofop-methyl), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phen- oxy]-propanoat (Fenoxaprop-(P)-ethyl),(R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxypropanoate (clodinafop-propargyl), methyl 2- [4- ( 2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phen-oxy] -propanoate (fenoxaprop- (P) -ethyl),
j) Dichloφhenoxysäurederivate:j) dichloφhenoxyacid derivatives:
2,4-Dichlor-phenoxyessigsäure (2,4-D), (R)-2-(2,4-Dichlor-phenoxy)-propan- säure (Dichloφrop-P), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2- (4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop),2,4-dichlorophenoxyacetic acid (2,4-D), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloφrop-P), (4-chloro-2-methylphenoxy ) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop),
k) Carboxamide:k) carboxamides:
N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen),N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) -pyridine-2-carboxamide (picolinafen),
1) Oxyacetamide:1) Oxyacetamide:
N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadiazol-2-yl- oxy)-acetamid (Flufenacet), (2-Chloro-N-[ 1 -[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro- 1 H-pyrazol-5-yl]- propancarbonsäureamid (CAS-Nummer 121750-12-2; SLA5599),N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), (2-Chloro-N- [1 - [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1 H-pyrazol-5-yl] propane carboxamide (CAS number 121750-12-2; SLA5599),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox),Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox),
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),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),
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl- ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),(4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl)
2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)),2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)),
N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropyl- ammonium),N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium),
N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate).N-phosphonomethyl-glycine trimethyl sulfonium (sulfosate).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 4 werden besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group 4:
5-Chlor-chinoxalin-8-oxy-essigsäure-( 1 -methylhexylester) (Cloquintocet), 1 -(2,4-Di- chlor-phenyl)-5-trichlormethyl-lH-l,2,4-triazol-3-carbonsäure-ethylester (Fenchlora- zol-ethyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl),5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (cloquintocet), 1 - (2,4-di-chlorophenyl) -5-trichloromethyl-1H-l, 2,4-triazole-3 -carboxylic acid ethyl ester (fenchlorazol-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl),
(4-Chlor-2-methylphenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methylphenoxy)-pro- pionsäure (Mecoprop), Diethyl- 1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- 1H- pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate. Erfindungsgemäß ganz besonders bevorzugt sind die oben genannten selektiv- herbiziden Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirk- stoffkombination umfassend(4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl 1 - (2,4-dichlorophenyl) -4,5- dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives. According to the invention, the above-mentioned selective herbicidal compositions, which are characterized by a content of an active ingredient combination, are very particularly preferred
a) mindestens ein Phenoxypyrimidin-Derivat aus der folgenden Gruppe von Verbindungen:a) at least one phenoxypyrimidine derivative from the following group of compounds:
2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribac- sodium, KEH 2023) der Formel2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribacsodium, KEH 2023) of the formula
Na .©Well. ©
Figure imgf000023_0001
Figure imgf000023_0001
oderor
Diphenyl-methanon-O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]- oxim (Pyribenzoxim) der Formel Diphenylmethanone-O- [2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoyl] oxime (pyribenzoxime) of the formula
Figure imgf000024_0001
Figure imgf000024_0001
b) der Verbindung Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH- 1,2,4-triazol-l-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone-sodium) der Formelb) the compound methyl-2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-1,2,4-triazol-l-yl) carbonyl] amino] sulfonyl] -benzoic acid, sodium salt (Propoxycarbazone-sodium) of the formula
Figure imgf000024_0002
Figure imgf000024_0002
sowiesuch as
c) zumindest einen der vorstehend genannten Wirkstoffe der Gruppe 3,c) at least one of the aforementioned Group 3 active ingredients,
sowie gegebenenfallsand if necessary
d) zumindest eine der vorstehend genannten, die Kultuφflanzen- Verträglichkeit verbessernden Verbindung der Gruppe 4, wobei solche Verbindungen bevorzugt sind, die vorstehend in bevorzugten Bereichen genannt wurden. Erfindungsgemäß am meisten bevorzugt sind selektiv-herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirkstoffkombination umfassendd) at least one of the above-mentioned compounds of group 4 which improve the compatibility with crop plants, preference being given to those compounds which have been mentioned above in preferred ranges. Most preferred according to the invention are selective herbicidal compositions which are characterized by a content of an active ingredient combination comprising
a) 2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribac- sodium) der Formela) 2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribac-sodium) of the formula
Figure imgf000025_0001
Figure imgf000025_0001
undand
b) Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy- 1 H- 1 ,2,4-triazol- 1 -yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone- sodium) der Formelb) Methyl-2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1 H-1, 2,4-triazole-1-yl) carbonyl] amino] sulfonyl] - benzoic acid, sodium salt (propoxycarbazone-sodium) of the formula
Figure imgf000025_0002
sowie
Figure imgf000025_0002
such as
c) zumindest eine weitere Verbindung ausgewählt aus den folgenden Wirkstoffen der Gruppe 3: a) Sulfonylharnstoffe:c) at least one further compound selected from the following active ingredients from group 3: a) Sulfonylureas:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamo- yl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl- 1 ,3,5-triazin-2-yl)- N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N- Methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- phenylsulfonyl)-harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluor- methoxy-l,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1 , 3,5-triazin-2-yl) - N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-l, 3.5 -triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl ) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron),
b) Triazolopyrimidine:b) Triazolopyrimidines:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin- 2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Metosulam),N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam),
c) Imidazolinone:c) Imidazolinones:
2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxy- methyl-pyridin-3 -carbonsäure (Imazamox),2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridin-3-carboxylic acid (imazamox),
d) Harnstoffe:d) ureas:
N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff(Isoproturon),N, N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproturon),
e) Triazindione:e) Triazinediones:
4-Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metribuzin), f) Triketone:4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (metribuzin), f) Triketones:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3 -dion (Sulcotrione),2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione),
g) Triazolinone:g) triazolinones:
Benzenecarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-lH- l,2,4-triazol-l-yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS 173980-17-1, HWH4991),Benzenecarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -lH- l, 2,4-triazol-l-yl] -2 - [(ethylsulfonyl) amino] - 5-fluoro- (CAS 173980-17-1, HWH4991),
(2-Chloro-N-[ 1 -[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro- 1 H-pyrazol-5-yl]- propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA 5599),(2-Chloro-N- [1 - [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1 H-pyrazol-5-yl] propane carboxamide (CAS number 121750-17-2; SLA 5599),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), undMethyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (Bifenox), and
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-l-methyl- ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),(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)
sowie gegebenenfallsand if necessary
d) zumindest eine der vorstehend genannten, die Kultuφflanzen-Verträglichkeit verbessernden Verbindung der Gruppe 4, wobei solche Verbindungen bevorzugt sind, die vorstehend in bevorzugten Bereichen genannt wurden.d) at least one of the above-mentioned compounds of group 4 which improve the compatibility with crop plants, preference being given to those compounds which have been mentioned above in preferred ranges.
Es wurde nun überraschend gefunden, dass die oben definierten Wirkstoffkombinationen aus den Phenoxypyrimidin-Derivaten der Formel (I) und dem Wirkstoff der Gruppe 2 in Kombination mit Wirkstoffen der Gruppe 3, gegebenenfalls in Kombinationen mit Wirkstoffen der Gruppe 4 bei sehr guter Nutzpflanzen- Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Nutz- pflanzenkulturen wie z. B. in Soja, Kartoffeln, Mais oder Reis und insbesondere in Getreide, wie z.B. Gerste, Roggen, Triticale und besonders Weizen zur selektiven Unkrautbekämpfung verwendet werden können.It has now surprisingly been found that the active substance combinations defined above from the phenoxypyrimidine derivatives of the formula (I) and the active substance from group 2 in combination with active substances from group 3, if appropriate in combinations with active substances from group 4, with very good crop plant tolerance have particularly high herbicidal activity and in various crops such as. B. in soy, potatoes, corn or rice and especially in Cereals such as barley, rye, triticale and especially wheat can be used for selective weed control.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirk- Stoffkombinationen aus Verbindungen der oben aufgeführten Gruppen 1, 2 und 3 erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active substance combinations according to the invention composed of compounds from groups 1, 2 and 3 listed above is considerably higher than the sum of the effects of the individual active substances.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungsergänzung. Die neuen Wirkstoffkombinationen sind in vielen Kulturen gut verträglich, wobei die neuen Wirkstoffkombinationen auch sonst schwer bekämpfbare Unkräuter gut bekämpfen. Die neuen Wirkstoffkombinationen stellen somit eine wertvolle Bereicherung der Selektivherbizide 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 selective herbicides.
Es wurde außerdem überraschend gefunden, dass die oben definierten Wirkstoff- kombinationen aus Phenoxypyrimidin-Derivaten der Formel (I) bzw. deren Salze und einem Safener/ Antidot ("Wirkstoffe der Gruppe 4") in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und Gruppe 3 bei sehr guter Nutzpflanzen- Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Getreide, vor allem Weizen, aber auch in Soja, Kartoffeln, Mais und Reis zur selektiven Unkrautbekämpfung verwendet werden können.It has also surprisingly been found that the active substance combinations defined above of phenoxypyrimidine derivatives of the formula (I) or their salts and a safener / antidote (“active substances of group 4”) in combination with one or more of the one or more Listed active ingredients of group 2 and group 3 with very good crop tolerance, have a particularly high herbicidal activity and can be used in various crops, in particular in cereals, especially wheat, but also in soybeans, potatoes, corn and rice for selective weed control.
Überraschenderweise wurde zudem gefunden, dass auch die herbizidwirksame Substanz MCPA sowie die Substanz 2,4-Dichlorophenoxy-essigsäure (2,4-D) und ihre Derivate die oben beschriebene Safeneraufgabe übernehmen können.Surprisingly, it was also found that the herbicidal substance MCPA and the substance 2,4-dichlorophenoxyacetic acid (2,4-D) and their derivatives can also take over the safener task described above.
Eine bevorzugte Ausführungsform ist daher auch eine Mischung enthaltend eine Verbindung der Formel (I) und/oder deren Salze einerseits und 2,4-D und/oder dessen Derivate andererseits, in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und 3. Typische Derivate von 2,4-D sind z.B. deren Ester. Eine bevorzugte Ausführungsform ist weiterhin eine Mischung enthaltend eine Verbindung der Formel (I) und/oder deren Salze einerseits und MCPA andererseits in Kombination mit dem oben angeführten Wirkstoff der Gruppe 2 und einem oder mehreren Verbindungen der Gruppe 3.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, in combination with one or more of the active ingredients or of the group mentioned above 2 and 3. Typical derivatives of 2,4-D are their esters. A preferred embodiment is also a mixture comprising a compound of formula (I) and / or its salts on the one hand and MCPA on the other hand in combination with the above-mentioned active ingredient of group 2 and one or more compounds of group 3.
Die Verbindungen Diethyl- 1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- lH-pyra- zole-3,5-dicarboxylate (Mefenpyr-diethyl), (l-methylhexyl)-[(5-chloro-8-quino- linyl)oxy]acetate (Cloquintocet-mexyl) und Ethyl-l-(2,4-dichlorophenyl)-5-(tri- chloromethyl)-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. (4-Chloro-2-methylphenoxy)- essigsäure (MCPA) ist ebenfalls ein bekanntes Herbizid.The compounds diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), (l-methylhexyl) - [(5th -chloro-8-quino-linyl) oxy] acetate (Cloquintocet-mexyl) and ethyl-l- (2,4-dichlorophenyl) -5- (tri- chloromethyl) -lH-l, 2,4-triazole-3- Carboxylates (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. (4-Chloro-2-methylphenoxy) acetic acid (MCPA) is also a well-known herbicide.
Als überraschend ist weiterhin anzusehen, dass aus einer Vielzahl von bekanntenIt is also surprising that from a large number of known
Safenern oder Antidots, die befähigt sind, die schädigende Wirkung eines Herbizids auf die Kultuφflanzen zu antagonisieren, gerade die oben aufgeführten Verbindungen der Gruppe 4 geeignet sind, die schädigende Wirkung von Verbindungen der Formel (I) und deren Salzen in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und 3, auf die Kultuφflanzen annähernd vollständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen.Safeners or antidots, which are capable of antagonizing the damaging effect of a herbicide on the cultivated plants, are particularly suitable for the group 4 compounds listed above, the damaging effect of compounds of the formula (I) and their salts in combination with one or more of the or the above-mentioned active ingredients of groups 2 and 3, to almost completely cancel the cultivated plants without impairing the herbicidal activity against the weeds.
Die erfindungsgemäßen Wirkstoffkombinationen können z.B. bei den folgenden Pflanzen verwendet werden:The active substance combinations according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria,Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria,
Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,
Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis,Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis,
Brassica, Lactuca, Cucumis, Cuburbita.Brassica, lactuca, cucumis, cuburbita.
Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,
Sciφus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.Sciφus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
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.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kultuφflanzen (einschließlich natürlich vorkommender Kultuφflanzen). Kultuφflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaftAccording 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 undesired wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including 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 parts and organs of plants, such as shoots, leaves, flowers and roots, examples being used
Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtköφer, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.Leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well Roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
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 Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgeneAs 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.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.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit bestimmten Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Bio- und Genotypen sein.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 certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht.The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”).
Beispiele für solche Eigenschaften sind 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 höherer Ernährungswert der Ernteprodukte, höhere Lagerfahigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle 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 Kultuφflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle,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, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products , Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. The important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton,
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 CryΙA(a), CrylA ), CryΙA(c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, CrySBb 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),Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton and rapeseed are particularly emphasized. The properties ("traits") that are particularly emphasized are the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CrylA), CryΙA ( c), CryllA, CrylHA, CryIIIB2, Cry9c, Cry2Ab, CrySBb 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 through systemic acquired resistance (SAR),
Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinothricin (z.B. "PAT"-Gen). Die jeweils die gewünschtenSystemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The traits are also particularly emphasized by the plants' increased tolerance to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The one you want
Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und 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 resistenteGenes conferring traits can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato). As examples of herbicide Tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rape), IMI® (tolerance to imidazolinones) and STS ® (tolerance to sulfonylureas such as corn) are sold. Resistant as a herbicide
(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").Plants (conventionally bred to herbicide tolerance) should also be mentioned the varieties sold under the name Clearfield® (e.g. 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").
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 GewichtsteilThe synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. Generally 1 part by weight
Wirkstoff der Formel (I) jeweils 0,001 bis 1000 Gewichtsteile, vorzugsweise jeweils 0,005 bis 200 Gewichtsteile und besonders bevorzugt jeweils 0,01 bis 100 Gewichtsteile Wirkstoff der Gruppe 2 und 3. Insbesondere entfallen auf 1 Gewichtsteil der Gruppe 1 jeweils 0,1 bis 1 Gewichtsteile der Wirkstoffe der Gruppe 2 und 3.Active ingredient of the formula (I) in each case 0.001 to 1000 parts by weight, preferably 0.005 to 200 parts by weight in each case and particularly preferably in each case 0.01 to 100 parts by weight of active ingredient of groups 2 and 3. In particular, 1 to 1 part by weight of group 1 each contains 0.1 to 1 part by weight of active substances in groups 2 and 3.
Der vorteilhafte Effekt der Kultuφflanzenverträglichkeit 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 allge- meinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I), seinen Salzen oder dessen Mischungen mit Wirkstoffen der Gruppe 2 und 3 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100 Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile einer der oben unter (d) genannten, die Kultuφflanzen Verträglichkeit verbessernden Verbindungen (Antidots/Safener). 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 Feinstverkapselungen in polymeren Stoffen.The advantageous effect of the compatibility of cultivated plants 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, 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 1 to 1 part by weight of active compound of the formula (I), its salts or mixtures thereof with active compounds of groups 2 and 3 Above under (d), the crop plants tolerability-improving compounds (antidots / safeners). The active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
Diese Formulierungen 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 Mit- teln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugendenThese formulations are prepared in a known manner, e.g. B. 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. Erdöl fraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.If 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 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 Tabakstengeln; 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, Alkyl- sulfonate, 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 Phospholi- pide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt,Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
Molybdän und Zink verwendet werden.Molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen einschließlich der safenden Wirkstoffe, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active ingredients, including the safing 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 An- wendung 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. However, the active substances contained in the active substance combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischungen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte Anwendungszwecke, insbesondere im Nachauflauf- Verfahren, kann es femer vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle oder Ammoniumsalze wie z.B. Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen.The new combinations of active ingredients, as such or in their formulations, can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. 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. For certain applications, particularly in the post-emergence process, it may also be advantageous to include plant-compatible mineral or vegetable oils 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 ge- brauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Stäuben oder Streuen.The new active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auf- laufen der Pflanzen appliziert werden, also im Vorauflauf und Nachauflauf- Verfahren. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compound combinations according to the invention can be applied before and after emergence of the plants, ie in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
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):The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, S.R .: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
Wenn X = % Schädigung durch Herbizid A (Wirkstoff der GruppeIf X =% damage from herbicide A (active ingredient in the group
1) bei p kg/ha Aufwandmenge1) at p kg / ha application rate
und Y = % Schädigung durch Herbizid B (Wirkstoff der Gruppe 2) bei q kg/ha Aufwandmenge und Z = % Schädigung durch Herbizid C (Wirkstoff derand Y =% damage by herbicide B (active ingredient of group 2) at an application rate of q kg / ha and Z =% damage by herbicide C (active ingredient in
Gruppe 3) bei r kg/ha AufwandmengeGroup 3) at r kg / ha application rate
und E = die erwartete Schädigung der Herbizide A B und C bei p, q und r kg/ha Aufwandmenge,and E = the expected damage to the herbicides A B and C at p, q and r kg / ha application rate,
dann ist E = X + Y + Z ^ (XY + XZ + YZ) (XYZthen E = X + Y + Z ^ (XY + XZ + YZ) (XYZ
+ 100 10,000+ 100 10,000
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.
Beispiele für synergistische Effekte bei den erfindungsgemäßen Mischungen, die wie vorstehend beschrieben beurteilt wurden, sind auf den nachfolgenden Seiten angegeben. Examples of synergistic effects in the mixtures according to the invention, which were assessed as described above, are given on the following pages.
BeispieleExamples
Beispiel 1example 1
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit Diflufenican, Picolinafen oder Fluroxypyr-meptylBispyribac-sodium and Propoxycarbazone-sodium in a mixture with Diflufenican, Picolinafen or Fluroxypyr-meptyl
Zur Untersuchung eines möglichen Synergismus wurden die Mischungen der Verbindungen Bispyribac-sodium (KTH 2023) mit Propoxycarbazone-sodium (MKH 6561) sowie einer der Verbindungen Diflufenican, Picolinafen und Fluoroxypyr-meptyl unter Gewächshausbedingungen gegen verschiedene Unkräuter geprüft.To investigate a possible synergism, the mixtures of the compounds bispyribac-sodium (KTH 2023) with propoxycarbazone-sodium (MKH 6561) and one of the compounds Diflufenican, Picolinafen and Fluoroxypyr-meptyl were tested under greenhouse conditions against various weeds.
Dazu wurden die jeweils nötigen Mengen der Formulierungen miteinander vermischt und gegebenenfalls andere Substanzen zugegeben, und anschließend mit Wasser auf die gewünschte Konzentration verdünnt.For this purpose, the required amounts of the formulations were mixed with one another and optionally other substances were added, and then diluted with water to the desired concentration.
Es wurden die folgenden Formulierungen verwendet:The following formulations were used:
Figure imgf000038_0001
Figure imgf000038_0001
Die Menge der Formulierung in den zu testenden Lösungen entspricht den gewünschten Aufwandmengen pro ha. VorauflaufThe amount of formulation in the solutions to be tested corresponds to the desired application rates per hectare. preemergence
Samen der Testpflanzen werden in normale Erde gesät. Nach 24 h wird die gewünschte Menge an aktiver Substanz als Formulierung auf die Bodenoberfläche aufgesprüht. Die Konzentration der aktiven Substanzen in der Spritzlösung wird so gewählt, dass die gewünschte Aufwandmenge in 500 1 Wasser/ha ausgebracht werden kann.Seeds of the test plants are sown in normal soil. After 24 hours, the desired amount of active substance is sprayed onto the soil surface as a formulation. The concentration of the active substances in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
Nachauflaufpostemergence
Testpflanzen werden unter kontrollierten Temperatur- und Lichtbedingungen angezogen. Das Besprühen mit der Testlösung findet statt, wenn die Pflanzen eine Höhe von 5 bis 15 cm erreicht haben.Test plants are grown under controlled temperature and light conditions. Spraying with the test solution takes place when the plants have reached a height of 5 to 15 cm.
Die Konzentration der aktiven Substanz in der Spritzlösung wird so gewählt, dass die gewünschte Aufwandmenge in 500 1 Wasser/ha ausgebracht werden kann.The concentration of the active substance in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
Die Bewertung erfolgt etwa drei Wochen nach der Applikation. Die herbizide Wirksamkeit wird visuell im Vergleich zur unbehandelten Kontrolle beurteilt. Es bedeutenThe evaluation takes place about three weeks after the application. The herbicidal activity is assessed visually in comparison to the untreated control. Mean it
0 % = keine herbizide Wirkung, entspricht der unbehandelten Kontrolle 100 % = völlige Vernichtung der Testpflanzen0% = no herbicidal activity, corresponds to the untreated control 100% = complete destruction of the test plants
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägtenThe mixtures tested showed a clearly pronounced in these experiments
Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen I-A bis I-E). Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet. I-A (Nachauflauf)Synergism in the action against various weeds (Tables IA to IE). The values marked with (*) were calculated according to Colby, 1967. IA (post-emergence)
Figure imgf000040_0001
Figure imgf000040_0001
I-B (Nachauflauf)I-B (post-emergence)
Figure imgf000040_0002
Figure imgf000040_0002
I-C (Nachauflauf)I-C (post-emergence)
Figure imgf000040_0003
I-D (Nachauflauf)
Figure imgf000040_0003
ID (post-emergence)
Figure imgf000041_0001
Figure imgf000041_0001
I-E (Nachauflauf)I-E (post-emergence)
Figure imgf000041_0002
Figure imgf000041_0002
Beispiel 2Example 2
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit Amidosulfuron oder Metsulforon-methylBispyribac-sodium and propoxycarbazone-sodium in a mixture with amidosulfuron or metsulforon-methyl
Die Untersuchung eines möglichen Synergismus bei den vorliegenden Mischungen wurde wie für Beispiel 1 beschrieben durchgeführt. Es wurden die folgenden Formulierungen verwendet:
Figure imgf000042_0001
The investigation of a possible synergism with the present mixtures was carried out as described for Example 1. The following formulations were used:
Figure imgf000042_0001
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägten Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen II-A bis II-F). Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet.In these experiments, the mixtures tested showed a clearly pronounced synergism in their action against various weeds (Tables II-A to II-F). The values marked with (*) were calculated according to Colby, 1967.
II-A (Nachauflauf)II-A (post-emergence)
Figure imgf000042_0002
Figure imgf000042_0002
II-B (Nachauflauf)II-B (post-emergence)
Figure imgf000043_0001
Figure imgf000043_0001
II-C (Nachauflauf)II-C (post-emergence)
Figure imgf000043_0002
Figure imgf000043_0002
II-D (Nachauflauf)II-D (post-emergence)
Figure imgf000043_0003
II-E (Nachauflauf)
Figure imgf000043_0003
II-E (post-emergence)
Figure imgf000044_0001
Figure imgf000044_0001
Beispiel 3Example 3
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit HWH 4991 oder Mecoprop-PBispyribac-sodium and propoxycarbazone-sodium in a mixture with HWH 4991 or Mecoprop-P
Die Untersuchung eines möglichen Synergismus bei den vorliegenden Mischungen wurde wie für Beispiel 1 beschrieben durchgeführt. Es wurden die folgenden Formulierungen verwendet:
Figure imgf000045_0001
The investigation of a possible synergism with the present mixtures was carried out as described for Example 1. The following formulations were used:
Figure imgf000045_0001
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägten Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen UI-A bis III-I). Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet.In these experiments, the mixtures tested showed a clearly pronounced synergism in their action against various weeds (Tables UI-A to III-I). The values marked with (*) were calculated according to Colby, 1967.
III-A (Nachauflauf)III-A (post-emergence)
Figure imgf000045_0002
III-C (Nachauflauf)
Figure imgf000045_0002
III-C (post-emergence)
Figure imgf000046_0001
Figure imgf000046_0001
III-D (Nachauflauf)III-D (post-emergence)
Figure imgf000046_0002
Figure imgf000046_0002
III-E (Nachauflauf)III-E (post-emergence)
Figure imgf000046_0003
III-F (Nachauflauf)
Figure imgf000046_0003
III-F (post-emergence)
Figure imgf000047_0001
III-I (Nachauflauf)
Figure imgf000047_0001
III-I (post-emergence)
Figure imgf000048_0001
Figure imgf000048_0001
Beispiel 4Example 4
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit Imazamox oder SulcotrioneBispyribac-sodium and Propoxycarbazone-sodium in a mixture with Imazamox or Sulcotrione
Die Untersuchung eines möglichen Synergismus bei den vorliegenden Mischungen wurde wie für Beispiel 1 beschrieben durchgeführt. Es wurden die folgendenThe investigation of a possible synergism with the present mixtures was carried out as described for Example 1. The following were
Formulierungen verwendet:Formulations used:
Figure imgf000048_0002
Figure imgf000048_0002
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägten Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen lN-A bis IV-G).In these experiments, the mixtures tested showed a clearly pronounced synergism in their action against various weeds (Tables IN-A to IV-G).
Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet. IV-A (Nachauflauf)The values marked with (*) were calculated according to Colby, 1967. IV-A (post-emergence)
Figure imgf000049_0001
IV-D (Nachauflauf)
Figure imgf000049_0001
IV-D (post-emergence)
Figure imgf000050_0001
Figure imgf000050_0001
IV-E (Nachauflauf)IV-E (post-emergence)
Figure imgf000050_0002
Figure imgf000050_0002
IV-F (Nachauflauf)IV-F (post-emergence)
Figure imgf000050_0003
IV-G (Nachauflauf)
Figure imgf000050_0003
IV-G (post-emergence)
Figure imgf000051_0001
Figure imgf000051_0001
Beispiel 5Example 5
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit Isoproturon oder MetribuzinBispyribac-sodium and propoxycarbazone-sodium in a mixture with isoproturon or metribuzin
Die Untersuchung eines möglichen Synergismus bei den vorliegenden Mischungen wurde wie für Beispiel 1 beschrieben durchgeführt. Es wurden die folgenden Formulierungen verwendet:The investigation of a possible synergism with the present mixtures was carried out as described for Example 1. The following formulations were used:
Figure imgf000051_0002
Figure imgf000051_0002
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägtenThe mixtures tested showed a clearly pronounced in these experiments
Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen V-A bis V-E). Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet. V-A (Nachauflauf)Synergism in the action against various weeds (tables VA to VE). The values marked with (*) were calculated according to Colby, 1967. VA (post-emergence)
Figure imgf000052_0001
Figure imgf000052_0001
V-B (Nachauflauf)V-B (post-emergence)
Figure imgf000052_0002
V-C (Nachauflauf)
Figure imgf000052_0002
VC (post-emergence)
Figure imgf000053_0001
Figure imgf000053_0001
V-D (Nachauflauf)V-D (post-emergence)
Figure imgf000053_0002
V-E (Nachauflauf)
Figure imgf000053_0002
VE (post-emergence)
Figure imgf000054_0001
Figure imgf000054_0001
Beispiel 6Example 6
Bispyribac-sodium und Propoxycarbazone-sodium in Mischung mit Tribenuron-methyl oder TritosulfuronBispyribac-sodium and propoxycarbazone-sodium in a mixture with tribenuron-methyl or tritosulfuron
Die Untersuchung eines möglichen Synergismus bei den vorliegenden Mischungen wurde wie für Beispiel 1 beschrieben durchgeführt. Es wurden die folgendenThe investigation of a possible synergism with the present mixtures was carried out as described for Example 1. The following were
Formulierungen verwendet:Formulations used:
Figure imgf000054_0002
Figure imgf000054_0002
Die getesteten Mischungen zeigten in diesen Versuchen einen deutlich ausgeprägten Synergismus in der Wirkung gegen verschiedene Unkräuter (Tabellen VI-A bis VI-F).In these experiments, the mixtures tested showed a clearly pronounced synergism in their action against various weeds (Tables VI-A to VI-F).
Die mit (*) gekennzeichneten Werte wurden nach Colby, 1967, berechnet. VI-A (Nachauflauf)The values marked with (*) were calculated according to Colby, 1967. VI-A (post-emergence)
Figure imgf000055_0001
Figure imgf000055_0001
VI-B (Nachauflauf)VI-B (post-emergence)
Figure imgf000055_0002
Figure imgf000055_0002
VI-C (Nachauflauf)VI-C (post-emergence)
Figure imgf000055_0003
VI-D (Nachauflauf)
Figure imgf000055_0003
VI-D (post-emergence)
Figure imgf000056_0001
Figure imgf000056_0001
VI-E (Nachauflauf)VI-E (post-emergence)
Figure imgf000056_0002
Figure imgf000056_0002
VI-F (Nachauflauf)VI-F (post-emergence)
Figure imgf000056_0003
Figure imgf000056_0003

Claims

Patentansprüche claims
Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination umfassendHerbicidal agents, characterized by comprising an effective content of an active ingredient combination
(a) zumindest ein Phenoxypyrimidin-Derivat der allgemeinen Formel (I)(a) at least one phenoxypyrimidine derivative of the general formula (I)
Figure imgf000057_0001
Figure imgf000057_0001
in welcherin which
R für Wasserstoff, -CH2CH2S(O)nR1 (wobei Rλ für CrC4-Alkyl und n für 0,1 oder 2 steht) oderR is hydrogen, -CH 2 CH 2 S (O) n R 1 (where R λ is C r C 4 alkyl and n is 0.1 or 2) or
/ 3 / 3rd
-N=C steht,-N = C stands,
\\
R„R "
wobeiin which
R2 für Wasserstoff, Halogen, Cyano, Phenyl, Cj-Cg-Alkyl, C C4-Alkoxy, C1-C4-Alkylthio, Cι-C4-Alkoxycarbonyl, Mono- oder Di-C1-C -Alkylaminocarbonyl, Phenyl-Cι-C4-Alkyl- aminocarbonyl steht, wobei die Phenylgruppe gegebenenfalls durch Halogen, Cj-C2-Alkyl oder Cι-C2-Alkoxy, Furyl- methylaminocarbonyl oder Phenyl substituiert sein kann, und R3 für jeweils gegebenenfalls durch Halogen, Cyano, Nitro, Cj- C4-Alkyl, ^-Alkoxy oder Allyloxy substituiertes Phenyl, für gegebenenfalls durch Cι-C4-Alkyl, Phenoxy, Benzyloxy oder Acetoxy substituiertes Amino, für C1-C4-Alkylthio oder für die Gruppierung -COR4 steht, wobei R4 für Cι-C4-Alkoxy, Cι-C4-Alkyl, Benzyloxy oder Benzylamino steht,R 2 for hydrogen, halogen, cyano, phenyl, Cj-Cg-alkyl, C C4-alkoxy, C 1 -C4-alkylthio, Cι-C4-alkoxycarbonyl, mono- or di-C 1 -C -alkylaminocarbonyl, phenyl-Cι -C4-alkyl- aminocarbonyl, where the phenyl group may optionally be substituted by halogen, C j -C2-alkyl or -C-C2 alkoxy, furylmethylaminocarbonyl or phenyl, and R3 for phenyl optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, ^ -alkoxy or allyloxy, for optionally substituted by C 1 -C 4 -alkyl, phenoxy, benzyloxy or acetoxy, for C 1 -C 4 -alkylthio or stands for the grouping -COR4, where R4 stands for C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl, benzyloxy or benzylamino,
A für Chlor oder Methoxy steht undA represents chlorine or methoxy and
D und E, die gleich oder unterschiedlich sein können, für Wasserstoff, Halogen, Ci-Cg-Alkyl, Cj-Cg-Alkoxy oder durch Halogen substituiertes C Cg-Alkoxy stehen,D and E, which may be the same or different, represent hydrogen, halogen, Ci-Cg-alkyl, C j -Cg-alkoxy or C Cg-alkoxy substituted by halogen,
und/oder einem Salz einer Verbindung der Formel (I) („Wirkstoffe der Gruppe 1"),and / or a salt of a compound of the formula (I) (“active compounds of group 1”),
undand
zumindest eine Verbindung aus einer weiteren Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:at least one compound from a further group of herbicides which contains the active compounds mentioned below:
Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy- 1 H- 1 ,2,4-triazol- 1-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone-sodium) der FormelMethyl-2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1 H-1, 2,4-triazol-1-yl) carbonyl] amino] sulfonyl] benzoic acid, Sodium salt (Propoxycarbazone-sodium) of the formula
Figure imgf000058_0001
Figure imgf000058_0001
und 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)- phenyl] sulfonyl]-lH-l,2,4-triazol-l-carboxamid, Natrium-Salz (Flucarbazone-sodium) der Formeland 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [[2- (trifluoromethoxy) phenyl] sulfonyl] -lH-l, 2,4-triazole-l-carboxamide, sodium salt (Flucarbazone-sodium) of the formula
Figure imgf000059_0001
Figure imgf000059_0001
(„Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
sowiesuch as
einer oder mehrerer Verbindungen aus einer weiteren Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:one or more compounds from a further group of herbicides which contains the active compounds mentioned below:
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoe- säure-Natriumsalz (Acifluorfen-sodium), 2-Chlor-6-nitro-3-phenoxy- benzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl- phenyl)-acetamid (Alachlor), N-Ethyl-N'-i-propyl-6-methylthio-l ,3,5- triazin-2,4-diamin (Ametryn), 4-Amino-N-(l,l-Dimethyl-ethyl)-4,5- dihydro-3-( 1 -methyl-ethyl)-5-oxo- 1 H- 1 ,2,4-triazol- 1 -carboxamid2-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-phenoxybenzenamine (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor ), N-ethyl-N'-i-propyl-6-methylthio-l, 3,5-triazine-2,4-diamine (ametryn), 4-amino-N- (l, l-dimethyl-ethyl) - 4,5-dihydro-3- (1-methyl-ethyl) -5-oxo-1 H-1, 2,4-triazole-1-carboxamide
(Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N- methylsulfonyl-sulfamoyl)-harnsto f (Amidosulfuron), 1H-1,2,4-Tri- azol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(l -isopropyl)-amino]- 2-oxo-ethyl]-O,O-dimethyl-phosphorodithioate (Anilofos), 6-Chlor-4- ethylamino-2-isopropylamino-l,3,5-triazin (Atrazin), 2-[2,4-Dichlor-(Amicarbazone), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1,2,4-tri - azol-3-amine (amitroles), S- [2 - [(4-chlorophenyl) - (l -isopropyl) -amino] - 2-oxo-ethyl] -O, O-dimethyl-phosphorodithioate (anilofos) , 6-chloro-4-ethylamino-2-isopropylamino-l, 3,5-triazine (atrazine), 2- [2,4-dichloro-
5-(2-propinyloxy)-phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]- pyridin-3(2H)-on (Azafenidin), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-[l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulfonyl]- harnstoff (Azimsulfüron), N-Benzyl-2-(4-fluor-3-trifluormethyl-phen- oxy)-butanamid (Beflubutamid), 4-Chlor-2-oxo-3(2H)-benzthiazol- essigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4-trifluormethyl- benzenamin (Benfluralin), 2,3-Dihydro-3,3-dimethyl-5-benzofuranyl- ethansulfonat (Benfüresate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-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] - urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole-acetic acid (benazoline), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzamine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulfonate (benfüresate), N- (4.6 dimethoxy-pyrimidin-2-yl) -N'
(2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuron- methyl), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thiobencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl- 1 (2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-pro- pansäure-methylester (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), Ethyl N-benzoyl-N- (3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-lH- 2,l,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlor- phenoxy)-2-nitro-benzoat (Bifenox), 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-benzaldehyd-O-(2,4-dinitro-phenyl)-oxim (Bromofen- oxim), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), N-Butoxy- methyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2-Chlor- 5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidi- nyl)-benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-tri- methyl-3-(l-oxo-butyl)-phenyl]-2-cyclohexen-l-on (Butroxydim), S-(2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuronmethyl), S - [(4-chlorophenyl) methyl] diethylthiocarbamate (benthiocarb, thiobencarb), 2- [2- [4- (3,6-dihydro -3-methyl-2,6-dioxo-4-trifluoromethyl-1 (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-methyl-benzoyl) -l , 3-dimethyl-1H-pyrazol-5-yl] - oxy] -l- (4-methylphenyl) ethanone (benzofenap), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL -alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2, l, 3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) -2- nitro-benzoate (bifenox), 5-bromo-6-methyl-3- (l-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-O- (2,4-dinitro-phenyl) -oxime (bromofenoxime), 3, 5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2 -chloro-N- (2,6-diethyl-phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H ) -pyrimidi- nyl) -benzoic acid- [1, 1 -dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (l-ethoximinopropyl) -3-hydroxy- 5- [2,4,6-trimethyl-3- (l-oxobutyl) phenyl] -2-cyclohexen-l-one (butroxydim), S-
Ethyl-bis-(2-methyl-propyl)-thiocarbamat (Butylate), N,N-Diethyl-3- (2,4,6-trimethyl-phenylsulfonyl)- 1 H- 1 ,2,4-triazol- 1 -carboxamid (Cafenstrole), 2-[ 1 -[(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3-hy- droxy-5 -(tetrahydro-2H-pyran-4-yl)-2-cyclohexen- 1 -on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl- ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-l,2,4-tri- azol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-l-(3-methoxy-4-nitro- phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoe- säure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2- ethoxycarbonyl-phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), 1,3,5- Trichlor-2-(4-nitro-phenoxy)-benzol (Chlornitrofen), N-(4-Methoxy-Ethyl bis (2-methyl-propyl) thiocarbamate (butylate), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) - 1 H-1, 2,4-triazole-1 - carboxamide (cafenstrole), 2- [1 - [(3-chloro-2-propenyl) -oxy-imino] -propyl] -3-hydroxy-5 - (tetrahydro-2H-pyran-4-yl) -2 -cyclohexen- 1 -one (caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-l, 2,4-tri- azol-3-one (Carfentrazone-ethyl), 2,4-dichloro-l- (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 3-amino-2,5-dichloro-benzoic acid ( Chloramben), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) -urea (chlorimuron-ethyl), 1,3,5-trichloro-2- ( 4-nitro-phenoxy) -benzene (chloronitrofen), N- (4-methoxy-
6-methyl-l,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfüron), N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harn- stoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(l,3,4,5,6,7-hexahydro-l,3- dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon- ethyl), Exo- 1 -methyl-4-isopropyl-2-(2-methyl-phenyl-methoxy)-7- oxabicyclo-[2.2.1]-heptan (Cinmethylin), N-(4,6-Dimethoxy-l,3,5-tri- azin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenylsulfonyl)-harnstoff (Cino- sulfüron), 2-[ 1 -[2-(4-Chlor-phenoxy)-propoxyaminobutyl]-5-(tetra- hydro-2H-thiopyran-3-yl)-l,3-cyclohexandion (Clefoxydim), (E,E)- (+)-2-[l-[[(3 -Chlor-2-propenyl)-oxy] -imino] -propyl] -3 -hydroxy-2- cyclohexen- 1 -on (Clethodim), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor- pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 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- 1 -phenyl-ethyl)-harnstoff (Cumyluron), 2-Chlor-4-ethylamino- 6-(l-cyano-l-methyl-ethylamino)-l,3,5-triazin (Cyanazine), N-(4,6- Dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenylsul- fonyl)-harnstoff (Cyclosulfamuron), 2-(l-Ethoximinobutyl)-3- hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen- 1 -on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propan- säure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4- Dichlor-phenoxy)-propansäure (Dichlo rop-P), Methyl-2-[4-(2,4-di- chlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), N-(2,6-Di- chlor-phenyl)-5-ethoxy-7-fluor-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2- sulfonamid (Diclosulam), l,2-Dimethyl-3,5-diphenyl-lH-pyrazolium- methylsulfat (Difenzoquat), N-(2,4-Difluor-phenyl)-2-(3-trifluor- methyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), 2-[l-[(3,5-Di- fluor-phenyl)-amino-carbonyl-hydrazono] -ethy 1] -pyridin-3 -carbonsäure (Diflufenzopyr), S-( 1 -Methyl- 1 -phenyl-ethyl)- 1 -piperidin-carbo- thioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-meth- oxy-ethyl)-acetamid (Dimethachlor), N-(l,2-Dimethyl-propyl)-N'- ethyl-6-methylthio-l,3,5-triazin-2,4-diamin (Dimethametryn), (S-) 2- Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy- 1 -methyl-ethyl)-acet- amid (S-) (Dimethenamid), 2-Amino-4-(l-ι"luor-l-methyl-ethyl)-6-(l- methyl-2-(3,5-dimethyl-phenoxy)-ethylamino)-l,3,5-triazin (Dimexy- flam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl-l ,3-diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[l,2-a:2', -c]pyrazindiium (Di- quat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethyl- pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor-phenyl)-N,N- dimethyl-harnstoff (Diuron), N-(4-Methyl-phenyl)-N'-(l -methyl- 1- phenyl-ethyl)-harnstoff (Dymron, Daimuron), 2-[2-(3-Chlor-phenyl)- oxiranylmethyl]-2-ethyl-lH-inden-l,3(2H)-dion (Epropodan), S- Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N-dimethyl-urea (chlorotoluron), 2-chloro-3- [2-chloro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindole-2 -yl) -phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), exo- 1 -methyl-4-isopropyl-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) urea (cinino sulfüron), 2- [1 - [2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) -1, 3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [l - [[(3-chloro-2-propenyl) -oxy] imino] propyl] -3-hydroxy-2-cyclohexen-1 -one (clethodim), (R. ) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (clodinafop-propargyl), 2- (2,4-dichloro-3 -methyl-phenoxy) -N-phenyl-propanamide (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-y l-sulfonyl) amino] - benzoate (chlorosulam-methyl), N - [(2-chlorophenyl) methyl] -N '- (l-methyl-1-phenyl-ethyl) urea (cumyluron), 2 -Chlor-4-ethylamino- 6- (l-cyano-l-methyl-ethylamino) -l, 3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N ' - (2-cyclopropylcarbonyl-phenylsulfonyl) urea (cyclosulfamuron), 2- (l-ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one ( Cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propanoic acid butyl ester (cyhalofop butyl), 2,4-dichlorophenoxyacetic acid (2,4- D), 3,6-dichloro-2-methoxybenzoic acid (dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichlorop-P), methyl-2- [4- ( 2,4-di-chlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-di- chlorophenyl) -5-ethoxy-7-fluoro- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (diclosulam), l, 2-dimethyl-3,5- diphenyl-lH-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [l- [ (3,5-di-fluoro-phenyl) -amino-carbonyl-hydrazono] -ethy 1] -pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl-ethyl) - 1 -piperidine- carbothioate (dimepiperate), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (2-methoxy-ethyl) -acetamide (dimethachlor), N- (1,2-dimethyl-propyl ) -N'- ethyl-6-methylthio-l, 3,5-triazine-2,4-diamine (dimethametryn), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) - N- (2-methoxy-1-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (l-ι " luor-l-methyl-ethyl) -6- (l- methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -l, 3,5-triazine (Dimexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-l, 3- diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', -c] pyrazinediium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-but yl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl-urea (diuron), N- (4-methyl-phenyl) -N '- (l -methyl-1-phenyl-ethyl) urea (Dymron, Daimuron), 2- [2- (3-chlorophenyl) -oxiranylmethyl] -2-ethyl-1H-indene-1,3 (2H) -dione (epropodane), S- ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N-
(l,2-dimethyl-propyl)-thiocarbamat (Esprocarb), N-Ethyl-N-(2- methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzenamin (Ethal- fluralin), (S)-(2-Ethoxy-l-methyl-2-oxoethyl)-2-chlor-5-(2-chlor-4-tri- fluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxy- sulfüron), N-(2,3-Dichlor-phenyl)-4-ethoxymethoxy-benzamid (Eto- benzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]- propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl- N-ethyl-4,5-dihydro-5-oxo- 1 H-tetrazol- 1 -carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flam- prop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L- alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4- fluor-phenoxy)-DL-alaninat (Flamprop-methyl), N-(2,6-Difluor- phenyl)-8-fluor-5-methoxy-[ 1 ,2,4]-triazolo-[ 1 ,5-c]-pyrimidin-2- sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl- oxy)-phenoxy]-propansäure-butylester (Fluazifop, -butyl, -P-butyl), 5-(1,2-dimethyl-propyl) -thiocarbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4-trifluoromethyl-benzenamine (ethal-fluralin), (S ) - (2-Ethoxy-l-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxy- pyrimidin-2-yl) -N '- (2-ethoxy-phenoxysulfonyl) urea (ethoxysulfuron), 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-chloro-phenyl) -N-cyclohexyl - N-ethyl-4,5-dihydro-5-oxo-1 H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N-benzoyl-N- (3-chloro-4-fluorophenyl) -DL-alaninate (Flamoprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L- alaninate (flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -DL-alaninate (flamprop-methyl), N- (2,6-difluorophenyl) - 8-fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyrimidine-2-sulfonamide (Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridine -2-yl-oxy) -phenoxy] -propanoic acid butyl ester (fluazifop, -butyl, -P-butyl), 5-
(4-Brom-l-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), N-(2,6-Difluor-phenyl)-5-methyl- 1 ,2,4-triazolo[ 1 ,5-a]-pyri- midin-2-sulfonamid (Flumetsulam), Pentyl-[2-chlor-4-fluor-5-(4-Bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluorobenzoic acid i-propyl ester (fluazolates), N- (4-fluoro-phenyl) -Ni propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) acetamide (flufenacet), N- (2,6-difluorophenyl) -5-methyl-1, 2, 4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), pentyl- [2-chloro-4-fluoro-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- 1 ,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- 1 ,3(2H)-dion (Flumipropyn),(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 - [(1-methyl-2-propynyl) -oxy] - phenyl] -4,5,6,7-tetrahydro-1H-isoindole-1,3 (2H ) -dione (flumipropyn),
3-Chlor-4-chlormethyl-l-(3-trifluormethyl-phenyl)-2-pyrrolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro- benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), 1 -(4- Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5-phenyl-lH- l,2,4-triazol-3-carboxamid (Flupoxam), l-Isopropyl-2-chlor-5-(3,6-di- hydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxy- carbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natrium- salz (Flupyrsulfuron-methyl-sodium), 9-Hydroxy-9H-fluoren-9- carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl- oxy)-essigsäure (-2-butoxy- 1 -methyl-ethylester, - 1 -methyl-hepty 1- ester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2- phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-füranon (Flurtamone),3-Chloro-4-chloromethyl-l- (3-trifluoromethyl-phenyl) -2-pyrrolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl ), 1 - (4-Chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-lH-l, 2,4-triazole-3-carboxamide (flupoxam) , l-Isopropyl-2-chloro-5- (3,6-di-hydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidyl) -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-1-methyl-ethyl ester , - 1-methyl-hepty-1-ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (Flurtamone),
Methyl-[(2-chlor-4-fluor-5-(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadi- azolo-[3,4-a]-pyridazin-l-yliden)-amino-phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl-phenoxy)-N-methylsulf- onyl-2-nitro-benzamid (Fomesafen), 2-[[[[(4,6-Dimethoxy-2-pyri- midinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formylamino-N,N-di- methyl-benzamid (Foramsulfuron), 2-Amino-4-(hydroxymethylphos- phinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N- Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, - isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluormethyl-pyridin-2- yl-oxy)-phenoxy]-propansäure (-methylester, -2-ethoxy-ethylester, - butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3- Cyclohexyl-6-dimethylamino- 1 -methyl- 1 ,3 ,5-triazin-2,4( 1 H,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo- lH-imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2- (4,5-Dihydro-4-methyl-4-isopropyl-5-oxo- 1 H-imidazol-2-yl)-5- methyl-pyridin-3 -carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo- 1 H-imidazol-2-yl)-5-methoxymethyl- pyridin-3 -carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-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[ 1 ,2-a]-pyridin-3-yl-sulfonyl)-harnstoff (Imazosulfuron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5- iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodo- sulfuron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (loxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3- (l-Ethyl-l-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 (Isoxa- flutole), 2- [2- [4- [3 ,5 -Dichlor-2-pyridinyl)-oxy] -phenoxy] - 1 -oxo- propyl]-isoxazolidin (Isoxapyrifop), (2-Ethoxy- 1 -methyl-2-oxo-ethyl)- 5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoat (Lactofen), N'-Methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-lH, 3H- [l, 3,4] thiadi-azolo- [3,4-a] pyridazin-l-ylidene ) -amino-phenyl] -thio-acetate (Fluthiacet-methyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) -N-methylsulf- onyl-2-nitro-benzamide (Fomesafen), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N -dimethyl-benzamide (foramsulfuron), 2-amino-4- (hydroxymethylphosphine) -butanoic acid (-ammonium salt) (glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, - isopropylammonium ), (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-1-methyl-1, 3, 5-triazine-2,4 (1 H, 3H) -dione (hexazinones), Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl) -5-methyl-pyridin-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl- 4-isopropyl-5-oxo-1 H-imidazol-2-yl) -5-methoxymethyl-pyridin-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl) 5-oxo-l H-imidazol-2-yl) -quinolin-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl) - 5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-chloro-imidazo [1, 2-a] pyridine-3- yl-sulfonyl) urea (imazosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea Sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (loxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N - (3- (l-Ethyl-l-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl - isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [2- [ 4- [3, 5 -Dichlor-2-pyridinyl) -oxy] -phenoxy] - 1-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2-oxo-ethyl) - 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N'-
(3,4-dichlor-phenyl)-N-methoxy-N-methyl-harnstoff (Linuron), (4- Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl- phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N- methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyri- midinyl)-amino] -carbonyl] -amino] -sulfonyl] -4- [ [(methylsulfonyl)- amino]methyl]-benzoesäure-methylester (Mesosulfuron), 2-(4-(3,4-dichlorophenyl) -N-methoxy-N-methyl-urea (Linuron), (4- Chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4- [[(methylsulfonyl) amino] methyl] benzoic acid -methyl ester (mesosulfuron), 2- (4-
Methylsulfonyl-2-nitro-benzoyl)- 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-( 1 H-pyrazol- 1 -yl-methyl)-acetamid (Metazachlor), N'-(4-(3 ,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H- 1 - benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-harnstoff (Meto- benzuron), N,-(4-Brom-phenyl)-N-methoxy-N-methylharastoff (Meto- bromuron), (S)-2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy- l-methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N-(2,6-Di- chlor-3-methyl-phenyl)-5,7-dimethoxy- 1 ,2,4-triazolo[ 1 ,5-a]- pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4-methoxy- phenyl)-N,N-dimethyl-harnstoff (Metoxuron), 4-Amino-6-tert-butyl- 3-methylthio-l,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-lH-azepin-1- carbothioat (Molinate), 2-(2-Naphthyloxy)-N-phenyl-propanamidMethylsulfonyl-2-nitro-benzoyl) - 1, 3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one (metamitron), 2- Chloro-N- (2,6-dimethyl-phenyl) -N- (1 H-pyrazole-1-yl-methyl) -acetamide (metazachlor), N '- (4- (3, 4-dihydro-2-methoxy -2,4,4-trimethyl-2H- 1 - benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl-urea (metobenzuron), N , - (4-bromo-phenyl) -N-methoxy-N-methylharastoff (metobromomuron), (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-1, 2,4-triazolo [1, 5-a] - pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4-methoxyphenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-l , 2,4-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl ) - urea (metsulfuron-methyl), S-ethyl-hexahydro-lH-azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N-phenyl-propanamide
(Naproanilide), N-Butyl-N'-(3,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarb- amoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfüron), 4-Chlor-5- methylamino-2-(3 -trifluormethyl-pheny l)-3 (2H)pyridazinon (Norflur- azon), S-(2-Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4-(Naproanilide), N-Butyl-N '- (3,4-dichlorophenyl) -N-methylurea (Neburon), N- (4,6-Dimethoxypyrimidin-2-yl) -N' - ( 3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfüron), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) pyridazinone (norflurazon), S- (2-chloro-benzyl) -N, N-diethyl-thiocarbamate (Orbencarb), 4-
Dipropylamino-3,5-dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Di- chlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-on (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- yl)-N'-(2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl)-harnstoff (Oxa- sulfuron), 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-benzen (Oxyfluorfen), l, -Dimethyl-4,4'-bipyridinium (Paraquat), l-Amino-N-(l-ethyl- propyl)-3 ,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t-Butyl)- N-(l-ethyl-propyl)-2,6-dinitro-benzenamin (Pendralin), 3-(4-Chlor-5- cyclopentyloxy-2-fluor-phenyl)-5-(l-methyl-ethyliden)-2,4-oxazoli- din-dion (Pentoxazone), 4-Amino-3,5,6-trichlor-pyridin-2-carbonsäure (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-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenyl- sulfonyl)-harnstoff (Primisulfuron-methyl), l-Chlor-N-[2-chlor-4- fluor-5-[(6S,7aR)-6-fluor-tetrahydro-l,3-dioxo-lH-pyrrolo[l,2-c]- imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Profluazol), 2-Chlor-Dipropylamino-3,5-dinitro-benzenesulfonamide (oryzalin), 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) -1,3,4-oxadiazole-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin-2-yl) -N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfone), 3 - [l - (3,5-dichlorophenyl) -l-i-propyl] -2,3-dihydro-6- methyl-5-phenyl-4H-l, 3-oxazin-4-one (oxaziclomefone), 2-chloro-l- (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), l, -Dimethyl-4,4'-bipyridinium (paraquat), l-amino-N- (l-ethyl-propyl) -3, 4-dimethyl-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl ) - N- (l-ethyl-propyl) -2,6-dinitro-benzenamine (pendralin), 3- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5- (l-methyl-ethylidene) -2,4-oxazolidinedione (pentoxazone), 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-l-piperidinyl) -2-oxoethyl] -O, O-dipropyl-phosphorodithioate (Piperophos), 2-chlorine -N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bis-difluoromethoxypyrimidin-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-pyrrolo [1,2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2 -Chlorine-
N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor- phenyl)-propanamid (Propanil), (R)-[2-[[(l-Methyl-ethyliden)- amino]-oxy]-ethyl]-2-[4-(6-chlor-2-chinoxalinyloxy)-phenoxy]-pro- panoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[( 1 - methyl-ethoxy)-methyl]-acetamid (Propisochlor), S-Phenylmethyl-N-isopropyl-N-phenyl-acetamide (propachlor), N- (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(l-methylethylidene) - amino] - oxy] ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(1 - methylethoxy) methyl] acetamide (propisochlor), 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 (Prosulfüron), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy-l- methyl-lH-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), l-(3-Chlor-4,5,6,7-tetrahydro-pyrazolo[l,5-a]pyridin-2-yl)-5-(methyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N , - (2- (3,3,3-trifluoro- propyl) phenylsulfonyl) urea (prosulfuron), ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] -acetate (pyraflufen-ethyl), l- (3-chloro-4,5,6,7-tetrahydro-pyrazolo [l, 5-a] pyridin-2-yl) -5- (methyl-
2-propinylamino)-lH-pyrazol-4-carbonitril (Pyraclonil, Pyrazogyl), 4- (2,4-Dichlor-benzoyl)-l,3-dimethyl-5-(4-methyl-phenylsulfonyloxy)- pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)-l ,3-dimethyl-5-(phenyl- carbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy-pyrimi- din-2-yl)-N'-(4-ethoxycarbonyl- 1 -methyl-pyrazol-5-yl-sulfonyl)-ham- stoff (Pyrazosulfüron-ethyl), Diphenylmethanon-O-[2,6-bis-(4,6- dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxim (Pyribenzoxim), O[3- (l,l-Dimethyl-ethyl)-phenyl]-(6-methoxy-2-pyridinyl)-methylthio- carbamat (Pyributicarb), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3-phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2- pyrimidinyl)-thio]-3-methyl-l(3H)-isobenzofuranon (Pyriftalid), 2- (4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-methylester (Pyr- iminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-ylthio)- benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor-chinolin- 8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbon- säure (Quinmerac), 2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]- propansäure (-ethylester, -tetrahydro-2-furanyl-methylester) (Quizalo- fop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfüron), 2- (1 -Ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-2-propynylamino) -lH-pyrazole-4-carbonitrile (pyraclonil, pyrazogyl), 4- (2,4-dichlorobenzoyl) -l, 3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates) , 4- (2,4-dichlorobenzoyl) -1, 3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxyfen), N- (4,6-dimethoxypyrimidine-2-yl) - N '- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenylmethanone-O- [2,6-bis- (4,6- dimethoxy-pyrimidin-2-yl-oxy) -benzoyl] -oxime (pyribenzoxime), O [3- (l, l-dimethyl-ethyl) -phenyl] - (6-methoxy-2-pyridinyl) -methylthio-carbamate ( Pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O- (6-chloro-3-phenyl-pyridazin-4-yl) -S-octyl-thiocarbonate (pyridate), 6-chloro-3 -phenyl-pyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-l (3H) -isobenzofuranone (pyriftalid), 2- (4,6 -Dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (pyr-iminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) -benzoic acid sodium salt (pyrithiobac-sodium ), 3,7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy) -phenoxy] - propanoic acid (-ethyl ester, -tetrahydro-2-furanyl-methyl ester) (quizalopop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidine-2- yl) - N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfüron), 2- (1-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cy clohexen-
1-on (Sethoxydim), 6-Chlor-2,4-bis-ethylamino-l,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino-phenyl)-4-di- fluormethyl-5-methyl-2,4-dihydro-3H-l ,2,4-triazol-3-on (Sulfentra- zone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]-carbonyl]- amino]-sulfonyl]-benzoate (Sulfometuron-methyl), N-Phosphono- methyl-glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[l,2-a]pyridin-3-sulfon- amid (Sulfosulfuron), 6-Chlor-4-ethylamino-2-tert-butylamino- 1,3,5- triazin (Terbuthylazine), 2-tert-Butylamino-4-ethylamino-6-methyl- thio-l,3,5-tτiazin (Terbutryn), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(3- methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl- 5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluormethyl- pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6- dimethyl-3H,5H-pyrrolo[2,l-c]-l,2,4-thiadiazol-3-ylidenamino)-7- fluor-4-(2-propinyl)-2H-l,4-benzoxazin-3(4H)-on (Thidiazimin), N- (4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethox- imino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-l- on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamo- thioat (Triallate), N-(4-Methoxy-6-methyl-l ,3,5-triazin-2-yl)-N'-[2-(2- chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N- (4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- phenylsulfonyl)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)-pyri- din-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2- trichlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2-pyrimidin- yl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid- Natriumsalz (Trifloxysulfüron), l-Amino-2,6-dinitro-N,N-dipropyl-4- trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2- trifluor-ethoxy)-l,3,5-triazin-2-yl]-N'-(2-methoxycarbonyl-phenyl- sulfonyl)-harnstoff (Triflusulfuron-methyl), N-(4-Methoxy-6-trifluor- methoxy-l,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)- harastoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]- carbonyl]-3-(N-methyl-N-methylsulfonyl-amino])-2-pyridinsulfon- amid, (vgl. WO-A-92/10660), 4-[4,5-Dihydro-4-methyl-5-oxo-(3-tri- fluormethyl)- 1H- 1 ,2,4-triazol- 1 -yl]-2-[(ethylsulfonyl)amino]-5-fluor- benzencarbothioamid (vgl. WO-A-95/30661), Phenylcarbothiamid-,4- [4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)- 1H- 1 ,2,4-triazol- 1 - yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991) und 2-Chloro-N-[l-[2,6-dichloro-4-(difluoromethyl)- phenyl]-4-nitro-lH-pyrazol-5-yl]-propancarbonsäureamid (CAS-1-one (Sethoxydim), 6-chloro-2,4-bis-ethylamino-l, 3,5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3 dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-di-fluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (Sulfentra zone), methyl 2 - [[[((4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoates (sulfometuron methyl), N-phosphonomethyl glycine-trimethylsulfonium (sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-1,3,5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-l, 3,5-tτiazine (terbutryn ), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro- methyl thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylate (thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H -pyrrolo [2, lc] -l, 2,4-thiadiazol-3-ylidenamino) -7- fl uor-4- (2-propynyl) -2H-l, 4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethox imino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) -diisopropylcarbamothioate (triallates), 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-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) pyridine-2-yl-oxyacetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloroethyl) -oxirane (tridiphane), N - [[(4,6-dimethoxy-2-pyrimidin-yl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt ( Trifloxysulfuron), l-amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -l , 3,5-triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (triflusulfuron-methyl), N- (4-Me thoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) - hara material (tritosulfuron), N - [[(4,6-dimethoxy-2- pyrimidinyl) amino] - carbonyl] -3- (N-methyl-N-methylsulfonylamino]) - 2-pyridinesulfonamide, (cf. WO-A-92/10660), 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -1H-1, 2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide (see WO-A-95/30661), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) - 1H- 1, 2,4-triazol-1 - yl] -2 - [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and 2-chloro-N- [l - [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propane carboxamide (CAS-
Nummer 121750-17-2; SLA5599).Number 121750-17-2; SLA5599).
("Wirkstoffe der Gruppe 3"),("Active substances of group 3"),
sowie gegebenenfalls zusätzlich (d) zumindest eine die Kultuφflanzen-Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:as well as, if necessary, additionally (d) at least one compound from the following group of compounds which improves compatibility with crop plants:
α-(l ,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), α- (Cyanomethoximino)-phenylacetonitril (Cyometrinil), 4-Chlor-N-α- (1,3-dioxolan-2-yl-methoximino) phenylacetonitrile (oxabetrinil), α- (cyanomethoximino) phenylacetonitrile (cyometrinil), 4-chloro-N-
(1 ,3-dioxolan-2-yl-methoxy)-α-trifluor-acetophenonoxim (Fluxo- fenim), 4,6-Dichlor-2-phenyl-pyrimidin (Fenclorim), 4-Dichloracetyl- 3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor), 5-Chlor- chinoxalin-8-oxy-essigsäure-( 1 -methyl-hexylester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)- acetamid (DKA-24), 1,8-Naphthalsäureanhydrid, l-(2,4-Dichlor- phenyl)-5 -trichlormethyl- 1 H- 1 ,2 ,4-triazol-3 -carbonsäure-ethy lester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure- phenylmethylester (Flurazole), 3-Dichloracetyl-5-(2-furanyι)-2,2-di- methyl-oxazolidin (Furilazole, MON-13900), 4-Dichloracetyl-l-oxa-(1,3-dioxolan-2-yl-methoxy) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro- 3-methyl-2H-l, 4-benzoxazine (Benoxacor), 5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo -2- (2-propenylamino) ethyl) -N- (2-propenyl) acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-dichlorophenyl) -5-trichloromethyl-1 H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5- (2- furanyι) -2,2-di-methyl-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-l-oxa-
4-aza-spiro[4.5]-decan (AD-67), 2-Dichlormethyl-2-methyl-l,3-di- oxolan (MG-191), 2,2-Dichlor-N-(l,3-dioxolan-2-yl-methyl)-N-(2- propenyl)-acetamid (PPG- 1292), 2,2-Dichlor-N,N-di-2-propenyl-acet- amid (Dichlormid), N-(4-Methyl-phenyl)-N'-(l -methyl- 1-phenyl- ethyl)-harnstoff (Dymron), l-Dichloracetyl-hexahydro-3,3,8a-tri- methylpyrrolo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), N-(2-Meth- oxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen- ethyl), (4-Chlor-2-methylphenoxy)-essigsäure (MCPA), 2-(4-Chlor-2- methylphenoxy)-propionsäure (Mecoprop), Diethyl-l-(2,4-dichloro- phenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate4-aza-spiro [4.5] decane (AD-67), 2-dichloromethyl-2-methyl-l, 3-dioxolane (MG-191), 2,2-dichloro-N- (l, 3- dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), N- ( 4-methyl-phenyl) -N '- (l-methyl-1-phenyl-ethyl) -urea (Dymron), l-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] - pyrimidin-6 (2H) -one (BAS-145138), N- (2-methoxybenzoyl) -4- (methylaminocarbonylamino) benzenesulfonamide, ethyl-4,5-dihydro-5,5-diphenyl-3- isoxazole carboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl-l- (2,4-dichloro- phenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives
("Wirkstoffe der Gruppe 4"). Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, das sie als Wirkstoffe der Gruppe 1 eine Verbindung der Formel (I) enthalten,("Active substances of group 4"). Herbicidal compositions according to Claim 1, characterized in that they contain a compound of the formula (I) as active ingredients in Group 1,
in welcherin which
R für Wasserstoff oderR for hydrogen or
R,R
-N=C-N = C
steht, wobeistands, where
R2 bevorzugt für Wasserstoff, Chlor, Cyano, Phenyl, Cj-Cg-Alkyl,R 2 preferably represents hydrogen, chlorine, cyano, phenyl, Cj-Cg-alkyl,
Methoxy, Methylthio, Cι-C2-Alkoxycarbonyl, Propylaminocarbonyl,Methoxy, methylthio, -C-C2-alkoxycarbonyl, propylaminocarbonyl,
Dimethylaminocarbonyl, Benzylaminocarbonyl (wobei die Benzyl- gruppe gegebenenfalls durch Chloro, Methyl oder Methoxy substituiert ist), 2'-Phenylethylaminocarbonyl oder Furylmethylamino- carbonyl steht, undDimethylaminocarbonyl, benzylaminocarbonyl (the benzyl group optionally being substituted by chloro, methyl or methoxy), 2'-phenylethylaminocarbonyl or furylmethylaminocarbonyl, and
R3 bevorzugt für gegebenenfalls durch Chlor, Fluor, Cyano, Nitro, Methyl, Methoxy, Ethoxy, Butoxy, Allyloxy, Methylthio, Dimethyl- amino, Phenoxy, Benzyloxy oder Acetoxy substituiertes Phenyl oder für -COR4 steht, worin R4 für Methoxy, Ethoxy, Methyl, Benzyloxy oder Benzylamino steht,R3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR 4 , where R 4 represents methoxy, ethoxy , Methyl, benzyloxy or benzylamino,
A bevorzugt für Chlor oder Methoxy steht undA preferably represents chlorine or methoxy and
D und E, die gleich oder unterschiedlich sein können, bevorzugt für Wasserstoff, Methoxy oder Ethoxy stehen. R2 steht besonders bevorzugt für Wasserstoff, Methyl, Methylthio, Cyano, Methoxycarbonyl oder Phenyl.D and E, which may be the same or different, are preferably hydrogen, methoxy or ethoxy. R2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
R3 steht besonders bevorzugt für gegebenenfalls durch Methyl oder Methoxy substituiertes Phenyl.R3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
A steht besonders bevorzugt für Methoxy.A particularly preferably represents methoxy.
D und E stehen besonders bevorzugt für Methoxy.D and E are particularly preferably methoxy.
R2 steht ganz besonders bevorzugt für Phenyl.R 2 very particularly preferably represents phenyl.
R3 steht ganz besonders bevorzugt für Phenyl.R3 very particularly preferably represents phenyl.
Herbizide Mittel gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 3 einen oder mehrere Wirkstoffe aus der folgenden Gruppe von Wirkstoffen enthält:Herbicidal composition according to claim 1 or 2, characterized in that it contains as active ingredient of group 3 one or more active ingredients from the following group of active ingredients:
4-Amino-N-(l,l-Dimethyl-ethyl)-4,5-dihydro-3-(l-methyl-ethyl)-5-oxo-lH- 1,2,4-triazol-l -carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron),4-amino-N- (l, l-dimethyl-ethyl) -4,5-dihydro-3- (l-methyl-ethyl) -5-oxo-lH- 1,2,4-triazole-l-carboxamide ( Amicarbazones), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron),
N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 3- i-Propyl- 1 H-2, 1 ,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-di- chlor-phenoxy)-2-nitro-benzoat (Bifenox), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phe- nyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- 1 ,2,4-triazol-3-on (Carfentra- zone-ethyl), N-(4-Methoxy-6-methyl- 1 ,3,5-triazin-2-yl)-N'-(2-chlor-phenyl- sulfonyl)-harnstoff (Chlorsulfüron), N'-(3-Chlor-4-methyl-phenyl)-N,N-di- methyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(l ,3,4,5,6,7-hexa- hydro- 1 ,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cini- don-ethyl), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phen- oxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy- benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlor- prop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop- methyl), l,2-Dimethyl-3,5-diphenyl-lH-pyrazolium-methylsulfat (Difenzo- quat), N-(2,4-Difluor-phenyl)-2-(3 -trifluormethyl-phenoxy)-pyridin-3 -carboxamid (Diflufenican), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phen- oxysulfonyl)-harnstoff (Ethoxysulfuron), (R)-Ethyl-2-[4-(6-chlor-benzoxazol- 2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N- cyclohexyl-N-ethyl-4,5-dihydro-5-oxo- 1 H-tetrazol- 1 -carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flam- prop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L-alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)- DL-alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy- [l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Florasulam), 5-(4-Brom-l- 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- 1 ,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), 5-(2-Chlor-4-trifluormethyl- phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen- ethyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluor- methyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl- sodium), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-but- oxy-1-methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)- füranon (Flurtamone), 2-Amino-4-(hydroxymethylphosphinyl)-butansäureN-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 3- i-propyl-1 H-2, 1, 3-benzothiadiazin-4 (3H) -one (bentazone), Methyl 5- (2,4-di-chlorophenoxy) -2-nitro-benzoate (bifenox), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 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 (Carfentra- zone-ethyl), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N'- (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlorotoluron), 2-chloro-3- [2-chloro-5- (l, 3,4,5,6,7 -hexa- hydro- 1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), (R) - (2-propynyl) -2- [4 - (5-chloro-3-fluoro-pyridin-2-yl-oxy) -phen- oxy-propanoate (clodinafop-propargyl), 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (Diclofop-methyl), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquate), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) -pyridine-3-carboxamide (diflufenican), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethoxy-phen-oxysulfonyl) -urea (ethoxysulfuron), (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-1 H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate (flamoprop -isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4- fluorophenoxy) - DL-alaninate (Flamprop-methyl), N- (2nd , 6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), 5- (4-bromo l-methyl-5-trifluoromethyl-lH-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), N- (4-fluorophenyl) -ni-propyl-2- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl ), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium ), (4-Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-but-oxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr , -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) - füranon (Flurtamone), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid
(-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), Methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-ben- zoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo- lH-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-(-ammonium salt) (glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-) oxo-lH-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2 -yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-
Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl- pyridin-3 -carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5- oxo-lH-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro- 4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2- methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron- methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (loxynil), N,N-Dimethyl- N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3-(l-Ethyl-l-methyl- propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2- methylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlor- tole), (5-Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl- phenyl)-methanon (Isoxaflutole), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2-(2- Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6-Di- methoxy-2-pyrimidinyl)-amino] -carbonyl] -amino] -sulfonyl] -4-[ [(methyl- sulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 4-Amino-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -5-methoxymethyl- pyridin-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquine), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4-methoxy- 6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5 -diiodobenzonitrile (loxynil), N, N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (l-ethyl-l-methyl-propyl) -isoxazole-5 -yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropyl -isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethylphenyl) -methanone (isoxaflutole), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2 -methyl-phenoxy) -propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl ) -amino] -carbonyl] -amino] -sulfonyl ] -4- [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 4-amino-
3-methyl-6-phenyl- 1 ,2,4-triazin-5(4H)-on (Metamitron), N-(2,6-Dichlor-3- methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Metosulam), 4- Amino-6-tert-butyl-3 -methylthio- 1 ,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6-methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxy- carbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), l-Amino-N-(l- ethyl-propyl)-3 ,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), N-(4-Fluor- phenyl)-6-(3 -trifluormethyl-phenoxy)-pyridin-2-carboxamid (Picolinafen), N- (3,4-Dichlor-phenyl)-propanamid (Propanil), Ethyl-[2-Chlor-5-(4-chlor-5-di- fluormethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflu- fen-ethyl), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion3-methyl-6-phenyl-1, 2,4-triazin-5 (4H) -one (metamitron), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam), 4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (Metribuzin), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (Metsulfuron-methyl), l- Amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2,6-dinitro-benzene (pendimethalin), N- (4-fluorophenyl) -6- (3-trifluoromethyl-phenoxy) pyridine -2-carboxamide (picolinafen), N- (3,4-dichlorophenyl) propanamide (propanil), ethyl- [2-chloro-5- (4-chloro-5-di-fluoromethoxy-l-methyl-1H -pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufene-ethyl), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1, 3-dione
(Sulcotrione), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N- (4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[l,2-a]pyridin- 3-sulfonamid (Sulfosulfuron), N-(4-Methoxy-6-methyl-l ,3,5-triazin-2-yl)-N'- (2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfüron-methyl), 2-(Ethoximino-proρyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-(Sulcotrione), N-phosphonomethyl-glycine trimethylsulfonium (sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3 -sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N'- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfüron -methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexene
1 -on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chlor- ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6- methyl-l,3,5-triazin-2-yl)-N,-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), l-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl- benzol (Trifluralin), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-1 -one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropyl carbamothioate (Triallates), 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) urea (tribenuron-methyl), l-amino- 2,6-dinitro-N, N-dipropyl-4-trifluoromethylbenzene (trifluralin), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N'-
(2-trifluormethyl-phenylsulfonyl)-hamstoff (Tritosulfuron), Phenylcarbothia- mid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-lH-l,2,4-triazol-l- yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991 ) und (2-Chloro-N-[ 1 -[2,6-dichloro-4-(difluoromethyl)phenyl]-4- nitro-lH-pyrazol-5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2;(2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), phenylcarbothiamide, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -IH-l, 2,4-triazole -l- yl] -2 - [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and (2-chloro-N- [1 - [2,6-dichloro-4 - (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2;
SLA5599).SLA5599).
4. Herbizide Mittel gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 3 einen oder mehrere Wirkstoffe aus einer oder mehrerer der folgenden Gruppen von Wirkstoffen enthält:4. Herbicidal composition according to one of claims 1 to 3, characterized in that it contains, as active ingredient of group 3, one or more active ingredients from one or more of the following groups of active ingredients:
a) Sulfonylharnstoffe:a) Sulfonylureas:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl- sulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-l,3,5- triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfüron),N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3 , 5- triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron),
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluor- methyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron- methyl-sodium), N-(4-Methoxy-6-methyl-l ,3,5-triazin-2-yl)-N'-(5- iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodo- sulfuron-methyl-sodium), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)- amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]- methyl]-benzoesäure-methylester (Mesosulfuron), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Metsulfuron-methyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(2-ethylsulfonyl-imidazo[l,2-a]pyridin-3-sulfonamid (Sulfosulf- uron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2 -methoxy- carbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfüron-methyl), N- (4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)- phenylsulfonylj-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluorrnethoxy- l,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium ), 2 - [[[[(4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester ( Mesosulfuron), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N- (4, 6-Dimethoxy-pyrimidin-2-yl) - N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron)), N- (4-methoxy-6-methyl-l , 3,5-triazin-2-yl) -N '- (2-methoxy- carbonyl-thien-3-yl-sulfonyl) urea (thifensulfüron-methyl), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- [2- (2 -chloro-ethoxy) - phenylsulfonylj-urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl ) - urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron),
b) Triazolopyrimidine:b) Triazolopyrimidines:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl- phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Metosulam),N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam),
c) Imidazolinone:c) Imidazolinones:
Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2- yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methyl-pyridin-3- carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl- 5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo- 1 H-imida- zol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4- methyl-4-i-propyl-5-oxo- 1 H-imidazol-2-yl)-5-ethyl-pyridin-3-carbon- säure (Imazethapyr),Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4 -isopropyl-5-oxo-lH-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo 1 H-imidazol-2-yl) quinoline-3-carboxylic acid (imazaquine), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1 H-imidazol-2 -yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr),
Harnstoffe:ureas:
N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron),N '- (3-chloro-4-methylphenyl) -N, N-dimethyl-urea (chlorotoluron),
N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), e) Triazindione:N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), e) Triazinediones:
4-Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metri- buzin),4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (metribuzin),
f) Triketone:f) Triketones:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion (Sulco- trione),2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione),
g) Triazolinone:g) triazolinones:
2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-di- fluormethyl-5-methyl-2,4-dihydro-3H- 1 ,2,4-triazol-3-on (Carfentra- zone-ethyl), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3- (trifluormethyl)- 1 H- 1 ,2,4-triazol-l -yl]-2-[(ethylsulfonyl)amino]-5- fluoro- (CAS-Nummer 173980-17-1, HWH4991),2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-di-fluoromethyl-5-methyl-2,4-dihydro-3H-1, 2, 4-triazol-3-one (Carfentra-zone-ethyl), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) - 1 H- 1, 2,4- triazol-l -yl] -2 - [(ethylsulfonyl) amino] -5- fluoro- (CAS number 173980-17-1, HWH4991),
h) Benzonitrile:h) Benzonitrile:
3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 4-Hydroxy-3,5-di- iod-benzonitril (loxynil),3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 4-hydroxy-3,5-di-iodo-benzonitrile (loxynil),
i) Phenoxypropionsäurederivate:i) Phenoxypropionic acid derivatives:
(R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-pro- panoat (Clodinafop-propargyl), Methyl-2-[4-(2,4-dichlor-phenoxy)- phenoxy]-propanoat (Diclofop-methyl), (R)-Ethyl-2-[4-(6-chlor-benz- oxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), j) Dichloφhenoxysäurederivate:(R) - (2-Propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (Clodinafop-propargyl), methyl 2- [4 - (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), (R) -ethyl-2- [4- (6-chloro-benz-oxazol-2-yl-oxy) phenoxy] -propanoate (fenoxaprop- (P) -ethyl), j) dichloφhenoxyacid derivatives:
2,4-Dichlor-phenoxyessigsäure (2,4-D), (®2-(2,4-Dichlor-phenoxy)- propansäure (Dichloφrop-P), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop),2,4-dichlorophenoxyacetic acid (2,4-D), (®2- (2,4-dichlorophenoxy) propanoic acid (Dichloφrop-P), (4-chloro-2-methylphenoxy) acetic acid ( MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop),
k) Carboxamide:k) carboxamides:
N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen),N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) -pyridine-2-carboxamide (picolinafen),
1) Oxyacetamide:1) Oxyacetamide:
N-(4-Fluor-phenyl)-N-i-propyl-2-(5 -trifluormethyl- 1 ,3 ,4-thiadiazol-2-yl- oxy)-acetamid (Flufenacet),N- (4-fluorophenyl) -N-i-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy) acetamide (flufenacet),
(2-Chloro-N-[l-[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-lH-pyrazol- 5-yl]-propancarbonsäureamid (CAS-Nummer 121750-12-2; SLA5599),(2-Chloro-N- [l- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-lH-pyrazol-5-yl] propane carboxamide (CAS number 121750-12-2; SLA5599 )
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox),Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox),
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),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),
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 - methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropyl- ammmoniumsalz), (Glyphosate, -isopropylammonium) oder N-Phosphono- methyl-glycin-trimethylsulfonium (Sulfosate). Herbizide Mittel gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 4 einen oder mehrere Wirkstoffe der folgenden Gruppe von Wirkstoffen enhält:(4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropyl ammonium salt), (glyphosate, isopropylammonium) or N-phosphono- methyl-glycine trimethyl sulfonium (sulfosates). Herbicidal agent according to one of claims 1 to 4, characterized in that it contains, as active ingredient in group 4, one or more active ingredients in the following group of active ingredients:
5-Chlor-chinoxalin-8-oxy-essigsäure-(l-methylhexylester) (Cloquintocet), 1- (2,4-Dichlor-phenyl)-5-trichlormethyl- 1 H- 1 ,2,4-triazol-3-carbonsäure-ethyl- ester (Fenchlorazol-ethyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarb- oxylat (Isoxadifen-ethyl), (4-Chlor-2-methylphenoxy)-essigsäure (MCPA), 2- (4-Chlor-2-methylphenoxy)-propionsäure (Mecoprop), Diethyl- 1 -(2,4-di- chlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr- diethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate.5-chloro-quinoxaline-8-oxyacetic acid (l-methylhexyl ester) (cloquintocet), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1 H-1, 2,4-triazole-3- ethyl carboxylate (fenchlorazole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA) , 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl 1 - (2,4-di-chlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5- dicarboxylate (mefenpyr diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
Herbizide Mittel gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass sieHerbicidal agent according to one of claims 1 to 5, characterized in that it
a) mindestens ein Phenoxypyrimidin-Derivat aus der folgenden Gruppe von Verbindungena) at least one phenoxypyrimidine derivative from the following group of compounds
2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribac-sodium, KIH 2023) der Formel2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribac-sodium, KIH 2023) of the formula
Na .©Well. ©
Figure imgf000078_0001
Figure imgf000078_0001
oder Diphenyl-methanon-O-[2,6-bis[(4,or Diphenyl-methanone O- [2,6-bis [(4
6-dimethoxy-2-pyrimidinyl)- oxy]benzoyl]oxim (Pyribenzoxim) der Formel6-dimethoxy-2-pyrimidinyl) oxy] benzoyl] oxime (pyribenzoxime) of the formula
Figure imgf000079_0001
Figure imgf000079_0001
b) die Verbindung Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy- lH-l,2,4-triazol-l-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone-sodium) der Formelb) the compound methyl-2 - [[((4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) carbonyl] amino] sulfonyl] -benzoic acid, sodium salt (Propoxycarbazone-sodium) of the formula
Figure imgf000079_0002
Figure imgf000079_0002
sowiesuch as
c) zumindest einen Wirkstoff der Gruppe 3 gemäß einem der Ansprüche 1 bis 4,c) at least one active ingredient of group 3 according to one of claims 1 to 4,
sowie gegebenenfalls d) zumindest eine die Kultuφflanzen-Verträglichkeit verbessernde Verbindung der Gruppe 4 gemäß Anspruch 1 oder 5,and if necessary d) at least one compound of group 4 which improves the compatibility with crop plants, according to claim 1 or 5,
umfassen.include.
7. Herbizide Mittel gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie7. Herbicidal agents according to one of claims 1 to 6, characterized in that they
a) 2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribac-sodium) der Formela) 2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribac-sodium) of the formula
Na .©Well. ©
Figure imgf000080_0001
Figure imgf000080_0001
undand
b) Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol- 1-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone-sodium) der Formelb) Methyl 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-l, 2,4-triazol-1-yl) carbonyl] amino] sulfonyl] benzoic acid , Sodium salt (Propoxycarbazone-sodium) of the formula
Figure imgf000080_0002
sowie c) zumindest eine weitere Verbindung ausgewählt aus der folgenden Gruppe von Verbindungen ("Wirkstoffe der Gruppe 3"):
Figure imgf000080_0002
such as c) at least one further compound selected from the following group of compounds (“active substances of group 3”):
a) Sulfonylharnstoffe:a) Sulfonylureas:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl- sulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl- 1,3,5- triazin-2-yl)-N' -(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N-Methyl-N-(4-methoxy-6-methyl-l ,3,5-triazin-2- yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron- methyl), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-(2- trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3 , 5- triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazine -2- yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N' - (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron),
b) Triazolopyrimidine:b) Triazolopyrimidines:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl- phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Metosulam),N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam),
c) Imidazolinone:c) Imidazolinones:
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-methoxymethyl-pyridine-3-carboxylic acid (imazamox),
d) Harnstoffe:d) ureas:
N,N-Dimethyl-N' -(4-isopropyl-phenyl)-harnstoff (Isoproturon), e) Triazindione:N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), e) Triazinediones:
4-Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metribuzin),4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (metribuzin),
f) Triketone:f) Triketones:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan- 1 ,3-dion (Sulcotrione),2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione),
g) Triazolinone:g) triazolinones:
B enzenecarbothiamid-,4- [4, 5 -dihydro-4-methyl-5 -oxo-3 -(trifluor- methyl)- 1 H- 1 ,2,4-triazol- 1 -yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS 173980-17- 1, HWH4991),B enzenecarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3 - (trifluoromethyl) - 1 H-1, 2,4-triazol-1-yl] -2 - [(ethylsulfonyl ) amino] -5-fluoro- (CAS 173980-17-1, HWH4991),
(2-Chloro-N-[l-[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-lH-pyrazol- 5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA 5599),(2-Chloro-N- [l- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-lH-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2; SLA 5599),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), undMethyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (Bifenox), and
(4- Amino-3 , 5 -dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 - methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),(4- amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl)
sowie gegebenenfallsand if necessary
d) zumindest eine der in Anspruch 1 oder 5 genannten, die Kulturpflanzen-Verträglichkeit verbessernden Verbindung der Gruppe 4d) at least one of the compounds of group 4 which improve crop plant tolerance and are mentioned in claim 1 or 5
umfassen. include.
8. Herbizide Mittel gemäß einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 4 MCPA oder 2,4-Dichloro- phenoxy-essigsäure (2,4-D) und ihre Derivate enthalten.8. Herbicidal compositions according to one of claims 1 to 7, characterized in that they contain MCPA or 2,4-dichlorophenoxyacetic acid (2,4-D) and their derivatives as the active ingredient of group 4.
9. Herbizide Mittel gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 19. Herbicidal composition according to one of claims 1 to 8, characterized in that it is an active ingredient in group 1
2,6-Bis [4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium) (Bispyribac- sodium)2,6-bis [4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium) (bispyribac-sodium)
enthalten.contain.
10. Herbizide Mittel gemäß einem der Ansprüche 1 bis 9, dadurch gekenn- zeichnet, dass sie als Wirkstoff der Gruppe 210. Herbicidal composition according to one of claims 1 to 9, characterized in that it is an active ingredient of group 2
Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-ρropoxy-lH-l,2,4-triazol-l-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone- sodiumMethyl 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-ρropoxy-lH-l, 2,4-triazol-l-yl) carbonyl] amino] sulfonyl] benzoic acid, sodium -Salt (Propoxycarbazone- sodium
enthalten.contain.
11. Herbizide Mittel gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass auf 1 Gewichtsteil Wirkstoff der Gruppe 1 oder seinen Salzen jeweils 0,001 bis 1000 Gewichtsteile der Wirkstoffe der Gruppe 2 und 3 entfallen.11. Herbicidal compositions according to one of claims 1 to 8, characterized in that 0.001 to 1000 parts by weight of the active ingredients of groups 2 and 3 are present for 1 part by weight of active ingredient of group 1 or its salts.
12. Herbizide Mittel gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass auf 1 Gewichtsteil Wirkstoff der Gruppe 1 oder seinen Salzen jeweils 0,1 bis 1 Gewichtsteil der Wirkstoffe der Gruppe 2 und 3 entfällt. 12. Herbicidal compositions according to one of claims 1 to 8, characterized in that 0.1 part to 1 part by weight of the active substances of groups 2 and 3 is present per 1 part by weight of active substance of group 1 or its salts.
13. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 12 zur Bekämpfung von unerwünschten Pflanzen.13. Use of an agent according to any one of claims 1 to 12 for controlling unwanted plants.
14. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekennzeichnet, dass man Mittel gemäß einen der Ansprüche 1 bis 12 auf die unerwünschten Pflanzen und/oder deren Lebensraum einwirken läßt. 14. A method for controlling unwanted plants, characterized in that agents according to one of claims 1 to 12 are allowed to act on the undesired plants and / or their habitat.
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