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EP1351571A2 - Selective herbicides based upon 2,6-disubstituted pyridine derivatives - Google Patents

Selective herbicides based upon 2,6-disubstituted pyridine derivatives

Info

Publication number
EP1351571A2
EP1351571A2 EP00971424A EP00971424A EP1351571A2 EP 1351571 A2 EP1351571 A2 EP 1351571A2 EP 00971424 A EP00971424 A EP 00971424A EP 00971424 A EP00971424 A EP 00971424A EP 1351571 A2 EP1351571 A2 EP 1351571A2
Authority
EP
European Patent Office
Prior art keywords
methyl
chloro
ethyl
phenyl
urea
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00971424A
Other languages
German (de)
French (fr)
Inventor
Arndt Wellmann
Dieter Feucht
Mathias Kremer
Birgit Krauskopf
Peter Dahmen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19960778A external-priority patent/DE19960778A1/en
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1351571A2 publication Critical patent/EP1351571A2/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the invention relates to new herbicidal, synergistic active substance combinations which consist of known 2,6-disubstituted pyridine derivatives on the one hand and known, herbicidally active compounds and / or safeners on the other hand and which can be used with particularly good success for selective weed control in various crops.
  • 2,6-disubstituted pyridine derivatives are the subject of broad-spectrum herbicides
  • the 2,6-disubstituted pyridine derivatives when used together with known herbicidally active compounds, when used together with the compounds (safeners / antidots) improving the crop plant tolerance described below, prevent the crop plants from being damaged very well and can be used particularly advantageously as a broadly effective combination preparation for the selective control of weeds in crops of useful plants, for example cereals.
  • the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
  • R 1 for an optionally mono- or polysubstituted by halogen and / or Ci-C -haloalkyl substituted 5 to 6-membered heterocycle containing 1 to 3 nitrogen atoms or for an optionally mono- or polysubstituted by halogen and / or -C-C3-haloalkyl substituted phenyl radical,
  • R 2 represents a phenoxy radical optionally substituted by halogen and / or C j -C 3 haloalkyl
  • R 3 represents a hydrogen atom or methyl
  • W represents oxygen or the group -CO-NH-
  • Chloro-2-methylphenoxy) propanoic acid (mecoprop), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and 2,4-dichloro-phenoxyacetic acid (2,4-D) and its derivatives
  • R 1 preferably represents a pyrazolyl radical which is optionally mono- or polysubstituted by trifluoromethyl and methyl or an optionally mono- or polysubstituted by fluorine.
  • R 2 preferably represents an optionally halogen- and / or C1-C3-
  • Haloalkyl substituted phenoxy
  • R 3 preferably represents a hydrogen atom or methyl.
  • W preferably represents oxygen or the group -CO-NH-.
  • compositions which are characterized by comprising an active ingredient combination
  • active compounds of group 2 one or more compounds from a second group of herbicides which contains the active compounds mentioned above under (b) (“active compounds of group 2”), wherein the compound from group (b) is not flufenacet if the compound (a) 2- (3,4-difluoropheneoxy) -4-methyl-6- (l-methyl-3-trifluoromethylpyrazol-5-yl ) -pyridine,
  • compositions which comprise picolinafen as a compound of the active ingredients of group 1.
  • the active compound combinations defined above from the 2,6-disubstituted pyridine derivatives of the formula (I) and the above-mentioned active compounds from group 2, if appropriate in combination with active compounds from groups 3 and 4, with very good useful plant Compatibility has a particularly high herbicidal activity and can be used in various crops, in particular in wheat, but also in rice, corn and barley for selective weed control.
  • 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 3 in combination with one or more of the active substances of the group mentioned above 2 with very good crop tolerance, have a particularly high herbicidal activity and in different Cultures, especially in cereals and maize, especially wheat, but also in soy, potatoes and rice can be used for selective weed control.
  • Safeners or antidots which are capable of antagonizing the damaging effect of a herbicide on the cultivated plants, are particularly suitable for the group 3 active substances listed above, the damaging effect of compounds of the formula (I), in combination with one or more of the abovementioned Active substances of group 2, to almost completely cancel the cultivated plants without impairing the herbicidal activity against the weeds.
  • the active compound combinations according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • 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 leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • 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 using the customary treatment methods, e.g. by dipping, spraying,
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, they can
  • Weight ratios of the active ingredients in the active ingredient combinations can be varied in relatively large ranges.
  • 1 to 1 part by weight of active compound of the formula (I) accounts for 0.01 to 1000 parts by weight, preferably 0.05 to 500 parts by weight and particularly preferably 0.1 to 100 parts by weight of active compound of group 2.
  • the advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is likewise particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I), its salts or its
  • 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, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes
  • Chloroethylene or methylene chloride Chloroethylene 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.
  • 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
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: e.g.
  • emulsifying and / or foam-generating agents are possible: for example nonionic and anionic African 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 leaching and methyl cellulose.
  • Haffstofffeld 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 ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • mineral-based or vegetable oils such as the commercial preparation "Oleo DuPont HE"
  • ammonium salts such as ammonium sulfate or ammonium rhodanide that are compatible with plants as additional additives in the formulations.
  • the new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
  • 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.
  • Test plants are grown under controlled conditions (temperature and light conditions) in the greenhouse. When a plant height of 5 to 15 cm is reached, the plants are sprayed with the test solution. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 l of water / ha.
  • the planters After spraying, the planters are placed in the greenhouse under constant light and temperature conditions.
  • the degree of damage to the cultivated plants is rated in% damage in comparison to the development of the untreated control.
  • Active ingredient preparation the active ingredients were formulated as 70 WG (70% w / w water-dispersible powder) or 75 WG (75% w / w water-dispersible powder) and suspended in water. The spray liquor was then applied in the usual amount of water.
  • the herbicidal activity was assessed visually approximately 8-10 weeks after application of the spray mixture. It means:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to novel, synergistic, herbicidal agent combinations, which comprise 2,6 di-substituted pyridine derivatives and known herbicidally effective compounds and/or safeners. Said combinations are particularly successful when used for selective weed control with various crop seedlings, in particular, cereals.

Description

Selektive Herbizide auf Basis von 2,6-disubstituierten Pyridin-DerivatenSelective herbicides based on 2,6-disubstituted pyridine derivatives
Die Erfindung betrifft neue herbizide, synergistische Wirkstoffkombinationen, die aus bekannten 2,6-disubstituierten Pyridin-Derivaten einerseits und bekannten, herbizid wirksamen Verbindungen und/oder 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 substance combinations which consist of known 2,6-disubstituted pyridine derivatives on the one hand and known, herbicidally active compounds and / or safeners on the other hand and which can be used with particularly good success for selective weed control in various crops.
2,6-disubstituierte Pyridin-Derivate sind als breit wirksame Herbizide Gegenstand einer2,6-disubstituted pyridine derivatives are the subject of broad-spectrum herbicides
Reihe von Patentanmeldungen (vgl. EP-A 447 004, WO-A 94/22833). Die bekannten Pyridin-Derivate weisen jedoch eine Reihe von Wirkungslücken auf. Die Verträglichkeit dieser Verbindungen gegenüber Kulturpflanzen ist ebenfalls nicht unter allen Bedingungen ganz zufriedenstellend.Series of patent applications (cf. EP-A 447 004, WO-A 94/22833). However, the known pyridine 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 2,6-disubstituierten Pyridin-Derivate bei gemeinsamer Anwendung mit bekannten herbizid wirksamen Verbindungen aus verschiedenen Stoffklassen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in Nutzpflanzenkulturen, wie z.B. Weizen, verwendet werden können.Surprisingly, it has now been found that a number of known active compounds from the series of 2,6-disubstituted pyridine derivatives, when used together with known herbicidally active compounds from different classes of substances, show pronounced synergistic effects with regard to the action against weeds and are particularly advantageous as broadly active combination preparations for the selective control of weeds in crops such as Wheat that can be used.
Überraschenderweise wurde ebenfalls gefunden, dass die 2,6-disubstituierten Pyridin- Derivate alleine oder zusammen mit bekannten herbizid wirksamen Verbindungen bei gemeinsamer Anwendung mit den im weiteren beschriebenen, die Kulturpflanzenver- träglichkeit verbessernden Verbindungen (Safenern/Antidots) ausgesprochen gut die Schädigung der Kulturpflanzen verhindern und besonders vorteilhaft als breit wirksames Kombinationspräparat zur selektiven Bekämpfung von Unkräutern in Nutz- pflanzenkulturen, z.B. Getreide, 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 2,6-disubstituted pyridine derivatives, alone or together with known herbicidally active compounds, when used together with the compounds (safeners / antidots) improving the crop plant tolerance described below, prevent the crop plants from being damaged very well and can be used particularly advantageously as a broadly effective combination preparation for the selective control of weeds in crops of useful plants, for example cereals. The invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
(a) zumindest ein 2,6-disubstituiertes Pyridin-Derivat der allgemeinen Formel (I)(a) at least one 2,6-disubstituted pyridine derivative of the general formula (I)
in welcher in which
R1 für einen gegebenenfalls einfach oder mehrfach durch Halogen- und/oder Ci-C -Halogenalkyl substituierten 5 bis 6 gliedrigen Hetero- zyklus enthaltend 1 bis 3 Stickstoffatome oder für ein gegebenenfalls einfach oder mehrfach durch Halogen- und/oder Cι-C3-Halogenalkyl substituierten Phenylrest steht,R 1 for an optionally mono- or polysubstituted by halogen and / or Ci-C -haloalkyl substituted 5 to 6-membered heterocycle containing 1 to 3 nitrogen atoms or for an optionally mono- or polysubstituted by halogen and / or -C-C3-haloalkyl substituted phenyl radical,
R2 für einen gegebenenfalls durch Halogen- und/oder Cj-C3-Halogenalkyl substituierten Phenoxyrest steht,R 2 represents a phenoxy radical optionally substituted by halogen and / or C j -C 3 haloalkyl,
R3 für ein Wasserstoffatom oder Methyl steht, undR 3 represents a hydrogen atom or methyl, and
W für Sauerstoff oder die Gruppe -CO-NH- steht,W represents oxygen or the group -CO-NH-,
(„Wirkstoffe der Gruppe 1")("Active substances of group 1")
undand
(b) eine oder mehrere Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält: (5-Trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-essigsäure-N-isopropyl-N-(4- fluorphenyl)-amid (flufenacet, DE-A-38 21 600), 2-(2-Methoxycarbonyl- phenylsulfonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4- triazol-3-on oder das Natriumsalz dieser Verbindung (propoxycarbazone- sodium, EP-A-507 171), 2-(2-Trifluormethoxy-phenylsulfonylaminocarbo- nyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (flucarbazone-sodium, EP-A-507 171), N- (3,4-Dichloφhenyl)propanamid (propanil, DE-A 1039779), N-2-Benzothia- zolyl-N,N'-dimethylharnstoff (methabenzthiazuron, GB-A 1085430), 4- Amino-6-( 1 , 1 -dimethylethyl)-3-(methylthio)- 1 ,2,4-triazin-5(4H)-on (metri- buzin, DE-A 1795784), 4-(2-Chlorphenyl)-N-cyclohexyl-N-ethyl-4,5- dihydro-5-oxo-lH-tetrazol-l-carboxamid (fentrazamide, EP-A 612735), 4- Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on (metamitron, DE-A 2138031), 2-(2-Benzothiazolyloxy)-N-methyl-N-phenylacetamid (mefenacet, DE-A 2822155), 4-Amino-6-(l,l-dimethylethyl)-3-(ethylthio)-l,2,4-triazin-(b) one or more compounds from a second group of herbicides, which contains the active compounds mentioned below: (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) acetic acid-N-isopropyl-N- (4-fluorophenyl) -amide (flufenacet, DE-A-38 21 600), 2- ( 2-methoxycarbonyl-phenylsulfonylaminocarbonyl) -4-methyl-5-n-propoxy-2,4-dihydro-3H-l, 2,4-triazol-3-one or the sodium salt of this compound (propoxycarbazone-sodium, EP-A- 507 171), 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2,4-dihydro-3H-l, 2,4-triazol-3-one or the sodium salt of this compound (flucarbazone -sodium, EP-A-507 171), N- (3,4-dichlorophenyl) propanamide (propanil, DE-A 1039779), N-2-benzothiazolyl-N, N'-dimethylurea (methabenzthiazuron, GB-A 1085430), 4- Amino-6- (1, 1-dimethylethyl) -3- (methylthio) - 1, 2,4-triazin-5 (4H) -one (metribuzin, DE-A 1795784), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-l-carboxamide (fentrazamide, EP-A 612735), 4-amino-3-methyl-6- phenyl-l, 2,4-triazin-5 (4H) -one (metamitron, DE-A 2138031), 2- (2-benzothiazolyloxy) -N-methyl-N-phenylacetamide (mefenacet, DE-A 2822155 ), 4-amino-6- (l, l-dimethylethyl) -3- (ethylthio) -l, 2,4-triazine
5(4H)-on (ethiozin, DE-A 1542873) oder 1-Methylethyl 5-[4-brom-l-methyl- 5-(trifluormethyl)-lH-pyrazol-3-yl]-2-chloro-4-fluorobenzoat (fluazolate, WO-A 9206962)5 (4H) -one (ethiozin, DE-A 1542873) or 1-methylethyl 5- [4-bromo-l-methyl-5- (trifluoromethyl) -lH-pyrazol-3-yl] -2-chloro-4- fluorobenzoate (fluazolate, WO-A 9206962)
(„Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
sowie gegebenenfallsand if necessary
(c) zusätzlich zumindest eine die Kultuφflanzenverträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:(c) additionally at least one compound from the following group of compounds which improves the compatibility with crop plants:
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-( 1 -methyl-hexyl- ester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N- (2-propenyl)-acetamid (DKA-24), 1 ,8-Naphthalinsäureanhydrid, 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 (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-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-quinoxalin-8-oxy-acetic acid- (1-methyl-hexyl- ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 1, 8-naphthalic anhydride , l- (2,4-Di-chlorophenyl) -5-trichloromethyl-lH-l, 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-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-l-oxa-4- aza-spiro [4.5] -decane (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N- (1,3-dioxolane-2- yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-di-chloro-N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methyl- phenyl) -N '- (l - methyl-l-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-
3,3,8a-trimethylpyrrolo[ 1 ,2-a]-pyrimidin-6(2H)-on (BAS- 145138), N-(2- Methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl- 4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), Diethyl-1 - (2,4-dichloφhenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Me- fenpyr-diethyl), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (+-)-2-(4-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (BAS-145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) -benzenesulfonamide, ethyl-4 , 5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl 1 - (2,4-dichloφhenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5- dicarboxylate (mefenpyr-diethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (+ -) - 2- (4-
Chlor-2-methylphenoxy)propansäure (Mecoprop), 3-Dichloracetyl-2,2,5-tri- methyl-oxazolidin (R-29148) und 2,4-Dichloφhenoxyessigsäure (2,4-D) und dessen DerivateChloro-2-methylphenoxy) propanoic acid (mecoprop), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and 2,4-dichloro-phenoxyacetic acid (2,4-D) and its derivatives
("Wirkstoffe der Gruppe 3"),("Active substances of group 3"),
sowie gegebenenfallsand if necessary
(d) zusätzlich eine oder mehrere Verbindungen aus einer dritten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(d) additionally one or more compounds from a third 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 (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid2-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 (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide
(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-(l-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), 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 (Azafen- idin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N' -[ 1 -methyl-4-(2-methyl-2H- tetrazol-5-yl)-lH-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfuron), N-Benzyl- 2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4-Chlor-2- oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4- trifluormethyl-benzenamin (Benfluralin), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N' -(2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuron), 2-[2- [4-(3 ,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1 (2H)-pyrimidinyl- phenoxy]methyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-(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- (l-methyl-ethyl) - 5-oxo-1 H-1, 2,4-triazole - 1-carboxamide (amicarbazone), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1, 2, 4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-l, 3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) - phenyl] -5,6,7,8-tetrahydro-l, 2,4-triazolo- [4,3-a] pyridin-3 (2H) -one (azafenidine), N- (4,6 -Dimethoxypyrimidin-2-yl) -N '- [1 -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-trifluoromethyl-benzenamine (benfluralin), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (2-methoxycarbonyl-phenylmethylsulfonyl) urea (bensulfuron), 2- [2- [ 4- (3, 6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidinyl phenoxy] methyl] -5-ethyl phenoxy methyl propanoate (benzfendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2.1] -oct-3-en-
2-on (Benzobicyclon), Ethyl N-benzoyl-N-(3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-lH-2,l,3-benzothiadiazin-4(3H)-on2-one (benzobicyclone), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-lH-2, l, 3-benzothiadiazin-4 (3H) -one
(Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 2,6- Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyri- bac-sodium), 2-Brom-3,3-dimethyl-N-(l-methyl-l-phenyl-ethyl)-butanamid(Bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), 2,6-bis (4,6-dimethoxypyrimidin-2-yl-oxy) benzoic acid -Sodium salt (bispyribac-sodium), 2-bromo-3,3-dimethyl-N- (l-methyl-l-phenyl-ethyl) -butanamide
(Bromobutide), 3,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-dinitro-phenyl)- oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), N- Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2-Chlor- 5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)-ben- zoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil- allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxo- butyl)-phenyl]-2-cyclohexen-l-on (Butroxydim), S-Ethyl-bis-(2-methyl- propyl)-thiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl-phenyl- sul fonyl)- 1 H- 1 ,2,4-triazol- 1 -carboxamid (Cafenstrole), 2- [ 1 -[(3 -Chlor-2- propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2- cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor- 2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-l-(3-methoxy-4-nitro- phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl- phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), l,3,5-Trichlor-2-(4-nitro- phenoxy)-benzol (Chlornitrofen), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)- N'-(2-chlor-phenylsulfonyl)-harnsto f (Chlorsulfuron), N'-(3-Chlor-4-methyl- ρhenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5- (l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure- ethylester (Cinidon-ethyl), N-(4,6-Dimethoxy-l,3,5-triazin-2-yl)-N'-(2-(2- methoxy-ethoxy)-phenylsulfonyl)-harnsto f (Cinosulfuron), 2-[ 1 -[2-(4-Chlor- phenoxy)-propoxyamino]butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclo- hexandion (Clefoxydim), (E,E)-(+)-2-[l-[[(3-Chlor-2-propenyl)-oxy]-imino]- ρropyl]-3-hydroxy-2-cyclohexen-l-on (Clethodim), (R)-(2-Propinyl)-2-[4-(5- chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl),(Bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) oxime (bromofenoxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N- Butoxymethyl-2-chloro-N- (2,6-diethyl-phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl- 1 (2H) -pyrimidinyl) -benzoic acid- [1, 1 -dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3 -hydroxy-5- [2,4,6-trimethyl-3- (l-oxobutyl) phenyl] -2-cyclohexen-l-one (butroxydim), S-ethyl-bis- (2-methylpropyl ) -thiocarbamate (butylates), 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-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-l - (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 3-amino-2,5-dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonylphenylsulfonyl) 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-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methyl-ρhenyl) -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), N- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2-methoxy-ethoxy ) -phenylsulfonyl) urea (cinosulfuron), 2- [1 - [2- (4-chlorophenoxy) propoxyamino] butyl] -5- (tetrahydro-2H-thiopyran-3-yl) -l, 3- cyclohexanedione (Clefoxydim), (E, E) - (+) - 2- [l - [[(3-chloro-2-propenyl) -oxy] -imino] - ρropyl] -3-hydroxy-2-cyclohexene -l-on ( Clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (clodinafop propargyl),
3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5-eth- oxy-7-fluor[l,2,4]triazolo[l,5-c]pyrimidin-2-yl-sulfonyl)-amino]-benzoat (Cloransulam-methyl), 2-Chlor-4-ethylamino-6-( 1 -cyano- 1 -methyl-ethyl- amino)-l ,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- cyclopropylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(l-3,6-dichloropyridine-2-carboxylic acid (clopyralide), methyl-3-chloro-2 - [(5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine -2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethyl-amino) -l, 3,5-triazine ( Cyanazines), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (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-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), 2-[l-[(3,5 -Difluor-phenyl)-amino-carbony 1-hydrazono] -ethyl] -pyridin-3 - carbonsäure (Diflufenzopyr), S-( 1 -Methyl- 1 -phenyl-ethyl)- 1 -piperidin-carbo- thioat (Dimepiperate), (S-) 2-Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2- methoxy-l-methyl-ethyl)-acetamid (S-) (Dimethenamid), 2-Amino-4-(l- fluor- 1 -methyl-ethyl)-6-( 1 -methyl-2-(3 ,5 -dimethyl-phenoxy)-ethylamino)- 1 ,3 ,5 -triazin (Dimexy flam), N3 ,N3 -Diethyl-2,4-dmitro-6-trifluormethyl- 1,3- diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[l,2-a:2',r-c]pyrazin- diium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethyl- pyridin-3 ,5 -dicarbothioat (Dithiopyr), N' -(3 ,4-Dichlor-phenyl)-N,N-di- methyl-harnstoff (Diuron), 2-[2-(3-Chlor-phenyl)-oxiranylmethyl]-2-ethyl- lH-inden-l,3(2H)-dion (Epropodan), S-Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l ,2-dimethyl-propyl)-thiocarbamat (Espro- carb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzen- amin (Ethalfluralin), (S)-(2-Ethoxy- 1 -methyl-2-oxoethyl)-2-chlor-5-(2-chlor- 4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxa- prop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5- oxo- 1 H-tetrazol- 1 -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-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-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-benzoe- säure-i-propylester (Fluazolate), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-Ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluoro- phenoxy) -phenoxy] -propanoic acid butyl ester (cyhalofop-butyl), 2,4-dichloro-phenoxyacetic 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-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [l - [(3,5-difluorophenyl) amino carbony 1-hydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl-ethyl) - 1 -piperidine-carbo- thioate (dimepiperate), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-Amino-4- (l-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) - 1, 3, 5 -triazine (Dimexy flam ), N3, N3 -diethyl-2,4-dmitro-6-trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', rc] pyrazine- diium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3, 5-dicarbothioate (dithiopyr), N '- (3, 4-dichlorophenyl) -N , N-dimethylurea (diuron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3, (2H) -dione (epropodane), S- Ethyl dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Espro-carb), N-ethyl-N- (2-methyl-2-propenyl ) -2,6-dinitro-4-trifluoromethyl-benzene-amine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4- trifluoromethyl-phenoxy) -benzoate (ethoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethoxy-phenoxysulfonyl) - urea (ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop- (P) -ethyl), 4- (2nd -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 (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- [l, 2, 4] -triazolo- [1,5-c] - pyrimidine-2-sulfonamide (Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) -phenoxy] -propanoic acid- butyl ester (fluazifop, butyl, P-butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1 H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid - i-propyl ester (fluazolates), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-
[(2-trifluormethoxy-phenyl)-sulfonyl]-l-H-l,2,4-triazol-l-carboxamid- Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)-N-i-propyl-2-(5- trifluormethyl- 1 ,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(2,6-Di- fluor-phenyl)-5-methyl-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Flu- metsulam), Pentyl-[2-chlor-4-fluor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H- isoindol-2-yl)-phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4-dihydro- 3-oxo-4-(2-propinyl)-2H-l,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-lH-iso- indol- 1 ,3 -dion (Flumioxazin), 2-[4-Chlor-2-fluor-5 - [( 1 -methyl-2-propinyl)- oxy]-phenyl]-4,5,6,7-tetrahydro-lH-isoindol-l,3(2H)-dion (Flumipropyn), 3- Chlor-4-chlormethyl-l-(3-trifluoπnethyl-phenyl)-2-pyrrolidinon (Fluoro- chloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure- ethoxycarbonylmethylester (Fluoroglycofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3- pentafluor-propoxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazol-3-carboxamid (Flupoxam), l-Isopropyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl-l(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sul- fonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 9-Hydroxy- 9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluor-pyridin- 2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl-ethylester, - 1 -methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluor- methyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4-fluor-5-[(2-trifluoromethoxy-phenyl) sulfonyl] -1Hl, 2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N- (4-fluoro-phenyl) -Ni-propyl-2- (5- trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (2,6-di-fluorophenyl) -5-methyl-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (fluoretsulam), pentyl- [2-chloro-4-fluoro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo- 2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro- 3-oxo-4- (2-propynyl) -2H-l, 4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(1-methyl-2-propynyl) - oxy] phenyl] -4,5,6,7-tetrahydro-lH-isoindole-1,3 (2H) -dione (flumipropyn), 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), l- (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-dihydro-3-methyl-2,6-dioxo-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 (flupyrsulfuron- methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy - 1-methyl-ethyl ester, - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -mept yl), 5-methylamino-2-phenyl-4- (3-trifluoromethylphenyl) -3 (2H) -furanone (flurtamone), methyl - [(2-chloro-4-fluoro-5-
(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadiazolo-[3,4-a]-pyridazin-l-yliden)- amino-phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl- phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fomesafen), 2-[[[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formylamino- N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4-(hydroxymethylphos- phinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phos- phonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropyl- ammonium), (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-l- methyl-l,3,5-triazin-2,4(lH,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro- 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-imid- azol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro- 4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridin-3- carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH- imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl- 4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazetha- pyr), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-chlor-imidazo[l,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-(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-l-methyl-l, 3,5 -triazin-2,4 (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-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-pyridine -3-carboxylic acid (Imazamethapy r), 2- (4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4th , 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- (4,6-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 -
Natriumsalz (lodosulfuron-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 (Isoxa- ben), (4-Chlor-2-methylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)- methanon (Isoxachlortole), (5-Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-Sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3rd - (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-trifluormethyl-phenyl)-methanon (Isoxaflutole), 2-[2-[4-[3,5-Dichlor-2- pyridinyl)-oxy]-phenoxy]-l-oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Eth- oxy-l-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitro- benzoat (Lactofen), N'-(3,4-dichlor-phenyl)-N-methoxy-N-methyl-harnstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2- methyl-phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N- methyl-N-phenyl-acetamid (Mefenacet), 2-(4-Methylsulfonyl-2-nitro- benzoyl)-l ,3-cyclohexandion (Mesotrione), 4-Amino-3-methyl-6-phenyl- 1 ,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(2,6-dimethyl-phenyl)-N- (lH-pyrazol-l-yl-methyl)-acetamid (Metazachlor), N'-(4-(3,4-Dihydro-2- methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N- methyl-harnstoff (Metobenzuron), N'-(4-Brom-phenyl)-N-methoxy-N- methylharnstoff (Metobromuron), (S)-2-Chlor-N-(2-ethyl-6-methyl-phenyl)- N-(2-methoxy-l-methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N- (2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]- pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4-methoxy-phenyl)-N,N- dimethyl-harnstoff (Metoxuron), 4-Amino-6-tert-butyl-3-methylthio- 1 ,2,4- triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6-methyl-l ,3,5-triazin-2-yl)- N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfüron-methyl), S- Ethyl-hexahydro-lH-azepin-1-carbothioat (Molinate), 2-(2-Naphthyloxy)-N- phenyl-propanamid (Naproanilide), N-Butyl-N'-(3,4-dichlor-phenyl)-N- methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-di- methylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfuron), S-(2- Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4-Dipropylamino-3,5- dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Dichlor-5-(2-propinyloxy)- phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-on (Oxadiargyl), 3-[2,4-Dichlor-5-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [2- [4- [3,5-dichloro-2-pyridinyl) -oxy] -phenoxy] -l-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-l-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3,4-dichlor -phenyl) -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-methylsulfonyl-2-nitro-benzoyl) -l, 3-cyclohexanedione (mesotrione), 4-amino -3-methyl-6-phenyl-1, 2,4-triazin-5 (4H) -one (metamitron), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (1H-pyrazole- l-yl-methyl) -acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy) - phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4-bromophenyl) -N-methoxy-N-methylurea (metobromuron), (S) -2-chloro-N- (2nd -ethyl-6-methyl-phenyl) - N- (2-methoxy-l-methyl-ethyl) -acet-amide (metolachlor, S-metolachlor), N- (2, 6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [l, 5-a] - pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4 -methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1, 2,4-triazin-5 (4H) -one (metribuzin), N - (4-Methoxy-6-methyl-l, 3,5-triazin-2-yl) - N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Metsulfüron-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-dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), S- ( 2-chloro-benzyl) -N, N-diethyl-thiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy) - phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5-
(l-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-phenylsul- fonyl)-harnstoff (Oxasulfuron), 3-[l-(3,5-Dichlor-phenyl)-l-i-propyl]-2,3-di- hydro-6-methyl-5-phenyl-4H-l,3-oxazin-4-on (Oxaziclomefone), 2-Chlor-l- (3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl-benzen (Oxyfluorfen), 1,1 '-Di- methyl-4,4 ' -bipyridinium (Paraquat), 1 - Amino-N-( 1 -ethyl-propyl)-3 ,4-di- methyl-2,6-dinitro-benzol (Pendimethalin), 4-(t-Butyl)-N-(l-ethyl-propyl)- 2,6-dinitro-benzenamin (Pendralin), 4-Amino-3,5,6-trichlor-pyridin-2-carbon- säure (Picloram), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acet- amid (Pretilachlor), N-(4,6-Bis-difluormethoxy-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-iso- propyl-N-phenyl-acetamid (Propachlor), N-(3 ,4-Dichlor-phenyl)-propanamid (Propanil), (R)-[2-[[(l-Methyl-ethyliden)-amino]-oxy]-ethyl]-2-[4-(6-chlor-2- chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6- methyl-phenyl)-N-[(l-methyl-ethoxy)-methyl]-acetamid (Propisochlor), 2- [[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]- amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone- sodium), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Prosulfocarb), N-(4-(l-methyl-ethoxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidine-2- yl) -N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [l- (3,5-dichlorophenyl) -li-propyl] -2.3 -di- hydro-6-methyl-5-phenyl-4H-l, 3-oxazin-4-one (oxaziclomefone), 2-chloro-l- (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl- benzene (oxyfluorfen), 1,1'-dimethyl-4,4'-bipyridinium (paraquat), 1 - amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2,6- dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (l-ethyl-propyl) - 2,6-dinitro-benzenamine (pendralin), 4-amino-3,5,6-trichloropyridine- 2-carboxylic acid (picloram), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bis -difluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (primisulfuron-methyl), 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-iso- propyl-N-phenyl-aceta mid (propachlor), N- (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(l-methylethylidene) amino] oxy] ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(l-methyl-ethoxy) - methyl] -acetamide (propisochlor), 2- [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) carbonyl] - amino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarbazone-sodium), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-
Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)-phenyl- sulfonyl)-harnstoff (Prosulfuron), 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 (Pyrazogyl), 4-(2,4-Dichlor- benzoyl)- 1 ,3-dimethyl-5-(4-methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxy fen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl- 1 - methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenyl- methanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxim (Pyribenzoxim), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3- phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl- pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl- 1 (3H)-isobenzofuranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)- benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy- pyrimidin-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Di- chlor-chinolin-8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8- carbonsäure (Quinmerac), 2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]- propansäure (-ethylester, -tetrahydro-2-furanyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-ethyl- sulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfüron), 2-(l-Ethoximino- butyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-l-on (Sethoxydim), 6- Chlor-2,4-bis-ethylamino-l ,3,5-triazin (Simazin), 2-(2-Chlor-4-methyl- sulfonyl-benzoyl)-cyclohexan-l,3-dion (Sulcotrione), 2-(2,4-Dichlor-5- methylsulfonylamino-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l ,2,4-triazol-3-on (Sulfentrazone), 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- 1 ,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),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), l- (3- Chloro-4,5,6,7-tetrahydro-pyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -lH-pyrazole-4-carbonitrile (pyrazogyl), 4- (2,4-dichlorobenzoyl) - 1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4- (2,4-dichlorobenzoyl) -1, 3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxy fen), 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), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O- (6-chloro-3-phenyl-pyridazin-4-yl) -S-octylthiocarbonate ( Pyridate), 6-chloro-3-phenylpyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H) -isobenzofuranone (pyriftalid ), 2- (4,6-Dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (Pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) -benzoic acid Sodium salt (pyrithiobac-sodium), 3,7-di-chloro-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-dimetho xy-pyrimidin-2-yl) -N '- (3-ethyl-sulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfüron), 2- (l-ethoximino-butyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-l-one (sethoxydim), 6-chloro-2,4-bis-ethylamino-l, 3,5-triazine (simazine), 2- (2-chloro-4-methyl- sulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylaminophenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one (sulfentrazone), N-phosphonomethyl-glycine-trimethyl-sulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethyl- sulfonyl) imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-1,3,5-triazine (terbuthylazine), 2-tert-butyl - amino-4-ethylamino-6-methylthio-l, 3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl ) -acetamide (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-l ,4-benzoxazin-3(4H)-on (Thidiazimin), N-(4-Methoxy-6- methyl- 1 ,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-l,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), l-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfuron- methyl), N-(4-Methoxy-6-trifluormethoxy- 1 ,3,5-triazin-2-yl)-N'-(2-trifluor- methyl-phenylsulfonyl)-harnstoff (Tritosulfüron), N-[[(4,6-Dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino)-2- pyridinsulfonamid (vgl. WO-A-92/10660), 2-[[[[(4,6-Dimethoxy-2-pyri- midinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]- methylj-benzoesäure-methylester (vgl. DE-A-4335297), 4-[4,5-Dihydro-4- methyl-5-oxo-(3-trifluormethyl)- 1 H- 1 ,2,4-triazol- 1 -yl]-2-[(ethylsulfonyl)- amino]-5-fluor-benzencarbothioamid (vgl. WO-A-95/30661)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-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl- thien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-tri- methyl-phenyl) -2-cyclohexen-l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-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), (3,5,6-trichloro) pyridin-2-yl-oxy -acetic acid (triclopyr), 2- (3,5-dichlorophenyl) -2- (2,2,2-trichloroethyl) oxirane (tridiphane), N - [[(4,6-dimethoxy- 2-pyrimidinyl) amino] - carbonyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), l-amino-2,6-dinitro-N, N- dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -l, 3,5-triazin-2-yl] -N '- (2nd -methoxycarbonyl-phenylsulfonyl) -urea (triflusulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) - urea (tritosulfuron), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N -methyl-N-methylsulfonyl-amino) -2-pyridinesulfonamide (cf. WO-A-92/10660), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino ] - methylj-benzoic acid methyl ester (cf. DE-A-4335297), 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -1 H-1, 2,4-triazole - 1 -yl] -2 - [(ethylsulfonyl) - amino] -5-fluorobenzenecarbothioamide (see WO-A-95/30661)
("Wirkstoffe der Gruppe 4"),("Active substances of group 4"),
wobei die Verbindung unter (b) nicht für Flufenacet steht, wenn die Verbindung unter (a) 2-(3,4-Difluoφhenoxy)-4-methyl-6-(l-methyl-3-trifluor- methylpyrazol-5-yl)-pyridin ist.where the compound under (b) is not flufenacet if the compound under (a) 2- (3,4-difluoropheneoxy) -4-methyl-6- (l-methyl-3-trifluoromethylpyrazol-5-yl) -pyridine is.
Bevorzugte Substituenten der in der vorstehend gezeigten Formel (I) aufgeführten Reste werden im folgenden erläutert. R1 steht bevorzugt für einen gegebenenfalls einfach oder mehrfach durch Trifluor- methyl und Methyl substituierten Pyrazolylrest oder für ein gegebenenfalls einfach oder mehrfach durch Fluor substituierten Phenylrest.Preferred substituents of the radicals listed in the formula (I) shown above are explained below. R 1 preferably represents a pyrazolyl radical which is optionally mono- or polysubstituted by trifluoromethyl and methyl or an optionally mono- or polysubstituted by fluorine.
R2 steht bevorzugt für einen gegebenenfalls durch Halogen- und/oder C1-C3-R 2 preferably represents an optionally halogen- and / or C1-C3-
Halogenalkyl substituierten Phenoxyrest.Haloalkyl substituted phenoxy.
R3 steht bevorzugt für ein Wasserstoffatom oder Methyl.R 3 preferably represents a hydrogen atom or methyl.
W steht bevorzugt für Sauerstoff oder die Gruppe -CO-NH-.W preferably represents oxygen or the group -CO-NH-.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group 3:
5-Chlor-chinoxalin-8-oxy-essigsäure-(l-methylhexylester) (Cloquintocet), l-(2,4-Di- chlor-phenyl)-5-trichlormethyl- 1 H- 1 ,2,4-triazol-3-carbonsäure-ethylester (Fenchlora- zol-ethyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), Diethyl-l-(2,4-dichlθφhenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichloφhenoxyessigsäure (2,4-D) und dessen Derivate.5-chloro-quinoxaline-8-oxyacetic acid (l-methylhexyl ester) (cloquintocet), l- (2,4-di-chlorophenyl) -5-trichloromethyl-1 H- 1, 2,4-triazole- 3-carboxylic acid ethyl ester (fenchlorazole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifene-ethyl), diethyl-l- (2,4-dichloro-phenyl) -4, 5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichloφhenoxyacetic acid (2,4-D) and its derivatives.
Wie beschrieben kann die Wirkung der oben beschrieben Kombinationen gegebenenfalls durch den Zusatz einer Verbindung aus der dritten Gruppe von Herbiziden ("Wirkstoffe der Gruppe 4") noch in ihren Eigenschaften verbessert werden. Als Mischungskomponenten aus der "Wirkstoffe der Gruppe 4" werden besonders hervorgehoben:As described, the properties of the combinations described above can be improved, if appropriate, by adding a compound from the third group of herbicides (“active compounds of group 4”). The following are particularly emphasized as mixture components from the "active ingredients of group 4":
4-Amino-N-(l , 1 -Dimethyl-ethyl)-4,5-dihydro-3-(l -methyl-ethyl)-5-oxo- 1H- 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), 2,6-Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure- Natriumsalz (Bispyribac-sodium), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)- benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5- methyl-2,4-dihydro-3H-l ,2,4-triazol-3-on (Carfentrazone-ethyl), 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-harnstoff (Chlortoluron), 2-Chlor-3-[2- chlor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure- ethylester (Cinidon-ethyl), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)- phenoxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clo- pyralid), 2-Chlor-4-ethylamino-6-(l -cyano-1 -methyl-ethylamino)-l ,3,5-triazin4-amino-N- (l, 1-dimethyl-ethyl) -4,5-dihydro-3- (l-methyl-ethyl) -5-oxo-1H- 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), 2,6-bis (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzoic acid sodium salt (bispyribac-sodium), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil) , 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) - benzoic acid- [1, 1-dimethyl-2-oxo-2 - (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (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-l, 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-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) phenoxy propanoate (Clodinafop propargyl), 3,6-dichloropyridine-2 -carboxylic acid (Clopyralid), 2-chloro-4-ethylamino-6- (l-cyano-1-methyl-ethylamino) -l, 3,5-triazine
(Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenyl- sulfonyl)-harnstoff (Cyclosulfamuron), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6- Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propan- säure (Dichloφrop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Di- clofop-methyl), l,2-Dimethyl-3,5-diphenyl-lH-pyrazolium-methylsulfat (Difenzoquat), (S)-(2-Ethoxy-l-methyl-2-oxoethyl)-2-chlor-5-(2-chlor-4-trifluormethyl-phen- oxy)-benzoat (Ethoxyfen), 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-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-(Cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 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), 1,2-dimethyl-3,5-diphenyl-lH-pyrazolium methyl sulfate (difenzoquat), (S) - (2- Ethoxy-l-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4-trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-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-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-fluorophosph enoxy) -DL-alaninate (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), 4,5-Dihydro-3-methoxy-4-methyl-5- oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]- 1 -H- 1 ,2,4-triazol- 1 -carboxamid- Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluor- methyl- 1 ,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(2,6-Difluor-phenyl)-5- methyl- 1 ,2,4-triazolo[ 1 ,5-a]-pyrimidin-2-sulfonamid (Flumetsulam), 5-(2-Chlor-4- trifluoπnethyl-phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoro- glycofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5- phenyl-lH-l,2,4-triazol-3-carboxamid (Flupoxam), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide (Florasulam), 5- (4-bromo-l-methyl -5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxy-phenyl) sulfonyl] - 1 -H-1, 2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N- (4-fluorophenyl) -Ni-propyl- 2- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) acetamide (flufenacet), N- (2,6-difluorophenyl) -5- methyl 1, 2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoro- glycofen-ethyl), 1- (4-chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-1,2,4-triazole-3-carboxamide (Flupoxam), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea -
Natriumsalz (Flupyrsulfuron-methyl-sodium), 9-Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-l- methyl-ethylester, -1 -methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5- Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flurtamone), 2- Amino-4-(hydroxymethylphosphinyl)-butansäure (-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-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbon- säure (Imazamox), 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 (lodosulfuron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl- N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3-(l -Ethyl- 1-methyl-propyl)- isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methyl-phenoxy)- essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2-(2- Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 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-l,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Met- sulfuron-methyl), l-Amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pen- dimethalin), N-(3,4-Dichlor-phenyl)-propanamid (Propanil), 2-[[[(4,5-Dihydro-4- methyl-5 -oxo-3 -propoxy- 1 H- 1 ,2,4-triazol- 1 -yl)-carbonyl] -amino] -sulfonyl]-benzoe- säure-methylester-Natriumsalz (Propoxycarbazone-sodium), S-Phenylmethyl-N,N- dipropyl-thiocarbamat (Prosulfocarb), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy- 1 -methyl- 1 H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 7-Chlor-3- methyl-chinolin-8-carbonsäure (Quinmerac), N-Phosphonomethyl-glycin-trimethyl- sulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl)-imid- azo[l,2-a]pyridin-3-sulfonamid (Sulfosulfuron), 2-tert-Butylamino-4-ethylamino-6- methylthio-l,3,5-triazin (Terbutryn), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-Sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid ( -2-butoxy-l-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanon (Flurtamone), 2-amino-4- (hydroxymethylphosphinyl) -butanoic acid (-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-1H-imidazol-2-yl) -5-methoxymethyl-pyridin-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-i -propyl-5-oxo-lH-imidazol-2-yl) -5-ethyl-pyridin-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-diiodobenz onitrile (ioxynil), N, N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (l-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 4-amino-3-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-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), l-amino-N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (Pen - dimethalin), N- (3,4-dichlorophenyl) propanamide (propanil), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1 H-1, 2,4-triazol-1 -yl) -carbonyl] -amino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarbazone-sodium), S-phenylmethyl-N , N-dipropyl thiocarbamate (prosulfocarb), ethyl- [2-chloro-5- (4-chloro-5-difluoromethoxy- 1-methyl-1 H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), N-phosphonomethyl-glycine -trimethyl-sulfonium (sulfosate), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethylsulfonyl) -imide-azo [l, 2-a] pyridine-3-sulfonamide (sulfosulfuron ), 2-tert-butylamino-4-ethylamino-6-methylthio-l, 3,5-triazine (terbutryn), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N
(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2- (Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-l-on (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 (Triasulfuron), N-Methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2- methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), N-[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfon- amid-Natriumsalz (Trifloxysulfuron), 1 - Amino-2,6-dinitro-N,N-dipropyl-4-trifluor- methyl-benzol (Trifluralin), N-(4-Methoxy-6-trifluormethoxy- 1 ,3,5-triazin-2-yl)-N'- (2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron)(2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexene -l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-triazine 2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-l, 3,5- triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3 - (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), 1 - amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin) , N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N'- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron)
Erfindungsgemäß ganz besonders bevorzugt sind selektiv-herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirkstoffkombination umfassendAccording to the invention, very particularly preferred are selective herbicidal compositions which are characterized by comprising an active ingredient combination
a) N-(4-Fluoφhenyl)-6-[3-(trifluormethyl)phenoxy]-2-pyridinecarboxamid (pico- linafen) oder 2-(3,4-Difluoφhenoxy)-4-methyl-6-(l-methyl-3-trifluormethyl- pyrazol-5-yl)-pyridina) N- (4-Fluoφhenyl) -6- [3- (trifluoromethyl) phenoxy] -2-pyridinecarboxamide (picoline) or 2- (3,4-difluorophenoxy) -4-methyl-6- (l-methyl -3-trifluoromethyl-pyrazol-5-yl) pyridine
undand
b) eine oder mehrere Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die vorstehend unter (b) genannten Wirkstoffe („Wirkstoffe der Gruppe 2") enthält, wobei die Verbindung aus der Gruppe (b) nicht für Flufenacet steht, wenn die Verbindung (a) 2-(3,4-Difluoφhenoxy)-4-methyl-6-(l-methyl-3-trifluor- methylpyrazol-5-yl)-pyridin ist,b) one or more compounds from a second group of herbicides which contains the active compounds mentioned above under (b) (“active compounds of group 2”), wherein the compound from group (b) is not flufenacet if the compound (a) 2- (3,4-difluoropheneoxy) -4-methyl-6- (l-methyl-3-trifluoromethylpyrazol-5-yl ) -pyridine,
sowie gegebenenfallsand if necessary
c) zumindest eine der vorstehend genannten, die Kultuφflanzenverträglichkeit verbessernden Verbindungen der Wirkstoffe der Gruppe 3, wobei solche Verbindungen bevorzugt sind, die vorstehend hervorgehoben wurden.c) at least one of the abovementioned compounds of the active compounds of group 3 which improve the compatibility with crop plants, preference being given to those compounds which have been emphasized above.
Erfindungsgemäß am meisten bevorzugt sind die selektiv-herbiziden Mittel, die als Verbindung der Wirkstoffe der Gruppe 1 Picolinafen enthalten.Most preferred according to the invention are the selective herbicidal compositions which comprise picolinafen as a compound of the active ingredients of group 1.
Hervorzuheben sind außerdem selektiv-herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirkstoffkombination umfassendAlso to be emphasized are selective herbicidal compositions which are characterized by a content of an active ingredient combination comprising
(a) Picolinafen und(a) Picolinafen and
(b) (5-Trifluoιmethyl-l,3,4-thiadiazol-2-yl-oxy)-essigsäure-N-isopropyl-N-(4- fluoφhenyl)-amid (flufenacet) und(b) (5-Trifluoιmethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetic acid-N-isopropyl-N- (4-fluoφhenyl) -amide (flufenacet) and
(c) gegebenenfalls eine oder mehrere Verbindungen aus der Gruppe 2,6-Bis-(4,6- dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyribac- sodium), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Florasulam), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(c) optionally one or more compounds from the group 2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac-sodium), N- (2,6-difluoro -phenyl) -8-fluoro-5-methoxy- [l, 2,4] -triazolo- [l, 5-c] - pyrimidine-2-sulfonamide (florasulam), N- (4,6-dimethoxy-pyrimidine- 2-yl) -N'
(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff- Natriumsalz (Flupyrsulfuron-methyl-sodium), N,N-Dimethyl-N'-(4-iso- propyl-phenyl)-harnstoff (Isoproturon), N-(2,6-Dichlor-3-methyl-phenyl)-5,7- dimethoxy- 1 ,2,4-triazolo[ 1 ,5-a]-pyrimidin-2-sulfonamid (Metosulam), 1 - Amino-N-( 1 -ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin) und Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy-l-methyl-lH-pyrazol-3-yl)- 4-fluor-phenoxy] -acetat (Pyraflufen-ethyl) .(3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), N, N-dimethyl-N '- (4-isopropylphenyl) urea ( Isoproturon), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1, 2,4-triazolo [1, 5-a] pyrimidine-2-sulfonamide (metosulam), 1 - Amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin) and ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl).
Hervorzuheben sind auch selektiv-herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirkstoffkombination umfassendAlso to be emphasized are selective herbicidal compositions which are characterized by a content of an active ingredient combination comprising
(a) Picolinafen und(a) Picolinafen and
(b) 2-(2-Methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-n- propoxy-2,4-dihydro-3H-l,2,4-triazol-3-on oder das Natriumsalz dieser(b) 2- (2-methoxycarbonyl-phenylsulfonylaminocarbonyl) -4-methyl-5-n-propoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one or the sodium salt thereof
Verbindung (propoxycarbazone-sodium) undCompound (propoxycarbazone-sodium) and
(c) gegebenenfalls eine oder mehrere Verbindungen aus der Gruppe N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harn- Stoff (Amidosulfuron), 2,6-Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoe- säure-Natriumsalz (Bispyribac-sodium), 2-(4-Chlor-2-fluor-5-(2-chlor-2- ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l,2,4-triazol-3-on (Carfentrazone-ethyl), 2-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-Chlor-4-ethylamino-6-( 1 -cyano- 1 -methyl-ethylamino)-(c) optionally one or more compounds from the group N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron) , 2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac-sodium), 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), 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 ), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino) -
1,3,5-triazin (Cyanazine), 2,4-Dichlor-phenoxyessigsäure (2,4-D), (R)-2-(2,4- Dichlor-phenoxy)-propansäure (Dichloφrop-P), N-(2,6-Difluor-phenyl)-8- fluor-5-methoxy-[ 1 ,2,4]-triazolo-[ 1 ,5-c]-pyrimidin-2-sulfonamid (Flora- sulam), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadiazol-2- yl-oxy)-acetamid (Flufenacet), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3- methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natrium- salz (Flupyrsulfuron-methyl-sodium), (4-Amino-3,5-dichlor-6-fluor-pyridin- 2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl-ethylester, - 1 -methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), N-(4-Methoxy-6-methyl-l,3,5-triazin- 2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz1,3,5-triazine (cyanazines), 2,4-dichlorophenoxyacetic acid (2,4-D), (R) -2- (2,4-dichlorophenoxy) propanoic acid (Dichloφrop-P), N - (2,6-difluorophenyl) -8- fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyrimidine-2-sulfonamide (Florasulam), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (4,6-dimethoxy-pyrimidine- 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-butoxy-1-methyl-ethyl ester, - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), N- (4-methoxy- 6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt
(lodosulfuron-methyl-sodium), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harn- stoff (Isoproturon), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 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), l-Amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimeth- alin), N-(4-Methoxy-6-methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-mefhyl), N-Methyl-N-(4- methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenyl- sulfonyl)-harnstoff (Tribenuron-methyl), N-[[(4,6-Dimethoxy-2-pyrimidinyl)- amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), N-(4-Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'- (2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfüron).(iodosulfuron-methyl-sodium), N, N-dimethyl-N '- (4-isopropyl-phenyl) -arn- substance (isoproturon), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2, 4-triazolo [1,5-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-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), l-amino-N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethaline), N- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-thien-3-yl-sulfonyl) urea (thifensulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2- yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2, 2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N'- (2-trifluoromethyl- phenylsulfonyl) urea (tritosulfuron).
Hervorzuheben sind auch selektiv-herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einer Wirkstoffkombination umfassendAlso to be emphasized are selective herbicidal compositions which are characterized by a content of an active ingredient combination comprising
(a) Picolinafen und(a) Picolinafen and
(b) 2-(2-Trifluormethoxy-phenylsulfonylaminocarbonyl)-4-methyl-5-methoxy-(b) 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-
2,4-dihydro-3H-l,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (flucarbazone-sodium) und2,4-dihydro-3H-l, 2,4-triazol-3-one or the sodium salt of this compound (flucarbazone-sodium) and
(c) gegebenenfalls eine oder mehrere Verbindungen aus der Gruppe 2,6-Bis-(4,6- dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyribac- sodium), 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-dihydro-3H- 1 ,2,4-triazol-3-on (Carfentrazone-ethyl), 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), (R)-(2-Proρinyl)-2-[4-(5-chlor-3-fluor-pyridin-2- yl-oxy)-phenoxy-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)-Ethyl-2-[4-(6-chlor-benzox- azol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), N-(2,6-Difluor- phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Florasulam), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadi- azol-2-yl-oxy)-acetamid (Flufenacet), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'- (3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff- Natriumsalz (Flupyrsulfuron-methyl-sodium), (4-Amino-3,5-dichlor-6-fluor- pyridin-2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl-ethylester, - 1 -methyl- heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), Methyl-2-(4,5-dihydro-4- methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-benzoat (Imazametha- benz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2- yl)-5-methoxymethyl-pyridin-3 -carbonsäure (Imazamox), N-(4-Methoxy-6- methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)- harnstoff-Natriumsalz (lodosulfuron-methyl-sodium), N,N-Dimethyl-N'-(4- isopropyl-phenyl)-harnstoff(Isoproturon), (4-Chlor-2-methyl-phenoxy)-essig- säure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 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), l-Amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimeth- alin), 2-[[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)- carbonyl]-amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxy- carbazone-sodium), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy- 1 -methyl-(c) optionally one or more compounds from the group 2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac-sodium), 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 (carfentrazone-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), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridine -2-yl-oxy) -phenoxy-propanoate (Clodinafop-propargyl), 3, 6-dichloropyridine-2- carboxylic acid (clopyralide), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -ethyl-2- [4- (6-chloro -benzox- azol-2-yl-oxy) phenoxy] propanoate (fenoxaprop- (P) -ethyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2 , 4] -triazolo- [l, 5-c] pyrimidine-2-sulfonamide (Florasulam), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-l, 3,4- thiadiazol-2-yl-oxy) -acetamide (flufenacet), 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-butoxy-1-methyl-ethyl ester , - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) - 4-methyl-benzoate (imazametha-benz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridin-3 -carboxylic acid (imazamox), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-me thoxycarbonyl-phenylsulfonyl) - urea sodium salt (iodosulfuron-methyl-sodium), N, N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproturon), (4-chloro-2-methyl-phenoxy) - acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 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-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), l-amino- N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethaline), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3 -propoxy-lH-l, 2,4-triazol-l-yl) -carbonyl] -amino] -sulfonyl] -benzoic acid-methyl ester sodium salt (propoxy-carbazone-sodium), ethyl- [2-chloro-5- ( 4-chloro-5-difluoromethoxy-1-methyl-
1 H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), N-(4,6-Di- methoxy-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 (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-1 H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-ethylsulfonyl) -imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N'- (2-methoxycarbonyl- thien-3-yl-sulfonyl) urea (thifensulfuron-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-Methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-meth- oxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), N-[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2- pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), N-(4-Methoxy-6-trifluor- methoxy- 1 ,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff1 -one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropyl carbamothioate (Triallate), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl ), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), N - (4-Methoxy-6-trifluoromethoxy-1, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea
(Tritosulfuron).(Tritosulfuron).
Es wurde nun überraschend gefunden, dass die oben definierten Wirkstoffkombinationen aus den 2,6-disubstituierten Pyridin-Derivaten der Formel (I) und den oben angeführten Wirkstoffen der Gruppe 2 gegebenenfalls in Kombination mit Wirkstoffen der Gruppe 3 und 4, bei sehr guter Nutzpflanzen- Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Weizen, daneben aber auch in Reis, Mais und Gerste zur selektiven Unkrautbekämpfung verwendet werden können.It has now surprisingly been found that the active compound combinations defined above from the 2,6-disubstituted pyridine derivatives of the formula (I) and the above-mentioned active compounds from group 2, if appropriate in combination with active compounds from groups 3 and 4, with very good useful plant Compatibility has a particularly high herbicidal activity and can be used in various crops, in particular in wheat, but also in rice, corn and barley for selective weed control.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirkstoffkombinationen aus Verbindungen der oben aufgeführten Gruppen 1 und 2 erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active compound combinations according to the invention from compounds of groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eineThere is therefore an unforeseeable synergistic effect and not just one
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.Addition of activities. 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 Wirkstoffkombinationen aus 2,6-disubstituierten Pyridin-Derivaten der Formel (I) und einem Safener/Antidot ("Wirkstoffe der Gruppe 3") in Kombination mit einem oder mehreren der oben angeführten Wirkstoffe der Gruppe 2 bei sehr guter Nutzpflanzen- Verträglich- keit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Getreide und Mais, vor allem Weizen, aber auch in Soja, Kartoffeln und Reis zur selektiven Unkrautbekämpfung verwendet werden können.It was also surprisingly found that the active substance combinations defined above from 2,6-disubstituted pyridine derivatives of the formula (I) and a safener / antidote (“active substances of group 3”) in combination with one or more of the active substances of the group mentioned above 2 with very good crop tolerance, have a particularly high herbicidal activity and in different Cultures, especially in cereals and maize, especially wheat, but also in soy, potatoes and rice can be used for selective weed control.
Überraschenderweise wurde zudem gefunden, dass auch die herbizidwirksame Sub- stanz 2,4-Dichlorophenoxy-essigsäure (2,4-D) und ihre Derivate die oben beschriebeneSurprisingly, it was also found that the herbicidal substance 2,4-dichlorophenoxy-acetic acid (2,4-D) and its derivatives also described the above
Safeneraufgabe übernehmen können.Can take over safener task.
Die Verbindungen Diethyl- 1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- 1 H-pyrazole- 3,5-dicarboxylate (Mefenpyr-diethyl), (l-Methylhexyl)-[(5-chloro-8-quinolinyl)oxy]- acetate (Cloquintocet-mexyl) und Ethyl- l-(2,4-dichlorophenyl)-5-(trichloromethyl)- lH-l,2,4-triazole-3-carboxylate (Fenchlorazole-ethyl) sind in den folgenden Patentanmeldungen beschrieben: DE-A-39 39 503, EP- A-191 736 bzw. DE-A-35 25 205. 2,4-D ist ein bekanntes Herbizid.The compounds diethyl 1 - (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1 H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), (l-methylhexyl) - [(5- chloro-8-quinolinyl) oxy] - acetate (Cloquintocet-mexyl) and ethyl l- (2,4-dichlorophenyl) -5- (trichloromethyl) - lH-l, 2,4-triazole-3-carboxylate (fenchlorazole- ethyl) are described in the following patent applications: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a known herbicide.
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 Wirkstoffe der Gruppe 3 geeignet sind, die schädigende Wirkung von Verbindungen der Formel (I), in Kombination mit einem oder mehreren der oben angeführten Wirkstoffe der Gruppe 2, auf die Kultuφflanzen annähernd vollständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen.Safeners or antidots, which are capable of antagonizing the damaging effect of a herbicide on the cultivated plants, are particularly suitable for the group 3 active substances listed above, the damaging effect of compounds of the formula (I), in combination with one or more of the abovementioned Active substances of group 2, to almost completely cancel the cultivated plants without impairing the herbicidal activity against the weeds.
Hervorgehoben sei hierbei die besonders vorteilhafte Wirkung der besonders bevorzugten Kombinationspartner von den Wirkstoffen der Gruppe 3, insbesondere hin- sichtlich der Schonung von Getreidepflanzen, wie z.B. Reis, Weizen, Gerste undThe particularly advantageous effect of the particularly preferred combination partners of the active ingredients of group 3, in particular with regard to the protection of cereal plants, such as, for example, Rice, wheat, barley and
Roggen, als Kultuφflanzen.Rye, as cultivated plants.
Die erfindungsgemäßen Wirkstoffkombinationen können z.B. bei den folgenden Pflanzen verwendet werden: Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria, 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.The active compound combinations according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , 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, Brassica, Lactuca, Cucumis, Cuburbita.Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, 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, Sciφus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasemumum, Sciumpalum , 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 beispielhaft 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.According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and 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 leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. 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,The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying,
Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.Evaporation, nebulization, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by means of single- or multi-layer coating.
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei be- stimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können dieThe synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, they can
Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) 0,01 bis 1000 Gewichtsteile, vorzugsweise 0,05 bis 500 Gewichtsteile und besonders bevorzugt 0,1 bis 100 Gewichtsteile Wirkstoff der Gruppe 2.Weight ratios of the active ingredients in the active ingredient combinations can be varied in relatively large ranges. In general, 1 to 1 part by weight of active compound of the formula (I) accounts for 0.01 to 1000 parts by weight, preferably 0.05 to 500 parts by weight and particularly preferably 0.1 to 100 parts by weight of active compound of group 2.
Der vorteilhafte Effekt der Kultuφflanzenverträglichkeit der erfindungsgemäßen Wirk- stoffkombinationen ist bei bestimmten Konzentrationsverhältnissen ebenfalls besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I), seinen Salzen oder dessenThe advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is likewise particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I), its salts or its
Mischungen mit Wirkstoffen der Gruppe 2 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100 Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile einer der oben unter (c) genannten, die 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, Wirkstoffimprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.Mixtures with active substances of group 2 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the compounds (antidots / safeners) which improve the tolerance to crop plants. 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 Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
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 Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole,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,
Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methyl- ethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Chloroethylene 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, 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 anio- nische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol- Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitab- laugen und Methylcellulose.e.g. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: 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; as emulsifying and / or foam-generating agents are possible: for example nonionic and anionic African 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 leaching and methyl cellulose.
Es können in den Formulierungen Haffmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexformige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Haffmittel 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 Metallphthalocyaninfarb- stoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen 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 Anwendung gemischt, d.h. in Form von Tankmischungen zur Anwendung gebracht werden.The active compound combinations according to the invention are generally used in the form of finished formulations. The active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischungen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akari- ziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte Anwendungs- zwecke, insbesondere im Nachauflauf-Verfahren, kann es ferner vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle (z.B. das Handelspräparat "Oleo DuPont HE") oder Ammoniumsalze wie z.B. Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen.The new combinations of active ingredients, as such or in their formulations, can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible. For certain application For purposes, especially in the post-emergence process, it may also be advantageous to include mineral-based or vegetable oils (such as the commercial preparation "Oleo DuPont HE") or ammonium salts such as ammonium sulfate or ammonium rhodanide that are compatible with plants as additional additives in the formulations.
Die neuen Wirkstoffkombinationen können als solche, in Form ihrer Formulierungen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Stäuben oder Streuen.The new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auflaufen der Pflanzen appliziert werden, also im Vorauflauf und Nachauflauf- Verfahren. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
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 Formel I) bei p kg/ha AufwandmengeIf X =% damage by herbicide A (active ingredient of formula I) at p kg / ha application rate
und Y = % Schädigung durch Herbizid B (Wirkstoff der Formeland Y =% damage by herbicide B (active ingredient of the formula
II) bei q kg/ha AufwandmengeII) at q kg / ha application rate
und E = die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge, dann ist E = X + Y - (X * Y/100).and E = the expected damage to herbicides A and B at p and q kg / ha application rate, then E = X + Y - (X * Y / 100).
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt. If the actual damage is greater than calculated, the effect of the combination is super-additive, that is, it shows a synergistic effect.
Anwendungsbeispiele:Application examples:
Es wurden übliche Formulierungen der involvierten Wirkstoffe benutzt. Propoxycarbazone-sodium wurde als 70 WG, Flufenacet als 60 WG und Picolinafen als 75 WG Formulierung eingesetzt . Aus den Wirkstoffen wurde eine wässrige Spritzbrühe mit 0,1 % des Additivs Renex-36 hergestellt.Usual formulations of the active substances involved were used. Propoxycarbazone-sodium was used as 70 WG, Flufenacet as 60 WG and Picolinafen as 75 WG formulation. An aqueous spray mixture containing 0.1% of the Renex-36 additive was prepared from the active ingredients.
Beispiel AExample A
Post-emergence/GewächshausPost-emergence / greenhouse
Testpflanzen werden unter kontrollierten Bedingungen (Temperatur- und Lichtverhältnisse) im Gewächshaus herangezogen. Bei Erreichen einer Pflanzenhöhe von 5 bis 15 cm werden die Pflanzen mit der Testlösung besprüht. Die Konzentration der Spritzbrühe wird so gewählt, dass in 500 1 Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden.Test plants are grown under controlled conditions (temperature and light conditions) in the greenhouse. When a plant height of 5 to 15 cm is reached, the plants are sprayed with the test solution. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 l of water / ha.
Nach der Spritzanwendung werden die Pflanzgefäße im Gewächshaus bei konstanten Licht- und Temperaturbedingungen untergebracht.After spraying, the planters are placed in the greenhouse under constant light and temperature conditions.
Nach ca. 3 Wochen wird der Schädigungsgrad der Kultuφflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After about 3 weeks, the degree of damage to the cultivated plants is rated in% damage in comparison to the development of the untreated control.
Es bedeuten: 0 % = keine Schädigung (wie unbehandelte Kontrolle)It means: 0% = no damage (like untreated control)
100 % = totale Vernichtung/Schädigung100% = total destruction / damage
Wirkstoffe, Aufwandmengen, Testpflanzen und Resultate gehen aus den nachfolgenden Tabellen hervor, wobei die in den Tabellen verwendeten Bezeichnungen die folgende Bedeutung haben: a.i. = active ingredient = Wirkstoff Tabelle A-lActive ingredients, application rates, test plants and results are shown in the following tables, the terms used in the tables having the following meaning: ai = active ingredient Table Al
Werte errechnet nach ColbyValues calculated according to Colby
Tabelle A-2Table A-2
* Werte errechnet nach Colby Tabelle A-3* Values calculated according to Colby Table A-3
* Werte errechnet nach Colby* Values calculated according to Colby
Tabelle A-4Table A-4
Werte errechnet nach Colby Tabelle A-5Values calculated according to Colby Table A-5
Werte errechnet nach ColbyValues calculated according to Colby
Tabelle A-6Table A-6
* Werte errechnet nach Colby Tabelle A-7* Values calculated according to Colby Table A-7
Tabelle A-8Table A-8
Tabelle A-9 Table A-9
Beispiel BExample B
Feldversuchefield trials
GetreideGrain
Nachauflauf FrühjahrPost-emergence spring
Zur Untersuchung eines möglichen Synergismus wurden die Verbindungen Picolinafen und Propoxycarbazone-sodium unter Freilandbedingungen in Getreide gegen wirtschaftlich bedeutende Ungräser geprüft. Die Anlage der Klein- parzellenversuche erfolgte auf Anbauflächen der landwirtschaftlichen Praxis. Es wurden Flächen mit gutem Unkrautbesatz ausgewählt.To investigate a possible synergism, the compounds picolinafen and propoxycarbazone-sodium were tested under field conditions in cereals against economically important weeds. The small parcel trials were set up on acreage in agricultural practice. Areas with good weeds were selected.
Die Applikation der Wirkstoffe erfolgte im Nachauflauf Frühjahr flächig im Spritzverfahren mit mittlerer Tropfengröße. Zur Herstellung einer zweckmäßigenThe active ingredients were applied extensively in the post-emergence spring with a medium drop size spray process. To produce a functional
Wirkstoffzubereitung wurden die Wirkstoffe als 70 WG (70 % w/w wasserdispergierbares Pulver) bzw. 75 WG (75 % w/w wasserdispergierbares Pulver) formuliert und in Wasser suspendiert. Anschließend wurde die Spritzbrühe in der praxisüblichen Wasseraufwandmenge ausgebracht.Active ingredient preparation, the active ingredients were formulated as 70 WG (70% w / w water-dispersible powder) or 75 WG (75% w / w water-dispersible powder) and suspended in water. The spray liquor was then applied in the usual amount of water.
Die herbizide Wirksamkeit wurde ca. 8 - 10 Wochen nach Applikation der Spritzbrühe visuell bonitiert. Es bedeuten:The herbicidal activity was assessed visually approximately 8-10 weeks after application of the spray mixture. It means:
0 % = Keine herbizide Wirkung, 100 % = totale Vernichtung der Kultur bzw. der Unkräuter.0% = no herbicidal activity, 100% = total destruction of the crop or weeds.
Die Wirkstoffmischungen zeigten in diesem Versuch einen deutlich ausgeprägten Synergismus in der Wirkung gegen verschiedene Unkräuter. Die Wirkung lag deutlich über dem nach der Colby-Formel (COLBY 1967) für die Mischung zu erwartenden Wert (siehe die folgenden Tabellen). Tabelle B-l:In this experiment, the active ingredient mixtures showed a clearly pronounced synergism in the action against various weeds. The effect was significantly higher than the value to be expected for the mixture according to the Colby formula (COLBY 1967) (see the following tables). Table Bl:
Tabelle B-2:Table B-2:
Tabelle B-3: Table B-3:
Tabelle B-4:Table B-4:
Tabelle B-5: Table B-5:
Tabelle B-6:Table B-6:
Tabelle B-7: Table B-7:

Claims

Patentansprüche claims
1. Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirk- stoffkombination umfassend1. Herbicidal agents, characterized by comprising an effective content of an active ingredient combination
(a) zumindest ein 2,6-disubstituiertes Pyridin-Derivat der allgemeinen Formel (I)(a) at least one 2,6-disubstituted pyridine derivative of the general formula (I)
in welcher in which
R1 für einen gegebenenfalls einfach oder mehrfach durch Halogen- und/oder Ci-Cß-Halogenalkyl substituierten 5 bis 6 gliedrigen Hetero- zyklus enthaltend 1 bis 3 Stickstoffatome oder für ein gegebenenfalls einfach oder mehrfach durch Halogen- und/oder Cι-C3-Halogenalkyl substituierten Phenylrest steht,R 1 for an optionally mono- or polysubstituted by halogen and / or Ci-C ß -haloalkyl substituted 5 to 6-membered heterocycle containing 1 to 3 nitrogen atoms or for an optionally mono- or polysubstituted by halogen and / or C 1 -C 3 Haloalkyl-substituted phenyl radical,
R2 für einen gegebenenfalls durch Halogen- und/oder Cι-C3-Halogenalkyl substituierten Phenoxyrest steht,R 2 represents a phenoxy radical which is optionally substituted by halogen and / or -CC3-haloalkyl,
R3 für ein Wasserstoffatom oder Methyl steht, undR 3 represents a hydrogen atom or methyl, and
W für Sauerstoff oder die Gruppe -CO-NH- steht,W represents oxygen or the group -CO-NH-,
(„Wirkstoffe der Gruppe 1")("Active substances of group 1")
und (b) eine oder mehrere Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:and (b) one or more compounds from a second group of herbicides, which contains the active compounds mentioned below:
(5-Trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-essigsäure-N-isopropyl-N-(4- fluoφhenyl)-amid (flufenacet), 2-(2-Methoxycarbonyl-phenylsulfonylamino- carbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (propoxycarbazone-sodium), 2-(2-Trifluor- methoxy-phenylsulfonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro- 3H-l,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (flucarbazone- sodium), N-(3,4-Dichloφhenyl)propanamid (propanil), N-2-Benzothiazolyl-(5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetic acid-N-isopropyl-N- (4-fluoro-phenyl) -amide (flufenacet), 2- (2-methoxycarbonyl-phenylsulfonylamino-carbonyl) -4-methyl-5-n-propoxy-2,4-dihydro-3H-l, 2,4-triazol-3-one or the sodium salt of this compound (propoxycarbazone-sodium), 2- (2-trifluoromethoxy- phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2,4-dihydro-3H-l, 2,4-triazol-3-one or the sodium salt of this compound (flucarbazone-sodium), N- (3,4-dichloφhenyl) propanamide (propanil), N-2-benzothiazolyl
N,N'-dimethylharnstoff (methabenzthiazuron), 4-Amino-6-( 1 , 1 -dimethyl- ethyl)-3-(methylthio)- 1 ,2,4-triazin-5(4H)-on (metribuzin), 4-(2-Chloφhenyl)- N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazol-l -carboxamid (fentraz- amide), 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on (metamitron), 2- (2-Benzothiazolyloxy)-N-methyl-N-phenylacetamid (mefenacet), 4-Amino-6-N, N'-dimethylurea (methabenzthiazuron), 4-amino-6- (1, 1-dimethyl-ethyl) -3- (methylthio) - 1, 2,4-triazin-5 (4H) -one (metribuzin), 4- (2-chloro-phenyl) - N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentraz amide), 4-amino-3-methyl-6-phenyl -l, 2,4-triazin-5 (4H) -one (metamitron), 2- (2-benzothiazolyloxy) -N-methyl-N-phenylacetamide (mefenacet), 4-amino-6-
(l,l-dimethylethyl)-3-(ethylthio)-l,2,4-triazin-5(4H)-on (ethiozin) oder 1- Methylethyl 5-[4-brom-l-methyl-5-(trifluormethyl)-lH-pyrazol-3-yl]-2- chloro-4-fluorobenzoat (fluazolate)(l, l-dimethylethyl) -3- (ethylthio) -l, 2,4-triazin-5 (4H) -one (ethiozine) or 1-methylethyl 5- [4-bromo-l-methyl-5- (trifluoromethyl ) -lH-pyrazol-3-yl] -2- chloro-4-fluorobenzoate (fluazolate)
(„Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
sowie gegebenenfallsand if necessary
(c) zusätzlich zumindest eine die Kultuφflanzenverträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:(c) additionally at least one compound from the following group of compounds which improves the compatibility with crop plants:
α-(l,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), α-(Cya- nomethoximino)-phenylacetonitril (Cyometrinil), 4-Chlor-N-( 1 ,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-( 1 -methyl-hexyl- ester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N- (2-propenyl)-acetamid (DKA-24), 1,8-Naphthalinsäureanhydrid, 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 (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'-( 1 - methyl-l-phenyl-ethyl)-harnstoff (Dymron), 1-Dichloracetyl-hexahydro-α- (1,3-Dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinil), α- (cyanomethoximino) -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-quinoxalin-8-oxy-acetic acid- (1-methyl-hexyl- ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) acetamide (DKA-24), 1,8-naphthalic anhydride , l- (2,4-Di-chlorophenyl) -5-trichloromethyl-lH-l, 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-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-l-oxa-4- aza-spiro [4.5] -decane (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N- (1,3-dioxolane-2- yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-di-chloro-N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methyl- phenyl) -N '- (1 - methyl-l-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-
3 ,3,8a-trimethylpyrrolo[ 1 ,2-a]-pyrimidin-6(2H)-on (BAS- 145138), N-(2- Methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl- 4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), Diethyl- 1 - (2,4-dichloφhenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Me- fenpyr-diethyl), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), (+-)-2-(4-3, 3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (BAS- 145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) -benzenesulfonamide, ethyl-4 , 5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl 1 - (2,4-dichloφhenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5- dicarboxylate (mefenpyr-diethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), (+ -) - 2- (4-
Chlor-2-methylphenoxy)propansäure (Mecoprop), 3-Dichloracetyl-2,2,5-tri- methyl-oxazolidin (R-29148) und 2,4-Dichloφhenoxyessigsäure (2,4-D) und dessen DerivateChloro-2-methylphenoxy) propanoic acid (mecoprop), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and 2,4-dichloro-phenoxyacetic acid (2,4-D) and its derivatives
("Wirkstoffe der Gruppe 3"),("Active substances of group 3"),
sowie gegebenenfallsand if necessary
(d) eine oder mehrere Verbindungen aus einer dritten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält:(d) one or more compounds from a third 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 (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid2-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 (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide
(Alachlor), N-Ethyl-N'-i-propyl-6-methylthio-l,3,5-triazin-2,4-diamin (Ametryn), 4-Amino-N-( 1 , 1 -Dimethyl-ethyl)-4,5-dihydro-3-(l -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), 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 (Azafen- idin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-[ 1 -methyl-4-(2-methyl-2H- tetrazol-5-yl)- 1 H-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulf ron), N-Benzyl- 2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4-Chlor-2- oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4- trifluormethyl-benzenamin (Benfluralin), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuron), 2-[2- [4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl- phenoxy]methyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2. l]-oct-3-en-(Alachlor), N-ethyl-N'-i-propyl-6-methylthio-l, 3,5-triazine-2,4-diamine (Ametryn), 4-amino-N- (1, 1-dimethyl-ethyl) -4,5-dihydro-3- (1-methyl-ethyl) - 5-oxo-1 H-1, 2,4-triazole - 1-carboxamide (amicarbazone), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1, 2, 4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-l, 3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) - phenyl] -5,6,7,8-tetrahydro-l, 2,4-triazolo- [4,3-a] pyridin-3 (2H) -one (azafenidine), N- (4,6 -Dimethoxypyrimidin-2-yl) -N '- [1 -methyl-4- (2-methyl-2H-tetrazol-5-yl) -1H-pyrazol-5-ylsulfonyl] urea (azimsulfon), 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), N- (4,6-dimethoxypyrimidin-2-yl) - N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuron), 2- [2 - [4- (3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) pyrimidinyl phenoxy] methyl] -5-ethyl phenox Methyl propanoic acid (benzfendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2. l] oct-3-ene
2-on (Benzobicyclon), Ethyl N-benzoyl-N-(3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-lH-2,l,3-benzothiadiazin-4(3H)-on2-one (benzobicyclone), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-lH-2, l, 3-benzothiadiazin-4 (3H) -one
(Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 2,6- Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyri- bac-sodium), 2-Brom-3,3-dimethyl-N-(l-methyl-l-phenyl-ethyl)-butanamid(Bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), 2,6-bis (4,6-dimethoxypyrimidin-2-yl-oxy) benzoic acid -Sodium salt (bispyribac-sodium), 2-bromo-3,3-dimethyl-N- (l-methyl-l-phenyl-ethyl) -butanamide
(Bromobutide), 3,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-dinitro-phenyl)- oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), N- Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2-Chlor- 5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinyl)-ben- zoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil- allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxo- butyl)-phenyl]-2-cyclohexen-l-on (Butroxydim), S-Ethyl-bis-(2-methyl- propyl)-fhiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl-phenyl- sulfonyl)- 1 H- 1 ,2,4-triazol- 1 -carboxamid (Cafenstrole), 2-[ 1 -[(3-Chlor-2- propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2- cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor- 2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-l-(3-methoxy-4-nitro- phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl- phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), l,3,5-Trichlor-2-(4-nitro- phenoxy)-benzol (Chlornitrofen), 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- (1, 3,4,5, 6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure- ethylester (Cinidon-ethyl), N-(4,6-Dimethoxy-l,3,5-triazin-2-yl)-N'-(2-(2- methoxy-ethoxy)-phenylsulfonyl)-harnstoff (Cinosulfuron), 2-[ 1 -[2-(4-Chlor- phenoxy)-propoxyamino]butyl]-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),(Bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) oxime (bromofenoxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N- Butoxymethyl-2-chloro-N- (2,6-diethyl-phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl- 1 (2H) -pyrimidinyl) -benzoic acid- [1, 1 -dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3 -hydroxy-5- [2,4,6-trimethyl-3- (l-oxobutyl) phenyl] -2-cyclohexen-l-one (butroxydim), S-ethyl-bis- (2-methylpropyl ) -fhiocarbamate (butylates), 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-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-l - (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 3-amino-2,5-dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonylphenylsulfonyl) urea (chlorimuron-ethyl), 1,3,5-trichloro-2- (4-nitro-phenoxy) benzene (chloronitrofen), 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- (1, 3,4,5, 6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) -phenyl] -2-propanoic acid, ethyl ester (cinidon-ethyl), N- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -N '- (2- (2-methoxy-ethoxy) -phenylsulfonyl) urea (cinosulfuron), 2- [1 - [2- (4-chlorophenoxy) propoxyamino] butyl] -5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclo- hexanedione (clefoxydim), (E, E) - (+) - 2- [l - [[(3-chloro-2-propenyl) -oxy] -imino] - propyl] -3-hydroxy-2-cyclohexene-l -O n (Clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (Clodinafop propargyl),
3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5-eth- oxy-7-fluor[l,2,4]triazolo[l,5-c]pyrimidin-2-yl-sulfonyl)-amino]-benzoat (Cloransulam-methyl), 2-Chlor-4-ethylamino-6-( 1 -cyano- 1 -me hyl-ethyl- amino)-l,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- cyclopropylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(l-3,6-dichloropyridine-2-carboxylic acid (clopyralide), methyl-3-chloro-2 - [(5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine -2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl ethyl-amino) -l, 3,5-triazine (Cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (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-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), 2-[ 1 -[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3- carbonsäure (Diflufenzopyr), S-( 1 -Methyl- 1 -phenyl-ethyl)- 1 -piperidin-carbo- thioat (Dimepiperate), (S-) 2-Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2- methoxy-l-methyl-ethyl)-acetamid (S-) (Dimethenamid), 2-Amino-4-(l- fluor- 1 -methyl-ethyl)-6-( 1 -methyl-2-(3 ,5-dimethyl-phenoxy)-ethylamino)- 1,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl-l,3- diamino-benzol (Dini tramine), 6,7-Dihydro-dip)τido[l,2-a:2',r-c]pyrazin- diium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethyl- pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor-phenyl)-N,N-di- methyl-harnsto f (Diuron), 2-[2-(3-Chlor-phenyl)-oxiranylmethyl]-2-ethyl- lH-inden-l,3(2H)-dion (Epropodan), S-Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(l ,2-dimethyl-propyl)-thiocarbamat (Espro- carb), N-Ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzen- amin (Ethalfluralin), (S)-(2-Ethoxy- 1 -methyl-2-oxoethyl)-2-chlor-5-(2-chlor- 4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-hamstoff (Ethoxysulfuron), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxa- prop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5- oxo-lH-tetrazol-1 -carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3- chlor-4-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-[l,2,4]-triazolo-[l,5-c]- pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-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-benzoe- säure-i-propylester (Fluazolate), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-Ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluoro- phenoxy) -phenoxy] -propanoic acid butyl ester (cyhalofop-butyl), 2,4-dichloro-phenoxyacetic 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-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [1 - [(3,5-difluorophenyl) aminocarbonylhydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl-ethyl) -1 piperidin-carbo- thioate (dimepiperate), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (l-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) - 1,3,5-triazine (dimexyflam) , N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-l, 3-diamino-benzene (diamine tramine), 6,7-dihydro-dip) τido [l, 2-a: 2 ', rc] pyrazidium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl-urea (diuron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3 (2H) -dione (epropodane) , S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Espro-carb), N-ethyl-N- (2-methyl- 2-propenyl) -2,6-dinitro-4-trifluoromethyl-benzene-amine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro - 4-trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (Ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxa-prop- (P) -ethyl), 4- (2- Chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N-benzoyl-N- (3-chloro-4-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- [l, 2,4] -triazolo- [l, 5-c] - pyrimidine-2-sulfonamide (Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) phenoxy] propanoic acid butyl ester ( Fluazifop, -butyl, -P-butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1 H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid-i- propyl ester (fluazolates), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-
[(2-trifluormethoxy-phenyl)-sulfonyl]- 1 -H- 1 ,2,4-triazol- 1 -carboxamid- Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)-N-i-propyl-2-(5- trifluormethyl- 1 ,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(2,6-Di- fluor-phenyl)-5-methyl-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Flu- metsulam), Pentyl-[2-chlor-4-fluor-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H- isoindol-2-yl)-phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4-dihydro- 3-oxo-4-(2-propinyl)-2H-l,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-lH-iso- indol-l,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(l-methyl-2-propinyl)- oxy]-phenyl]-4,5,6,7-tetrahydro-lH-isoindol-l,3(2H)-dion (Flumipropyn), 3- Chlor-4-chlormethyl- 1 -(3-trifluormethyl-phenyl)-2-pyrrolidinon (Fluoro- chloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure- ethoxycarbonylmethylester (Fluoroglycofen-ethyl), l-(4-Chlor-3-(2,2,3,3,3- pentafluor-propoxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazol-3-carboxamid (Flupoxam), l-Isopropyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl-l(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy- pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sul- fonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 9-Hydroxy- 9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluor-pyridin- 2-yl-oxy)-essigsäure (-2-butoxy- 1 -methyl-ethylester, - 1 -methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluor- methyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4-fluor-5-[(2-trifluoromethoxy-phenyl) sulfonyl] -1 -H-1, 2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N- (4-fluorophenyl) -Ni-propyl-2 - (5- trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (2,6-di-fluorophenyl) -5-methyl-l, 2,4- triazolo [l, 5-a] pyrimidine-2-sulfonamide (fluoretsulam), pentyl- [2-chloro-4-fluoro-5- (l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro- 3-oxo-4- (2-propynyl) -2H-l, 4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(l-methyl-2-propynyl) - oxy] phenyl] -4,5,6,7-tetrahydro-lH-isoindole-1,3 (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl-1 - (3-trifluoromethyl-phenyl) -2-pyrrolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro -benzoic acid- ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), l- (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-dihydro-3-methyl-2,6-dioxo-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 (flupyrsulfuron- methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy - 1-methyl-ethyl ester, - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5 -Methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (flurtamone), methyl - [(2-chloro-4-fluoro-5-
(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadiazolo-[3,4-a]-pyridazin-l-yliden)- amino-phenyl]-thio-acetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl- phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fomesafen), 2-[[[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formylamino- N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4-(hydroxymethylphos- phinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phos- phonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropyl- ammonium), (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-l- methyl-l,3,5-triazin-2,4(lH,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro- 4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-benzoat (Imaza- methabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imid- azol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro- 4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridin-3- carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH- imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl- 4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazetha- pyr), 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- 1 ,3,5- triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-(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-l-methyl-l, 3,5 -triazin-2,4 (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4 -methyl benzoate (imaza- methabenz-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- 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-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea -
Natriumsalz (lodosulfuron-methyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N- (3-( 1 -Ethyl- 1 -methyl-propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxa- ben), (4-Chlor-2-methylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)- methanon (Isoxachlortole), (5-Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-Sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3rd - (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxabene), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl- isoxazol-4-yl) - methanone (isoxachlortole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-
4-trifluormethyl-phenyl)-methanon (Isoxaflutole), 2-[2-[4-[3,5-Dichlor-2- pyridinyl)-oxy]-phenoxy]-l-oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Eth- oxy-l-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitro- benzoat (Lactofen), N'-(3,4-dichlor-phenyl)-N-methoxy-N-methyl-harnstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2- methyl-phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N- methyl-N-phenyl-acetamid (Mefenacet), 2-(4-Methylsulfonyl-2-nitro- benzoyl)- 1 ,3-cyclohexandion (Mesotrione), 4-Amino-3-methyl-6-phenyl- 1 ,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(2,6-dimethyl-phenyl)-N- (lH-pyrazol-l-yl-methyl)-acetamid (Metazachlor), N'-(4-(3,4-Dihydro-2- methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N- methyl-harnstoff (Metobenzuron), N'-(4-Brom-phenyl)-N-methoxy-N- methylharnstoff (Metobromuron), (S)-2-Chlor-N-(2-ethyl-6-methyl-phenyl)- N-(2-methoxy-l-methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N- (2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]- pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4-methoxy-phenyl)-N,N- dimethyl-harnstoff (Metoxuron), 4- Amino-6-ten-butyl-3 -methylthio- 1 ,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-propanamid (Naproanilide), N-Butyl-N'-(3 ,4-dichlor-phenyl)-N- methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-di- methylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfüron), S-(2- Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4-Dipropylamino-3,5- dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Dichlor-5-(2-propinyloxy)- phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-on (Oxadiargyl), 3-[2,4-Dichlor-5-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), 2- [2- [4- [3,5-dichloro-2-pyridinyl) -oxy] -phenoxy] -l-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-l-methyl-2-oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3,4-dichlor -phenyl) -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-methylsulfonyl-2-nitrobenzoyl) - 1, 3-cyclohexanedione (mesotrione), 4-amino -3-methyl-6-phenyl-1, 2,4-triazin-5 (4H) -one (metamitron), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (1H-pyrazole- l-yl-methyl) -acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-l-benzopyran-7-yl-oxy) - phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4-bromophenyl) -N-methoxy-N-methylurea (metobromuron), (S) -2-chloro-N- (2nd -ethyl-6-methyl-phenyl) - N- (2-methoxy-l-methyl-ethyl) -acetamide (metolachlor, S-metolachlor), N- (2nd , 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-ten-butyl-3-methylthio-1, 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-dichlorophenyl) -N- methyl urea (neburon), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), S- ( 2-chloro-benzyl) -N, N-diethyl-thiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy) - phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5-
(l-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-phenylsul- fonyl)-harnstoff (Oxasulfuron), 3-[ 1 -(3,5-Dichlor-phenyl)- 1 -i-propyl]-2,3-di- hydro-6-methyl-5-phenyl-4H-l ,3-oxazin-4-on (Oxaziclomefone), 2-Chlor-l - (3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl-benzen (Oxyfluorfen), l,l'-Di- methyl-4,4'-bipyridinium (Paraquat), 1 -Amino-N-(l -ethyl-propyl)-3,4-di- methyl-2,6-dinitro-benzol (Pendimethalin), 4-(t-Butyl)-N-(l -ethyl-propyl)- 2,6-dinitro-benzenamin (Pendralin), 4-Amino-3,5,6-trichlor-pyridin-2-carbon- säure (Picloram), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acet- amid (Pretilachlor), N-(4,6-Bis-difluormethoxy-pyrimidin-2-yl)-N'-(2- methoxycarbonyl-phenylsulfonyl)-harnstoff (Primisulfüron-methyl), 1 -Chlor- N-[2-chlor-4-fluor-5-[(6S,7aR)-6-fluor-tetrahydro- 1 ,3-dioxo- 1 H-pyrrolo[ 1 ,2- c]imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Profluazol), 2-Chlor-N-iso- propyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor-phenyl)-propanamid (Propanil), (R)-[2-[[(l-Methyl-ethyliden)-amino]-oxy]-ethyl]-2-[4-(6-chlor-2- chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6- methyl-phenyl)-N-[( 1 -methyl-ethoxy)-methyl]-acetamid (Propisochlor), 2- [[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]- amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone- sodium), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Prosulfocarb), N-(4-(l-methyl-ethoxy) phenyl] -5- (t-butyl) -l, 3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidine-2- yl) -N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [1 - (3,5-dichlorophenyl) -1-i-propyl] -2 , 3-di-hydro-6-methyl-5-phenyl-4H-l, 3-oxazin-4-one (oxaziclomefone), 2-chloro-l - (3-ethoxy-4-nitro-phenoxy) -4- trifluoromethyl-benzene (oxyfluorfen), l, l'-dimethyl-4,4'-bipyridinium (paraquat), 1-amino-N- (l-ethyl-propyl) -3,4-dimethyl-2, 6-dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (l -ethyl-propyl) - 2,6-dinitro-benzene amine (pendralin), 4-amino-3,5,6-trichloro- pyridine-2-carboxylic acid (picloram), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6 -Bis-difluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (primisulfuron-methyl), 1-chloro-N- [2-chloro-4-fluoro-5 - [(6S , 7aR) -6-fluoro-tetrahydro-1,3-dioxo-1 H-pyrrolo [1,2-c] imidazole-2 (3H) -yl] -phenyl] methanesulfonamide (profluazole), 2-chloro-N -isopropyl-N-phen yl-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-methyl-ethoxy ) -methyl] -acetamide (propisochlor), 2- [[((4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) carbonyl ] - amino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarbazone-sodium), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-
Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)-phenyl- sulfonyl)-harnstoff (Prosulfuron), Ethyl-[2-Chlor-5-(4-chlor-5-difluor- methoxy-l-methyl-lH-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen- ethyl), l-(3-Chlor-4,5,6,7-tetrahydro-pyrazolo[ 1 ,5-a]pyridin-2-yl)-5-(methyl- 2-propinylamino)-lH-pyrazol-4-carbonitril (Pyrazogyl), 4-(2,4-Dichlor- benzoyl)- 1 ,3-dimethyl-5-(4-methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)-l,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl- 1 - methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenyl- methanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxim (Pyribenzoxim), 6-Chlor-3-phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3- phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl- pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl- 1 (3H)-isobenzoftιranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)- benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy- ρyrimidin-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Di- chlor-chinolin-8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8- carbonsäure (Quinmerac), 2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]- propansäure (-ethylester, -tetrahydro-2-füranyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-ethyl- sulfonyl-pyridin-2-yl-sulfonyl)-harnsto f (Rimsulfuron), 2-(l-Ethoximino- butyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-l-on (Sethoxydim), 6- Chlor-2,4-bis-ethylamino-l,3,5-triazin (Simazin), 2-(2-Chlor-4-methyl- sulfonyl-benzoyl)-cyclohexan-l ,3-dion (Sulcotrione), 2-(2,4-Dichlor-5- methylsulfonylamino-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- l,2,4-triazol-3-on (Sulfentrazone), N-Phosphonomethyl-glycin-trimethyl- sulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethyl- sulfonyl)-imidazo[ 1 ,2-a]pyridin-3-sulfonamid (Sulfosulfuron), 6-Chlor-4- ethylamino-2-tert-butylamino- 1 ,3,5-triazin (Terbuthylazine), 2-tert-Butyl- amino-4-ethylamino-6-methylthio- 1 ,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6- dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor),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-l-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), l- (3-chloro -4,5,6,7-tetrahydro-pyrazolo [1, 5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -lH-pyrazole-4-carbonitrile (pyrazogyl), 4- ( 2,4-dichlorobenzoyl) - 1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4- (2,4-dichlorobenzoyl) -1, 3-dimethyl-5- (phenylcarbonylmethoxy) pyrazole (pyrazoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (4th -ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenyl-methanone-O- [2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy ) -benzoyl] -oxime (pyribenzoxime), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O- (6-chloro-3-phenyl-pyridazin-4-yl) -S-octyl-thiocarbonate (pyridates ), 6-chloro-3-phenylpyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H) -isobenzoftιranon (pyriftalid) , 2- (4,6-Dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (Pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-ρyrimidin-2-ylthio) -benzoic acid- Sodium salt (pyrithiobac-sodium), 3,7-di-chloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chlorine -2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester, tetrahydro-2-furanyl methyl ester) (quizalofop, ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dime thoxy-pyrimidin-2-yl) -N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) urea f (rimsulfuron), 2- (l-ethoximino-butyl) -5- (2-ethylthiopropyl ) -3-hydroxy-2-cyclohexen-l-one (sethoxydim), 6-chloro-2,4-bis-ethylamino-l, 3,5-triazine (simazine), 2- (2-chloro-4-methyl - sulfonyl-benzoyl) -cyclohexane-l, 3-dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-l , 2,4-triazol-3-one (sulfentrazone), N-phosphonomethyl-glycine-trimethyl-sulfonium (sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethyl - sulfonyl) -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-1, 3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl- methyl) acetamide (thenylchlor),
2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluor- methyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6- dimethyl-3H,5H-pyrrolo[2,l-c]-l,2,4-thiadiazol-3-ylidenamino)-7-fluor-4-(2- propinyl)-2H-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)-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 (Trifloxysulfuron), l-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfuron- methyl), N-(4-Methoxy-6-trifluormethoxy- 1 ,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, 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]- amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]methyl]-benzoesäure-methyl- ester, 4-[4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-lH-l,2,4-triazol-l- yl]-2-[(ethylsulfonyl)amino]-5-fluor-benzencarbothioamid2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6- ( 6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2, lc] -l, 2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) -2H- 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- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-tri- methyl-phenyl) -2-cyclohexen-l-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy-6-methyl-l, 3,5-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), (3,5,6-trichloro) pyridin-2-yl-oxy -acetic acid (triclopyr), 2- (3,5-dichlorophenyl) -2- (2,2,2-trichloroethyl) oxirane (tridiphane), N - [[(4,6-dimethoxy- 2-pyrimidinyl) amino] - carbonyl] -3- (2,2,2-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-methoxy-6-trifluoromethoxy-1, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea ( Tritosulfuron), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N- methyl-N-methylsulfonylamino) -2-pyridinesulfonamide, 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) -amino] methyl] -benzoic acid methyl ester, 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -lH-l, 2,4-triazol-l-yl] - 2 - [(ethylsulfonyl) amino] -5-fluoro-benzencarbothioamid
("Wirkstoffe der Gruppe 4"),("Active substances of group 4"),
wobei die Verbindung unter (b) nicht für Flufenacet steht, wenn die unter (a) 2-(3,4-Difluoφhenoxy)-4-methyl-6-(l-methyl-3-trifluormethylpyrazol-5-yl)- pyridin ist.wherein the compound under (b) is not flufenacet if the one under (a) is 2- (3,4-difluoropheneoxy) -4-methyl-6- (l-methyl-3-trifluoromethylpyrazol-5-yl) pyridine ,
2. Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass sie als Wirkstoff der Gruppe 1 ein 2,6-disubstituiertes Pyridin-Derivat der allgemeinen Formel (I) enthalten,2. Herbicidal compositions according to claim 1, characterized in that they contain a 2,6-disubstituted pyridine derivative of the general formula (I) as active ingredient of group 1,
in welcher R1 für einen gegebenenfalls durch Trifluormethyl und Methyl substituierten Pyrazolylrest oder für ein gegebenenfalls einfach oder mehrfach durch Fluor substituierten Phenylrest steht,in which R 1 represents a pyrazolyl radical optionally substituted by trifluoromethyl and methyl or a phenyl radical which is optionally monosubstituted or polysubstituted by fluorine,
R2 für einen gegebenenfalls durch Halogen- und oder Cj-C3-Halogenalkyl substituierten Phenoxyrest steht,R 2 represents a phenoxy radical which is optionally substituted by halogen and or C j -C3-haloalkyl,
R3 für ein Wasserstoffatom oder Methyl steht, undR 3 represents a hydrogen atom or methyl, and
W für Sauerstoff oder die Gruppe -CO-NH- steht.W stands for oxygen or the group -CO-NH-.
3. Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass sie als Wirkstoffe der Gruppe 13. Herbicidal compositions according to claim 1, characterized in that they are active ingredients of group 1
N-(4-Fluoφhenyl)-6-[3-(trifluormethyl)phenoxy]-2-pyridinecarboxamidN- (4-Fluoφhenyl) -6- [3- (trifluoromethyl) phenoxy] -2-pyridinecarboxamid
(picolinafen) oder 2-(3 ,4-Difluoφhenoxy)-4-methyl-6-( 1 -methyl-3 -trifluor- methylpyrazol-5-yl)-ρyridin enthalten.(picolinafen) or 2- (3, 4-Difluoφhenoxy) -4-methyl-6- (1-methyl-3-trifluoromethylpyrazol-5-yl) -ρyridine contain.
4. Herbizide Mittel gemäß einem der Ansprüche 1 bis 3, dadurch gekenn- zeichnet, dass sie als Wirkstoff der Gruppe 3 zumindest eine die Kulturpflanzen-Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen enthalten:4. Herbicidal compositions according to one of claims 1 to 3, characterized in that they contain, as active ingredient in group 3, at least one compound from the following group of compounds which improves the tolerance of crop plants:
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), Diethyl-l-(2,4-dichloφhenyl)-4,5-dihydro-5-me- thyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlor- phenoxyessigsäure (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), diethyl l- (2,4-dichloφhenyl) -4, 5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
5. Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass sie5. Herbicidal composition according to claim 1, characterized in that it
als Wirkstoff der Gruppe 1 Picolinafen undas an active ingredient in group 1 picolinafen and
als Wirkstoff der Gruppe 2 (5-Trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)- essigsäure-N-isopropyl-N-(4-fluoφhenyl)-amid (flufenacet) undas active ingredient of group 2 (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) - acetic acid-N-isopropyl-N- (4-fluoφhenyl) -amide (flufenacet) and
gegebenenfalls als weiteren Wirkstoff oder weitere Wirkstoffe eine oder mehrere Verbindungen aus der Gruppe 2,6-Bis-(4,6-dimethoxy-pyrimidin-2- yl-oxy)-benzoesäure-Natriumsalz (Bispyribac-sodium), N-(2,6-Difluor- phenyl)-8-fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamidoptionally one or more compounds from the group 2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac-sodium), N- (2, 6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine-2-sulfonamide
(Florasulam), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6- trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfüron- methyl-sodium), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoprot- uron), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]- pyrimidin-2-sulfonamid (Metosulam), 1 -Amino-N-( 1 -ethyl-propyl)-3,4-di- methyl-2,6-dinitro-benzol (Pendimethalin) und Ethyl-[2-Chlor-5-(4-chlor-5- difluormethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflu- fen-ethyl) enthalten.(Florasulam), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (Flupyrsulfüron-methyl-sodium ), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-l, 2,4-triazolo [1,5-a] - pyrimidine-2-sulfonamide (metosulam), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6-dinitro- benzene (pendimethalin) and ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyrafluene-ethyl ) contain.
6. Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass sie6. Herbicidal compositions according to claim 1, characterized in that they
als Wirkstoff der Gruppe 1 Picolinafen undas an active ingredient in group 1 picolinafen and
als Wirkstoff der Gruppe 2 2-(2-Methoxycarbonyl-phenylsulfonylamino- carbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H- 1 ,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (propoxycarbazone-sodium) undas active ingredient of group 2 2- (2-methoxycarbonyl-phenylsulfonylamino-carbonyl) -4-methyl-5-n-propoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one or the sodium salt thereof Compound (propoxycarbazone-sodium) and
gegebenenfalls als weiteren Wirkstoff oder weitere Wirkstoffe eine oder mehrere Verbindungen aus der Gruppe N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), 2,6- Bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-Natriumsalz (Bispyribac-sodium), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)- 4-difluormethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-on (Carfentrazone- ethyl), 2-Chlor-3 -[2-chlor-5-( 1 ,3 ,4,5 ,6,7-hexahydro- 1 ,3 -dioxo-2H-isoindol-2- yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl), 2-Chlor-4-ethylamino- 6-( 1 -cyano- 1 -methyl-ethylamino)- 1 ,3,5-triazin (Cyanazine), 2,4-Dichlor- phenoxyessigsäure (2,4-D), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Di- chloφrop-P), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[l ,2,4]-triazolo-[l ,5- c]-pyrimidin-2-sulfonamid (Florasulam), N-(4-Fluor-phenyl)-N-i-propyl-2-(5- trifluormethyl- 1 ,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2- yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), (4- Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-l-methyl- ethylester, -1 -methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), N-optionally one or more compounds from the group N- (4,6-dimethoxy-pyrimidin-2-yl) as a further active ingredient or other active ingredients - N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 2,6-bis (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzoic acid sodium salt (bispyribac-sodium) , 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), 2-chloro-3 - [2-chloro-5- (1, 3, 4,5, 6,7-hexahydro- 1, 3 -dioxo-2H-isoindole- 2-yl) -phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), 2-chloro-4-ethylamino- 6- (1-cyano-1-methyl-ethylamino) - 1, 3,5-triazine (cyanazines ), 2,4-dichlorophenoxyacetic acid (2,4-D), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), N- (2,6-difluoro -phenyl) -8-fluoro-5-methoxy- [l, 2,4] -triazolo- [l, 5- c] -pyrimidine-2-sulfonamide (Florasulam), N- (4-fluorophenyl) -Ni -propyl-2- (5- trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), 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-di chloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-l-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), N-
(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl- phenylsulfonyl)-harnstoff-Natriumsalz (lodosulfuron-methyl-sodium), N,N- Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), 2-(4-Chlor-2- methyl-phenoxy)-propionsäure (Mecoprop), N-(2,6-Dichlor-3-methyl- phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidin-2-sulfonamid (Meto- sulam), 4-Amino-6-tert-butyl-3-methylthio- 1 ,2,4-triazin-5(4H)-on (Metri- buzin), 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-dimethyl-2,6-dinitro-benzol (Pendimethalin), N-(4-Methoxy-6- methyl- 1 ,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harn- stoff (Thifensulfuron-methyl), N-Methyl-N-(4-methoxy-6-methyl- 1 ,3,5- triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron- methyl), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-tri- fluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), N-(4- Methoxy-6-trifluormethoxy-l,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenyl- sulfonyl)-harnstoff (Tritosulfuron) enthalten. Herbizide Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass sie(4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 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-l, 3,5-triazin-2-yl) -N '- (2nd -methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), N- (4-methoxy -6- methyl- 1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl), N - [[(4,6-dimethoxy -2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-tri-fluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxy sulfuron), N- (4-methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron). Herbicidal agents according to claim 1, characterized in that they
als Wirkstoff der Gruppe 1 Picolinafen undas an active ingredient in group 1 picolinafen and
als Wirkstoff der Gruppe 2 2-(2-Trifluormethoxy-phenylsulfonylaminocarbo- nyl)-4-methyl-5-methoxy-2,4-dihydro-3H- 1 ,2,4-triazol-3-on oder das Natriumsalz dieser Verbindung (flucarbazone-sodium) undas active ingredient of group 2 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one or the sodium salt of this compound ( flucarbazone-sodium) and
gegebenenfalls als weiteren Wirkstoff oder weitere Wirkstoffe eine oder mehrere Verbindungen aus der Gruppe 2,6-Bis-(4,6-dimethoxy-pyrimidin-2- yl-oxy)-benzoesäure-Natriumsalz (Bispyribac-sodium), 3,5-Dibrom-4- hydroxy-benzonitril (Bromoxynil), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxy- carbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-l,2,4- triazol-3-on (Carfentrazone-ethyl), 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)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)- phenoxyj-propanoat (Fenoxaprop-(P)-ethyl), N-(2,6-Difluor-phenyl)-8-fluor- 5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Florasulam), N- (4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)- acetamid (Flufenacet), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxy- carbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-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), Methyl-2-(4,5-dihydro-4-methyl-4-iso- propyl-5-oxo- 1 H-imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz- methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5- methoxymethyl-pyridin-3-carbonsäure (Imazamox), N-(4-Methoxy-6-methyl- l,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff- Natriumsalz (lodosulfuron-methyl-sodium), N,N-Dimethyl-N'-(4-isopropyl- phenyl)-harnstoff (Isopro turon), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), N-(2,6- Dichlor-3-methyl-phenyl)-5,optionally as a further active ingredient or other active ingredients, one or more compounds from the group 2,6-bis (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzoic acid sodium salt (bispyribac sodium), 3,5-dibromo -4-hydroxy-benzonitrile (bromoxynil), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonylethyl) phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-l, 2,4-triazol-3-one (carfentrazone-ethyl), 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-dichloro-pyridine-2-carboxylic acid (clopyralide), 2,4-dichloro-phenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phenoxyj- propanoate (fenoxaprop- (P) -ethyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidine -2-sulfonamide (Florasulam), N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethy ll, 3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxy-carbonyl-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-butoxy -l -methyl-ethyl ester, -1-methyl-heptyl ester) (corridor oxypyr, -butoxypropyl, -meptyl), methyl-2- (4,5-dihydro-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- methoxymethyl-pyridine-3-carboxylic acid (imazamox), N- (4-methoxy-6-methyl- l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), N, N-dimethyl-N' - (4th -isopropylphenyl) urea (isopropyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), N- (2,6-dichloro-3-methylphenyl) -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-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 2- [[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]- amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone- sodium), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy-l-methyl-lH-pyrazol- 3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), N-(4,6-Dimethoxy-pyrimi- din-2-yl)-N'-(2-ethylsulfonyl)-imidazo[ 1 ,2-a]pyridin-3-sulfonamid (Sulfo- sulfuron), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbo- nyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethoximino- propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen- 1 -on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamothioat (Triallate), N- Methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl- phenylsulfonyl)-harnstoff (Tribenuron-methyl), N-[[(4,6-Dimethoxy-2-pyri- midinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid- Natriumsalz (Trifloxysulfuron), N-(4-Methoxy-6-trifluormethoxy-l,3,5- triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron) enthalten.7-dimethoxy-l, 2,4-triazolo [l, 5-a] pyrimidine-2-sulfonamide (metosulam), 4-amino-6-tert-butyl-3-methylthio-l, 2,4-triazine 5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl ), 1 -Amino- N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), 2- [[[(4,5-dihydro-4-methyl-5 -oxo-3-propoxy-lH-l, 2,4-triazol-l-yl) -carbonyl] - amino] -sulfonyl] -benzoic acid-methyl ester sodium salt (propoxycarbazone-sodium), ethyl- [2-chloro-5 - (4-chloro-5-difluoromethoxy-l-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), N- (4,6-dimethoxy-pyrimididine) 2-yl) -N '- (2-ethylsulfonyl) imidazo [1, 2-a] pyridine-3-sulfonamide (sulfosulfone), 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-trimethyl-phenyl) -2-cyclohexen- 1 -one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triall ate), N-methyl-N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N - [[(4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), N- (4th -Methoxy-6-trifluoromethoxy-l, 3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron) contain.
8. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 7 zur Bekämpfung von unerwünschten Pflanzen.8. Use of an agent according to any one of claims 1 to 7 for controlling unwanted plants.
9. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekenn- zeichnet, dass man Mittel gemäß einem der Ansprüche 1 bis 7 auf die unerwünschten Pflanzen und/oder ihren Lebensraum einwirken lässt. 9. A method for controlling unwanted plants, characterized in that agents according to one of claims 1 to 7 are allowed to act on the undesired plants and / or their habitat.
0. Verfahren zur Herstellung eines herbiziden Mittels, dadurch gekennzeichnet, dass man ein Mittel gemäß einem der Ansprüche 1 bis 7 mit oberflächenaktiven Mitteln und/oder Streckmitteln vermischt. 0. A process for the preparation of a herbicidal agent, characterized in that an agent according to any one of claims 1 to 7 is mixed with surface-active agents and / or extenders.
EP00971424A 1999-11-17 2000-11-06 Selective herbicides based upon 2,6-disubstituted pyridine derivatives Withdrawn EP1351571A2 (en)

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DE19960778 1999-12-16
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