EP3599856A1 - Mélanges herbicides contenant 2-[(2,4-dichlorophényl)méthyl]4,4-diméthyl-3-isoxazolidinone, pyroxasulfone et méfenpyr-diéthyle - Google Patents

Mélanges herbicides contenant 2-[(2,4-dichlorophényl)méthyl]4,4-diméthyl-3-isoxazolidinone, pyroxasulfone et méfenpyr-diéthyle

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Publication number
EP3599856A1
EP3599856A1 EP18711124.0A EP18711124A EP3599856A1 EP 3599856 A1 EP3599856 A1 EP 3599856A1 EP 18711124 A EP18711124 A EP 18711124A EP 3599856 A1 EP3599856 A1 EP 3599856A1
Authority
EP
European Patent Office
Prior art keywords
methyl
sodium
ethyl
herbicidal
plants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP18711124.0A
Other languages
German (de)
English (en)
Inventor
Thomas Auler
Jan Dittgen
Thomas Wilde
Herve TOSSENS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Bayer CropScience AG
Original Assignee
Bayer AG
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/EP2017/069701 external-priority patent/WO2018024839A1/fr
Application filed by Bayer AG, Bayer CropScience AG filed Critical Bayer AG
Publication of EP3599856A1 publication Critical patent/EP3599856A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to herbicidal mixtures comprising (i) 2 - [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-3-isoxazolidinone, (ii) pyroxasulfone and (iii) mefenpyr-diethyl and herbicidal compositions containing these mixtures , Furthermore, the present invention relates to a process for the preparation of these herbicidal mixtures and compositions containing these mixtures. Furthermore, the invention relates to the use of said mixtures and compositions in the field of agriculture for controlling harmful plants.
  • 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 biological incompatibility occur quite often, e.g. lack of stability in a Coformuherung, decomposition of an active substance or antagonism of the active ingredients.
  • Desired, however, are combinations of active ingredients with favorable effect profile, high stability and synergistically enhanced as possible effect, which allows a reduction in the application rate compared to the single application of the active ingredients to be combined.
  • Combinations of active ingredients which generally increase crop plant tolerance and / or can be used in special production techniques are also desirable. This includes, for example, a reduction in the sowing depth, which can often not be used for reasons of cultural compatibility.
  • the object of the present invention was to improve the application profile of the herbicidal active ingredient 2 - [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-3-isoxazolidinone with regard to:
  • An object of the invention are thus herbicide mixtures containing:
  • a further aspect of the present invention are herbicide mixtures which, in addition to the components (i), (ii) and (iii), contain at least one further group I herbicide. definitions
  • plant growth regulators as possible mixing partners are:
  • AS / ha As far as the abbreviation "AS / ha” is used in this description, this means “active substance per hectare", based on 100% active ingredient. All percentages in the specification are by weight (acronym: “% by weight”) and, unless otherwise defined, refer to the relative weight of each component based on the total weight of the herbicidal mixture / composition (e.g., as the formulation).
  • the herbicidal compositions according to the invention comprise the components according to the invention of the mixture, ie (i), (ii), and (iii) and optionally further herbicides and contain further constituents, e.g. agrochemical active substances from the group of insecticides and fungicides and / or additives customary in crop protection and / or formulation auxiliaries.
  • the herbicidal mixtures / 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, however, they can often be detected even with split-off application (splitting). It is also possible to use the individual herbicides or the herbicide combinations in several portions (sequence application), e.g. Pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the joint or timely use of the active compounds of the herbicidal mixtures / compositions according to the invention.
  • 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 period of application and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and ecologically more beneficial weed control systems.
  • the application rate of the herbicidal components in the herbicidal mixtures / compositions can vary within wide ranges. In applications with application rates of from 21 to 5500 g AS / ha of the herbicide components, a relatively wide spectrum of annual and perennial weeds, grass weeds and cyperaceae is combated in the pre-emergence and post-emergence processes.
  • the application rates of the herbicidal components in the mixtures / compositions are in the following weight ratio to one another: (i) in general (1- 2000) :( 1-100), preferably (1-40) :( 1-25), more preferably (1-10) :( 1-10).
  • Component (ii) generally 5-1000 g AS / ha, preferably 10-500 g AS / ha, more preferably 25-250 g AS / ha pyroxasulfone.
  • the application rate of the safener (iii) is generally 5-2400 g AS / ha, preferably 25-1200 g AS / ha and more preferably 50-600 g AS / ha.
  • the weight percentages (% by weight) of the herbicidal components based on the total weight of the herbicidal compositions can be calculated from the above-mentioned application rates, which may additionally also contain further constituents.
  • the mixtures / compositions according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial harmful plants, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling undesirable plants or regulating the growth of plants, preferably in plant crops, wherein the mixtures / compositions according to the invention are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seed ( For example, grains, seeds or vegetative propagules such as tubers or Sprossmaschine with buds) or the area on which the plants grow (eg the acreage) are applied.
  • the mixtures / compositions according to the invention can be used, for example. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinen be applied.
  • mixtures / compositions according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die off completely after three to four weeks , This is also the case when the application method IBS (Incorporated By Sowing) is applied.
  • IBS Incorporated By Sowing
  • the herbicidal mixture / composition is introduced into the seedbed during sowing.
  • the herbicidal mixtures / compositions according to the invention can also be applied to the water in rice and are then absorbed via soil, shoot and root.
  • the herbicidal mixtures / compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • the rainfastness of the active ingredients in the mixtures / compositions according to the invention is generally favorable.
  • a particular advantage is that the dosages of components (i), (ii) and (iii) used and effective in the mixtures / compositions according to the invention can be adjusted so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contamination is also virtually avoided.
  • the combination of active substances according to the invention enables a considerable reduction in the required application rate of the active substances.
  • the synergistic effects allow a higher and / or longer potency (lasting effect); the combating a broader spectrum of weeds, 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; Extension of the period of application and / or a reduction in the number of necessary individual applications or a reduction in the total amount applied and - as a result for the user - economically and ecologically more advantageous weed control systems.
  • mixtures / compositions according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple , Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, depending on the structure of the compounds in the respective mixtures / compositions containing compounds and their application rate only insignificantly or not at all damaged.
  • crops of economically important crops e.g. dicotyledonous
  • mixtures / compositions according to the invention may have partial growth-regulatory properties in the crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as crop losses during storage can be reduced or completely prevented.
  • the mixtures / compositions according to the invention can also be used for controlling 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 (i) and (ii) in the mixtures / compositions according to the invention), for example by resistance to pest insects, plant diseases or pathogens of plant diseases such as certain microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, and the composition of special ingredients.
  • 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 special properties may include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
  • the mixtures / compositions according to the invention can also be employed for controlling harmful plants in crops of known or yet to be developed plants obtained by mutant selection, as well as from crosses of mutagenic and transgenic plants.
  • genetic engineering of crops has been described in several cases to modify the starch synthesized in the plants (eg WO 92/011376 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.
  • Transgenic crops such as corn or soybean with the trade name or designation Optimum TM GAT TM (Glyphosate ALS Tolerant); transgenic crops, for example cotton, having the ability Bacillus thuringiensis toxins (Bt toxins ), which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A); transgenic crops with modified fatty acid composition (WO 91/013972 A), genetically modified crops with new content or secondary substances, eg new phytoalexins, which have a cause increased disease resistance (EP 0309862 A, EP 0464461 A); genetically modified plants with reduced photorespiration ion, 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 crops characterized by a combination
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • base exchanges can be made, partial sequences removed or natural or synthetic sequences added.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • 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.
  • 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, i. both monocotyledonous and dicotyledonous plants.
  • the present invention furthermore relates to a method for controlling undesired plant growth (eg harmful plants), preferably in crops such as cereals (eg hard and soft wheat, barley, rye, oats, crossings thereof, such as triticale, planted or sown rice under 'upland' or 'paddy' conditions, maize, millet such as sorghum), sugar beet, sugarcane, oilseed rape, cotton, Sunflowers, soya, potato, tomatoes, beans such as bush and horse bean, flax, grass, orchards, plantation crops, green areas and lawns, as well as residential and industrial sites, railway tracks, most preferably in monocotyledonous crops such as wheat, barley, Rye, oats, crossbreeds thereof such as triticale, rice, maize and millet, and dicotyledonous crops such as sunflowers, soya, potatoes, tomatoes, peas, carrots and fennel, comprising the components (i), (
  • the invention also provides the use of the herbicidal compositions according to the invention comprising the components (i), (ii) and (iii) for controlling harmful plants, preferably in plant crops, preferably in the abovementioned crops. Furthermore, the invention also relates to the use of the herbicidal compositions according to the invention comprising the components (i), (ii) and (iii) for controlling herbicide-resistant harmful plants (eg TSR and EMR resistance in ALS and ACCase), preferably in plant cultures, preferably in the above-mentioned crops. The invention also provides the process with the herbicidal compositions according to the invention comprising the components (i), (ii) and (iii) for the selective control of harmful plants in plant crops, preferably in the abovementioned crops, and their use.
  • herbicide-resistant harmful plants eg TSR and EMR resistance in ALS and ACCase
  • the invention also provides the process for controlling undesired plant growth with the herbicidal compositions according to the invention comprising the components (i), (ii) and (iii), and the use thereof, in plant cultures which have been genetically modified (transgenic) or obtained by mutation selection , and against which growth inhibitors, such as 2,4 D, Dicamba or against herbicides, the essential plant enzymes, eg Acetolactatsynthasen (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit, respectively against herbicides from the group Sulfonylureas, the glyphosate, glufosinate or Benzoylisoxazole and analogous drugs, or against any combination of these agents, resistant.
  • the essential plant enzymes eg Acetolactatsynthasen (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyr
  • the herbicidal compositions according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. Most preferably, the herbicidal compositions of the invention in transgenic crops such.
  • the invention also provides the use of the herbicidal compositions according to the invention comprising the components (i), (ii) and (iii) for controlling harmful plants, preferably in plant crops, preferably in the abovementioned crops.
  • the herbicidal compositions of the invention may also be used non-selectively to control undesired plant growth, e.g. in plantation crops, on roadsides, squares, industrial plants or railway facilities; 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 (i), (ii) and (iii) and optionally with further agrochemical active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or be prepared as so-called tank mixes by co-diluting the separately formulated or partially separately formulated components with water. Under certain circumstances, the mixed formulations may be diluted with other liquids or solids, or used undiluted.
  • the components (i), (ii) and (iii) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are given.
  • suitable formulation options are: wettable powder (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), dispersions, oil dispersions (OD), suspoemulsions (SE), dusts (DP), mordants, granules for soil or litter application (GR) or water-dispersible granules (WG), ultra-low-volume formulations, microcapsules - or wax dispersions.
  • WP wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsions
  • SC Suspension concentrates
  • 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.
  • Injectable powders are preparations which are uniformly dispersible in water and 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.
  • Emulsifiable concentrates are prepared by dissolving the active ingredients in an organic solvent or mixture of solvents, e.g. Butanol, cyclohexanone, dimethylformamide, acetophenone, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic and / or nonionic surfactants (emulsifiers) produced.
  • organic solvent or mixture of solvents e.g. Butanol, cyclohexanone, dimethylformamide, acetophenone, xylene or higher-boiling aromatics or hydrocarbons.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. 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. In addition to the suspended active ingredient or active ingredients, other active ingredients in the formulation may also be present dissolved.
  • 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 grinding by means of commercially available bead mills and, if appropriate, addition of further surfactants (wetting agents, dispersants), as already listed above, for example, in the other types of formulation. In addition to the suspended active ingredient or active ingredients, other active ingredients in the formulation may also be present dissolved.
  • oil 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 grinding by means of commercially available bead mills and, if appropriate, addition of further surfactants (wetting agents, dispersants), as already listed above, for example, in the other types of formulation.
  • surfactants wetting agents, dispersants
  • other active ingredients in the formulation may also be present
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • the active ingredients are present in dissolved form.
  • Granules can either be prepared by atomizing the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites, 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.
  • the agrochemical formulations generally contain from 0.1 to 99% 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 adhesion, wetting, dispersing, emulsifying, preserving, antifreeze and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors and agents which have the pH value or the Influence 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 section.
  • 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 metal salts (eg sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts such as magnesium salts, such as C 12 / Ci4-fatty alcohol diglycol ether 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.
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2 - 20, preferably 3 - 15 ethylene oxide units containing (CIO Cis) -, preferably (Cio-Ci4) fatty alcohol polyglycol ethers (for example isotridecyl alcohol polyglycol ether), for example from the Genapol ® X series, such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • 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 (i) and (ii) 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) may be present.
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X - C 2 / C 4 fatty alcohol diglycol ether sulfate sodium (Genapol ® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3 are preferably -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 polyglycol ether sulfates), are also suitable as penetration aids and activity enhancers for a number of other herbicides, inter alia also for herbicides from the series of imidazolinones (see, for example, EP-A -0,502,014).
  • the herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils.
  • vegetable oils refers to 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, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C 10 -C 22, preferably C 12 -C 20 fatty acids.
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 20 -fatty acids, in particular having an even number of carbon atoms, eg erucic acid, lauric acid, palmitic acid and especially cis fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cio-C 22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 -fatty acids, as contained, for example, in oils from oil-yielding plant species, or Ci-C 2 o-alkyl-CioC 22 fatty acid esters, as for example by transesterification of the aforementioned glycerol or glycol-Cio-C22 fatty acid esters with C1-C20 alcohols (eg, methanol, ethanol, propanol or butanol ) can be obtained.
  • the transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • Ci-C2o-alkyl-Cio-C 22 fatty acid esters are preferably Methylester, ethyl ester, propyl ester, butyl ester, 2-ethyl-hexyl and dodecyl.
  • Preferred glycol and glycerol-C 10 -C 22 -fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C 10 -C 22 -fatty acids, in particular those fatty acids having an even number of carbon atoms, eg erucic acid, lauric acid, palmitic acid and especially cis-fatty acids such as stearic acid, oleic 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: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter called ActirobB, main ingredient: Rapsölmethylester), Rako-binol ® (Bayer AG, Germany, referred to as Rako-binol called main constituent: rapeseed oil), Renol ® (Stefes, Germany, termed Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes , Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester) may be contained.
  • Hasten ® Vanictorian Chemical Company, Australia, hereinbelow termed
  • the present invention includes in a further embodiment, combinations of components (i), (ii) and (iii) 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 ®.
  • vegetable oils such as rapeseed oil
  • 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.
  • a common herbicidal formulation of the herbicidal compositions according to the invention with the components (i), (ii) and (iii) has the advantage of easier applicability because the amounts of the components are already set in the correct ratio.
  • the adjuvants in the formulation can be optimally matched to one another.
  • a duster is obtained by mixing 10 parts by weight of an active ingredient / active ingredient mixture and 90 parts by weight of talc as inert material and comminuted in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of an active substance mixture, 64 parts by weight of kaolin-containing clay as inert material, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of sodium oleoylmethyltaurine as mesh and dispersing agent and grinding in a pin mill.
  • a suspension concentrate which is readily dispersible in water is obtained by mixing 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 of lignosulfonate sodium (Vanisperse CB) and 74 parts by weight Mix water and grind to a fineness of less than 5 microns in a ball mill.
  • Soprophor BSU tristyrylphenol polyglycol ether
  • Vanisperse CB lignosulfonate sodium
  • An oil dispersion which is readily dispersible in water is obtained by mixing 20 parts by weight of an active substance / active substance mixture with 6 parts by weight of alkylphenol polyglycol ether ( Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic mineral oil (boiling range, for example, about 255 to 277 ° C) and milled in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active compound / active substance mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granules are obtained by
  • a water-dispersible granule is also obtained by
  • the seeds of different weeds and weed grasses were seeded in a pot of 8-13 cm diameter filled with natural soil of a standard field soil (loamy silt; non-sterile) and covered with a covering layer of the soil of about 1 cm.
  • 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 on a laboratory spraying track with spray mixtures with the mixtures / compositions according to the invention or with the individually applied components.
  • the application of the active ingredients or combinations of active substances formulated as WG, WP, EC or otherwise took place at the corresponding growth stages of the plants.
  • the amount of water used for the spray application was 100-600 1 ha. After treatment, the plants were placed back in the greenhouses.
  • h light hours of illumination time
  • g AS / ha grams of active ingredient per hectare
  • 1 / ha liters per hectare
  • S sensitive
  • R resistant
  • 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 with the mixtures / compositions according to the invention or with the individually used components as WG, WP, EC or other formulations in BBCH stage 00-10 of the seeds / plants on a laboratory spray lane with spray mixtures.
  • the amount of water used for the spray application was 100-600 1 / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed.
  • Post-emergence weeds Seeds of different weeds and weeds 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) and covered with a cover layer of the soil of about 1 cm. The pots were then cultivated in a greenhouse (12-16h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were grown at different BBCH stages between 11-25 seeds / plants, i. usually between two to three weeks after the beginning of cultivation, treated on a laboratory sprayer with spray mixtures with the mixtures / compositions according to the invention or with the individually applied components as WG, WP, EC or other formulations. The amount of water used for the spray application was 100-600 1 ha. After the treatment, the plants were again placed in the greenhouses and fertilized and irrigated as needed.
  • 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.
  • Pre-emergence selectivity Seeds of different crops (origins) were grown in a pot filled with natural soil from a standard field soil (loamy silt, non-sterile) seeded 8-13 cm in diameter and covered with a covering layer of the soil of about 1cm. 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 with the mixtures / compositions according to the invention or with the individually used components as WG, WP, EC or other formulations in BBCH stage 00-10 of the seeds / plants on a laboratory spray lane with spray mixtures. The amount of water used for the spray application was 100-600 1 / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed.
  • Postemergence selectivity Seeds of different cultivars (origins) were seeded in a pot of 8-13 cm diameter filled with natural soil of a standard field soil (loamy silt; non-sterile) and covered with a cover layer of the soil of about 1 cm. 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 at different BBCH stages 11-32 of the seeds / plants, i. usually between two to four weeks after the beginning of cultivation, treated on a laboratory sprayer with spray mixtures with the mixtures / compositions according to the invention or with the individually applied components as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 100-600 1 / 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)
  • Seedling and postemergence weeds under different cultivation conditions seeds of different weeds and weed Biotypes (origins) were seeded in a natural soil of a standard field soil (loamy silt, non-sterile) filled pot of 8-13 cm in diameter and covered with a layer of soil from covered about 1cm. 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 at different BBCH stages 00-25 the seeds / plants treated with spray mixtures with the inventive mixtures / compositions or with the individually applied components as WG, WP, EC or other formulations on a laboratory sprayer. The amount of water used for the spray application was 100-600 1 ha.
  • the plants were again placed in the greenhouses and fertilized and irrigated 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 supplied with water in gradations ranging from above the PWP (permanent wilting point) and up to the maximum field capacity level.
  • Seed weeds and weeds in different irrigation conditions Seeds of different weeds and weeds Biotypes (origins) were seeded in a pot of 8-13 cm diameter filled with natural soil of a standard field soil (loamy silt, non-sterile) and covered with soil from covered about 1cm. 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 different BBCH stages 00-25 of the seeds / plants on a laboratory spray lane with spray mixtures with the mixtures / compositions according to the invention or with the individually used components as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 100-600 1 ha. After the treatment, the plants were again placed in the greenhouses and fertilized and irrigated 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 exposed to different irrigation techniques. Irrigation was done either from below or in increments from above (simulated irrigation).
  • the pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray lane with spray mixtures with the mixtures / compositions according to the invention or with the individually used components as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 100-600 1 / 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 20-22 ° C, night 15-18 ° C). 10.
  • the pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray lane with spray mixtures with the mixtures / compositions according to the invention or with the individually used components as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 300 1 / 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). 11.
  • Stages 00-25 of the seeds / plants are treated with spray mixtures with the mixtures / compositions according to the invention or with the individually applied components as WG, WP, EC or other formulations on a laboratory sprayer.
  • the amount of water used for the spray application was 100-600 1 / 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 20-22 ° C, night 15-18 ° C).
  • the pots were at different BBCH stages 00-10 of the seeds / plants on a laboratory sprayer with spray mixtures with the mixtures / compositions according to the invention or with the individually applied components treated as WG, WP, EC or other formulations.
  • the amount of water used for the spray application was 100-600 1 ha.
  • the plants were again placed in the greenhouses and fertilized and irrigated as needed.
  • the pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C).
  • Table 1 shows the degree of crop tolerability in pre-emergence winter wheat after 7, 10, 13 and 22 days.
  • both mixtures pyroxasulfone + clomazone and pyroxasulfone + 2 - [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-3-isoxazolidinone
  • This also applies to the mixture of pyroxasulfone + clomazone at lower application rates (25 + 400 g AS / ha). Even the safener does not change this fact.

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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)
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Abstract

La présente invention concerne des mélanges herbicides contenant (i) 2-[(2,4-dichlorophényl)méthyl]-4,4-diméthyl-3-isoxazolidinone, (ii) pyroxasulfone et (iii) méfenpyr-diéthyle et des compositions herbicides contenant ces mélanges. L'invention concerne par ailleurs un procédé de préparation de ces mélanges et compositions contenant ces mélanges. L'invention a également pour objet l'utilisation desdits mélanges et desdites compositions dans l'agriculture pour lutter contre des végétaux nuisibles.
EP18711124.0A 2017-03-24 2018-03-20 Mélanges herbicides contenant 2-[(2,4-dichlorophényl)méthyl]4,4-diméthyl-3-isoxazolidinone, pyroxasulfone et méfenpyr-diéthyle Withdrawn EP3599856A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP17162724.3A EP3378315A1 (fr) 2017-03-24 2017-03-24 Mélanges herbicides contenant 2-[2,4-dichlorphenyl)methyl]-4,4-dimethyl-3-isoxazolidinon
PCT/EP2017/069701 WO2018024839A1 (fr) 2016-08-04 2017-08-03 Suspensions concentrées aqueuses en capsules à base de 2-(2,4-dichlorophényl)méthyl-4,4-diméthyl-3-isoxazolidinone
PCT/EP2018/056964 WO2018172325A1 (fr) 2017-03-24 2018-03-20 Mélanges herbicides contenant 2-[(2,4-dichlorophényl)méthyl]4,4-diméthyl-3-isoxazolidinone, pyroxasulfone et méfenpyr-diéthyle

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EP3599856A1 true EP3599856A1 (fr) 2020-02-05

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EP17162724.3A Withdrawn EP3378315A1 (fr) 2017-03-24 2017-03-24 Mélanges herbicides contenant 2-[2,4-dichlorphenyl)methyl]-4,4-dimethyl-3-isoxazolidinon
EP18711124.0A Withdrawn EP3599856A1 (fr) 2017-03-24 2018-03-20 Mélanges herbicides contenant 2-[(2,4-dichlorophényl)méthyl]4,4-diméthyl-3-isoxazolidinone, pyroxasulfone et méfenpyr-diéthyle

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AR (1) AR111250A1 (fr)
AU (1) AU2018240339A1 (fr)
BR (1) BR112019019638A2 (fr)
CA (1) CA3057392A1 (fr)
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WO2020172305A1 (fr) 2019-02-19 2020-08-27 Gowan Company, L.L.C. Compositions liquides stables et leurs procédés d'utilisation
CN114041470A (zh) * 2021-11-29 2022-02-15 陕西上格之路生物科学有限公司 一种含二氯异噁草酮的除草组合物
CN116762817A (zh) * 2022-03-11 2023-09-19 青岛清原作物科学有限公司 包含灭草松的除草组合物及其应用
CN116762816A (zh) * 2022-03-11 2023-09-19 青岛清原作物科学有限公司 一种除草组合物及其应用
WO2024073019A1 (fr) * 2022-09-30 2024-04-04 Fmc Corporation Compositions stables au stockage à base de bixlozone et de beflubutamide
WO2024073021A1 (fr) * 2022-09-30 2024-04-04 Fmc Corporation Compositions de granules à base de de bixlozone dispersibles dans l'eau
CN116326589A (zh) * 2023-02-01 2023-06-27 青岛瀚生生物科技股份有限公司 农用除草剂组合物及其应用

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JP2020511489A (ja) 2020-04-16
US20200022369A1 (en) 2020-01-23
CL2019002682A1 (es) 2020-02-21
US10932467B2 (en) 2021-03-02
WO2018172325A1 (fr) 2018-09-27
EA201992239A1 (ru) 2020-03-26
AR111250A1 (es) 2019-06-19
CN110461158B (zh) 2021-12-10
EP3378315A1 (fr) 2018-09-26
CN110461158A (zh) 2019-11-15
UA124816C2 (uk) 2021-11-24
CA3057392A1 (fr) 2018-09-27
AU2018240339A1 (en) 2019-09-26
BR112019019638A2 (pt) 2020-04-14

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