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WO2025132266A1 - Combinaisons herbicides et compositions - Google Patents

Combinaisons herbicides et compositions Download PDF

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Publication number
WO2025132266A1
WO2025132266A1 PCT/EP2024/086659 EP2024086659W WO2025132266A1 WO 2025132266 A1 WO2025132266 A1 WO 2025132266A1 EP 2024086659 W EP2024086659 W EP 2024086659W WO 2025132266 A1 WO2025132266 A1 WO 2025132266A1
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WO
WIPO (PCT)
Prior art keywords
methyl
dioxo
dihydropyrimidin
chloro
fluoro
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PCT/EP2024/086659
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English (en)
Inventor
Jens Frackenpohl
Hendrik Helmke
Klaus Haaf
Stefan Lehr
Anna REINGRUBER
Elmar Gatzweiler
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Bayer AG
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Bayer AG
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Priority claimed from EP24155124.1A external-priority patent/EP4595756A1/fr
Application filed by Bayer AG filed Critical Bayer AG
Publication of WO2025132266A1 publication Critical patent/WO2025132266A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • A01N43/72—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

  • BCS231030 FC NR/ed 14.10.2024 - 1 -
  • Herbicidal combinations and compositions The invention relates to novel herbicidal active compound combinations and/or compositions which comprise substituted isoxazoline-carboxamides or agrochemical acceptable salts thereof and substituted N-phenyluraciles. They can be used with particularly good results for the control of weeds in various crops of useful plants. Substituted N-phenyluracile are already known as effective herbicides e.g.
  • the compounds can be used either non-selective or selective depending on the timing and crops. However, the activity and compatibility with crop plants are not entirely satisfactory under all conditions.
  • certain substituted isoxazoline-carboxamides when used together with substituted N-phenyluraciles described below, can be used particularly advantageously as broad-spectrum combination preparations for the control of weeds in crops of useful plants, for example, in cereals, maize and soybean excersing a significant synergistic effect.
  • C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1- methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1- dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-eth
  • Alkenyl means unsaturated straight-chain or branched hydrocarbyl radicals having the number of carbon atoms specified in each case and one double bond in any position, e.g. C 2 - C 6 -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1- butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-
  • Alkynyl represents a straight-chain or branched hydrocarbyl groups having 2 to 8, preferably 2 to 6, carbon atoms and one triple bond in any position.
  • Non-limiting examples include BCS231030 FC NR/ed 14.10.2024 - 11 - ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, 1-methylbut-2-ynyl, 1-methylbut-3-ynyl, 2-methylbut-3-ynyl, 3-methylbut-1-ynyl, 1,1-dimethylprop-2-ynyl, 1-ethylprop-2-ynyl, hex- 1-ynyl, hex-2-ynyl, hex-3-
  • Alkoxy means saturated straight-chain or branched alkoxy radicals having the number of carbon atoms specified in each case, for example C 1 -C 6 -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2- trimethylpropoxy, 1-eth
  • C 1 -C 2 -haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-1,2- BCS231030 FC NR/ed 14.10.2024 - 12 - difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy.
  • the invention also relates to all stereoisomers and mixtures thereof which are encompassed by the formula (I) but not defined specifically.
  • compounds of the formula (I) might have acidic properties and can form salts, and if appropriate also internal salts or adducts with inorganic or organic bases or with metal ions. If the compounds of the formula (I) bear hydroxyl, carboxyl or other groups which induce acidic properties, these compounds can be reacted with bases to give salts.
  • Suitable bases are, for example, hydroxides, carbonates, hydrogencarbonates of the alkali metals and alkaline earth metals, especially those of sodium, potassium, magnesium and calcium, and also ammonia, primary, secondary and tertiary amines having (C 1 -C 4 )-alkyl groups, mono-, di- and trialkanolamines of (C 1 -C 4 )- alkanols, choline and chlorocholine, and organic amines, such as trialkylamines, morpholine, piperidine or pyridine.
  • salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR ⁇ R ⁇ ⁇ R ⁇ ⁇ ] + in which R to R ⁇ ⁇ ⁇ are each independently an organic radical, especially alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts.
  • Some of the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids, for example HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, for example p-toluenesulfonic acid, onto a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino.
  • these salts comprise the conjugate base of the acid as the anion.
  • Suitable substituents present in deprotonated form for example sulfonic acids or carboxylic BCS231030 FC NR/ed 14.10.2024 - 13 - acids, may form internal salts with groups which for their part can be protonated, such as amino groups.
  • the preparation of the compounds of the herbicidal combination is known. Compounds (a) are prepared according to the procedure disclosed in WO 2018/228985 A1.
  • Preferred substituents of the radicals given in the formulae mentioned above are herbicidal combinations wherein compound of formula (I) is one compounds of the formula (Ia) or agrochemical acceptable salts thereof in which X 3 , X 5 , R 3 and G are as described above;
  • Z means Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-5a, Z-6a, Z-7a, Z-8a,
  • BCS231030 FC NR/ed 14.10.2024 - 14 - ; wherein Z-4a means the mixture of both structures Z-4b and Z-4c; and wherein Z-8a means the mixture of both structures Z-8b and Z-8c ; and wherein the arrow means a bond to the group CO-G in formula (Ia).
  • herbicidal combinations wherein compound of formula (Ia) is one of the compounds of table 2 or agrochemical acceptable salts thereof BCS231030 FC NR/ed 14.10.2024 - 15 - with Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-4c, Z-4b, Z-5a, Z-6a, Z-7a, Z-8a being as defined (Ia) above.
  • Table 2 Examples for compounds of the formula (Ia) No. X 3 X 5 R 3 1.1 F F (R)-CH 2 Cl 1.2 F CN (R)-CF 3 1.3 F F (R)-CF 3 1.4 F H (R)-CH 3 1.5 Cl CN (R)-CH 3 1.6 F H (S)-vinyl 1.7 F F (R)-CF 3 BCS231030 FC NR/ed 14.10.2024 - 16 - No.
  • Preferred is a combination comprising No.1.68 of formula (Ia) and B26. Preferred is a combination comprising No.1.68 of formula (Ia) and B27. Preferred is a combination comprising No.1.68 of formula (Ia) and B28. Preferred is a combination comprising No.1.68 of formula (Ia) and B29. Preferred is a combination comprising No.1.68 of formula (Ia) and B30. Preferred is a combination comprising No.1.68 of formula (Ia) and B31. Preferred is a combination comprising No.1.68 of formula (Ia) and B32. Preferred is a combination comprising No.1.68 of formula (Ia) and B33.
  • Preferred is a combination comprising No.1.68 of formula (Ia) and B34. Preferred is a combination comprising No.1.68 of formula (Ia) and B35. BCS231030 FC NR/ed 14.10.2024 - 25 - Preferred is also a combination comprising No.1.100 of formula (Ia) and B1. Preferred is also a combination comprising No.1.100 of formula (Ia) and B2. Preferred is also a combination comprising No.1.100 of formula (Ia) and B3. Preferred is also a combination comprising No.1.100 of formula (Ia) and B4. Preferred is also a combination comprising No.1.100 of formula (Ia) and B5.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B6.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B7.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B8.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B9.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B10.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B11.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B12.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B13.
  • Preferred is also a combination comprising No.1.100 of formula (Ia) and B22. Preferred is also a combination comprising No.1.100 of formula (Ia) and B23. Preferred is also a combination comprising No.1.100 of formula (Ia) and B24. Preferred is also a combination comprising No.1.100 of formula (Ia) and B25. Preferred is also a combination comprising No.1.100 of formula (Ia) and B26. Preferred is also a combination comprising No.1.100 of formula (Ia) and B27. Preferred is also a combination comprising No 1.100 of formula (Ia) and B28. Preferred is also a combination comprising No.1.100 of formula (Ia) and B29.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.
  • the synergistic effects are observed in the case of joint deployment of active ingredients (a) and (b), but can also frequently occur in the case of offset application (splitting).
  • one or more pre-emergence applications may be followed by a post-emergence application, or an early post-emergence application may be followed by a moderately late or late post-emergence application.
  • Preference is given to the simultaneous or immediately successive application of the active ingredients of the respective combination, if appropriate in several portions.
  • the active compound combinations according to the invention can be used, for example, in connection with the following plants: Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthe- mis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
  • the invention furthermore relates to a method of reducing crop damage by treating the seed of the crop with the safener before sowing.
  • the active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkyl- naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl- formamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene or alkyl- naphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes
  • Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, BCS231030 FC NR/ed 14.10.2024 - 29 - alkylsul
  • novel active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by washing, spraying, atomizing, dusting or scattering.
  • BCS231030 FC NR/ed 14.10.2024 - 30 - The advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is particularly highly pronounced at certain amounts of herbicide and safener.
  • the amounts of the active compound combinations according to the invention applied can be varied within a certain range; they depend, inter alia, on the weather and on soil factors.
  • the spectrum of action extends to species such as, for example, Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erodium, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Geranium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sin
  • the active ingredient combinations of the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop growing and ultimately die completely after three to four weeks have passed. If the active ingredients are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, and so this eliminates competition by the weeds, which is harmful to the crop plants, very early and in a sustained manner. BCS231030 FC NR/ed 14.10.2024 - 39 - The herbicidal products of the invention are notable for a rapid onset and long duration of herbicidal action.
  • the expected activity for a given combination of two active ingredients can be calculated according to S.R. Colby (“Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15 (1967), 20-22) (see below).
  • the synergistic effects therefore permit, for example, a reduction in the application rates of the individual active ingredients, a higher efficacy at the same application rate, the control of species of harmful plants which are as yet uncovered (gaps), elevated residual action, an extended period of efficacy, an elevated speed of action, an extension of the period of application and/or a reduction in the number of individual applications required and - as a result for the user - weed control systems which are more advantageous economically and ecologically.
  • the combinations of the invention have excellent herbicidal activity with respect to mono- and dicotyledonous weeds, many economically important crop plants, depending on the structure of the respective active ingredient combinations of the invention and the application rate thereof, are damaged only insignificantly, if at all.
  • Economically important crops here are, for example, dicotyledonous crops from the genera of Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or BCS231030 FC NR/ed 14.10.2024 - 40 - monocotyledonous crops from the genera of Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum and Zea.
  • the combination/compositions of the invention in some cases have outstanding growth-regulating properties in crop plants. They intervene in the plants’ own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example 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 in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since this can reduce or completely prevent lodging. Owing to their herbicidal and plant growth-regulatory properties, the combinations/compositions can be used to control harmful plants in known plant crops or in tolerant crop plants still to be developed, modified by conventional mutagenesis or modified by genetic engineering.
  • transgenic plants feature particular advantageous properties in addition to resistances to the combinations/compositions of the invention, for example resistances to plant diseases or the organisms that cause plant diseases such as certain insects, or microorganisms such as fungi, bacteria or viruses.
  • Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, combinations/composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid combinations/composition in the harvested material.
  • Other particular properties may be tolerance or resistance to abiotic stressors, for example heat, low temperatures, drought, salinity and ultraviolet radiation.
  • the active ingredient combinations of the invention can preferably be used as herbicides in crops of crop plants that are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.
  • the active ingredient combinations of the invention can preferably be used in transgenic crops that are tolerant or have been rendered tolerant to the active ingredients used.
  • the active ingredient combinations of the invention can preferably also be used in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides BCS231030 FC NR/ed 14.10.2024 - 41 - from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
  • growth regulators for example dicamba
  • herbicides which inhibit essential plant enzymes for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides BCS231030 FC NR/ed 14.10.2024 - 41 - from the
  • the invention therefore also provides a method of controlling unwanted plant growth, optionally in crops of crop plants, preferably on uncultivated land or in plantation crops, characterized in that one or more herbicides of type (a) is/are applied with one or more herbicides of type (b) to the harmful plants, parts of plants or plant seeds (seed) or to the growing area.
  • the invention also provides for the use of the novel combinations of compounds (a)+(b) for control of harmful plants, optionally in crops of crop plants, preferably on uncultivated land and plantation crops, but also for control of harmful plants before the sowing of the subsequent crop plant, such as, in particular, for preparation for seeding ("burn-down application").
  • the active ingredient combinations of the invention may either take the form of mixed formulations of the two components, if appropriate with further active ingredients, additives and/or customary formulation auxiliaries, which are then applied in a customary manner diluted with water, or can be prepared as what are called tankmixes by joint dilution of the separately formulated or partially separately formulated components with water.
  • the compounds (a) and (b) or their combinations can be formulated in various ways according to which biological and/or physicochemical parameters are required.
  • WP wettable powders
  • SP water-soluble powders
  • EW emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsions
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsions
  • OD oil-difiable concentrates
  • SC aqueous solutions
  • EW emulsions
  • OD oil-in-water and water-in-oil emulsions
  • sprayable solutions or emulsions sprayable solutions or emulsions
  • dispersions based on oil or water oil dispersions
  • SC suspoemulsions
  • SC suspension concentrates
  • SC oil-miscible solutions
  • capsule suspensions CS
  • dusting products DP
  • dressings granules for soil application or scattering
  • GR granules
  • GR granules in the form
  • the invention therefore also provides herbicidal and plant-growth-regulating compositions containing the active ingredient combinations of the invention.
  • the individual types of formulation are known in principle and are described, for example, in: Winnacker-kuchler, "Chemische TECH” [Chemical Technology], Volume 7, C. BCS231030 FC NR/ed 14.10.2024 - 42 - Hanser Verlag Kunststoff, 4th Ed. 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.
  • the formulation auxiliaries required are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ.
  • pesticidally active substances such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactericides, viricides etc.), and also with fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix.
  • Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate.
  • surfactants of the ionic and/or nonionic type for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxy
  • emulsifiers which BCS231030 FC NR/ed 14.10.2024 - 43 - may be used are: calcium alkylarylsulfonate 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 condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or for example polyoxyethylene sorbitan fatty acid esters.
  • calcium alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorb
  • the active ingredient formulations mentioned optionally comprise the respectively customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, evaporation inhibitors and pH- or viscosity-modifying agents.
  • the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or broadcasting and sprayable solutions are not normally diluted further with other inert substances prior to application.
  • the bottles were capped and then placed in an overhead shaker (set at medium speed for ca. 60 minutes) so that the seeds were evenly coated with the slurry.
  • the bottles were uncapped and the seeds were either placed on paper and dried for an interval of 3-4 hours prior to sowing, or directly sown. Seeds were placed in sandy loam soil in pots of a diameter of 7-8 cm, and covered with soil. Pre-emergence application of the specified herbicides was done subsequently, on two sets of plants: a) seed treatment with safener, as described above b) no safener treatment The herbicides were formulated as WP and was sprayed onto the soil surface as an aqueous suspension at an equivalent water application rate of 300 l/ha.
  • the bottles were uncapped and the seeds were either placed on paper and dried for an interval of 3-4 hours prior to sowing, or directly sown. Seeds were placed in sandy loam soil in pots of a diameter of 7-8 cm, covered with soil, and cultivated in a greenhouse under good growth conditions. Post-emergence application of the specified herbicides was done when the plants had reached growth stage BBCH11-13, on two sets of plants: a) seed treatment with safener, as described above b) no safener treatment The herbicides were formulated as WP and sprayed onto the green parts of the plants as an aqueous suspension at an equivalent water application rate of 300 l/ha, with addition of wetting agent and adjuvants (e.g.
  • Water-dispersible granules are obtained by mixing 75 parts by weight of an active ingredient/active ingredient mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.
  • Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, 25 parts by weight of an active ingredient/active ingredient mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water, then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.
  • a colloid mill 25 parts by weight of an active ingredient/active ingredient mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water, then
  • the observed values (E A ) from the experiments, given suitable low dosages, show an effect of the combinations exceeding the expected values according to Colby ( ⁇ ). 1.
  • Post-emergence action against weeds (Method 1 - used for the data shown in table 4) Seeds or rhizome pieces of mono- and dicotyledonous weeds are placed in sandy loam in pots, covered with soil and grown in a greenhouse under good growth conditions (temperature, air humidity, water supply). Approximately three weeks after sowing, the test plants are treated at the three-leaf stage with the combination/compositions of the invention.
  • the combination/compositions of the invention formulated as spray powders or as emulsion concentrates, are sprayed onto the green plant parts in various dosages with an application rate equivalent to 300 to 800 l/ha of water.
  • the combination /compositions of the invention also have good post-emergence herbicidal activity against a broad spectrum of economically important weed grasses and broadleaved weeds. Effects of the combinations of the invention that exceed the formal sum total of the effects in the case of individual application of the herbicides are frequently observed here. The observed values from the experiments, given suitable low dosages, show an effect of the combinations exceeding the expected values according to Colby. 2.
  • Herbicidal pre-emergence and post-emergence action BCS231030 FC NR/ed 14.10.2024 - 51 - The experiments were conducted on outdoor plots in accordance with the greenhouse experiments from section 1. The rating was analogous to the experiment in section 1. 3.
  • Herbicidal action and crop plant compatibility Crop plants were grown in outdoor plots under natural outdoor conditions, by laying out seeds or rhizome pieces of typical harmful plants or utilizing natural weed flora.
  • the treatment with the combinations/compositions of the invention followed the emergence of the harmful plants and of the crop plants, generally at the 2- to 4-leaf stage; in some cases (as specified), individual active ingredients or active ingredient combinations were applied pre- emergence or as a sequential treatment partly pre-emergence and/or post-emergence.
  • individual active ingredients or active ingredient combinations were applied pre- emergence or as a sequential treatment partly pre-emergence and/or post-emergence.
  • the active ingredients in general, only the soil between the individual crop plants was treated with the active ingredients.
  • the combination /compositions of the invention also have synergistic herbicidal activity in field trials against a broad spectrum of economically important weed grasses and broadleaved weeds.
  • BCS231030 FC NR/ed 14.10.2024 - 52 - Table 4 shows the synergistic effect ( ⁇ ) for herbicidal binary combinations comprising (a) 1.68 a substituted isoxazoline-carboxamides of the formula (I) and (b) one of B1 to B35, applied by Post-emergence action against weeds (s. Method 1 above). The following weeds were selected for testing (see table 3): Table 3 Target Bayer code Alopecurus myosuroides ALOMY_R resistant to herbicidally active compounds of the HRAC groups A and B; population mixture of field origin having increased metabolic resistance (IMR) and some target site resistance (TSR).
  • IMR metabolic resistance
  • TSR target site resistance

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  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne de nouvelles combinaisons de composés actifs herbicides et/ou des compositions qui comprennent des isoxazoline-carboxamides substitués ou des sels agrochimiques acceptables de ceux-ci et des N-phényluraciles substitués. Les nouvelles combinaisons peuvent être utilisées avec des résultats particulièrement bons pour la lutte contre les mauvaises herbes dans diverses cultures de plantes utiles.
PCT/EP2024/086659 2023-12-22 2024-12-16 Combinaisons herbicides et compositions Pending WO2025132266A1 (fr)

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WO2023228935A1 (fr) 2022-05-25 2023-11-30 住友化学株式会社 Composition herbicide et procédé de lutte contre les mauvaises herbes
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