WO2015086605A1 - Agents herbicides contenant du flufénacet, du picolinafen et de la métribuzine - Google Patents

Agents herbicides contenant du flufénacet, du picolinafen et de la métribuzine Download PDF

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Publication number
WO2015086605A1
WO2015086605A1 PCT/EP2014/077065 EP2014077065W WO2015086605A1 WO 2015086605 A1 WO2015086605 A1 WO 2015086605A1 EP 2014077065 W EP2014077065 W EP 2014077065W WO 2015086605 A1 WO2015086605 A1 WO 2015086605A1
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Prior art keywords
plants
herbicidal
component
components
crops
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PCT/EP2014/077065
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German (de)
English (en)
Inventor
Thomas Wilde
Thomas Auler
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Bayer Cropscience Ag
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Priority to EP14809400.6A priority Critical patent/EP3079471A1/fr
Publication of WO2015086605A1 publication Critical patent/WO2015086605A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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 is in the technical field of pesticides which are useful against harmful plants e.g. can be used in crops and contain as active ingredients in the herbicidal compositions a combination of Flufenacet and several other herbicides.
  • the herbicidal active ingredient Flufenacet belongs to the group of heteroaryloxy-acetamides and is characterized by a broad
  • planted agricultural or horticultural crops and non-crops e.g., cereals such as wheat, barley, rye, oats, triticale, rice, corn, millet, sugarbeet, sugarcane, rapeseed,
  • Flufenacet is commercially available, for example, under the trade names Cadou®, Drago®, Define® and Tiara®.
  • Cadou® As an individual active ingredient, Flufenacet is commercially available, for example, under the trade names Cadou®, Drago®, Define® and Tiara®.
  • Cadou® As an individual active ingredient, Flufenacet is commercially available, for example, under the trade names Cadou®, Drago®, Define® and Tiara®.
  • Weed populations contain biotypes with a site-specific resistance, i. by natural mutations in the gene sequence, the binding site changes at the site of action, so that the drugs can no longer or insufficiently bind and act accordingly) and 'Enhanced Metabolism Resistance' (abbreviation: EMR, whereby the weed populations contain biotypes with a metabolic resistance, ie the plants possess the ability of enzyme complexes
  • One way to improve the application profile of a herbicide may be to combine the active ingredient with one or more other suitable agents.
  • phenomena of chemical, physical and chemical phenomena often occur in the combined use of several active substances
  • Production techniques can be used. This includes, for example, a reduction in the sowing depth, which can often not be used for reasons of cultural compatibility. This generally achieves a faster casserole of the crop, reduces its risk of casserole diseases (such as Pythium and Rhizoctonia), improves overwintering ability and the degree of tillering. This also applies to late-seed, which would otherwise not be possible due to the risk of cultural compatibility.
  • casserole diseases such as Pythium and Rhizoctonia
  • the object of the present invention was to improve the
  • Soils with different soil properties e.g.
  • This object has been achieved by providing herbicidal compositions containing flufenacet and the other herbicides picolinafen and metribuzin.
  • herbicidal compositions comprising:
  • herbicidally active ingredients component A, B and C are hereinafter referred to collectively as "(single) agents", “(single) herbicides” or as “herbicidal components” and are used as individual substances or as a mixture e.g. known from "The Pesticide Manual", 15th edition (s.o.) and have the following
  • Component A Flufenacet (PM # 392), syn. thiafluamide, e.g. N- (4-fluorophenyl) -N- (1-methylethyl) -2 - [[5- (trifluoromethyl) -1, 3,4-thiadiazol-2-yl] oxy] acetamide;
  • Component B Picolinafen (PM # 685), e.g. N- (4-fluorophenyl) -6- [3- (trifluoromethyl) phenoxy] -2-pyridinecarboxamide;
  • Component C metribuzin (PM # 593), eg 4-amino-6- (1,1-dimethylethyl) -3- (methylthio) -1,2,4-triazine-5 (4H) -one. If the abbreviated form of the "common name" of an active substance is used in the context of this description, then all current derivatives, such as the esters and salts, and isomers, in particular optical isomers, if applicable, are used, in particular the commercial form or forms , Will with the
  • “Common name” denotes an ester or salt, so are all other common derivatives such as other esters and salts, the free acids and neutral compounds, and isomers, in particular optical isomers, in particular the commercial form or forms.
  • the chemical link names given refer to at least one of the "common name” compounds, often a preferred compound.
  • Component based on the total weight of the herbicidal agent (e.g., as a formulation).
  • the herbicidal compositions according to the invention have a herbicidally active content of the components A, B and C and may contain further constituents, e.g. agrochemical active substances from the group of insecticides, fungicides and safeners and / or additives customary in crop protection and / or
  • Formulation aids or used together with these.
  • the herbicidal compositions according to the invention contain the abovementioned components as the only herbicidally active constituents.
  • the herbicidal compositions according to the invention have synergistic effects as an improvement of the application profile. These synergistic effects can be observed, for example, when the herbicidal components are applied together, but they can often also be detected in the case of splitting. It is also possible Application of the individual herbicides or herbicide combinations in several portions (sequence application), eg pre-emergence applications, followed by postemergence applications or early postemergence applications, followed by
  • the synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency at the same rate, the control of previously unrecognized species (gaps), an extension of the
  • the application rate of the herbicidal components and their derivatives in the herbicidal composition can vary within wide limits. In applications with application rates of 21 to 5500 g AS / ha of herbicide components is in the pre and
  • Postemergence control a relatively wide range of annual and perennial weeds, grass weeds and Cyperaceae.
  • the application rates of the herbicidal components are in the herbicidal composition in the following weight ratio to each other:
  • the application rates of the respective herbicidal components in the herbicidal composition are:
  • Component A generally 10 to 2000 g AS / ha, preferably 30 to 400 g AS / ha, more preferably 50 to 300 g AS / ha flufenacet;
  • Component B generally 1 to 500 g AS / ha, preferably 10 to 300 g
  • AS / ha more preferably 30-200 g AS / ha picolinafen
  • Component C generally 10 to 3000 g AS / ha, preferably 30 to 400 g AS / ha, more preferably 50 to 300 g AS / ha metribuzin.
  • Total weight of herbicidal agents are calculated, which may additionally contain other ingredients.
  • the herbicidal compositions of the present invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds, such as weeds, grass weeds or cyperaceans, including species resistant to herbicidal active compounds, e.g.
  • the substances may be e.g. be applied in pre-sowing, pre-emergence or post-emergence, e.g. together or separately.
  • Called weed flora which can be controlled by the herbicidal compositions according to the invention, without being limited by naming a restriction to certain species.
  • Echinochloa spp. Leptochloa spp., Fimbristylis spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and Cyperus species from the contendle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusart well.
  • the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp. , Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. Eclipta spp., Sesbania spp., Aeschynomene spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds.
  • Plant parts postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the stage of growth existing at the time of application or die completely after a period of time, so that eliminated in this way harmful to crops weed competition very early and sustainable becomes.
  • herbicidal compositions according to the invention can also be applied in rice in the water and are then taken up via soil, shoot and root.
  • the herbicidal compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • the rainfastness of the active ingredients in the compositions according to the invention is generally favorable.
  • a particular advantage is the fact that the effective and used in the compositions of the invention dosages of components A, B and C can be set so low that their soil effect is optimally low.
  • herbicidal compositions according to the invention are significantly exceeded in terms of the properties described.
  • the herbicidal compositions according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.
  • the agents according to the invention can be partially
  • compositions of the invention can also be used to control harmful plants in known crops or to be developed tolerant or genetically engineered culture and
  • GMOs transgenic plants
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides (such as resistance to components A, B and C in the
  • Harmful insects, plant diseases or pathogens of plant diseases such as certain microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality,
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop or increased vitamin content or energy properties are known. More special
  • Properties may be in tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
  • abiotic stressors e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
  • the agents according to the invention can also be used for combating harmful plants in cultures of known or yet to be developed by mutant selection
  • Plants are used, and from crosses of mutagenic and transgenic plants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044 A, EP 0131624 A). In several cases, for example, genetic engineering was described
  • Gene stacking are resistant, such as transgenic crops such as corn or soybean with the trade name or the name Optimum TM GAT TM (Glyphosate ALS Tolerant); transgenic
  • Crops for example cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) that target the plants
  • Crop plants with modified fatty acid composition (WO 91/013972 A); genetically engineered crops with new content or secondary substances, e.g. new phytoalexins which cause increased disease resistance (EP 0309862 A, EP 0464461 A); genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398 A); transgenic crops that produce pharmaceutically or diagnostically important proteins ("molecular pharming"), transgenic crops characterized by higher yields or better quality, transgenic crops
  • Crop plants which are characterized by a combination e.g. the o.g. characterize new properties ("gene stacking").
  • nucleic acid molecules can be introduced into plasmids containing a
  • Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. Also possible is the use of DNA sequences that have a high degree of homology to the coding
  • the synthesized protein may be located in any compartment of the plant cell.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those of skill in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available that changed
  • the present invention also provides a process for
  • crops such as cereals (e.g., hard and soft wheat, barley, rye, oats, crosses thereof such as triticale, planted or sown rice under 'upland' or 'paddy' conditions, corn, millet such as
  • Sorghum sugar beet, cane, canola, cotton, sunflower, soya,
  • Potato tomatoes, beans such as bush bean and horse bean,
  • Crosses thereof such as triticale, rice, maize and millet, and dicotyledonous crops such as sunflower, soybean, potato, tomato, pea, carrot and fennel, wherein components A, B and C of the herbicidal compositions of the invention are taken together or separately, e.g. in pre-emergence (very early to late), post-emergence or pre-emergence, on the plants, e.g. Harmful plants, plant parts, plant seeds or the area on which the plants grow, e.g. applied the acreage.
  • the invention also provides the use of the herbicidal compositions according to the invention comprising the components A, B and C for controlling harmful plants, preferably in plant crops, preferably in the abovementioned plant crops. Furthermore, the invention also relates to the use of the herbicidal compositions according to the invention comprising components A, B and C for controlling herbicidally-resistant harmful plants (eg TSR and EMR resistance in ALS and ACCase), preferably in plant crops, preferably in the abovementioned crops. The invention also provides the process with the herbicidal compositions according to the invention comprising the components A, B and C for the selective
  • the invention also provides the method for controlling
  • Mutation selection were obtained, and which against growth substances, such. 2,4 D, dicamba or against herbicides containing essential plant enzymes, e.g.
  • Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit, respectively against herbicides from the group of sulfonylureas, glyphosate, glufosinate or
  • Benzoylisoxazole and analogues, or against any combination of these agents, are resistant.
  • the benzoylisoxazole and analogues, or against any combination of these agents are resistant.
  • the benzoylisoxazole and analogues, or against any combination of these agents are resistant.
  • the benzoylisoxazole and analogues, or against any combination of these agents are resistant.
  • Herbicidal agents according to the invention are used in transgenic crops which are resistant to a combination of glyphosates and glufosinates,
  • Glyphosaten and sulfonylureas or imidazolinones are resistant. Most preferably, the herbicidal compositions of the invention in transgenic crops such. B. corn or soybean with the trade name or the
  • the invention also provides the use of the herbicidal compositions according to the invention comprising the components A, B and C for controlling harmful plants, preferably in plant crops, preferably in the abovementioned plant crops.
  • the herbicidal compositions of the invention may also be non-selective to
  • Plantation crops on roadsides, squares, industrial plants or Rail installations; or selectively used to control undesired plant growth in crops for energy production (biogas, bio-ethanol).
  • the herbicidal compositions according to the invention can be present both as mixed formulations of components A, B and C and optionally with further agrochemical active ingredients, additives and / or customary formulation auxiliaries which are then diluted with water in the customary manner, or as so-called tank mixtures by joint dilution the separately formulated or partially separately formulated components are prepared with water. Under certain circumstances, the mixed formulations with others
  • Liquids or solids diluted or used undiluted Liquids or solids diluted or used undiluted.
  • the components A, B and C or their sub-combinations can be formulated in various ways, depending on which biological and / or chemical-physical parameters are given. As a general
  • Formulation options are, for example: wettable powders (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions , Suspension concentrates (SC),
  • WP wettable powders
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsions
  • SC Suspension concentrates
  • Dispersions oil dispersions (OD), suspoemulsions (SE), dusts (DP), mordants, granules for soil or litter application (GR) or
  • Microcapsule or wax dispersions are known in principle and will be
  • the necessary formulation auxiliaries such as inert materials, surfactants,
  • Solvents and other additives are also known and are for example, Watkins, “Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; Hv Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, NY Marsden, “Solvents Guide”, 2nd Ed., Interscience, NY 1950; McCutcheon's, “Detergents and Emulsifiers Annual", MC Publ. Corp., Ridegewood NJ; Sisley and Wood, “Encyclopedia of Surface Active Agents", Chem. Publ. Co.
  • Preparations which, in addition to the active substances other than one or more diluents or inert substances, also contain ionic and / or nonionic surfactants (wetting agents, dispersants), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, propylene oxide-ethylene oxide copolymers, alkanesulfonates or alkylbenzenesulfonates or alkylnaphthalenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalene-sodium sulfonate or sodium oleoylmethyltaurine.
  • ionic and / or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines,
  • Emulsifiable concentrates are made by dissolving the active ingredients in one
  • organic solvent or solvent mixture e.g. Butanol, Cydohexanon, dimethylformamide, acetophenone, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic and / or nonionic surfactants (emulsifiers) produced.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters,
  • Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates are water-based suspensions of active ingredients. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of further surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • surfactants as described, for example, in US Pat. are already listed above for the other formulation types.
  • Oil dispersions are oil-based suspensions of active ingredients, where by oil is meant any organic liquid, e.g. As vegetable oils, aromatic or aliphatic solvents, or fatty acid alkyl esters. They can be prepared, for example, by wet milling using commercially available bead mills and, if appropriate, addition of further surfactants (wetting agents, dispersants), as described, for example, in US Pat. are already listed above for the other formulation types. In addition to the suspended drug or agents, other drugs in the
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers from mixtures of water and water-immiscible organic solvents and optionally other surfactants, as described e.g. listed above for the other formulation types.
  • the active ingredients are present in dissolved form.
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinite, chalk or granulated inert material. Also suitable active ingredients in the usual way for the production of fertilizer granules - if desired in mixture with fertilizers - be granulated.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • Percent by weight, in particular from 2 to 95% by weight, of active substances of the herbicidal components Percent by weight, in particular from 2 to 95% by weight, of active substances of the herbicidal components, the following concentrations being customary depending on the type of formulation:
  • the active compound concentration is e.g. about 10 to 95 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the drug concentration may be e.g. 5 to 80 wt .-%, amount.
  • Dusty formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 0.2 to 25 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers,
  • Evaporation inhibitors and agents that affect the pH or viscosity are Evaporation inhibitors and agents that affect the pH or viscosity.
  • the herbicidal action of the herbicidal combinations according to the invention can be improved, for example, by surface-active substances, for example by Wetting agent from the series of fatty alcohol polyglycol ethers.
  • the fatty alcohol polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part.
  • the fatty alcohol polyglycol ethers may be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates or phosphates, which are used, for example, as alkali salts (eg sodium and potassium salts) or ammonium salts, or else as alkaline earth salts such as magnesium salts, such as C 12 / Ci-4 fatty alcohol diglykolethersulfat- sodium (Genapol ® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988).
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2 to 20, preferably 3 to 15,
  • Ethylene oxide-containing (C10- Cis) -, preferably (Cio-Ci 4) -Fettalkohol- polyglycol ethers for example isotridecyl alcohol polyglycol ether
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X-060, Genapol ® X -080 or Genapol ® X-150 (all from Clariant GmbH).
  • the present invention further comprises the combination of components A, B and C with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (For example, as fatty alcohol polyglycol ether) may be present.
  • fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (For example, as fatty alcohol polyglycol ether) may be present.
  • Ci 2 / Ci fatty alcohol diglycol ether Nathum (Genapol ® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3-15 ethylene oxide units, for example from the Genapol ® X series, such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 and Genapol ® X-150 (all from Clariant GmbH).
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 and Genapol ® X-150 (all from Clariant GmbH).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol Polyglykolethersulfate) as a penetration aid and
  • herbicides from the series of imidazolinones are also suitable for a number of other herbicides, including herbicides from the series of imidazolinones (see, for example, EP-A-0502014).
  • the herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils.
  • vegetable oils under the term
  • Vegetable oils are oils from oil-supplying plant species such as soybean oil, rapeseed oil, Corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, especially rapeseed understood, and their
  • Transesterification products e.g. Alkyl esters such as rapeseed oil methyl ester or Rapsolethylester.
  • the vegetable oils are preferably esters of C10-C22, preferably C12-C20
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 -fatty acids, in particular having an even number of carbon atoms, e.g. Erucic acid, lauric acid, palmitic acid and especially cis fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cio-C22 fatty acid esters are esters obtained by reacting glycerol or glycol with the C 10 -C 22 fatty acids, as described e.g. in oils derived from oil-producing plant species or C 1 -C 20 -alkyl-C 10 -C 22 -fatty acid esters, as described, for example, in US Pat. by transesterification of the abovementioned glycerol or glycol-C 10 -C 22 -fatty acid esters with C 1 -C 20 -alcohols (for example methanol, ethanol, propanol or .alpha
  • Butanol can be obtained.
  • the transesterification can be carried out by known methods, such as e.g. are described in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • Preferred C 1 -C 20 -alkyl-C 10 -C 22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters.
  • Glycerol-Cio-C22-fatty acid esters preferred are the uniform or mixed glycol esters and glycerol esters of Cio-C22 fatty acids, especially those
  • carbon fatty acids e.g. Erucic acid, lauric acid, palmitic acid and in particular cis-fatty acids such as stearic acid, oleic acid,
  • Linoleic acid or linolenic acid Linoleic acid or linolenic acid.
  • the vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: Rapsolethylester) Actirob ® B
  • ActirobB (Novance, France, hereinafter referred to ActirobB, main component:
  • Rapsölmethylester Rapsölmethylester
  • Rako-Binol ® (Bayer AG, Germany, referred to as Rako-Binol called rapeseed oil)
  • Renol ® Stefes, Germany, hereinbelow referred to as Renol, vegetable oil constituent: called, main constituent Rapsölmethylester
  • Stefes Mero ® Stefes, Germany, hereinbelow referred to Mero, main constituent:
  • Rapeseed oil methyl ester may be included.
  • Vegetable oils such as rapeseed oil, preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ®, ® Actirob B, Rako-Binol ®, Renol ® or Stefes Mero ®.
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-form preparations, soil or spreading granulates, as well as sprayable formulations are usually no longer diluted with further inert substances before use.
  • the active substances can be applied to the plants, plant parts, plant seeds or the acreage (field soil), preferably to the green plants and plant parts and optionally additionally to the field soil.
  • One possibility of application is the joint application of the active ingredients in the form of tank mixes, with the optimally formulated concentrated
  • Formulations of the individual active ingredients are mixed together in the tank with water and the resulting spray mixture is discharged.
  • a common herbicidal formulation of the herbicidal compositions according to the invention with the components A, B and C has the advantage of easier applicability, because the amounts of the components are already set in the correct ratio to each other.
  • the adjuvants in the formulation can be optimally matched to one another.
  • a dust is obtained by adding 10 parts by weight of a
  • a wettable powder easily dispersible in water is obtained by adding 25 parts by weight of an active ingredient mixture, 64 parts by weight of kaolin clay as an inert, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurine as a mesh and dispersing agent and grinding in a pin mill.
  • An easily water-dispersible suspension concentrate is obtained by adding 20 parts by weight of an active substance / active substance mixture with 5 parts by weight of tristyrylphenol polyglycol ether (Soprophor BSU), 1 part by weight
  • Lignosulfonate sodium (Vanisperse CB) and 74 parts by weight of water mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An easily dispersible in water oil dispersion is obtained by adding 20 parts by weight of an active ingredient / active ingredient mixture with 6 parts by weight
  • Isotridecanolpolyglykolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277 ° C) and mixed in a
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • Active ingredient / active substance mixture 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • f) A water-dispersible granules are obtained by
  • a water-dispersible granules are also obtained by
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were placed on a laboratory sprayer with spray liquors containing the
  • inventive compositions mixtures of the prior art or treated with the individually applied components.
  • the amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were placed back in the greenhouses.
  • Pre-emergence weed effect seeds of different weeds and weeds
  • Biotypes (origins) were found in one with natural soil
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were treated at BBCH stage 00-10 of the seeds / plants on a laboratory spray track with spray mixtures with the agents according to the invention, mixtures or with the individually used components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed.
  • the pots were then placed in a greenhouse (12-16h light, Temperature day 20-22 ° C, night 15-18 ° C) until the application time.
  • the pots were placed at different BBCH stages between 1 1 -25 of the seeds / plants, ie usually between two to three weeks after the beginning of the culture on a laboratory spray lane with spray liquors
  • Pre-emergence weed action with and without drug incorporation Seeds of different weeds and weed Biotypes (origins) were seeded in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt, non-sterile). The pots with seeds were compared either at BBCH stage 00-10 of the seeds / plants, i. usually between two to three weeks after starting to grow, on one
  • Treated mixtures or with the individually applied components as WG, WP, EC or other formulations, or an equivalent amount of the inventive compositions, mixtures or individually applied components as WG, WP, EC or other formulations were incorporated into the top layer of 1 cm.
  • the amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were placed in a greenhouse (12-16 h light,
  • Treated mixtures or with the individually applied components as WG, WP, EC or other formulations Treated mixtures or with the individually applied components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) Weeding action in the pre-sowing application: Seeds of different weeds and weed biotypes (origins) were grown in one with natural soil
  • the pots with the seeds were treated prior to sowing on a laboratory sprayer with spray mixtures with the compositions of the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha. After sowing, the pots were placed in the greenhouses and as needed fertilized and watered. The pots were cultured in a greenhouse (12-16 h light temperature day 20-22 ° C, night 15-18 ° C).
  • Biotypes (origins) were found in one with natural soil
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray
  • the amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) Irrigation was varied according to the question. The individual comparison groups were graded in a range from above the PWP (permanent wilting point) and up to the level of the maximum
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray
  • inventive compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations were 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). The individual comparison groups were different
  • Soil conditions seeds of different weeds and weed Biotypes (origins) were seeded in a natural soil filled pot of 8-13 cm diameter and covered with a cover layer of the soil of about 1 cm.
  • the plants were cultured in different cultivation soil, from a sandy soil to heavy clay soil and various organic substance contents.
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were grown to different BBCH stages 00-25 of the seeds / plants on one
  • Treated mixtures or with the individually applied components as WG, WP, EC or other formulations Treated mixtures or with the individually applied components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). , Pre and postemergence weed action to control resistant weed / weed species: Seeds of different weeds and weed Biotypes (origins) with different resistance mechanisms to different
  • Standard field soil (loamy silt, LSI; pH 7.4;% C org 2.2) seeded pot of 8 cm diameter and covered with a covering layer of the soil of covered about 1 cm. The pots were then placed in a greenhouse (12-16 h light, temperature day about 23 ° C, night about 15 ° C) until the
  • the pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray lane with spray mixtures with the compositions according to the invention, mixtures or with the individually used components as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 300 l / ha.
  • the plants were again placed in the greenhouses and fertilized and watered as needed.
  • the pots were cultured in a greenhouse (12-16 h light, temperature day about 23 ° C, night about 15 ° C). , Weed effect and culture selectivity in the pre- and postemergence at
  • Treated mixtures or with the individually applied components as WG, WP, EC or other formulations Treated mixtures or with the individually applied components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). , Weed action in the pre- and post-emergence at different pH values of the soil: Seeds of different weeds and weed Biotypes (origins) were sown in a natural soil filled pot of 8-13 cm in diameter and covered with a covering layer of the soil of about 1 cm. For a comparison of the herbicidal activity, the plants were grown in potting soil, from a standard field soil (loamy silt, not sterile) with
  • the pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application.
  • the pots were grown to different BBCH stages 00-10 of the seeds / plants on one
  • Treated mixtures or with the individually applied components as WG, WP, EC or other formulations Treated mixtures or with the individually applied components as WG, WP, EC or other formulations.
  • Water application rate for the spray application was 100-600 l / ha.
  • compositions of the invention Harmful plants before or after sowing the crops or before or after emergence of the harmful plants, the compositions of the invention, mixtures of the prior art or the individual components applied and in the period of 4 weeks to 8 months after treatment compared to
  • BBCH BBCH code provides information about the morphological developmental stage of a plant.
  • the abbreviation stands officially for the Federal Biological Research Center, Federal Plant Variety Office and Chemical Industry.
  • the range of BBCH 00-10 stands for Stages of germination of seeds to penetration of a surface.
  • the range of BBCH 1 1 -25 stands for the stages of the sheet development up to the
  • PE pre-emergence application on the ground; BBCH of seeds / plants 00-10.
  • HRAC 'Herbicide Resistance Action Committee', which classifies the approved active ingredients according to their mode of action (MoA).
  • HRAC group A acetylcoenzyme A carboxylase inhibitors (MoA: ACCase).
  • HRAC group B acetolactate synthase inhibitors (MoA: ALS).
  • AS active substance (based on 100% active ingredient, syn. A.i. (English)).
  • ALOMY_DEU12053 refers to a Biotype with increased metabolic resistance to ALS (EMR) without ALS Target Site Resistance (TSR).
  • ALOMY_DEU12061 refers to a biotype with elevated metabolic
  • EMR ACCase Resistance
  • TSR ACCase Target Site Resistance
  • ALOMY_R35 refers to a biotype sensitive to herbicides with ALS or ACCase mechanism of action (MoA).
  • A, B, C in each case the effect of the components A or B or C in percent at a dosage of a or b or c gram AS / ha;
  • E c expected value according to Colby in% at a dosage of a + b + c gram AS / ha.
  • the agent according to the invention showed a clear synergistic action against the ALS and ACCase-EMR-resistant biotypes ( ⁇ + 15% and ⁇ + 23%, respectively).

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

Abstract

L'invention concerne des agents herbicides présentant une teneur efficace en flufénacet et en d'autres herbicides, à savoir le picolinafen et la métribuzine. Ces agents herbicides présentent un profil d'utilisation amélioré.
PCT/EP2014/077065 2013-12-11 2014-12-09 Agents herbicides contenant du flufénacet, du picolinafen et de la métribuzine WO2015086605A1 (fr)

Priority Applications (1)

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EP14809400.6A EP3079471A1 (fr) 2013-12-11 2014-12-09 Agents herbicides contenant du flufénacet, du picolinafen et de la métribuzine

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3395172A1 (fr) * 2017-04-25 2018-10-31 Rotam Agrochem International Company Limited Procédé de régulation de la croissance de plantes tolérantes aux pds

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4223465A1 (de) * 1992-07-16 1994-01-20 Bayer Ag Herbizide Mittel auf Basis von Heteroaryloxyacetamiden
WO2001035740A2 (fr) * 1999-11-17 2001-05-25 Bayer Aktiengesellschaft Herbicides selectifs a base de derives de pyridine 2,6-disubstituee
WO2001039597A2 (fr) * 1999-12-03 2001-06-07 Bayer Aktiengesellschaft Herbicide a base de n-aryl-uraciles
WO2001074157A2 (fr) * 2000-04-04 2001-10-11 Basf Ag Melanges herbicides synergiques
WO2011082958A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4223465A1 (de) * 1992-07-16 1994-01-20 Bayer Ag Herbizide Mittel auf Basis von Heteroaryloxyacetamiden
WO2001035740A2 (fr) * 1999-11-17 2001-05-25 Bayer Aktiengesellschaft Herbicides selectifs a base de derives de pyridine 2,6-disubstituee
WO2001039597A2 (fr) * 1999-12-03 2001-06-07 Bayer Aktiengesellschaft Herbicide a base de n-aryl-uraciles
WO2001074157A2 (fr) * 2000-04-04 2001-10-11 Basf Ag Melanges herbicides synergiques
WO2011082958A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3395172A1 (fr) * 2017-04-25 2018-10-31 Rotam Agrochem International Company Limited Procédé de régulation de la croissance de plantes tolérantes aux pds
WO2018196640A1 (fr) * 2017-04-25 2018-11-01 Rotam Agrochem International Company Limited Procédé de lutte contre la croissance de végétaux tolérants aux inhibiteurs de pds
CN110248546A (zh) * 2017-04-25 2019-09-17 江苏龙灯化学有限公司 控制pds耐受性植物生长的方法
CN110248546B (zh) * 2017-04-25 2022-04-15 江苏龙灯化学有限公司 控制pds耐受性植物生长的方法

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