EP1298996A1 - Selective heteroaryloxy-acetamide-based herbicides - Google Patents

Selective heteroaryloxy-acetamide-based herbicides

Info

Publication number
EP1298996A1
EP1298996A1 EP01943335A EP01943335A EP1298996A1 EP 1298996 A1 EP1298996 A1 EP 1298996A1 EP 01943335 A EP01943335 A EP 01943335A EP 01943335 A EP01943335 A EP 01943335A EP 1298996 A1 EP1298996 A1 EP 1298996A1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
chloro
phenyl
dihydro
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Withdrawn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
EP01943335A
Other languages
German (de)
French (fr)
Inventor
Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
Mathias Kremer
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 DE10041619A external-priority patent/DE10041619A1/en
Priority to EP10158932A priority Critical patent/EP2243369A3/en
Priority to EP10158913.3A priority patent/EP2243361B1/en
Priority to EP10158918A priority patent/EP2243365A3/en
Priority to EP10158933A priority patent/EP2243370A2/en
Priority to DK05005219.0T priority patent/DK1552746T3/en
Priority to EP10158925A priority patent/EP2243367A3/en
Priority to EP10158915.8A priority patent/EP2243362B1/en
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP10158917.4A priority patent/EP2243364B1/en
Priority to EP10158924A priority patent/EP2243366A3/en
Priority to EP10158916.6A priority patent/EP2243363B1/en
Priority to EP05005219.0A priority patent/EP1552746B1/en
Priority to EP10158929A priority patent/EP2243368A3/en
Publication of EP1298996A1 publication Critical patent/EP1298996A1/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Withdrawn legal-status Critical Current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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • the invention relates to new selective herbicidal, synergistic active ingredient combinations which consist of known heteroaryloxyacetamides on the one hand and known herbicidally active compounds and / or compounds which improve the tolerance of crop plants on the other hand and which are used with particularly good success for selective weed control in various crop plants can.
  • Heteroaryloxyacetamides as strong herbicides which are particularly effective against monocotyledon weeds, are the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP -A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323).
  • EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP -A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323 are the subject of a number of patent applications.
  • active substance combinations are heteroaryloxyacetamides and other herbicidally active compounds to achieve a synergistic effect (cf. WO-A 94/02014, WO-A-96/07323, WO-A-96/11575, WO-A-96/17519 , WO-A-
  • the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • Ar represents phenyl which is optionally substituted by halogen, C 4 -C 4 -alkyl or C 4 -C 4 -haloalkyl,
  • Het is thiadiazolyl which is substituted by halogen or by C1-C4-alkyl or phenyl which is optionally substituted by halogen, and
  • R represents alkyl, alkenyl or alkynyl each having up to 4 carbon atoms
  • Ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate isoxadifen-ethyl
  • diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole -3,5-dicarboxy-lat mefenpyr-diethyl
  • 2-dichloromethyl-2-methyl-1,3-dioxolane MG-191, 1,8-naphthalic acid anhydride, ⁇ - (1,3-dioxolane-2 -yl-methoximino) -phenylaceto-nitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-2
  • Ar preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
  • Het preferably stands for 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which by fluorine, chlorine, bromine or by optionally by fluorine and / or Chlorine substituted methyl, ethyl, n- or i-propyl or phenyl is substituted.
  • R preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1- Methyl 2-propynyl, 2-butynyl.
  • Ar particularly preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • Het is particularly preferably 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by fluorine, chlorine, bromine or by methyl, ethyl or phenyl which are optionally substituted by fluorine and / or chlorine.
  • R particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • Ar very particularly preferably represents phenyl optionally substituted by fluorine or chlorine.
  • Het very particularly preferably represents 1,3,4-thiadiazolyl which is substituted by chlorine, bromine or by fluorine- and / or chlorine-substituted methyl.
  • R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • Examples of the compounds of the formula (I) to be used as mixture partners according to the invention are: Ni-propyl-N-phenyl- ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (2-chlorophenyl) - ⁇ - (5th -trifluora ⁇ ethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (3-chlorophenyl) - ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2 -yl-oxy) -acetamide, Ni-propyl-N- (4-chlorophenyl) - ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) - acetamide, Ni Propyl-N- (2-fluoro-phenyl) - ⁇ - (5-trifluoromethyl-1, 3,
  • the active substances of group 2 can be assigned to their chemical structure according to the following active substance classes:
  • Amides e.g. beflubutamide
  • aryl heterocycles e.g. azafenidin, benzfendizone
  • Butroxydim, Clefoxydim, Cycloxydim), dinitroanilines e.g. Benfluralin, Oryzalin
  • imidazoxones e.g. Imazamoxolinone
  • Isoxachlortole e.g. Isoxachlortole
  • pyridines e.g. Thiazopyr
  • pyrimidinyl (thio) benzoates e.g. Pyribenz-oxim, Pyriftalid, Pyriminobac-methyl, Pyrithiobac-sodium
  • sulfonylureas e.g.
  • Azimsulfuron Flupyrsulfuron-methyl-sodium, Foramsulfuron-methyl- Iodosulfuron sodium, mesosul Someon, trifloxysulfuron, triflusulfuron-methyl), tetrazolinones (e.g.
  • Fentrazamides Fentrazamides
  • triazoles e.g. amitroles
  • triazolinones e.g. flucarbazone-sodium, Procarbazone-sodium
  • triazolopyrimidines e.g. cloransulam-methyl, diclosulam, florasulam
  • triketones e.g. mesotrione
  • mixture components from the active ingredients of group 2 are:
  • Azimsulfuron Beflubuta id, Butafenacil-allyl, Cinidon-ethyl, Cloransulam-methyl, Clefoxydim, Diclosulam, Fenoxaprop-P-ethyl, Florasulam, Flupyrsul possiblyon-methyl-sodium, Foramsulmron, Imazamox, Iodosulfuron-methyl-sodium, Oxox, Isox , Procarbazone-sodium, pyriftalid, pyrithiobac-sodium, quinclorac, trifloxysulfuron.
  • beflubutamide is of particular interest as a mixture component.
  • butafenacil-allyl is of particular interest as a mixture component.
  • cinidon-ethyl is of particular interest as a mixture component.
  • Clefoxydim is also of particular interest as a mixture component.
  • cloransulam-methyl is also of particular interest as a mixture component.
  • flupyrsulfuron-methyl-sodium is of particular interest as a mixture component.
  • imazamox is also of particular interest as a mixture component.
  • iodosulfuron-methyl-sodium is of particular interest as a mixture component.
  • mesosullayson is also of particular interest as a mixture component.
  • oxaziclomefone is also of particular interest as a mixture component.
  • Procarbazone-sodium from this group is of particular interest as a mixture component.
  • agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally an active substance from group 3.
  • the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
  • Active ingredients of group 2 with a largely good crop tolerance have a particularly high herbicidal activity and can be used in various crops, in particular in barley, potatoes, corn, rice, soybeans and wheat, for the selective control of monocotyledonous and dicotyledonous weeds and that they can also be used for Control of monocot and dicot weeds in the semi and non-selective range can be used.
  • the herbicidal activity of the active compound combinations according to the invention consisting of compounds from groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
  • the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active Substance of the formula (I) 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight of active ingredient or active ingredients of group 2.
  • the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate also in combination with one or more of the active ingredients of group 2 mentioned above, to be completely removed from the crop plants without impairing the herbicidal activity against the weeds.
  • the advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I) or mixtures thereof are present
  • 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 active substance or active substances of group 3.
  • Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and
  • Roots, tubers and rhiozomes are listed.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, by - or multi-layer wrapping.
  • the plants obtained by biotechnological and genetic engineering methods or by a combination of these methods those plants are emphasized which tolerate so-called 4-HPPD, EPSP and / or PPO materials, such as, for example, acuron plants.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and with the minimum tillage process become. They are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates,
  • Alkyl sulfates, aryl sulfonates and protein hydrolyzates Possible dispersants are: e.g. Lignin sulfate leachate and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarinv, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarinv, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active substances contained in the active substance combinations can, however, also be mixed in individual formulations when used, that is to say applied in the form of tank mixtures.
  • the new combinations of active ingredients can furthermore 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 or vegetable oils which are compatible with plants (e.g. the commercial preparation "Oleo DuPont 11E") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new combinations of active substances 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 ingredient 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.
  • X % damage by herbicide A (active ingredient of the formula I) at p kg / ha
  • Y % damage by herbicide B (active ingredient of the formula II) at q kg / ha
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.

Abstract

The invention relates to novel herbicidal, synergistic active agent combinations which consist of heteroaryloxy acetamides and known herbicidal compounds and/or safeners as listed in the description and which can be used particularly effectively for selective weed control in various crop cultures.

Description

Selektive Herbizide auf Basis yon Heteroaryloxy-acetamidenSelective herbicides based on heteroaryloxy acetamides
Die Erfindung betrifft neue selektiv-herbizide, synergistische Wirkstoffkombinatio- nen, die aus bekannten Heteroaryloxy-acetamiden einerseits und bekannten, herbizid wirksamen Verbindungen und/oder die Kulturpflanzen-Verträglichkeit verbessernden Verbindungen andererseits bestehen und mit besonders gutem Erfolg zur selektiven Unkrautbekämpfung in verschiedenen Nutzpflanzenkulturen verwendet werden können.The invention relates to new selective herbicidal, synergistic active ingredient combinations which consist of known heteroaryloxyacetamides on the one hand and known herbicidally active compounds and / or compounds which improve the tolerance of crop plants on the other hand and which are used with particularly good success for selective weed control in various crop plants can.
Heteroaryloxyacetamide sind als starke, besonders gegen monokotyle Unkräuter wirksame Herbizide Gegenstand einer Reihe von Patentanmeldungen (vgl. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323). Die Wirkung dieser Verbindungen und/oder ihre Verträglichkeit gegenüber Kulturpflanzen sind jedoch nicht immer ganz zufriedenstellend.Heteroaryloxyacetamides, as strong herbicides which are particularly effective against monocotyledon weeds, are the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP -A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323). However, the action of these compounds and / or their compatibility with crop plants are not always entirely satisfactory.
Weiter sind Wirkstoffkombinationen aus Heteroaryloxy-acetamiden und anderen herbizid wirksamen Verbindungen zum Erzielen einer synergistischen Wirkung (vgl. WO-A 94/02014, WO-A-96/07323, WO-A-96/11575, WO-A-96/17519, WO-A-Also active substance combinations are heteroaryloxyacetamides and other herbicidally active compounds to achieve a synergistic effect (cf. WO-A 94/02014, WO-A-96/07323, WO-A-96/11575, WO-A-96/17519 , WO-A-
98/08383, vgl. auch US-A-5858920, US-A-5945379, US-A-5985797) bzw. aus Heteroaryloxy-acetamiden und Verbindungen, welche die Kulturpflanzen- Verträglichkeit von Herbiziden verbessern können (vgl. DE-A 3418167, vgl. auch US-A-5858920) bekannt geworden. Auch bei diesen Kombinationsprodukten sind jedoch die Anwen- dungseigenschaften nicht immer vollständig befriedigend.98/08383, cf. also US-A-5858920, US-A-5945379, US-A-5985797) or from heteroaryloxyacetamides and compounds which can improve the crop tolerance of herbicides (cf. DE-A 3418167, cf. also US Pat. A-5858920). However, the application properties of these combination products are not always completely satisfactory.
Überraschenderweise wurde nun gefunden, dass eine Reihe von bekannten Wirkstoffen aus der Reihe der Heteroaryloxy-acetamide bei gemeinsamer Anwendung mit bekannten herbizid wirksamen Verbindungen aus verschiedenen Stoffklassen und/oder die Kulturpflanzen-Verträglichkeit verbessernden Verbindungen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und/oder die Kulturpflanzen- Verträglichkeit signifikant verbessern und besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in Nutzpflanzenkulturen, wie z.B. in Baumwolle, Gerste, Mais, Kartoffeln, Raps, Reis, Soja, Sonnenblumen, Weizen und Zuckerrohr verwendet werden können.Surprisingly, it has now been found that a number of known active compounds from the series of heteroaryloxyacetamides, when used together with known herbicidally active compounds from different classes of substances and / or compounds which improve the tolerance to crop plants, show pronounced synergistic effects with regard to the action against weeds and / or the Significantly improve crop tolerance and can be used particularly advantageously as a broadly effective combination preparation for the selective control of weeds in crops such as, for example, cotton, barley, corn, potatoes, rapeseed, rice, soybeans, sunflowers, wheat and sugar cane.
Gegenstand der Erfindung sind selektiv-herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend ausThe invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
(a) einem Heteroaryloxy-acetamid der allgemeinen Formel (I)(a) a heteroaryloxyacetamide of the general formula (I)
RR
Het- o-^Y N .Het- o- ^ YN.
•Ar ( • Ar (
OO
in welcherin which
Ar für gegebenenfalls durch Halogen, C \ -C4- Alkyl oder C \ -C4-Halogen- alkyl substituiertes Phenyl steht,Ar represents phenyl which is optionally substituted by halogen, C 4 -C 4 -alkyl or C 4 -C 4 -haloalkyl,
Het für Thiadiazolyl steht, welches durch Halogen oder durch jeweils gegebenenfalls durch Halogen substituiertes C1-C4- Alkyl oder Phenyl substituiert ist, undHet is thiadiazolyl which is substituted by halogen or by C1-C4-alkyl or phenyl which is optionally substituted by halogen, and
R für Alkyl, Alkenyl oder Alkinyl mit jeweils bis zu 4 Kohlenstoffatomen steht,R represents alkyl, alkenyl or alkynyl each having up to 4 carbon atoms,
("Wirkstoffe der Gruppe 1 ") und("Active substances of group 1") and
(b) einer oder mehrerer Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe enthält: lH-l,2,4-triazol-3-amin (Amitrole), 2-[2,4-Dichlor-5-(2-propinyloxy)-phe- nyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-on (Azafenidin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-[l-methyl-4-(2-methyl-2H-tetrazol-5- yl)-lH-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfuron), N-Benzyl-2-(4-fluor- 3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), N-Butyl-N-ethyl-2,6- dinitro-4-trifluormethyl-benzenamin (Benfluralin), 2- [2- [4-(3 ,6-Dihydro-3 - methyl-2,6-dioxo-4-trifluormethyl-l(2H)-pyrimidinylphenoxy]methyl]-5- ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-me- thylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2. l]-oct-3-en-2-on (Benzobi- cyclon), 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)- pyrimidinyl)-benzoesäure-[l,l-dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3- (l-oxo-butyl)-phenyl]-2-cyclohexen-l-on (Butroxydim), 2-[l-[(3-Chlor-2- propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2- cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-Chlor-3-[2-chlor-5-(b) one or more compounds from a second group of herbicides which contain the active compounds mentioned below: 1H-l, 2,4-triazol-3-amine (amitrole), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-l , 2,4-triazolo- [4,3-a] pyridin-3 (2H) -one (azafenidin), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [l-methyl -4- (2-methyl-2H-tetrazol-5-yl) -lH-pyrazol-5-ylsulfonyl] urea (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethylphenoxy) butanamide (Beflubutamide), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzamine (benfluralin), 2- [2- [4- (3,6-dihydro-3 - methyl-2,6- dioxo-4-trifluoromethyl-l (2H) -pyrimidinylphenoxy] methyl] -5-ethyl-phenoxy-propanoic acid methyl ester (benzfendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo - [3.2. L] -oct-3-en-2-one (benzobicyclone), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoic acid- [l, l-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (l-ethoximino-propyl) -3-hydroxy- 5- [2,4,6-trimethyl-3- (l-oxo-butyl) phenyl] -2-cyclohexen-l-one (butroxydim), 2- [l - [(3-chloro-2-propenyl) oxy-imino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1-one (caloxydim, tepraloxydim), 2-chloro-3- [2-chloro-5-
(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure- ethylester (Cinidon-ethyl), 2-[l-[2-(4-Chlor-phenoxy)]-propoxyaminobutyl]- 5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclohexandion (Clefoxydim), (E,E)- (+)-2- [ 1 -[[(3 -Chlor-2-propenyl)-oxy] -imino] -propyl] -3 -hydroxy-2-cyclo- hexen-1-on (Clethodim), 3-chloro-2-[[(5-ethoxy-7-fluoro[l,2,4]triazolo[l,5- c]pyrimidin-2-yl) sulfonyl]amino]-benzoesäuremethylester (Cloransulam- methyl), 2-( 1 -Ethoximinobutyl)-3 -hydroxy-5 -(tetrahydro-2H-thiopyran-3 -yl)- 2-cyclohexen-l-on (Cycloxydim), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor- [l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 2-[l-[(3,5-Di- fluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3-carbonsäure (Di- flufenzopyr), (S)-2-Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-l- methyl-ethyl)-acetamid (Dimethenamid-P), 2-[2-(3-Chlor-phenyl)-oxiranyl- methyl]-2-ethyl-lH-inden-l,3(2H)-dion (Epropodan), (R)-Ethyl-2-[4-(6- chlor-benzoxazol-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), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl-oxy)-phen- oxy]-propansäure-butylester (Fluazifop-P-butyl), 4,5-Dihydro-3-methoxy-4- methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]- 1H- 1 ,2,4-triazol- 1 - carboxamid-Natriumsalz (Flucarbazone-sodium), Ethyl-[2-chloro-4-fluoro-5- (5-methyl-6-oxo-4-trifluoromethyl-l(6H)-pyridazinyl)-phenoxy]-acetate (Flu- fenpyr), 2-[7-Fluor-3 ,4-dihydro-3-oxo-4-(2-propinyl)-2H- 1 ,4-benzoxazin-6- yl]-4,5,6,7-tetrahydro-lH-isoindol-l,3-dion (Flumioxazin), N-(4,6-Di- methoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2- yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 2- [[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4- formylamino-N,N-dimethyl-benzamid (Foramsulfuron), (R)-2-[4-(3-Chlor-5- trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure (-methylester, -2-eth- oxy-ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, - butyl), 2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo-lH-imidazol-2-yl]- 5- (methoxymethyl)-3-pyridincarbonsäure (Imazamox), N-(4-Methoxy-6- methyl- 1 ,3 ,5-triazin-2-yl)-N' -(5-iod-2-methoxycarbonyl-phenylsulfonyl)- harnstoff-Natriumsalz (Iodosulfuronme- thyl-sodium), (4-Chlor-2-methyl- sulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), 2- [[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4- [[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfüron), 2-(4-Methylsulfonyl-2-nitro-benzoyl)-l,3-cyclohexandion (Mesotrione), 3-[l-(l, 3,4,5,6,7-hexahydro-l, 3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid, ethyl ester (cinidon-ethyl), 2- [l- [ 2- (4-chlorophenoxy)] - propoxyaminobutyl] - 5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [ 1 - [[(3-Chloro-2-propenyl) -oxy] -imino] -propyl] -3-hydroxy-2-cyclohexen-1-one (Clethodim), 3-chloro-2 - [[(5 -ethoxy-7-fluoro [l, 2,4] triazolo [l, 5- c] pyrimidin-2-yl) sulfonyl] amino] -benzoic acid methyl ester (chlorosulam-methyl), 2- (1-ethoximinobutyl) -3-hydroxy -5 - (tetrahydro-2H-thiopyran-3 -yl) - 2-cyclohexen-l-one (cycloxydim), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro- [1,2 , 4] -triazolo- [l, 5-c] pyrimidine-2-sulfonamide (diclosulam), 2- [l - [(3,5-di-fluorophenyl) amino carbonyl hydrazono] ethyl] -pyridine-3-carboxylic acid (diflufenzopyr), (S) -2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-l-methyl-ethyl) -acetamide ( Dimethenamid-P), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3, (2H) -dione (epropodane), (R) -ethyl-2 - [4- (6-chloro-benzoxazol-2-yl-oxy) phenox y] propanoate (fenoxaprop-P-ethyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] -triazolo- [l, 5-c] - pyrimidin-2-sulfonamide (florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) -phen- butyl oxy] propanoate (fluazifop-P-butyl), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), ethyl- [2-chloro-4-fluoro-5- (5-methyl-6-oxo-4-trifluoromethyl-l (6H) -pyridazinyl) -phenoxy] -acetate (flufenpyr), 2- [7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazin-6- yl] -4 , 5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6- trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 2- [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl ] -4- formylamino-N, N-dimethyl-benzamide (foramsulfuron), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy) -phenoxy] -propanoic acid (- methyl ester, -2-eth-oxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, - butyl), 2- [4,5-dihydro-4-methyl-4- (l- methylethyl) -5-oxo-1H-imidazol-2-yl] - 5- (methoxymethyl) -3-pyridinecarbo Acid (imazamox), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfuronme- thyl-sodium), (4-chloro-2-methylsulfonylphenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), 2- [[[(4,6-dimethoxy-2 -pyrimidinyl) -amino] -carbonyl] -amino] -sulfonyl] -4- [[(methylsulfonyl) -amino] methyl] -benzoic acid methyl ester (mesosulfuron), 2- (4-methylsulfonyl-2-nitro-benzoyl) - l, 3-cyclohexanedione (mesotrione), 3- [l-
(3,5-Dichlor-phenyl)-l-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-l,3- oxazin-4-on (Oxaziclomefone), 2-Chlor-l-(3-ethoxy-4-nitro-phenoxy)-4-tri- fluormethyl-benzen (Oxyfluorfen), 2-(2,2-Difluor-ethoxy)-N-(5,8-dimethoxy- [l,2,4]Mazolo[l,5-c]pyrimidm-2-yl)-6-trifluormethyl-benzolsulfonamid (Pen- oxsulam), 2-Chloro-N-(2-ethoxy-ethyl)-N-(2-methyl- 1 -phenyl- 1 -propenyl)- acetamide (Pethoxamid), 2-[[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy- 1H- l,2,4-triazol-l-yl)-carbonyl]-amino]-sulfonyl]-benzoesäure-methylester- Natriumsalz (Procarbazone-sodium), 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), (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]-acet- amid (Propisochlor), l-(3-Chlor-4,5,6,7-tetrahydropyrazolo[l,5-a]pyridin-2- yl)-5-(methyl-2-propinylamino)-lH-pyrazol-4-carbonitril (Pyraclonil), Ethyl [2-Chloro-5-(4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3-yl)-4- fluoro-phenoxy]-acetate (Pyraflufen-ethyl), 6-Chlor-3-phenyl-pyridazin-4-ol(3,5-dichlorophenyl) -li-propyl] -2,3-dihydro-6-methyl-5-phenyl-4H-l, 3-oxazin-4-one (oxaziclomefone), 2-chloro-l- (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethylbenzene (oxyfluorfen), 2- (2,2-difluoro-ethoxy) -N- (5,8-dimethoxy- [1,2,4 ] Mazolo [1,5-c] pyrimidm-2-yl) -6-trifluoromethyl-benzenesulfonamide (penoxsulam), 2-chloro-N- (2-ethoxy-ethyl) -N- (2-methyl-1 - phenyl-1-propenyl) -acetamide (pethoxamide), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-l, 2,4-triazol-l-yl) -carbonyl] -amino] -sulfonyl] -benzoic acid methyl ester sodium salt (procarbazone-sodium), 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), (R) - [2 - [[(l-methylethylidene ) -amino] -oxy] -ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) -phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methyl-phenyl) -N - [(l-methyl-ethoxy) -methyl] -acetamide (propisochlor), l- (3-chloro-4,5, 6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -IH-pyrazole-4-carbonitrile (pyraclonil), ethyl [2-chloro-5- (4th -chloro-5-difluoromethoxy-l-methyl-1H-pyrazol-3-yl) -4- fluoro-phenoxy] -acetate (pyraflufen-ethyl), 6-chloro-3-phenyl-pyridazin-4-ol
(Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl- 1 (3H)-iso- benzofuranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoe- säure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimi- din-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobac-sodium), 3,7-Dichlor- chinolin- 8 -carbonsäure (Quinchlorac), (R)-2-[4-(6-Chlor-2-chinoxalinyloxy)- phenoxyj-propansäure (-ethylester, -tetrahydro-2-furanyl-methylester) (Qui- zalofop-P-ethyl, -P-tefuryl), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4- (2-methyl-propyl)-6-trifluormethyl-pyridin-3-carbonsäure-methylester (Thi- azopyr), (3,5,6-Trichlor)-pyridin-2-yl-oxy-essigsäure (Triclopyr), N-[[(4,6- Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2- pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), N-[4-Dimethylamino-6- (2,2,2-trifluor-ethoxy)-l,3,5-triazin-2-yl]-N'-(2-methoxycarbonyl-phenyl- sulfonyl)-harnstoff (Triflusulfuron-methyl), N-[[(4,6-Dimethoxy-2-pyrimidin- yl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino])-2-pyridin- sulfonamid (vgl. WO-A-92/10660),(Pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H) -isobenzofuranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidine-2 -yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidine-2-ylthio) -benzoic acid sodium salt (pyrithiobac-sodium), 3, 7-dichloro-quinoline-8-carboxylic acid (quinchlorac), (R) -2- [4- (6-chloro-2-quinoxalinyloxy) - phenoxyj-propanoic acid (ethyl ester, -tetrahydro-2-furanyl methyl ester) (Qui - zalofop-P-ethyl, -P-tefuryl), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3 -carboxylic acid methyl ester (thiazopyr), (3,5,6-trichloro) pyridin-2-yl-oxyacetic acid (triclopyr), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino ] -carbonyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -l , 3,5-triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (triflusulfuron-methyl), N - [[(4,6-dimethoxy-2-pyrimidin-yl) - amino] carbonyl] -3- ( N-methyl-N-methylsulfonylamino]) - 2-pyridine sulfonamide (cf. WO-A-92/10660),
("Wirkstoffe der Gruppe 2")("Active substances of group 2")
sowie gegebenenfalls zusätzlichas well as, if necessary, additionally
(c) einer die Kulturpflanzen- Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:(c) a crop-tolerance-improving compound from the following group of compounds:
4-Dichloracetyl- 1 -oxa-4-aza-spiro[4.5]-decan (AD-67), 1 -Dichloracetyl-hexa- hydro-3,3,8a-trimethylpyrrolo[l,2-a]-pyrimidm-6(2H)-on (Dicyclonon, BAS-4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexa- hydro-3,3,8a-trimethylpyrrolo [1,2-a] -pyrimidm-6 (2H) -one (dicyclonone, BAS-
145138), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxa- cor), 5-Chlor-chinolin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet- mexyl), α-(Cyanomethoximino)-phenylacetonitril (Cyometrinil), 2,2-Dichlor- N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamid (DKA-24), 2,2-Dichlor-N,N-di-2-proρenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)- N'-(l -methyl- l-phenyl-ethyl)-harnstoff (Dymron), 4,6-Dichlor-2-phenyl- pyrimidin (Fenclorim), l-(2,4-Dichlor-ρhenyl)-5-trichlormethyl-lH-l,2,4-tri- azol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl- thiazol-5-carbonsäure-phenylmethylester (Flurazole), 4-Chlor-N-(l ,3-di- oxolan-2-yl-methoxy)-α-trifluor-acetophenonoxim (Fluxofenim), 3-Dichlor- acetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furilazole, MON-13900),145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (benoxa- cor), 5-chloro-quinoline-8-oxy-acetic acid (l-methyl-hexyl ester) (cloquintocet-mexyl), α- (cyanomethoximino) phenylacetonitrile (cyometrinil), 2,2-dichloro-N- (2- oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), N - (4-methylphenyl) - N '- (l -methyl-l-phenyl-ethyl) -urea (Dymron), 4,6-dichloro-2-phenylpyrimidine (fenclorim), l- (2,4 -Dichloro-ρhenyl) -5-trichloromethyl-lH-l, 2,4-tri-azole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole ), 4-chloro-N- (1,3-di-oxolan-2-yl-methoxy) -α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2.2 dimethyl oxazolidine (Furilazole, MON-13900),
Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), Di- ethyl-l-(2,4-dichlorphenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxy- lat (Mefenpyr-diethyl), 2-Dichlormethyl-2-methyl-l,3-dioxolan (MG-191), 1 , 8 -Naphthalsäureanhy drid, α-( 1 ,3 -Dioxolan-2-yl-methoximino)-phenylaceto- nitril (Oxabetrinil), 2,2-Dichlor-N-(l,3-dioxolan-2-yl-methyl)-N-(2- propenyl)-acetamid (PPG-1292), 3-Dichloracetyl-2,2-dimethyl-oxazolidin (R- 28725), 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148), l-(2-Chlor- phenyl)-5 -phenyl- 1 H-pyrazol-3 -carbonsäure-methylester und N-(2-Methoxy- benzoyl)-4-[(methylamino-carbonyl)-amino]-benzolsulfonamidEthyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole -3,5-dicarboxy-lat (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalic acid anhydride, α- (1,3-dioxolane-2 -yl-methoximino) -phenylaceto-nitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), l- (2-chlorophenyl) -5 -phenyl- 1 H-pyrazole-3-carboxylic acid methyl ester and N- (2-methoxy-benzoyl) -4 - [(methylamino-carbonyl) -amino] -benzenesulfonamide
("Wirkstoffe der Gruppe 3").("Active substances of group 3").
Bevorzugte Bedeutungen der in der vorstehend gezeigten Formel (I) aufgeführten Reste werden im folgenden erläutert.Preferred meanings of the radicals listed in the formula (I) shown above are explained below.
Ar steht bevorzugt für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl oder Trifluormethyl substituiertes Phenyl.Ar preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
Het steht bevorzugt für 1,2,4-Thiadiazolyl oder 1,3,4-Thiadiazolyl, welches durch Fluor, Chlor, Brom oder durch jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl oder Phenyl substituiert ist.Het preferably stands for 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which by fluorine, chlorine, bromine or by optionally by fluorine and / or Chlorine substituted methyl, ethyl, n- or i-propyl or phenyl is substituted.
R steht bevorzugt für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, 2- Propenyl, l-Methyl-2-propenyl, 2-Butenyl, 2-Propinyl, l-Methyl-2-propinyl, 2-Butinyl.R preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1- Methyl 2-propynyl, 2-butynyl.
Ar steht besonders bevorzugt für gegebenenfalls durch Fluor, Chlor, Brom, Methyl oder Trifluormethyl substituiertes Phenyl.Ar particularly preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl.
Het steht besonders bevorzugt für 1,2,4-Thiadiazolyl oder 1,3,4-Thiadiazolyl, welches durch Fluor, Chlor, Brom oder durch jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl oder Phenyl substituiert ist.Het is particularly preferably 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by fluorine, chlorine, bromine or by methyl, ethyl or phenyl which are optionally substituted by fluorine and / or chlorine.
R steht besonders bevorzugt für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-R particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
Butyl, 2-Propenyl, l-Methyl-2-propenyl, 2-Butenyl, 2-Propinyl, l-Methyl-2- propinyl, 2-Butinyl.Butyl, 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-propynyl, l-methyl-2-propynyl, 2-butynyl.
Ar steht ganz besonders bevorzugt für gegebenenfalls durch Fluor oder Chlor substituiertes Phenyl.Ar very particularly preferably represents phenyl optionally substituted by fluorine or chlorine.
Het steht ganz besonders bevorzugt für 1,3,4-Thiadiazolyl, welches durch Chlor, Brom oder durch Fluor- und/oder Chlor-substituiertes Methyl substituiert ist.Het very particularly preferably represents 1,3,4-thiadiazolyl which is substituted by chlorine, bromine or by fluorine- and / or chlorine-substituted methyl.
R steht ganz besonders bevorzugt für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl.R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
Als Beispiele für die als erfindungsgemäße Mischungspartner zu verwendenden Verbindungen der Formel (I) seien genannt: N-i-Propyl-N-phenyl-α-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamid, N-i- Propyl-N-(2-chlor-phenyl)-α-(5-trifluoraιethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamid, N-i-Propyl-N-(3-chlor-phenyl)-α-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-acet- amid, N-i-Propyl-N-(4-chlor-phenyl)-α-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)- acetamid, N-i-Propyl-N-(2-fluor-phenyl)-α-(5-trifluormethyl- 1 ,3,4-thiadiazol-2-yl- oxy)-acetamid, N-i-Propy l-N-(3 -fluor-phenyl)-α-(5 -trifluormethyl- 1 ,3 ,4-thiadiazol-2- yl-oxy)-acetamid, N-i-Propyl-N-(4-fluor-phenyl)-α-(5-trifluormethyl-l,3,4-thiadia- zol-2-yl-oxy)-acetamid.Examples of the compounds of the formula (I) to be used as mixture partners according to the invention are: Ni-propyl-N-phenyl-α- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (2-chlorophenyl) -α- (5th -trifluoraιethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (3-chlorophenyl) -α- (5-trifluoromethyl-l, 3,4-thiadiazol-2 -yl-oxy) -acetamide, Ni-propyl-N- (4-chlorophenyl) -α- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) - acetamide, Ni Propyl-N- (2-fluoro-phenyl) -α- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propy lN- (3-fluorophenyl) -α - (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) acetamide, Ni-propyl-N- (4-fluorophenyl) -α- (5-trifluoromethyl-l, 3,4- thiadiazol-2-yl-oxy) acetamide.
Die Verbindung N-i-Propyl-N-(4-fluor-phenyl)-α-(5-trifluormethyl-l,3,4-thiadiazol-The compound N-i-propyl-N- (4-fluorophenyl) -α- (5-trifluoromethyl-l, 3,4-thiadiazole-
2-yl-oxy)-acetamid (Flufenacet) - im Folgenden als Verbindung (I-l) bezeichnet - sei als Mischungskomponente der Formel (I) besonders hervorgehoben.2-yl-oxy) -acetamide (Flufenacet) - hereinafter referred to as compound (I-1) - is particularly emphasized as a mixture component of formula (I).
Die Verbindungen der Formel (I) sind in den oben angegebenen Patentanmeldungen bzw. Patentschriften beschrieben.The compounds of formula (I) are described in the above-mentioned patent applications and patents.
Die Wirkstoffe der Gruppe 2 können ihrer chemischen Struktur entsprechend folgenden Wirkstoffklassen zugeordnet werden:The active substances of group 2 can be assigned to their chemical structure according to the following active substance classes:
Amide (z.B. Beflubutamid), Arylheterocyclen (z.B. Azafenidin, Benzfendizone,Amides (e.g. beflubutamide), aryl heterocycles (e.g. azafenidin, benzfendizone,
Butafenacil-allyl, Cinidon-ethyl, Fluazolate, Flumioxazin, Oxaziclomefone, Proflu- azol, Pyraflufen-ethyl, Pyridatol), Aryloxyphenoxypropionate (z.B. Fenoxaprop-P- ethyl, Fluazifop-P-butyl, Haloxyfop-P-methyl, Quizalofop-P-ethyl), Carbonsäurederivate (z.B. Quinclorac, Triclopyr), Chloracetamide (z.B. Dimethenamid-P, Prop- isochlor), Cyclohexandione (z.B. Butroxydim, Clefoxydim, Cycloxydim), Dinitro- aniline (z.B. Benfluralin, Oryzalin), Imidazolinone (z.B. Imazamox), Isoxazole (z.B. Isoxachlortole), Pyridine (z.B. Thiazopyr), Pyrimidinyl(thio)benzoate (z.B. Pyribenz- oxim, Pyriftalid, Pyriminobac-methyl, Pyrithiobac-sodium), Sulfonylharnstoffe (z.B. Azimsulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfuron, Iodosulfuron-methyl- sodium, Mesosulfüron, Trifloxysulfuron, Triflusulfuron-methyl), Tetrazolinone (z.B.Butafenacil-allyl, cinidon-ethyl, fluazolate, flumioxazin, oxaziclomefone, profluazol, pyraflufen-ethyl, pyridatol), aryloxyphenoxypropionate (e.g. fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, quizalofop-P ethyl), carboxylic acid derivatives (e.g. Quinclorac, Triclopyr), chloroacetamides (e.g. Dimethenamid-P, prop-isochlor), cyclohexanediones (e.g. Butroxydim, Clefoxydim, Cycloxydim), dinitroanilines (e.g. Benfluralin, Oryzalin), imidazoxones (e.g. Imazamoxolinone) (e.g. Isoxachlortole), pyridines (e.g. Thiazopyr), pyrimidinyl (thio) benzoates (e.g. Pyribenz-oxim, Pyriftalid, Pyriminobac-methyl, Pyrithiobac-sodium), sulfonylureas (e.g. Azimsulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfuron-methyl- Iodosulfuron sodium, mesosulfüron, trifloxysulfuron, triflusulfuron-methyl), tetrazolinones (e.g.
Fentrazamide), Triazole (z.B. Amitrole), Triazolinone (z.B. Flucarbazone-sodium, Procarbazone-sodium), Triazolopyrimidine (z.B. Cloransulam-methyl, Diclosulam, Florasulam), Triketone (z.B. Mesotrione).Fentrazamides), triazoles (e.g. amitroles), triazolinones (e.g. flucarbazone-sodium, Procarbazone-sodium), triazolopyrimidines (e.g. cloransulam-methyl, diclosulam, florasulam), triketones (e.g. mesotrione).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 2 seien besonders her- vorgehoben:Particularly noteworthy as mixture components from the active ingredients of group 2 are:
Azimsulfuron, Beflubuta id, Butafenacil-allyl, Cinidon-ethyl, Cloransulam-methyl, Clefoxydim, Diclosulam, Fenoxaprop-P-ethyl, Florasulam, Flupyrsulfüron-methyl- sodium, Foramsulmron, Imazamox, Iodosulfuron-methyl-sodium, Isoxachlortole, Mesosulfüron, Oxaziclomefone, Procarbazone-sodium, Pyriftalid, Pyrithiobac- sodium, Quinclorac, Trifloxysulfuron.Azimsulfuron, Beflubuta id, Butafenacil-allyl, Cinidon-ethyl, Cloransulam-methyl, Clefoxydim, Diclosulam, Fenoxaprop-P-ethyl, Florasulam, Flupyrsulfüron-methyl-sodium, Foramsulmron, Imazamox, Iodosulfuron-methyl-sodium, Oxox, Isox , Procarbazone-sodium, pyriftalid, pyrithiobac-sodium, quinclorac, trifloxysulfuron.
Aus dieser Gruppe ist Beflubutamid als Mischungskomponente von ganz besonderem Interesse.From this group, beflubutamide is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Butafenacil-allyl als Mischungskomponente von ganz besonderem Interesse.Of this group, butafenacil-allyl is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Cinidon-ethyl als Mischungskomponente von ganz besonderem Interesse.From this group, cinidon-ethyl is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Clefoxydim als Mischungskomponente von ganz besonderem Interesse.From this group, Clefoxydim is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Cloransulam-methyl als Mischungskomponente von ganz besonderem Interesse.From this group, cloransulam-methyl is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Diclosulam als Mischungskomponente von ganz besonderem Interesse. Aus dieser Gruppe ist weiter Florasulam als Mischungskomponente von ganz besonderem Interesse.From this group, diclosulam is also of particular interest as a mixture component. Florasulam from this group is of particular interest as a mixture component.
Aus dieser Gruppe ist Flupyrsulfuron-methyl-sodium als Mischungskomponente von ganz besonderem Interesse.From this group, flupyrsulfuron-methyl-sodium is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Foramsulfuron als Mischungskomponente von ganz besonderem Interesse.From this group, foramsulfuron is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Imazamox als Mischungskomponente von ganz besonderem Interesse.From this group, imazamox is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Iodosulfuron-methyl-sodium als Mischungskomponente von ganz besonderem Interesse.From this group, iodosulfuron-methyl-sodium is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Isoxachlortole als Mischungsko ponente von ganz besonderem Interesse.From this group, isoxachlorotole as a mixture component is of particular interest.
Aus dieser Gruppe ist weiter Mesosulfüron als Mischungskomponente von ganz besonderem Interesse.Of this group, mesosulfüron is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Oxaziclomefone als Mischungskomponente von ganz besonderem Interesse.From this group, oxaziclomefone is also of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Procarbazone-sodium als Mischungskomponente von ganz besonderem Interesse.Procarbazone-sodium from this group is of particular interest as a mixture component.
Aus dieser Gruppe ist weiter Trifloxysulfuron als Mischungskomponente von ganz besonderem Interesse. Vorzugsweise enthalten die erfindungsgemäßen Mittel einen oder zwei Wirkstoffe der Gruppe 1, ein bis drei Wirkstoffe der Gruppe 2 und gegebenenfalls einen Wirkstoff der Gruppe 3.From this group, trifloxysulfuron is also of particular interest as a mixture component. The agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally an active substance from group 3.
Insbesondere enthalten die erfindungsgemäßen Mittel einen Wirkstoff der Gruppe 1, einen oder zwei Wirkstoffe der Gruppe 2 und gegebenenfalls einen Wirkstoff der Gruppe 3.In particular, the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
Es wurde nun überraschend gefunden, dass die oben definierten Wirkstoffkombina- tionen aus den Heteroaryloxy-acetamiden der Formel (I) und den oben angeführtenIt has now surprisingly been found that the active substance combinations defined above from the heteroaryloxyacetamides of the formula (I) and those mentioned above
Wirkstoffen der Gruppe 2 bei weitgehend guter Nutzpflanzen- Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Gerste, Kartoffeln, Mais, Reis, Soja und Weizen zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern verwendet werden können und dass sie auch zur Bekämpfung von monokotylen und dikotylen Unkräutern im semi- und nicht-selektiven Bereich verwendet werden können.Active ingredients of group 2 with a largely good crop tolerance, have a particularly high herbicidal activity and can be used in various crops, in particular in barley, potatoes, corn, rice, soybeans and wheat, for the selective control of monocotyledonous and dicotyledonous weeds and that they can also be used for Control of monocot and dicot weeds in the semi and non-selective range can be used.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirkstoffkombinationen aus Verbindungen der oben aufgeführten Gruppen 1 und 2 er- heblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active compound combinations according to the invention consisting of compounds from groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungsergänzung. Die neuen Wirkstoffkombinationen sind in vielen Kulturen gut verträglich, wobei die neuen Wirkstoffkombinationen auch sonst schwer bekämpf- bare Unkräuter gut bekämpfen. Die neuen Wirkstoffkombinationen stellen somit eine wertvolle Bereicherung der Herbizide dar.There is therefore an unforeseeable synergistic effect and not just an addition. The new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control. The new active ingredient combinations thus represent a valuable addition to the herbicides.
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirk- stoff der Formel (I) 0,01 bis 1000 Gewichtsteile, vorzugsweise 0,02 bis 500 Gewichtsteile und besonders bevorzugt 0,05 bis 100 Gewichtsteile Wirkstoff oder Wirkstoffe der Gruppe 2.The synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active Substance of the formula (I) 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight of active ingredient or active ingredients of group 2.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden besonders hervorgehoben:The following are particularly emphasized as mixture components from the active ingredients of group 3:
5-Chlor-chinolin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet-mexyl),5-chloro-quinoline-8-oxy-acetic acid (l-methyl-hexyl ester) (Cloquintocet-mexyl),
Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl) und Diethyl- l-(2,4-dichlor-phenyl)-4,5-dihydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) zur Verbesserung der Verträglichkeit in Getreide, sowie 4-Dichloracetyl- l-oxa-4-aza-spiro[4.5]-decan (AD-67), l-Dichloracetyl-hexahydro-3,3,8a-trimethyl- pyrrolo[l,2-a]-pyrimidin-6(2H)-on (BAS-145138), 4-Dichloracetyl-3,4-dihydro-3- methyl-2H- 1 ,4-benzoxazin (Benoxacor), 2,2-Dichlor~N,N-di-2-propenyl-acetamid (Dichlormid), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)- acetamid (DKA-24), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furil- azole, MON-13900), 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148) zur Verbesserung der Verträglichkeit in Mais.Ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl) and diethyl-l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole -3,5-dicarboxylate (mefenpyr-diethyl) to improve the tolerance in cereals, as well as 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] -decane (AD-67), l-dichloroacetyl-hexahydro-3 , 3,8a-trimethyl-pyrrolo [1,2-a] -pyrimidin-6 (2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4- benzoxazine (Benoxacor), 2,2-dichloro ~ N, N-di-2-propenyl-acetamide (dichlormid), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) - N- (2-propenyl) acetamide (DKA-24), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazoles, MON-13900), 3-dichloroacetyl-2, 2,5-trimethyl-oxazolidine (R-29148) to improve tolerance in maize.
Als Beispiele für die erfindungsgemäßen Wirkstoffkombinationen - gegebenenfalls auch mit Safenern - seien genannt:The following may be mentioned as examples of the active compound combinations according to the invention - optionally also with safeners:
Flufenacet + Azimsulfuron, Flufenacet + Beflubutamid, Flufenacet + Beflubutamid + Mefenpyr-diethyl, Flufenacet + Beflubutamid + Cloquintocet-mexyl, Flufenacet + Butafenacil-allyl, Flufenacet + Cinidon-ethyl, Flufenacet + Clefoxydim, Flufenacet +Flufenacet + azimsulfuron, Flufenacet + Beflubutamid, Flufenacet + Beflubutamid + Mefenpyr-diethyl, Flufenacet + Beflubutamid + Cloquintocet-mexyl, Flufenacet + Butafenacil-allyl, Flufenacet + Cinidon-ethyl, Flufenacet + Flufenacet + Clefacetim
Diclosulam, Flufenacet + Fenoxaprop-P-ethyl + Mefenpyr-diethyl, Flufenacet + Florasulam, Flufenacet + Florasulam + Mefenpyr-diethyl, Flufenacet + Florasulam + Cloquintocet-mexyl, Flufenacet + Flupyrsulfuron-methyl-sodium, Flufenacet + Flupyrsulfuron-methyl-sodium + Mefenpyr-diethyl, Flufenacet + Flupyrsulfuron-methyl- sodium + Cloquintocet-mexyl, Flufenacet + Foramsulfuron, Flufenacet + Foramsulfü- ron + Mefenpyr-diethyl, Flufenacet + Foramsulfuron + Cloquintocet-mexyl, Flufenacet + Foramsulfuron + Benoxacor, Flufenacet + Foramsulfuron + Dichlormid, Flufenacet + Foramsulfuron + R-29148, Flufenacet + Foramsulfuron + AD-67, Flufenacet + Imazamox, Flufenacet + lodosulfuron-methyl-sodium, Flufenacet + lodosulfuron-methyl-sodium + Mefenpyr-diethyl, Flufenacet + Iodosulf ron-methyl- sodium + Cloquintocet-mexyl, Flufenacet + Isoxachlortole, Flufenacet +Diclosulam, flufenacet + fenoxaprop-P-ethyl + mefenpyr-diethyl, flufenacet + florasulam, flufenacet + florasulam + mefenpyr-diethyl, flufenacet + florasulam + cloquintocet-mexyl, flufenacet + flupyrsulfuron-methyl-sodium-methyl-sodium, fl Mefenpyr-diethyl, Flufenacet + Flupyrsulfuron-methyl- sodium + Cloquintocet-mexyl, Flufenacet + Foramsulfuron, Flufenacet + Foramsulfuron + Mefenpyr-diethyl, Flufenacet + Foramsulfuron + Cloquintocet-mexyl, Flufenacet + Foramsulfuron + Benoxacor, Flufenacet + Foramsulfuron + Dichlormid, Flufenacet + Foramsulfuron + R-29148, Flufenacet + Foramsulfuron + AD-67, Flufenacet + Imazamox, Flufenacet + lodosulfuron-methyl-sodium, Flufenacefen + podsulfuron + diethyl, flufenacet + iodosulfon-methyl-sodium + cloquintocet-mexyl, flufenacet + isoxachlortole, flufenacet +
Mesosulfüron, Flufenacet + Oxaziclomefone, Flufenacet + Procarbazone-sodium, Flufenacet + Procarbazone-sodium + Mefenpyr-diethyl, Flufenacet + Procarbazone- sodium + Cloquintocet-mexyl, Flufenacet + Pyriftalid, Flufenacet + Pyrithiobac- sodium, Flufenacet + Quinclorac, Flufenacet + Trifloxysulfuron.Mesosulfüron, Flufenacet + Oxaziclomefone, Flufenacet + Procarbazone-sodium, Flufenacet + Procarbazone-sodium + Mefenpyr-diethyl, Flufenacet + Procarbazone-sodium + Cloquintocet-mexyl, Flufenacet + Pyriftalid, Flufenacet + Pyrithiacacacififonuronclonefulfonox
Es ist als überraschend anzusehen, dass aus einer Vielzahl von bekannten Safenern oder Antidots, die befähigt sind, die schädigende Wirkung eines Herbizids auf die Kulturpflanzen zu antagonisieren, gerade die oben aufgeführten Verbindungen der Gruppe 3 geeignet sind, die schädigende Wirkung von Wirkstoffen der Formel (I) und deren Salzen, gegebenenfalls auch in Kombination mit einem oder mehreren der oben angeführten Wirkstoffe der Gruppe 2, auf die Kulturpflanzen annähernd vollständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen.It is surprising that from a large number of known safeners or antidots which are capable of antagonizing the harmful effect of a herbicide on the crop plants, the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate also in combination with one or more of the active ingredients of group 2 mentioned above, to be completely removed from the crop plants without impairing the herbicidal activity against the weeds.
Die folgende Wirkstoffe der Gruppe 3 erwiesen sich erfindungsgemäß auch ohneAccording to the invention, the following active ingredients of group 3 also proved to be without
Zusatz eines Wirkstoffes der Gruppe 2 als hervorragend geeignet, die Kulturpflanzenverträglichkeit der Wirkstoffe der Formel (I) zu erhöhen:Addition of an active ingredient of group 2 is outstandingly suitable for increasing the crop plant tolerance of the active ingredients of the formula (I):
1 -Dichloracetyl-hexahy dro-3 ,3 , 8 a-trimethylpyrrolo [ 1 ,2-a] -p yrimidin-6(2H)-on (Di- cyclonon, BAS-145138), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat1 -Dichloroacetyl-hexahy dro-3, 3, 8 a-trimethylpyrrolo [1, 2-a] -p yrimidin-6 (2H) -one (dicyclonone, BAS-145138), ethyl-4,5-dihydro- 5,5-diphenyl-3-isoxazolecarboxylate
(Isoxadifen-ethyl), Diethyl-l-(2,4-dichlorphenyl)-4,5-dihydro-5-methyl-lH-pyrazol- 3,5-dicarboxylat (Mefenpyr-diethyl), 3-Dichloracetyl-2,2-dimethyl-oxazolidin (R- 28725), 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148) und l-(2-Chlor-ρhe- nyl)-5-phenyl-lH-pyrazol-3-carbonsäure-methylester. Der vorteilhafte Effekt der KulturpflanzenverträgHchkeit der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen ebenfalls besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) oder dessen Mischungen mit(Isoxadifen-ethyl), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 3-dichloroacetyl-2,2 -dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and l- (2-chloro-pyrenyl) -5-phenyl-1H-pyrazole-3 carboxylic acid-methylester. The advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I) or mixtures thereof are present
Wirkstoffen der Gruppe 2 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100 Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile Wirkstoff oder Wirkstoffe der Gruppe 3.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 active substance or active substances of group 3.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. UnterAccording to the invention, all plants and parts of plants can be treated. Under
Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Pflanzenteile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowiePlants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and
Wurzeln, Knollen und Rhiozome aufgeführt werden. Zu den Pflanzenteilen gehört auch vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.Roots, tubers and rhiozomes are listed. The plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfmdungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen weiterhin durch ein- oder mehrschichtiges Umhüllen. Unter den durch biotechnologische und gentechnologische Methoden oder durch Kombination dieser Methoden erhaltenen Pflanzen werden solche Pflanzen hervorgehoben, die sog. 4-HPPD-, EPSP- und/oder PPO-He mstoffe tolerieren, wie z.B. Acuron-Pflanzen.The treatment according to the invention of the plants and parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, by - or multi-layer wrapping. Among the plants obtained by biotechnological and genetic engineering methods or by a combination of these methods, those plants are emphasized which tolerate so-called 4-HPPD, EPSP and / or PPO materials, such as, for example, acuron plants.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden:The active compounds according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,
Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Plantaago, Pharb Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,
Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dikotyle Kulturen der Gattungen: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monokotyle Unkräuter der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriocha, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium,
Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monokotyle Kulturen der Gattungen: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea. Die Verwendung der erfindungsgemäßen Wirkstoffkombmationen ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea. However, the use of the active compound combinations according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
Die erfindungsgemäß zu verwendenden Wirkstoffkombinationen können sowohl in konventionellen Anbauverfahren (Reihenkulturen mit geeigneter Reihenweite) in Plantagenkulturen (z.B. Wein, Obst, Zitrus) sowie in Industrie- und Gleisanlagen, auf Wegen und Plätzen, aber auch zur Stoppelbehandlung und beim Minimum-Tillage- Verfahren eingesetzt werden. Sie eignen sich weiterhin als Abbrenner (Krautabtötung z.B. in Kartoffeln) oder als Defoliantien (z.B. in Baumwolle). Ferner sind sind sie für den Einsatz auf Bracheflächen geeignet. Weitere Einsatzgebiete sind Baumschulen, Forst, Grünland und Zierpflanzenbau.The active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and with the minimum tillage process become. They are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing.
Die Wirkstoffkombinationen können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The 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 made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organischeIf water is used as an extender, e.g. also organic
Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaph- thaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzlicheSolvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methyl-isobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage:The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktio- nierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate,e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates,
Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfϊtablaugen und Methylcellulose.Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfate leachate and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexformige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarinv, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarinv, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen, vorzugsweise zwischen 0,5 und 90 %. Die erfindungsgemäßen Wirkstoffkombinationen werden im allgemeinen in Form von Fertigformulierungen zur Anwendung gebracht. Die in den Wirkstoffkombmationen enthaltenen Wirkstoffe können aber auch in Einzelformulierungen bei der An- wendung gemischt, d.h. in Form von Tankmischungen zur Anwendung gebracht werden.The formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%. The active compound combinations according to the invention are generally used in the form of finished formulations. The active substances contained in the active substance combinations can, however, also be mixed in individual formulations when used, that is to say applied in the form of tank mixtures.
Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischimgen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte Anwendungszwecke, insbesondere im Nachauflauf- Verfahren, kann es ferner vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle (z.B. das Handelspräparat "Oleo DuPont 11E") oder Ammoniumsalze wie z.B. Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen.The new combinations of active ingredients, as such or in their formulations, can furthermore also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible. For certain applications, particularly in the post-emergence process, it may also be advantageous to add mineral or vegetable oils which are compatible with plants (e.g. the commercial preparation "Oleo DuPont 11E") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
Die neuen Wirkstoffkombmationen 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 combinations of active substances 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 Wirkstoffkombmationen 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 ingredient 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 appliziertenA herbicide always has a synergistic effect if the herbicidal action of the active ingredient combination is greater than that of the individual agents applied
Wirkstoffe. Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl. COLBY, S.R.: "Calculating synergistic and antago- nistic responses of herbicide combinations", Weeds 15, Seiten 20 - 22, 1967):Agents. The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, SR: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
WennIf
X = % Schädigung durch Herbizid A (Wirkstoff der Formel I) bei p kg/haX =% damage by herbicide A (active ingredient of the formula I) at p kg / ha
Aufwandmengeapplication rate
undand
Y = % Schädigung durch Herbizid B (Wirkstoff der Formel II) bei q kg/haY =% damage by herbicide B (active ingredient of the formula II) at q kg / ha
Aufwandmengeapplication rate
undand
E = die erwartete Schädigung der Herbizide A und B bei p und q kg/haE = expected damage to herbicides A and B at p and q kg / ha
Aufwandmenge,Application rate,
dann ist E = X + Y - (X * Y/100).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.
Die Wirkstoffkombinationen der vorliegenden Erfindung weisen in der Tat dieThe combinations of active ingredients of the present invention indeed have the
Eigenschaft auf, dass ihre gefundene herbizide Wirkung stärker ist als die berechnete, das heißt, dass die neuen Wirkstoffkombinationen synergistisch wirken. Characteristic that their herbicidal activity found is stronger than the calculated one, that is, that the new active ingredient combinations act synergistically.

Claims

Patentansprtiche Patentansprtiche
1. Mittel enthaltend einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus1. Agent containing an effective content of an active ingredient combination consisting of
(a) einem Heteroaryloxy-acetamid der allgemeinen Formel (I)(a) a heteroaryloxyacetamide of the general formula (I)
in welcherin which
Ar für gegebenenfalls durch Halogen, Cχ-C4-Alkyl oder C1-C4- Halogenalkyl substituiertes Phenyl steht,Ar represents phenyl optionally substituted by halogen, Cχ-C4-alkyl or C1-C4-haloalkyl,
Het für Thiadiazolyl steht, welches durch Halogen oder durch jeweils gegebenenfalls durch Halogen substituiertes C1-C4- Alkyl oder Phenyl substituiert ist, undHet is thiadiazolyl which is substituted by halogen or by C1-C4-alkyl or phenyl which is optionally substituted by halogen, and
R für Alkyl, Alkenyl oder Alkinyl mit jeweils bis zu 4 Kohlen- Stoffatomen steht,R represents alkyl, alkenyl or alkynyl each having up to 4 carbon atoms,
("Wirkstoffe der Gruppe 1") und("Active substances of group 1") and
(b) einer oder mehrerer Verbindungen aus einer zweiten Gruppe von Her- biziden, welche die nachstehend genannten Wirkstoffe enthält:(b) one or more compounds from a second group of herbicides which contain the active compounds mentioned below:
1H-1 ,2,4-triazol-3-amin (Amitrole), 2-[2,4-Dichlor-5-(2-propinyloxy)- phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-on (Azafenidin), N-(4,6-Dimethoxy-ρyrimidin-2-yl)-N'-[l-methyl-4-(2- methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfuron), N-B enzyl-2-(4-fluor-3 -trifluormethyl-phenoxy)-butanamid (Beflubutamid), N-Butyl-N-ethyl-2,6-dinitro-4-trifluormethyl-benzen- amin (Benfluralin), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-tri- fluormethyl- 1 (2H)-pyrimidinylphenoxy]methyl]-5-ethyl-phenoxy-pro- pansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl- benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-on (Benzobicyclon), 2-Chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-l(2H)- pyrimidinyl)-benzoesäure-[ 1 , 1 -dimethyl-2-oxo-2-(2-propenyloxy)j- ethylester (Butafenacil-allyl), 2-(l-Ethoximino-propyl)-3-hydroxy-5-1H-1, 2,4-triazol-3-amine (amitrole), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2 , 4-triazolo- [4,3-a] pyridin-3 (2H) -one (azafenidin), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- [l-methyl-4 - (2- methyl-2H-tetrazol-5-yl) -lH-pyrazol-5-ylsulfonyl] urea (azimsulfuron), NB enzyl-2- (4-fluoro-3-trifluoromethylphenoxy) butanamide (beflubutamide), N-butyl -N-ethyl-2,6-dinitro-4-trifluoromethyl-benzene-amine (benfluralin), 2- [2- [4- (3,6-dihydro-3-methyl-2,6-dioxo-4-tri - fluoromethyl-1 (2H) -pyrimidinylphenoxy] methyl] -5-ethyl-phenoxy-propanoic acid methyl ester (benzfendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2 .1] oct-3-en-2-one (benzobicyclone), 2-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) j- ethyl ester (butafenacil-allyl), 2- (l-ethoximino-propyl) -3-hydroxy-5-
[2,4,6-trimethyl-3 -(1 -oxo-butyl)-phenyl] -2-cyclohexen- 1 -on (Butroxy- dim), 2-[l-[(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5- (tetrahydro-2H-pyran-4-yl)-2-cyclohexen-l-on (Caloxydim, Tepral- oxydim), 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-[l-[2,4,6-trimethyl-3 - (1-oxo-butyl) phenyl] -2-cyclohexen-1-one (butroxy-dim), 2- [l - [(3-chloro-2-propenyl) -oxy-imino] -propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-l-one (caloxydim, tepraloxydim), 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 - [l-
[2-(4-Chlor-phenoxy)]-propoxyaminobutyl]-5-(tetrahydro-2H-thio- pyran-3-yl)-l,3-cyclohexandion (Clefoxydim), (E,E)-(+)-2-[l-[[(3- Chlor-2-propenyl)-oxy] -imino] -propyl] -3 -hydroxy-2-cyclohexen- 1 -on (Clethodim), 3-chloro-2-[[(5-ethoxy-7-fluoro[l,2,4]triazolo[l,5-c]py- rimidin-2-yl) sulfonyl]amino]-benzoesäuremethylester (Cloransulam- methyl), 2-(l-Ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopy- ran-3-yl)-2-cyclohexen-l-on (Cycloxydim), N-(2,6-Dichlor-phenyl)-5- ethoxy-7-fluor-[l,2,4]-triazolo-[l,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 2-[ 1 - [(3 , 5 -Difluor-phenyl)-amino-carbonyl-hydrazono] -ethyl] - pyridin-3-carbonsäure (Diflufenzopyr), (S)-2-Chlor-N-(2,4-dimethyl-[2- (4-chlorophenoxy)] - propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) -l, 3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [l - [[(3-chloro-2-propenyl) -oxy] -imino] -propyl] -3 -hydroxy-2-cyclohexen- 1 -one (Clethodim), 3-chloro-2 - [[( 5-ethoxy-7-fluoro [l, 2,4] triazolo [l, 5-c] pyrimidin-2-yl) sulfonyl] amino] -benzoic acid methyl ester (chlorosulam-methyl), 2- (l-ethoximinobutyl) - 3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one (cycloxydim), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro - [l, 2,4] -triazolo- [l, 5-c] -pyrimidine-2-sulfonamide (diclosulam), 2- [1 - [(3, 5-difluorophenyl) -amino-carbonyl-hydrazono] -ethyl] - pyridine-3-carboxylic acid (diflufenzopyr), (S) -2-chloro-N- (2,4-dimethyl-
3 -thienyl)-N-(2-methoxy- 1 -methyl-ethyl)-acetamid (Dimethenamid- P), 2-[2-(3-Chlor-phenyl)-oxiranylmethyl]-2-ethyl-lH-inden-l,3(2H)- dion (Epropodan), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)- phenoxy]-propanoat (Fenoxaprop-P-ethyl), N-(2,6-Difluor-phenyl)-8- fluor-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidm-2-sulfonamid3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamid-P), 2- [2- (3-chlorophenyl) -oxiranylmethyl] -2-ethyl-lH-inden- 1,3 (2H) - dione (epropodan), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop-P-ethyl), N - (2,6-difluorophenyl) -8-fluoro-5-methoxy- [l, 2,4] triazolo- [l, 5-c] pyrimidm-2-sulfonamide
(Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl-oxy)-phenoxy]- propansäure-butylester (Fluazifop-P-butyl), 4,5-Dihydro-3-methoxy- 4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]- 1H- 1 ,2,4- triazol-1-carboxamid-Natriumsalz (Flucarbazone-sodium), Ethyl-[2- chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-l(6H)-pyrid- azinyl)-phenoxy]-acetate (Flufenpyr), 2-[7-Fluor-3,4-dihydro-3-oxo-4-(Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) phenoxy] - butyl propanoate (fluazifop-P-butyl), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] - 1H-1, 2.4 - triazole-1-carboxamide sodium salt (Flucarbazone-sodium), ethyl- [2-chloro-4-fluoro-5- (5-methyl-6-oxo-4-trifluoromethyl-l (6H) -pyrid-azinyl) - phenoxy] acetates (flufenpyr), 2- [7-fluoro-3,4-dihydro-3-oxo-4-
(2-propinyl)-2H-l,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-lH-isoindol- 1,3-dion (Flumioxazin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3- methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff- Natriumsalz (Flupyrsulfuron-methyl-sodium), 2-[[[[(4,6-Dimethoxy- 2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formylamino-(2-propynyl) -2H-l, 4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-lH-isoindole-1,3-dione (flumioxazin), N- (4,6-dimethoxy -pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 2 - [[[(4,6 -Dimethoxy-2-pyrimidinyl) -amino] -carbonyl] -amino] -sulfonyl] -4-formylamino-
N,N-dimethyl-benzamid (Foramsulfuron), (R)-2-[4-(3-Chlor-5-tri- fluormethyl-pyridm-2-yl-oxy)-phenoxy] -propansäure (-methylester, -2-ethoxy-ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 2-[4,5-dihydro-4-methyl-4-(l -methylethyl)-5- oxo-lH-imidazol-2-yl]-5-(methoxymethyl)-3-pyridincarbonsäureN, N-dimethyl-benzamide (foramsulfuron), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridm-2-yl-oxy) phenoxy] propanoic acid (methyl ester, -2 -ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 2- [4,5-dihydro-4-methyl-4- (l -methylethyl) -5-oxo -lH-imidazol-2-yl] -5- (methoxymethyl) -3-pyridinecarboxylic acid
(Imazamox), N-(4-Methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(5-iod-2- methoxycarbonyl-phenylsulfonyl)-hamstoff-Natriumsalz (Iodosul- füronme-thyl-sodium), (4-Chlor-2-methylsulfonyl-phenyl)-(5-cyclo- propyl-isoxazol-4-yl)-methanon (Isoxachlortole), 2-[[[[(4,6-Dimeth- oxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methyl- sulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfüron), 2- (4-Methylsulfonyl-2-nitro-benzoyl)-l,3-cyclohexandion (Mesotrione), 3-[l-(3,5-Dichlor-phenyl)-l-i-propyl]-2,3-dihydro-6-methyl-5-phenyl- 4H- 1 ,3 -oxazin-4-on (Oxaziclomefone), 2-Chlor- 1 -(3 -ethoxy-4-nitro- phenoxy)-4-trifluormethyl-benzen (Oxyfluorfen), 2-(2,2-Difluor- ethoxy)-N-(5 , 8 -dimethoxy [ 1 ,2,4 jtriazolo [ 1 , 5 -c]pyrimidin-2-yl)-6-tri- fluormethyl-benzolsulfonamid (Penoxsulam), 2-Chloro-N-(2-ethoxy- ethyl)-N-(2-methyl- 1 -phenyl- 1 -propenyl)-acetamide (Pethoxamid), 2- [[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)- carbonyl]-amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz(Imazamox), N- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfonate) -thyl-sodium), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), 2 - [[[[(4,6-dimeth- oxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 2- (4-methylsulfonyl-2- nitro-benzoyl) -l, 3-cyclohexanedione (mesotrione), 3- [l- (3,5-dichlorophenyl) -li-propyl] -2,3-dihydro-6-methyl-5-phenyl- 4H- 1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1 - (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), 2- (2,2-difluoro-ethoxy ) -N- (5, 8 -dimethoxy [1, 2,4-jtriazolo [1, 5 -c] pyrimidin-2-yl) -6-trifluoromethyl-benzenesulfonamide (penoxsulam), 2-chloro-N- (2nd -ethoxy-ethyl) -N- (2-methyl-1-phenyl-1-propenyl) -acetamide (pethoxamide), 2- [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy -lH-l, 2,4-triazol-l-yl) carbonyl] amino] sulfonyl] benzoic acid methyl lester sodium salt
(Procarbazone-sodium), l-Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)-6- fluor-te rahydro- 1 ,3-dioxo- lH-pyrrolo [ 1 ,2-c]imidazol-2(3H)-yl]- phenyl]-methansulfonamid (Profluazol), (R)-[2-[[(l-Methyl-ethyli- den)-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), l-(3-Chlor-(Procarbazone-sodium), l-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6- fluor-te rahydro-1, 3-dioxo-lH-pyrrolo [1, 2-c] imidazole-2 (3H) -yl] - phenyl] methanesulfonamide (profluazole), (R) - [2 - [[(l -Methyl-ethyli- den) -amino] -oxy] -ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) -phenoxy] - propanoate (propaquizafop), 2-chloro-N- (2-ethyl -6-methyl-phenyl) -N- [(l-methyl-ethoxy) -methyl] -acetamide (propisochlor), l- (3-chloro-
4,5,6,7-tetrahydropyrazolo[l,5-a]pyridin-2-yl)-5-(methyl-2-propinyl- amino)-lH-pyrazol-4-carbonitril (Pyraclonil), Ethyl [2-Chloro-5-(4- chloro-5 -difluoromethoxy- 1 -methyl- 1 H-pyrazol-3 -yl)-4-fluoro- phenoxyj-acetate (Pyraflufen-ethyl), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl-l(3H)- isobenzofuranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)- benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-di- methoxy-pyrimidin-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobac- sodium), 3,7-Dichlor-chinolin-8-carbonsäure (Quinchlorac), (R)-2-[4- (6-Chlor-2-chinoxalinyloxy)-phenoxy] -propansäure (-ethylester,4,5,6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -lH-pyrazole-4-carbonitrile (pyraclonil), ethyl [2- Chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1 H-pyrazol-3-yl) -4-fluorophenoxyj-acetate (Pyraflufen-ethyl), 6-chloro-3-phenyl-pyridazine- 4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-l (3H) - isobenzofuranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidine) 2-yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxypyrimidin-2-ylthio) -benzoic acid sodium salt (pyrithiobac-sodium), 3.7 -Dichloro-quinoline-8-carboxylic acid (quinchlorac), (R) -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester,
-tetrahydro-2-füranyl-methylester) (Quizalofop-P-ethyl, -P-tefuryl), 2- Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-tri- fluormethyl-pyridin-3-carbonsäure-methylester (Thiazopyr), (3,5,6- Trichlor)-pyridin-2-yl-oxy-essigsäure (Triclopyr), N-[[(4,6-Di- methoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluor-ethoxy)-2- pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), N-[4-Dimethyl- amino-6-(2,2,2-trifluor-ethoxy)-l,3,5-triazin-2-yl]-N'-(2-methoxy- carbonyl-phenylsulfonyl)-harnstoff (Triflusulfuron-methyl), N-[[(4,6- Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methyl- sulfonyl-amino])-2-pyridinsulfonamid (vgl. WO-A-92/10660),-tetrahydro-2-foranyl-methyl ester) (Quizalofop-P-ethyl, -P-tefuryl), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl ) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), (3,5,6-trichloro) -pyridin-2-yl-oxyacetic acid (triclopyr), N - [[(4,6 -Dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -l, 3,5-triazin-2-yl] -N '- (2-methoxycarbonylphenylsulfonyl) urea (triflusulfuron-methyl), N - [[( 4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino]) - 2-pyridinesulfonamide (cf. WO-A-92/10660),
("Wirkstoffe der Gruppe 2")("Active substances of group 2")
sowie gegebenenfalls zusätzlich (c) einer die Kulturpflanzen- Verträglichkeit verbessernde Verbindung aus der folgenden Gruppe von Verbindungen:and, if necessary, additionally (c) a crop-tolerance-improving compound from the following group of compounds:
4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1-Dichlor- acetyl-hexahydro-3 ,3 , 8a-trimethylpyrrolo [ 1 ,2-a]-pyrimidm-6(2H)-on4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexahydro-3, 3, 8a-trimethylpyrrolo [1, 2-a] pyrimidm-6 (2H) -one
(Dicyclonon, BAS-145138), 4-Dichloracetyl-3,4-dihydro-3-methyl- 2H-l,4-benzoxazin (Benoxacor), 5-Chlor-chinolin-8-oxy-essigsäure- ( 1 -methyl-hexylester) (Cloquintocet-mexyl), α-(Cy anomethoximino)- phenylacetonitril (Cyometrinil), 2,2-Dichlor-N-(2-oxo-2-(2-propenyl- amino)-ethyl)-N-(2-propenyl)-acetamid (DKA-24), 2,2-Dichlor-N,N- di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-(l- methyl-l-phenyl-ethyl)-harnstoff (Dymron), 4,6-Dichlor-2-phenyl- pyrimidin (Fenclorim), l-(2,4-Dichlor-phenyl)-5-trichlormethyl-lH- 1 ,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4- trifluormethyl-thiazol-5-carbonsäure-phenylmethylester (Flurazole),(Dicyclonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 5-chloro-quinoline-8-oxyacetic acid- (1-methyl- hexyl ester) (cloquintocet-mexyl), α- (cy anomethoximino) - phenylacetonitrile (cyometrinil), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2 -propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N- di-2-propenyl-acetamide (dichloromide), N- (4-methylphenyl) -N '- (l-methyl- l-phenyl-ethyl) urea (Dymron), 4,6-dichloro-2-phenyl-pyrimidine (Fenclorim), l- (2,4-dichloro-phenyl) -5-trichloromethyl-1H-1, 2.4 -triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid-phenylmethyl ester (flurazole),
4-Chlor-N-( 1 ,3 -dioxolan-2-yl-methoxy)-α-trifluor-acetophenonoxim (Fluxofenim), 3-Dichloracetyl-5-(2-füranyl)-2,2-dimethyl-oxazolidin (Furilazole, MON- 13900), Ethyl-4,5-dihydro-5,5-diρhenyl-3-isoxazol- carboxylat (Isoxadifen-ethyl), Diethyl-l-(2,4-dichlorphenyl)-4,5-di- hydro-5-methyl-lH-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl), 2-4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole , MON-13900), ethyl 4,5-dihydro-5,5-diρhenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro -5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-
Dichlormethyl-2-methyl-l,3-dioxolan (MG-191), 1,8-Naphthalsäure- anhydrid, α-(l,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxa- betrinil), 2,2-Dichlor-N-(l,3-dioxolan-2-yl-methyl)-N-(2-propenyl)- acetamid (PPG- 1292), 3-Dichloracetyl-2,2-dimethyl-oxazolidin (R- 28725), 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148), l-(2-Dichloromethyl-2-methyl-l, 3-dioxolane (MG-191), 1,8-naphthalic anhydride, α- (l, 3-dioxolan-2-yl-methoximino) -phenylacetonitrile (oxa- betrinil), 2, 2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725 ), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), l- (2-
Chlor-phenyl)-5-phenyl-lH-pyrazol-3-carbonsäure-methylester und N-(2-Methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzol- sulfonamidChlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester and N- (2-methoxy-benzoyl) -4 - [(methylamino-carbonyl) -amino] -benzenesulfonamide
("Wirkstoffe der Gruppe 3"). ("Active substances of group 3").
2. Mittel nach Anspruch 1, dadurch gekennzeichnet, dass in der Formel (I)2. Composition according to claim 1, characterized in that in the formula (I)
Ar für gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl oder Tri- fluormethyl substituiertes Phenyl steht,Ar represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl,
Het für 1,2,4-Thiadiazolyl oder 1,3,4-Thiadiazolyl steht, welches durch Fluor, Chlor, Brom oder durch jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl oder Phenyl substituiert ist, undHet stands for 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by fluorine, chlorine, bromine or by methyl, ethyl, n- or i-propyl or phenyl which are optionally substituted by fluorine and / or chlorine is and
R für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, 2-Propenyl, l-Methyl-2-propenyl, 2-Butenyl, 2-Propinyl, l-Methyl-2-propinyl, 2- Butinyl steht.R is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-propynyl, l-methyl- 2-propynyl, 2-butynyl.
3. Mittel nach Anspruch 1, dadurch gekennzeichnet, dass das Heteroaryloxy- acetamid der allgemeinen Formel (I) die Verbindung N-i-Propyl-N-(4-fluor- phenyl)-α-(5-trifluormethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet) ist.3. Composition according to claim 1, characterized in that the heteroaryloxyacetamide of the general formula (I) the compound Ni-propyl-N- (4-fluorophenyl) -α- (5-trifluoromethyl-l, 3,4- thiadiazol-2-yl-oxy) -acetamide (Flufenacet).
4. Mittel nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass die4. Composition according to one of claims 1 to 3, characterized in that the
Verbindungen aus der zweiten Gruppe von Herbiziden (Komponente (b)) aus den nachstehend genannten Wirkstoffe ausgewählt sind:Compounds from the second group of herbicides (component (b)) are selected from the active substances mentioned below:
Azimsulfuron, Beflubutamid, Butafenacil-allyl, Cinidon-ethyl, Clefoxydim, Cloransulam-methyl, Diclosulam, Fenoxaprop-P-ethyl, Florasulam, Flupyrsulfuron-methyl-sodium, Foramsulfuron, Imazamox, lodosulfuron-methyl- sodium, Isoxachlortole, Mesosulfüron, Oxaziclomefone, Procarbazone- sodium, Pyriftalid, Pyrithiobac-sodium, Quinclorac, Trifloxysulfuron. Azimsulfuron, beflubutamide, butafenacil-allyl, cinidon-ethyl, clefoxydim, cloransulam-methyl, diclosulam, fenoxaprop-P-ethyl, florasulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, iodosulfuron-methyl-sodium, mesazachlurl, mesoxachlone, mesoxachl Procarbazone-sodium, pyriftalid, pyrithiobac-sodium, quinclorac, trifloxysulfuron.
5. Mittel nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass die die Kxilturpflanzen- Verträglichkeit verbessernden Verbindungen (Komponente (c)) aus den nachstehend genannten Wirkstoffen ausgewählt sind:5. Composition according to one of claims 1 to 4, characterized in that the compounds which improve the compatibility with plants (component (c)) are selected from the active ingredients mentioned below:
5-Chlor-chinolin-8-oxy-essigsäure-(l-methyl-hexylester) (Cloquintocet- mexyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen- ethyl) und Diethyl-l-(2,4-dichlor-phenyl)-4,5-dihydro-5-methyl-lH-pyrazol- 3,5-dicarboxylat (Mefenpyr-diethyl) zu Verbesserung der Verträglichkeit in Getreide, sowie 4-Dichloracetyl-l-oxa-4-aza-spiro[4.5]-decan (AD-67), 1-Di- chloracetyl-hexahydro-3,3,8a-trimethylpyrrolo[l ,2-a]-pyrimidin-6(2H)-on5-chloro-quinoline-8-oxyacetic acid (l-methyl-hexyl ester) (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl) and diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) to improve the tolerance in cereals, and 4-dichloroacetyl-l- oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one
(BAS-145138), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin (Benoxacor), 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid), 2,2- Dichlor-N-(2-oxo-2-(2-ρropenylamino)-ethyl)-N-(2-propenyl)-acetamid (DKA-24), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Puril- azole, MON-13900), 3-Dichloracetyl-2,2,5-trimethyl-oxazolidin (R-29148).(BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide ), 2,2-dichloro-N- (2-oxo-2- (2-ρropenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 3-dichloroacetyl-5- (2- furanyl) -2,2-dimethyl-oxazolidine (Purilazole, MON-13900), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148).
6. Mittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass auf einen Gewichtsteil Wirkstoff der Formel (I) 0,01 bis 1000 Gewichtsteile des Wirkstoffs oder der Wirkstoffe aus der zweiten Gruppe von Herbiziden (Komponente (b)) entfallen.6. Composition according to one of claims 1 to 5, characterized in that 0.01 to 1000 parts by weight of the active ingredient or active ingredients from the second group of herbicides (component (b)) are present per part by weight of active ingredient of the formula (I).
7. Mittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass auf einen Gewichtsteil Wirkstoff der Formel (I) oder dessen Mischungen mit Wirkstoffen aus der zweiten Gruppe von Herbiziden (Komponente (b)) 0,001 bis 1000 Gewichtsteile des die die Kulturpflanzen- Verträglichkeit verbessernden Wirkstoffs oder der die Kulturpflanzen-Verträglichkeit verbessernden Wirkstoffe (Komponente (c)) entfallen.7. Composition according to one of claims 1 to 5, characterized in that 0.001 to 1000 parts by weight of the the crop plants- to one part by weight of active compound of the formula (I) or mixtures thereof with active compounds from the second group of herbicides (component (b)). Compatibility-improving active ingredient or the crop plant tolerance-enhancing active ingredients (component (c)) are eliminated.
8. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 7 zur Be- kämpfung von unerwünschten Pflanzen. 8. Use of an agent according to one of claims 1 to 7 for controlling unwanted plants.
. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekennzeichnet, dass man Mittel gemäß einem der Ansprüche 1 bis 7 auf die unerwünschten Pflanzen und/oder ihren Lebensraum einwirken lässt., Process 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.
10. 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. 10. A process for the preparation of a herbicidal composition, characterized in that a composition according to one of claims 1 to 7 is mixed with surface-active agents and / or extenders.
EP01943335A 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides Withdrawn EP1298996A1 (en)

Priority Applications (12)

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EP10158929A EP2243368A3 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158915.8A EP2243362B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158918A EP2243365A3 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158933A EP2243370A2 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
DK05005219.0T DK1552746T3 (en) 2000-05-22 2001-05-09 Selective herbicides based on heteroaryloxy-acetamides
EP10158925A EP2243367A3 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158917.4A EP2243364B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158932A EP2243369A3 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158913.3A EP2243361B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158924A EP2243366A3 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158916.6A EP2243363B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP05005219.0A EP1552746B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides

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DE10041619A DE10041619A1 (en) 2000-05-22 2000-08-24 Selective herbicides based on heteroaryloxyacetamides
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EP10158917.4A Division EP2243364B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
EP10158915.8A Division EP2243362B1 (en) 2000-05-22 2001-05-09 Selective heteroaryloxy-acetamide-based herbicides
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