WO2014001361A1 - Agents herbicides contenant du flufénacet - Google Patents

Agents herbicides contenant du flufénacet Download PDF

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Publication number
WO2014001361A1
WO2014001361A1 PCT/EP2013/063318 EP2013063318W WO2014001361A1 WO 2014001361 A1 WO2014001361 A1 WO 2014001361A1 EP 2013063318 W EP2013063318 W EP 2013063318W WO 2014001361 A1 WO2014001361 A1 WO 2014001361A1
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Prior art keywords
herbicidal
plants
component
crops
components
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PCT/EP2013/063318
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German (de)
English (en)
Inventor
Dominique Schreiber
Dirk BRÜGGEMANN
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Bayer Cropscience Ag
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Publication of WO2014001361A1 publication Critical patent/WO2014001361A1/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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
    • 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
    • A01N43/72—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 mixtures of this group with other herbicides are known from the literature: for example (for example) US 5945397 B, US 5593942 B, US 581 1373 B, US 6967188 B. In US 5858920 B among others
  • the herbicidal active ingredient flufenacet is characterized by a broad activity against monocotyledonous and dicotyledonous harmful plants and is used e.g. used in pre-sowing, pre-emergence or postemergence agriculture in sown and / or planted agricultural or horticultural crops and non-crops (eg in cereals such as wheat, barley, rye, oats, triticale, rice, corn, millet, sugar beet, sugarcane, Oilseed rape, cotton, sunflower, soya, potato, tomatoes, beans, flax, pasture grass, fruit growing plants, plantation crops, green areas and lawns, as well as residential and industrial sites, railway tracks).
  • cereals such as wheat, barley, rye, oats, triticale, rice, corn, millet, sugar beet, sugarcane, Oilseed rape, cotton, sunflower, soya, potato, tomatoes, beans, flax, pasture grass, fruit growing plants, plantation crops, green areas and
  • 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®.
  • Single agents are also known from mixtures of flufenacet with other herbicides (for example US 5985797 B, US 5912206 B, US 6492301 B, US 6864217 B, US 6486096 B, US 2003/0069138 A, WO 2002/058472 A, US 6365550 B, US Pat.
  • Crystal®, Malibu Pack® with atrazine and metribuzin (e.g., Axiom AT®) and with diflufenican and flurtamones (e.g., Baccara FORTE®).
  • atrazine and metribuzin e.g., Axiom AT®
  • diflufenican and flurtamones e.g., Baccara FORTE®
  • 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 ones Active ingredients exist.
  • Active ingredients exist.
  • phenomena of physical and biological 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.
  • An object of the invention are thus herbicidal compositions containing as the only herbicidally active ingredients:
  • the herbicidally active components component A, B, C and D are in
  • Entry number / "sequential entry number" - Component A: Flufenacet (PM # 381), syn. thiafluamide, e.g. N- (4-fluorophenyl) -N- (1-methylethyl) -2 - [[5- (trifluoromethyl) -1, 3,4-thiadiazol-2-yl] oxy] acetamide;
  • Component B Aclonifen (PM # 9), e.g. 2-chloro-6-nitro-3-phenoxybenzeneamines;
  • Component C diflufenican (PM # 258), e.g. A / - (2,4-difluorophenyl) -2- [3- (trifluoromethyl) phenoxy] -3-pyridinecarboxamide;
  • Component D metribuzin (PM # 573), eg, 4-amino-6- (1,1-dimethylethyl) -3- (methylthio) -1,2,4-triazine-5 (4 / - /) --one.
  • PM # 573 metribuzin
  • 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.
  • the herbicidal compositions according to the invention have a herbicidally active content of the components A, B, C and D 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 have synergistic effects as an improvement of the application profile. These synergistic effects can e.g. co-application of the herbicidal components, but they can often be detected even in case of splitting. It is also possible
  • 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 26 to 12500 g AS / ha of the 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 weight ratio indicated below (component: Kmp.): (Range Kmp. A): (range Kmp. B): (range Kmp. C): (range Kmp. D) im general (1 - 2000): (1 - 100): (1 - 500): (1 - 5000),
  • 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 10 to 5000 g AS / ha, preferably 80 to 3000 g AS / ha, more preferably 80 to 1000 g AS / ha aclonifen;
  • Component C generally 1 to 500 g AS / ha, preferably 10 to 300 g
  • AS / ha more preferably 30-200 g AS / ha diflufenican;
  • Component D generally 5-5000 g AS / ha, preferably 20-500 g AS / ha, more preferably 30-300 g AS / ha metribuzin. Accordingly, from the above-mentioned application rates
  • 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., Stellaha 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 after a certain time completely off, 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 absorbed by 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, C and D can be set so low that their soil effect is optimally low.
  • the effect in the combinations is stronger than the expected sum of the effects of the individual herbicides used.
  • the synergistic effects allow a higher and / or longer potency (lasting effect); the control of a broader spectrum of weeds, grass weeds and cyperaceans, sometimes with only one or a few applications; faster onset of herbicidal activity; Control of previously unrecognized species (gaps); Control, for example, of species that have tolerances or resistances to single or multiple herbicides;
  • 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.
  • agents according to the invention can be partially or completely identical
  • compositions according to the invention can also be used for combating harmful plants in known plant crops or tolerant or genetically modified crop and energy crops to be developed.
  • the transgenic plants (GMOs) are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides (such as resistance to the components A, B, C and D 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.
  • Other particular properties may include tolerance or resistance to 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.
  • Genetic engineering methods are produced (see for example EP 0221044 A, EP 0131624 A). In several cases, for example, genetic engineering was described Alterations of crops to modify the starch synthesized in the plants (eg WO 92/01 1376 A, WO 92/014827 A, WO 91/019806 A); transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US Pat. No.
  • 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 that are characterized by higher yields or better quality; transgenic
  • 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
  • Mutagenesis or a sequence change by recombination of DNA sequences allow.
  • standard methods e.g.
  • 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. However, to achieve localization in a particular compartment, e.g. the coding region is linked to DNA sequences which 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 whole by known techniques
  • transgenic plants are regenerated.
  • the transgenic plants may in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.
  • 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 bushbeam and horse bean, flax, pasture grass, orchards, plantation crops, lawns and lawns, as well as residential and industrial sites, railway tracks, most preferably in monocotyledonous crops such as cereals, e.g. Wheat, barley, rye, oats,
  • Crosses thereof such as triticale, rice, maize and millet, and dicotyledonous crops such as sunflower, soybean, potato, tomato, pea, carrot and fennel, wherein the components A, B, C and D of the herbicidal compositions of the invention
  • pre-emergence very early to late
  • post-emergence pre-emergence
  • pre-emergence on the plants
  • the invention also provides the use of the herbicidal compositions according to the invention comprising the components A, B, C and D for controlling harmful plants, preferably in plant crops, preferably in the abovementioned crops.
  • the invention furthermore also relates to the use of the herbicidal compositions according to the invention comprising components A, B, C and D for controlling herbicidally-resistant harmful plants (eg TSR and EMR resistances in ALS and ACCase), preferably in plant crops, preferably in the abovementioned plant crops.
  • herbicidally-resistant harmful plants eg TSR and EMR resistances in ALS and ACCase
  • the invention also provides the process with the herbicidal compositions according to the invention comprising the components A, B, C and D for the selective Control of harmful plants in plant crops, preferably in the above-mentioned crops, and its use.
  • the invention also provides the method for controlling
  • herbicidal compositions according to the invention containing the components A, B, C and D, and its use, in
  • 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
  • Hydoxyphenylpyruvate Dioxygenases 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, C and D for controlling harmful plants, preferably in plant crops, preferably in the abovementioned crops.
  • herbicidal compositions of the invention may also be non-selective to
  • Plantation crops on roadsides, squares, industrial plants or
  • the herbicidal compositions according to the invention can be present both as mixed formulations of components A, B, C and D and optionally with further agrochemical active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water in a customary manner, or as so-called tank mixes common dilution of the separately formulated or partially separately formulated components 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, C and D 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 Microcapsule or wax dispersions.
  • the necessary formulation auxiliaries such as inert materials, surfactants,
  • Solvents and other additives are also known and are described in, for example, Watkins, Handbook of Insecticides 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.
  • agrochemical active substances such as fungicides, insecticides, as well as safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
  • Spray powders are uniformly dispersible in water
  • 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 by means of commercial bead mills and, if appropriate, addition of further surfactants, as already listed above, for example, for the other types of formulation.
  • 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. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • 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. For the preparation of plate, fluidized bed, extruder and spray granules see, for example
  • the agrochemical formulations usually contain from 0.1 to 99
  • 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 substance 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 agents 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, C and D 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 (eg as fatty alcohol polyglycol ether sulfates) 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 (eg as fatty alcohol polyglycol ether sulfates) may be present.
  • nonionic or ionic eg as fatty alcohol polyglycol ether sulfates
  • Ci 2 / Ci fatty alcohol diglycol ether sulfate sodium (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. Under the term
  • Vegetable oils are oils from oil-supplying plant species such as soybean oil, rapeseed oil,
  • 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 fatty acids.
  • 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. can be obtained by transesterification of the aforementioned glycerol or glycol-Cio-C22 fatty acid esters with C 1 -C 20 -alcohols (for example, methanol, ethanol, propanol or butanol). 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:
  • Rako-Binol ® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ® (Stefes, Germany, hereinbelow Renol called, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes, Germany, termed Mero, main ingredient:
  • Rapeseed oil methyl ester may be included.
  • the present invention comprises in a further embodiment
  • Combinations of the components A, B, C and D with the previously mentioned 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.
  • 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, C and D 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 oleoylmethyltaurine sodium as a net 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
  • 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 effect in pre- and post-emergence at different
  • 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). The 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 placed in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until application time cultured.
  • the pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray
  • Soil conditions Seeds of different weeds and weed Biotypes (origins) were grown in a natural soil-filled pot of 8-13 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 Mechanisms of action were in one with natural earth
  • 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
  • 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). field trials
  • 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 the stages of germination of the seeds until the surface is pierced.
  • 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.
  • PO postemergence application to the green plant parts; BBCH of plants 1 1 - 25.
  • HRAC 'Herbicide Resistance Action Committee', which classifies the approved active substances 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 ai (English)).
  • Dose g AS / ha application rate in grams of active substance per hectare.
  • E c expected value according to Colby in% at a dosage of a + b and c + d gram AS / ha.
  • Table 1 Comparison of the effect of the mixture on resistant biotypes of Lolium spp. after a postemergence treatment (PO, BBCH 1 1).

Abstract

L'invention concerne des agents herbicides ayant une teneur active en flufénacet et autres agents herbicides aclonifen, diflufénican et métribuzine. Ces agents herbicides présentent un profil d'utilisation amélioré.
PCT/EP2013/063318 2012-06-27 2013-06-25 Agents herbicides contenant du flufénacet WO2014001361A1 (fr)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2017068587A1 (fr) * 2015-10-22 2017-04-27 Adama Agan Ltd. Mélange herbicide et formulation à utiliser sur des pommes de terre
EP3338551A1 (fr) * 2016-12-21 2018-06-27 Bayer CropScience Aktiengesellschaft Combinaisons herbicides
EP3395172A1 (fr) * 2017-04-25 2018-10-31 Rotam Agrochem International Company Limited Procédé de régulation de la croissance de plantes tolérantes aux pds

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