Use of isoxazoline carboxamides as pre-emergence herbicides in dicot crops

Abstract

The present invention relates to the field of crop protection, more specifically to the use of (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester (I) and / or salts thereof for controlling unwanted vegetation at the site of planting of dicot crop plants by application before emergence of the dicot crop plants.

Description

[0001] This invention relates to the field of crop protection, and more specifically, to (2R) 4R Methyl tetrahydrofuran-2-carboxylate (I) and / or its salts are used for the prevention of unwanted vegetation at the planting site of dicotyledonous crops by application before the emergence of dicotyledonous crop plants.

[0002] Compounds of the substituted isoxazoline carboxamide class are known as herbicides by WO2018 / 228985 and WO2019 / 145245 for the control of broad-spectrum weeds in burn applications. It is also known to combine this herbicidal active ingredient with other herbicides for weed control, see, for example, WO 2020 / 114932.

[0003] For the purpose of controlling weeds in dicotyledonous crops, the herbicides used must exhibit selective action against weeds without significantly harming crops that emerge in the same spatial location as the weeds. However, many herbicides used for weed control management do not exhibit the required level of selectivity. Some herbicides need to be used in combination with a safener to achieve sufficient selectivity. For example, as known from WO 2021 / 245004, substituted isoxazoline carboxamide can be used as a pre-emergence herbicide for monocotyledonous crops when applied in combination with a safener. Other agricultural chemicals are inadequate in controlling weed plants, or fail to control some weed species at all.

[0004] Therefore, new and alternative methods are needed to effectively protect dicotyledonous crops from weeds without reducing crop quality.

[0005] Therefore, the object of the present invention is to provide an improvement and control of unwanted vegetation in dicotyledonous crops (such as sunflower, flax, peanut, potato, lentil, soybean, kidney bean, broad bean, pea, chickpea, safflower, carrot, lettuce, edamame, chicory, caraway, ginseng, chicory, artichoke, chamomile, goldenrod, and cotton).

[0006] This objective has been achieved through the use of (2R) 4R Methyl tetrahydrofuran-2-carboxylate (I) (which exists in two stereoisomers: (Ia) of formula (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isooxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate and (Ib) of formula (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isooxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate) and / or its salts, is used to control unwanted vegetation at the planting site of dicotyledonous crops by application before emergence of dicotyledonous crops. .

[0007] Surprisingly, isoxazoline carboxamide of formula (I) has been found to exhibit high herbicidal activity against a broad spectrum of monocot and dicot weeds, and shows virtually no phytotoxicity to dicot crops if applied before emergence. Co-application of a safener is not necessary to achieve high levels of selectivity. This is particularly suitable when a mixture of compound (I) and a surfactant (e.g., methylated seed oil) is applied at a rate of 300 g of active ingredient per hectare or less.

[0008] Another object of the present invention is to include (2R) 4R Compositions of methyl tetrahydrofuran-2-carboxylate (I) and / or its salts are used for the prevention of unwanted vegetation at the planting site of dicotyledonous crops by application prior to the emergence of dicotyledonous crop plants.

[0009] According to the present invention, the compound of formula (I) exhibits excellent and desirable effects in weed control in dicotyledonous crops during pre-emergence treatment (i.e., application before emergence of dicotyledonous crops) without causing any or substantial damage to the crop or its quality.

[0010] This treatment can be carried out shortly before or after sowing or planting, but before the emergence of dicotyledonous crops. The soil may already have unwanted vegetation. However, it is preferable to apply it to bare soil with broadleaf crop seeds underground. As used herein, the term "seed" also includes planted plant parts or tubers, such as in the case of potatoes. The compound (I) according to the invention can be used to control existing and newly emerging weeds.

[0011] Preferably, the compound of formula (I) and / or its salt is applied to the soil of the planting area after sowing or planting and before the emergence of the dicotyledonous crop, i.e., on the day of sowing or planting or until the BBCH stage 09 of the crop, more preferably until the BBCH stage 08 of the crop. More preferably, the compound of formula (I) and / or its salt is applied to a moist and firm seedbed of the dicotyledonous crop immediately after planting or sowing the crop.

[0012] This treatment can be applied once or repeatedly.

[0013] Suitable dicotyledonous crops include sunflower, flax, peanut, potato, lentil, soybean, kidney bean, broad bean, pea, chickpea, safflower, carrot, lettuce, edamame, chicory, caraway, ginseng, chicory, artichoke, chamomile, goldenrod, and cotton.

[0014] Preferably, the dicotyledonous crops are selected from sunflower, flax, peanut, potato, lentil, soybean, common bean, broad bean, pea, chickpea, safflower, sesame, rapeseed, and cotton. Particularly preferred dicotyledonous crops are sunflower, flax, peanut, potato, lentil, soybean, common bean, broad bean, pea, and chickpea.

[0015] Crop plants can be plants that can be obtained through conventional breeding and optimization methods or through biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMOs or transgenic plants) and plant cultivars that are protected or not protected by plant breeders' rights.

[0016] Plant Cultivation This should be understood to mean plants that possess new characteristics ("traits") and have been obtained through conventional breeding, mutagenesis, or recombinant DNA techniques. These can be cultivars, varieties, biotypes, or genotypes.

[0017] The compounds of formula (I) and their salts of the present invention can be advantageously used to treat transgenic plants, cultivars, or plant parts that have received genetic material that confers advantageous and / or useful characteristics (traits) to these plants, cultivars, or plant parts. Therefore, it is conceivable to combine the present invention with one or more recombinant traits or transgenic events, or combinations thereof. For the purposes of this application, a transgenic event is produced by inserting a specific recombinant DNA molecule into a specific location (site) on a plant genome chromosome. This insertion creates a new DNA sequence referred to as a “line,” characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to / flanked at both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, wherein the trait is determined relative to plants lacking such a trait or transgenic event. Specific examples of such advantageous and / or useful traits are better plant growth, vigor, stress tolerance, uprightness, lodging resistance, nutrient uptake, plant nutrition and / or yield, especially improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated ripening, higher yield, higher quality and / or higher nutritional value of harvested products, better storage life and / or processability of harvested products, and enhanced resistance to animal and microbial pests (e.g., insects, arachnids, nematodes, mites, slugs and snails).

[0018] As used herein, the term "unwanted vegetation" (also known as "weeds") should be understood to include any vegetation growing where crops are planted or where sown crops and other desired crops are located, wherein said vegetation is any plant species other than sown crops or desired dicotyledonous crops, including their germinating seeds, seedlings, and rooted vegetation. In the broadest sense, weeds are considered plants that are undesirable in a particular location.

[0019] Some representative examples of monocotyledonous and dicotyledonous weed communities that can be controlled by the compounds of formula (I) of the present invention are as follows, but it is not intended to limit the enumeration to specific genera and species.

[0020] The following genera are considered harmful monocotyledonous plants: *Aegilops*, *Agropyron*, *Agrostis*, *Alopecurus*, *Apera*, *Avena*, *Brachiaria*, *Bromus*, *Cenchrus*, *Commelina*, *Cynodon*, *Cyperus*, *Dactyloctenium*, *Digitaria*, *Echinochloa*, *Eleocharis*, *Eleusine*, and *Eragrosti*. s), Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochooria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0021] The following genera of dicotyledonous weeds are listed: *Abutilon*, *Amaranthus*, *Ambrosia*, *Anoda*, *Anthemis*, *Aphanes*, *Artemisia*, *Atriplex*, *Bellis*, *Bidens*, *Capsella*, *Carduus*, *Cassia*, *Centaurea*, *Chenopodium*, and *Thistle*. (Cirsium), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Linde *Rnia*, *Matricaria*, *Mentha*, *Mercurialis*, *Mullugo*, *Myosotis*, *Papaver*, *Pharbitis*, *Plantago*, *Polygonum*, *Portulaca*, *Ranunculus*, *Raphanus*, *Rorippa*, *Rotala*, *Rumex*, *Salvia* (Salsola), Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thraspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0022] According to the present invention, the compound of formula (I) may be used on its own or in the form of an agriculturally chemically acceptable salt. An agriculturally chemically acceptable salt includes an acid addition salt of a suitable inorganic or organic acid (e.g., inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid and nitric acid, or organic acids such as carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acid, e.g. p-toluenesulfonic acid).

[0023] According to the present invention, the compound of formula (I) is used in the form of a mixture of stereoisomers (Ia) and (Ib). This mixture can be prepared according to the steps described in WO2018 / 228985. Preferably, the stereoisomers (Ia) and (Ib) are present in a weight ratio (Ia) / (Ib) in the range of 30:70 to 70:30, more preferably in the range of 45:55 to 55:45.

[0024] According to the present invention, in order to control unwanted vegetation, an effective amount of a compound of formula (I) and / or its salts is applied to the planting site of dicotyledonous crops, preferably to the entire planting area. As used herein, the term "effective amount" means an amount sufficient to control unwanted vegetation without causing substantial damage to the dicotyledonous crops.

[0025] The application rate of herbicidal compounds of formula (I) or its salts can vary over a wide range and generally depends on the treatment type, such as, for example, spraying or sprinkling, weather conditions, period of year, application time, specific dicotyledonous crop, and whether the compound of formula (I) is combined with other herbicides. Suitable application rates of compounds of formula (I) for selective control of harmful vegetation in dicotyledonous crops are in the range of 10 to 500 g ai / ha, preferably 10 to 350 g ai / ha, and most preferably 25 to 200 g ai / ha.

[0026] If the dicotyledonous crop is soybean, the compound of formula (I) and / or its salt is preferably applied at a rate in the range of 25 to 150 g ai / ha.

[0027] Compound (I) can be applied using a composition containing compound (I) and / or its salts. This composition is preferably applied to the entire planted area via a spray or infusion (sprayable) formulation or a soluble or dispersible formulation. Spraying and infusion application at a water volume of 50-10,000 liters per hectare can be performed using all conventional application equipment, such as large-motor-driven specialized sprayers, backpack sprayers, hose-end applicators, RTU pump sprayers, aerosol cans, ULV applicators, or sprinkler cans.

[0028] This application can be carried out by broadcasting, covering the entire cultivation and planting or sowing area, or by broadcasting only within sections, strips, strips, or points within the cultivation area. The application can also be targeted at specific areas, based on camera identification of emerging weeds, or, in cases of uneven crop emergence, around emerging crop plants, based on a georeferenced weed map generated from previous season records of emerging weeds or weed infestation, based on weed identification, yield decline, or monitoring of previous crop growth.

[0029] The application rate can be kept constant or adjusted based on weed density and species composition, topography, and soil type.

[0030] In addition, the composition can be applied by spraying or as a granular formulation (active ingredient on an inert material or fertilizer). For all application methods, the product can also be watered with additional irrigation after application.

[0031] In one embodiment, the composition comprising a compound of formula (I) or a salt thereof is applied to the planting area in the form of a sprayable liquid formulation. In another embodiment, the composition is applied to the planting area in a granular formulation. Suitable granules include inert granules and fertilizer granules. The active ingredient may be dispersed throughout the granule, impregnated into the interior of the granule, or coated on the surface of the granule.

[0032] The herbicidal effect of the compound of formula (I) of the present invention can be enhanced by using a surfactant, preferably selected from vegetable oil-based surfactants.

[0033] The term "vegetable oil-based surfactant" should be understood to refer to oils from oilseed plant species, such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, or castor oil, especially soybean oil or rapeseed oil, and their transesterification products, such as alkyl esters, like rapeseed oil methyl ester and rapeseed oil ethyl ester (e.g., Stevie's Mero). ® ), or methylated soybean oil (such as Destiny) ® HC).

[0034] Plant oil-based surfactants are preferably C 10 -C 22 Fatty acid esters, preferably C 12 -C 20 Fatty acid esters. C 10 -C 22 Fatty acid esters are, for example, unsaturated or saturated C-type fatty acids, especially those with an even number of carbon atoms. 10 -C 22 Fatty acids (such as erucic acid, lauric acid, palmitic acid) and especially C 18 Esters of fatty acids (such as stearic acid, oleic acid, linoleic acid, or linolenic acid).

[0035] C 10 -C 22 Examples of fatty acid esters are those made by combining glycerol or ethylene glycol with C, which is present in, for example, oils of oilseed plants. 10 -C 22 Esters obtained from fatty acid reactions, or through the aforementioned glycerol or ethylene glycol C 10 -C 22 Fatty acid esters and C1-C 20 C60 is obtained by transesterification of alcohols (such as methanol, ethanol, propanol, or butanol). 10 -C 22 Fatty acid C1-C 20 Alkyl esters. Transesterification reactions can be carried out by known methods, for example, as described in the following literature: Römpp Chemie Lexikon, 9th edition, Vol. 2, p. 1343, Thieme Verlag Stuttgart.

[0036] Preferred C 10 -C 22 Fatty acid C1-C 20 Alkyl esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters, and dodecyl esters. Preferred are ethylene glycol and glycerol C. 10 -C 22 Fatty acid esters are C 10 -C 22 Fatty acids (especially those with an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and especially C-type fatty acids) 18 A homogeneous or mixed ethylene glycol ester and glycerol ester of fatty acids (such as stearic acid, oleic acid, linoleic acid or linolenic acid).

[0037] In the herbicidal mixtures / compositions of the present invention, the vegetable oil-based surfactants may be present, for example, in the form of commercially available vegetable oil-based surfactants, particularly those based on soybean oil, such as Destiny. ® HC (Winfield United, main ingredient: methylated soybean oil), or those surfactants based on rapeseed oil, such as Hasten. ® (Victorian Chemical Company, Australia, hereinafter referred to as Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter referred to as ActirobB, main ingredient: rapeseed oil methyl ester), Rako-Binol ® (Bayer AG, Germany, hereinafter referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ®(Stefes, Germany, hereinafter referred to as Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero ® (Stefes, Germany, hereinafter referred to as Mero, main ingredient: rapeseed oil methyl ester).

[0038] Methylated seed oils, such as methylated soybean oil or rapeseed oil methyl esters, are particularly preferred. Methylated seed oils are produced through the esterification of vegetable-based oils with methanol. The methylation process increases the hydrophilic / lipophilic balance (HLB) of the seed oil. HLB describes the ability of a surfactant to associate with both hydrophilic and lipophilic compounds. Suitable methylated seed oils preferably have an HLB value of at least 12.

[0039] The appropriate application rate of the surfactant is in the range of 0.1 to 10 L / ha, preferably in the range of 0.2 to 5 L / ha, and most preferably in the range of 0.5 to 3.0 L / ha.

[0040] Therefore, another object of the present invention is the use of a composition comprising (i) a compound of formula (I) and / or its salt and (ii) a surfactant for the prevention of unwanted vegetation at the planting site of dicotyledonous crops by application prior to emergence of the dicotyledonous crop, wherein the surfactant is preferably selected from vegetable oil-based surfactants as described above. A composition comprising a compound of formula (I) and / or its salt and a surfactant based on methylated seed oil is preferred.

[0041] The compounds and compositions of formula (I) of the present invention can be formulated in various ways according to desired biological and / or physicochemical parameters. Examples of common alternative formulations are as follows: wettable powder (WP), water-soluble concentrate, emulsifiable concentrate (EC), aqueous solution (SL), emulsion (EW) (such as oil-in-water and water-in-oil emulsions), sprayable solution or sprayable emulsion, suspension concentrate (SC), dispersion, oil dispersion (OD), suspension emulsion (SE), dust (DP), seed-dressing product, granules (GR) for soil application or broadcasting or water-dispersible granules (WG), ultra-low volume formulations, microencapsulated dispersants or waxy dispersants.

[0042] The individual types of formulations are known in principle and described, for example, in the following literature: "Manual on Development and Use of FAO and WHO Specifications for Pesticides", FAO and WHO, Rome, Italy, 2002; Winnacker-Küchler, "Chemische Technologie" [Chemical Engineering], Vol. 7, C. Hanser Verlag Munich, 4th ed., 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker NY 1973; K. Martens, "Spray Drying Handbook", 3rd ed., 1979, G. Goodwin Ltd. London.

[0043] The required formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described in, for example, the following literature: "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to ClayColloid Chemistry", 2nd ed., J. Wiley & Sons, NY; Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte [Interface-active ethylene oxide adducts]", Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker Küchler, "ChemischeTechnologie [Chemical Engineering]", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986.

[0044] Wettable powders (sprayable powders) are products that can be uniformly dispersed in water. In addition to active ingredients and one or more diluents or inert substances, they also include ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylene alkylphenols, polyethoxylated fatty alcohols or fatty amines, propylene oxide / ethylene oxide copolymers, alkyl sulfonates or alkylbenzene sulfonates or alkylnaphthalene sulfonates, sodium lignin sulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoylmethyl taurate.

[0045] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent or solvent mixture, such as butanol, cyclohexanone, dimethylformamide, acetophenone, xylene, or an aromatic hydrocarbon with a higher boiling point, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include: calcium alkyl aryl sulfonates (such as calcium dodecylbenzene sulfonate), nonionic emulsifiers (such as fatty acid polyethylene glycol esters), alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, or polyoxyethylene sorbitan esters.

[0046] Powders are obtained by grinding active compounds with finely ground solids, such as talc, natural clays like kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0047] Suspension concentrates are aqueous suspensions of active compounds. They can be prepared by wet milling, for example, using a commercially available bead mill, and optionally by adding other surfactants as listed above for other formulation types. In addition to one or more suspended active compounds, other active compounds may also be present in the formulation in a dissolved form.

[0048] Oil dispersants are oil-based suspensions of active compounds. Here, "oil" refers to any organic liquid, such as vegetable oils, aromatic or aliphatic solvents, or alkyl esters of fatty acids. They can be prepared by wet milling, for example, using a commercially available bead mill, and, if appropriate, other surfactants (wetting agents, dispersants) as mentioned above when discussing other formulation types may be added. In addition to one or more active compounds in suspension, other active compounds may also exist in a dissolved form in the formulation.

[0049] Emulsions, such as oil-in-water emulsions (EWs), can be prepared from a mixture of water and a water-immiscible organic solvent using a stirrer, colloid mill, and / or static mixer. If appropriate, other surfactants, as mentioned above when discussing other formulation types, may also be added. Here, the active compound exists in dissolved form.

[0050] Granules can be prepared by spraying an active compound onto an absorbent granular inert material, or by applying a concentrate of the active compound to the surface of a carrier (e.g., sand, kaolin, chalk, or granular inert material) using an adhesive (e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oil). Suitable active compounds can also be granulated using methods conventional for preparing fertilizer granules—if desired—as a mixture with fertilizer. Water-dispersible granules are generally prepared using conventional methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without a solid inert material. For the preparation of disc pellets, fluidized bed pellets, extruder pellets, and spray pellets, see, for example, the processes described in the following literature: "Spray-Drying Handbook," 3rd edition, 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration," Chemical and Engineering 1967, p. 147 and subsequent pages; "Perry's Chemical Engineer's Handbook," 5th edition, McGraw Hill, New York, 1973, pp. 8-57.

[0051] For further details on crop protection composition formulations, see, for example: GC Klingmam, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; JD Freyer, SA Evans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0052] Agricultural chemical formulations typically contain 0.1 to 99 wt% of the active compound of the herbicide component, particularly 2 to 95 wt%, with the following concentrations being conventional depending on the formulation type: In wettable powders, the concentration of the active compound is, for example, about 10 to 95 wt%, with the balance consisting of conventional formulation components up to 100 wt%. In emulsifiable concentrates, the concentration of the active compound can be, for example, 5 to 80 wt%. In most cases, powder formulations contain 5 to 20 wt% of the active compound, and sprayable solutions contain about 0.2 to 25 wt% of the active compound. In the case of granules (such as dispersible granules), the content of the active compound depends in part on whether the active compound is in liquid or solid form, and what granulation aids and fillers are used. In the case of water-dispersible granules, the content is typically between 10 and 90 wt%.

[0053] In addition, the above-mentioned active compound formulations may optionally include corresponding conventional adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors, pH adjusters or viscosity adjusters.

[0054] When applied, formulations containing compounds of formula (I) are diluted in a conventional manner where appropriate, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powder formulations, soil application granules, spreadable granules, and sprayable formulations are generally not diluted with other inert substances before application.

[0055] General Formulation Examples a) The powder is obtained by mixing 10 parts by weight of the active compound / active compound mixture with 90 parts by weight of talc (as an inert substance) and pulverizing the mixture in a hammer mill.

[0056] b) A wettable powder that is easily dispersible in water is obtained by mixing 25 parts by weight of an active compound / active compound mixture, 64 parts by weight of kaolin-containing clay (as an inert substance), 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleomethyl taurate (as a wetting agent and dispersant), and grinding the mixture in a nail disc mill.

[0057] c) A suspension concentrate that is easily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture, 5 parts by weight of tristyrylphenol polyethylene glycol ether (Soprophor BSU), 1 part by weight of sodium lignosulfonate (Vanisperse CB), and 74 parts by weight of water, and grinding the mixture in a friction ball mill to a fineness of less than 5 micrometers.

[0058] d) An oil dispersant that is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture, 6 parts by weight of an alkylphenol polyethylene glycol ether (Triton® X 207), 3 parts by weight of an isotridecyl polyethylene glycol ether (8 EO), and 71 parts by weight of a paraffin mineral oil (boiling range, for example, about 255 to 277°C), and grinding the mixture in a friction ball mill to a fineness of less than 5 microns.

[0059] e) The emulsifiable concentrate is obtained by mixing 15 parts by weight of the active compound / active compound mixture, 75 parts by weight of cyclohexanone (as a solvent), and 10 parts by weight of ethoxylated nonylphenol (as an emulsifier).

[0060] f) Water-dispersible granules are obtained by mixing the following components. 75 parts by weight of active compound / mixture of active compounds 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, The mixture is ground in a nail-disc mill and granulated into powder in a fluidized bed by spraying water (as a granulation liquid).

[0061] g) Water-dispersible granules are also obtained by homogenizing and pre-powdering the following components in a colloid mill. 25 parts by weight of active compound / mixture of active compounds 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate 2 parts by weight of sodium oleoylmethyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water, The mixture is then ground in a bead mill, and the resulting suspension is atomized and dried in a spray tower using a single-phase nozzle.

[0062] Compounds of formula (I) may also be used in combination with other active ingredients or nutrients (e.g., insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators), or in combination with compounds or compositions containing other active ingredients or nutrients.

[0063] According to the invention, the term "combination" refers to various combinations of compound (I) and other active ingredients or nutrients, such as in a single "premix" form, as a combined spray mixture consisting of a single formulation of a single active compound, such as a "tank mix," and when a single active ingredient is used in combination in a sequential manner, i.e., applied sequentially over a reasonable period of time, such as several hours or days. Preferably, the order in which the active compounds are applied is not important for carrying out the invention.

[0064] In some preferred embodiments of the invention, the compound of formula (I) is used in combination with at least one other herbicide, preferably in the form of a composition comprising the compound of formula (I) and at least one other herbicide.

[0065] Therefore, another object of the present invention is to include (i)(2R) 4R The use of a composition of methyl tetrahydrofuran-2-carboxylate (I) and / or its salts and (ii) at least one other herbicide for the prevention of unwanted vegetation at the planting site of dicotyledonous crops by application prior to the emergence of dicotyledonous crop plants.

[0066] As used herein, unless otherwise stated, the term "herbicide" refers to a compound produced, sold, or used in the field to kill or inhibit the growth of unwanted plants (such as, but not limited to, harmful or bothersome weeds, unwanted broadleaf plants, grasses, and sedges), and it can be used for crop protection, building protection, or lawn protection. The term "herbicide" includes herbicide products for end-use. Such compositions can be pure compounds, solutions of chemical compounds, mixtures of chemical compounds, emulsions, suspensions, solid-liquid mixtures, or liquid-liquid mixtures. The term "herbicide" also refers to products delivered commercially from the manufacturer to the end-user, who may apply the herbicide in its commercial form to the affected field or mix it with other adjuvants.

[0067] Examples of herbicides that can be used in combination with compounds of formula (I) are: Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazone, amidochlor, amidosulfuron, 4 -Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrol, ammonium aminosulfonate (AM) oniumsulfamate), ailofos, asulam, asulam-potassium, asulamsodium, atrazin, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benzolin, benzolin-ethyl, benzolin- Benazolin-dimethylammonium, benzolin-potassium, benzfluralin, benzuresate, benzsulfuron, benzsulfuron-methyl, benzulide, benzalkonium chloride, benzalkonium chloride sodium, benzobicyclon, benzofenap, and bicyclopyron.Bifenox, bilanafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozon, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim, bromoxynil, bromobutide Bromoxynil-butyrat, bromoxynil-potassium, bromoxynil-heptanoate, and bromoxynil-octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, and chlorpyrifos. fenstrole, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamin, chloramben-methyl, chloramben-methylammonium, chloramben-sodium Sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethylChlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cyhalothrin (i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1] [Heptane], exo-(-)-cycloheptanyl (i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, cromazine, comeprop, clopyralid, methyl clopyralid (c Clopyralid-methyl, clopyralid-olamin, clopyralid-potassium, clopyralid-tripomin, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuro n), cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (and ammonium salts), 2,4-D-butoxyethyl ester (2,4-D-butoyl), 2,4-D-butyl ester, 2,4-D-choline, 2,4-D-dimethylammonium, 2,4-D-diethylammonium, 2,4-D-diolamine, 2,4-D-doboxyl, 2,4-D-dodecylammonium, 2,4-D-etexyl, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-heptylammonium, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester,2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl ester, 2,4-D-potassium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-triisopropanolammonium, 2,4-D-tripromine and 2,4-D-trolamine salts), 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium salt (dal apon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decyl alcohol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts (e.g., dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butoxyethyl ester). dicamba-cholin, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamine, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine ne), dicamba-olamin, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, and dichlorprop-butotyl.Dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isooctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, and purified dichlorprop-P are all dichlorpropamides. Dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, difenzoquat- Metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, doxycycline Inoterb, dinoterb-acetate, diphenamid, diquat, diquat-dibromid, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endothal, endothal-diammoniumEndothal-dipotassium, Endothal-disodium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, F-5231 (i.e., N-[2- Chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasul fone), fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyraux ifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralinFluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, sodium tetrafluoropropionate ( Flupropanate-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron-sodium. Sodium glufosinate, fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate.Glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium, and glyphosate-trimesium H-9201 (O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, and haloxyfop. Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Haloxyfop-sodium, Hexazinone, HNPC-A8169 (i.e., (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propionic acid prop-2-yn-1-yl ester), HW-02 ( Specifically, 1-(dimethoxyphosphoryl)-ethyl(2,4-dichlorophenoxy)acetate, hydantocidin, isoxaflutole, isoxaflutole-methyl, imidacloprid, imidacloprid-methyl, methoxyimidacloprid, methoxyimidacloprid-ammonium, imidacloprid-nicotinic acid, imidacloprid-ammonium, and imidacloprid-nicotinic acid.Imidazopyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin-methyl, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iodosulfuron, iodine Iodosesulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, ioxynil-octanoate, ioxynil-potassium, and ioxynil-sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, and isoxaflutole. xaben), isoxaflutole, karbutilate, KUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, ketospiradox-potassium, lactoferrin, lenacil, linuron, MCPA, MCPA-butotyl, MCPA-bu MCPA-2-ethylhexyl ester, MCPA-ethyl ester, MCPA-isobutyl ester, MCPA-isoctyl ester, MCPA-isopropyl ester, MCPA-isopropylammonium, MCPA-methyl ester, MCPA-olamin ester, MCPA-potassium esterMCPA-sodium and MCPA-trolamin, MCPB, MCPB-methyl, MCPB-ethyl and MCPB-sodium, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), 2-methyl-4-chloropropionic acid dimethylammonium (mecoprop-dimethylammonium), 2-methyl-4-chloropropionic acid diethanolamine (mecoprop-diolamin), mecoprop- etexyl, mecoprop-ethadyl, isooctyl 2-methyl-4-chloropropionate, methyl 2-methyl-4-chloropropionate, potassium 2-methyl-4-chloropropionate, sodium 2-methyl-4-chloropropionate, triethanolamine 2-methyl-4-chloropropionate, purified 2-methyl-4-chloropropionic acid, purified butoxyethyl 2-methyl-4-chloropropionate, dimethyl 2-methyl-4-chloropropionate Mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mefluidide-diolamin, mefluidide-potassium, mesosulfuron, mesosulfuron-methionine l), mesosulfuron-sodium, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron.Metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclon, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron-methyl, MT-5950 (i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), neburon, nicosulfuron, pelargonic acid acid, norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam Pentachlorophenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamin, picloram-potassium, picloram-triethylammoniumPicloram-tripromin, picloram-trolamin, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, and doxychlor. (propachlor), propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyrazosulfuron Pyraflufen, pyraflufen-ethyl, pyraquinat, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyrimidinoxime-pyrazosulfuron (pyribenzoxim), pyributicarb, pyridafol, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quincloracQuinclorac-dimethylammonium, quinclorac-methyl (methyl quinclorac), quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201 (i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one), rimsulfuron, saflufenacil, olefins Sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioimidazolidine-4,5-dione), 2,3,6-TBA, TCA Trichloroacetic acid and its salts (such as ammonium trichloroacetate, calcium trichloroacetate, ethyl trichloroacetate, magnesium trichloroacetate, sodium trichloroacetate), tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron.Thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron-methyl, tribensulfuric acid, tribensulfuric acid, trilopyr, trilopyr-butotyl, triclopyr Trilopyr-cholin, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate sulfate), Vernolate, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), methyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydroxypyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydroxypyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydroxypyrimidin-1) Ethyl (2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carboxylic acid, ethyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydroxypyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carboxylic acid, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether,2-(3,4-Dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophene-5-yl)methyl ketone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophene-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate, 4-{2-chloro-3- [(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-(methanesulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylate, cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid prop-2-ynyl 1-yl ester, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, benzyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine 2-Carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl-4-amino-3-chloro-6-[1-(2,2-dimethylpropionyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl-4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl] Pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolin-2-one4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazoline-2-one, 6-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methanesulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohexyl-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl) Pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazine-3-yl)pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 4-(pyridazine-3-yl)-1-(2-sulfoethyl)pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazolyl-2-yl)pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazolyl-2-yl)pyridazine-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate). 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazine-1-onium salt (with a suitable anion, such as chloride, acetate or trifluoroacetate), 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, 2-ethoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylic acid, 2-methoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylic acid, 2-methoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6- Dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropane carboxylic acid, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopentane[d][1,2]oxazolidin-6a-carboxylic acid methyl ester,3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopentane[d][1,2]oxazol-6a-carboxylic acid ethyl ester.

[0068] Preferred herbicides that can be used in combination with compounds of formula (I) are selected from acetochlor, aclofen, ametryn, amitrole, bentazone, chlorimuron, chlorimuron-ethyl, clonzone, cloransulam, cloransulam-methyl, dimenthenamid, diflufenican, flufenacet, flumioxazin, fluometuron, and flufenacet. Ridone, Fomesafen, Fomesafen-sodium, Foramsulfuron, Glyphosate, Glyphosate-ammonium, Glyphosate-isopropylammonium, Glyphosate-diammonium, Glyphosate-dimethylammonium, Glyphosate-potassium, Glyphosate-sodium, Glyphosate-sodiumglyphosate-trimesium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, isoxaflutole The following herbicide names are listed: ole), mesotrione, metribuzin, metolachlor, norflurazon, oryzalin, oxadiargyl, oxadiazon, oxaziclomefon, oxyfluorfen, pendimethalin, phenmedipham, propyzamide, prosulfocarb, pyraflufen, pyraflufen-ethyl, pyrasulfotole, rimsulfuron, saflufenacil, simazine, sulfentrazone, and S-metolachlor.

[0069] The herbicides mentioned in this article are those known, for example, from The Pesticide Manual, 16th edition, 2012.

[0070] Compounds of formula (I) may be used in combination with other active ingredients selected from: insecticides, acaricides, nematicides, fungicides, safeners, fertilizers and / or growth regulators and their compounds or compositions.

[0071] Examples of suitable plant growth regulators include:Abscisic acid and related analogues [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexyl-2-en-1-yl]-3-methylpent-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexyl-2-en-1-yl]-3-methylpent-2,4-dienoic acid (dienoate), (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-dienoic acid)] -Oxycyclohexyl-2-en-1-yl)pent-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexyl-2-en-1-yl)-3-(trifluoromethyl)pent-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexyl-2-en-1-yl)-3-(trifluoromethyl)pent-2,4-dienoic acid methyl ester, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1]).[0] Heptan-3-en-2-yl)-3-methylpentane-2,4-dienoic acid], activated ester (acibenzolar), activated ester (acibenzolar-S-methyl), S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (isopropylidene)-aminooxyacetic acid-2-(methoxy [(Isopropyl)-2-oxoethyl ester, (isopropyl)-aminooxyacetic acid-2-(hexyloxy)-2-oxoethyl ester, (cyclohexyl)-aminooxyacetic acid-2-(isopropoxy)-2-oxoethyl ester], 1-aminocyclopropyl-1-ylcarboxylic acid and its derivatives (e.g., disclosed in DE3335514, EP30287, DE2906507 or US5123951), 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bik Inin, brassinolide, brassinolide-ethyl, L-canaline, catechins, and catechines (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-benzopyran-3,5,7-triol), chitooligosaccharide (CO; CO differs from LCO in that it lacks a fatty acid side chain, a characteristic of LCO. CO (sometimes called N-acetylchitosan) also contains GlcNAc residues, but has side chain modifications that distinguish it from chitin molecules [(C8H]). 13 NO5) n [CAS No. 1398-61-4] and chitosan molecules [(C5H] 11 NO4) n[CAS No. 9012-76-4]), chitosan compounds, chlormequat chloride chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamyl]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamyl]cyclohexanecarboxylic acid, daminozide, dazomet, sodium dazomet, n-decanol, dikegulac, dikegulac-sodium, yumpolyacrylic acid, dipotassium yumpolyacrylic acid, disodium yumpolyacrylic acid, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, chlormequat chloride, butyl fluorene, methyl fluorene, flurprimidol, forchlorfenuron, gibberellic acid acid), indo-3-acetic acid (IAA), 4-indo-3-ylbutyric acid, isoprethiolane, probenazole, jasmonic acid, jasmonic acid or its derivatives (e.g., methyl jasmonic acid, ethyl jasmonic acid), lipo-chitooligosaccharide (LCO, sometimes referred to as a symbiotic nodule (Nod) signal (or Nod factor) or Myc factor, consisting of an oligosaccharide backbone having an N-linked fatty acyl chain condensed at a non-reducing end with β-1,4-linked N-acetyl-D-glucosamine (“GlcNAc”) residues. As understood in the art, LCOs vary in the number of GlcNAc residues in the backbone, the length and saturation of the fatty acyl chain, and the substitution of reducing and non-reducing sugar residues), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride), mepiquatpentaborate, 1-methylcyclopropene, 3-methylcyclopropene, 1-ethylcyclopropene, 1-n-propylcyclopropene, 1-cyclopropenylmethanol, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinoline-6-yl)methylsulfonamide and related substituted tetrahydroquinoline-6-yl)methylsulfonamide, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-inden[1,2-b]furan-2-one and related lactones as outlined in EP2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its salts (e.g., sodium 4-phenylbutyrate, potassium 4-phenylbutyrate), phenylalanine, N-phenylphthalic acid, prohexadione, prohexadione-calcium, putrescine, prohydrojasmon, rhizobitoxin, salicylic acid, methyl salicylate, sarcosine, cycloprop-1-ene-1 Sodium 3-(cycloprop-2-en-1-yl)acetate, sodium 3-(cycloprop-2-en-1-yl)propionate, sodium 3-(cycloprop-1-en-1-yl)propionate, sidefungin, spermidine, spermine, strigolactone, tetrachloronitrobenzene, thidiazuron, triacontanol, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purine-6-amine.

[0072] A safener is a compound that prevents or reduces damage to beneficial plants without significantly affecting the weed-controlling effect of the compound of formula (I) on unwanted vegetation. Safeners can be applied before sowing (e.g., on seed treatment, buds, or seedlings) or before emergence in dicotyledonous crops. Safeners and compounds of formula (I) can be applied simultaneously or sequentially.

[0073] However, it is preferable to apply the compound of formula (I) and / or its salt in the absence of any safener.

[0074] Compounds of formula (I) can be used in combination with one or more suitable nutrients and / or fertilizers, such as organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), macrominerals (e.g., phosphorus, calcium, magnesium, potassium, sodium, iron, etc.), microminerals (e.g., boron, cobalt, chlorine, chromium, copper, fluorine, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), vitamins (e.g., vitamin A, B complex (i.e., vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9 ... 12 The compounds and compositions according to the invention can be combined with macronutrients and micronutrients of plants or microorganisms, including phosphorus, boron, chlorine, copper, iron, manganese, molybdenum, and / or zinc. According to certain embodiments, the compounds and compositions according to the invention can be used in combination with one or more beneficial micronutrients. Non-limiting examples of micronutrients used in the compositions described herein may include vitamins (e.g., vitamin A, B complex (i.e., vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B12, choline), vitamin C, vitamin D, vitamin E, vitamin K, carotenoids (α-carotene, β-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), macrominerals (e.g., phosphorus, calcium, magnesium, potassium, sodium, iron, etc.), microminerals (e.g., boron, cobalt, chlorine, chromium, copper, fluorine, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), and combinations thereof (e.g., BAYFOLAN secure, BAYFOLAN complete, BAYFOLAN energy, BAYFOLAN from Aglukon GmbH, Germany). In one particular aspect, the composition may include phosphorus, boron, chlorine, copper, iron, manganese, molybdenum and / or zinc, and combinations thereof. For compositions containing phosphorus, it is contemplated that any suitable phosphorus source may be used. For example, phosphorus may be derived from phosphate rock sources such as monoammonium phosphate, diammonium phosphate, monocalcium phosphate, superphosphate, triple superphosphate and / or polyammonium phosphate, organic phosphorus sources, or phosphorus sources that can be dissolved by one or more microorganisms (such as Penicillium mbilaiae).

[0075] The combination of compounds of formula (I) with other active compounds can be administered in the form of a tank mix, wherein optimally formulated concentrated formulations of each active compound are mixed together with water in a tank, and the resulting spray is applied. This has the advantages that the combination of active compounds can be applied more easily because the amounts of the components have been adjusted to the correct proportions to each other. Furthermore, the adjuvants in the formulation can be mutually optimized.

[0076] The present invention also relates to a method for controlling unwanted vegetation at planting sites of dicotyledonous crops, the method comprising applying a herbicidal effective amount (2R) before the dicotyledonous crop seedlings emerge. 4R Methyl tetrahydrofuran-2-carboxylate (I) (which exists in two stereoisomers: (Ia) of formula (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate and (Ib) of formula (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate and / or its salts are brought to the planting site. .

[0077] The information, preferred scope, and preferred embodiments given above regarding the uses of the present invention also apply to the methods of the present invention.

[0078] In particular, the following are especially preferred for the uses and methods of the present invention: - The dicotyledonous plants mentioned are selected from sunflower, flax, peanut, potato, lentil, soybean, kidney bean, broad bean, pea, chickpea, safflower, and cotton. Compound of formula (I) and / or its salts are applied at a rate of 10 to 350 g ai / ha, more preferably 25 to 200 g ai / ha. Compound of formula (I) and / or its salts are applied to the soil of the planting area after sowing or planting and before the emergence of dicotyledonous crop seedlings. The compound of formula (I) and / or its salt is applied in the form of a composition comprising the compound of formula (I) and / or its salt and a surfactant selected from vegetable oils, preferably methylated seed oils.

[0079] If the dicotyledonous crop is soybean, then the compound of formula (I) and / or its salt is preferably applied in the following form: - Apply at a rate ranging from 25 to 150 g ai / ha. - To be applied in the form of a composition comprising a compound of formula (I) and / or its salts and a vegetable oil-based surfactant, preferably methylated seed oil. - Apply to the soil in the planting area after sowing or planting and before the emergence of dicotyledonous crops.

[0080] Example In repeated field trials, the selectivity of compound (I) in controlling broad-spectrum weeds in dicotyledonous crops was determined by application before emergence of dicotyledonous crops and compared with commercially available herbicides.

[0081] The compound of formula (I) is used as a suspension concentrate (200 g / L) containing a mixture of stereoisomers (Ia) and (Ib), which is prepared according to the method described in WO2018 / 228985.

[0082] For comparative trials, the following commercially available formulations were used: Metribuzin: Suspension concentrate (600 g / L or 480 g / L) Aclonifen: Suspension concentrate (600 g / L) Clomazone: Microcapsule suspension (360 g / L) Flufenacet + Metribuzin: Water-dispersible granules (containing 240 g / kg flufenacet) + water-dispersible granules (containing 175 g / kg metribuzin) Pyroxasulfone: Water-dispersible granules (850 g / kg) Dimethenamid-P: EC (720 g / L) S-Metolachlor: EC (960 g / L) Pendimethalin: Microcapsule suspension (455 g / L) Sulfentrazone: Suspension concentrate (480 g / L) Glyphosate + isoxaflutole mixture: suspension concentrate (containing 480 g / L glyphosate acid, in the form of 588 g / L glyphosate potassium salt) + water-dispersible granules (containing 750 g / kg isoxaflutole) Example 1: Peanut (Arachis hypogaea) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for peanuts, a field trial was conducted in the spring under typical peanut-growing conditions in the southern United States. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using commercial tractor-pulled planting equipment, after which peanut seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting the peanuts. The treatments, as described in the table below, were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 187 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Destiny® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of peanuts per plot. The spray was calibrated to an application rate of 187 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0083] Twenty days after application (equivalent to 21 days after planting), the weed control effect on the established weeds was visually evaluated as a percentage (%), compared to the normally formed and untreated weeds growing in untreated soil. Rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control (meaning no visible emergence or death).

[0084] During the period from 13 to 63 days after application (13-63 DAA), the maximum damage to the resulting peanut plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as the weeds mentioned above.

[0085] The results are summarized in Table 1 below.

[0086] Table 1: g ai / ha: grams of active ingredient per hectare ARHHY: Peanuts AMAPA: Long-awned amaranth (Amaranthus palmeri) CONSS: Convolvulus spp. ECHCG: Barnyard grass (Echinochloa crus-galli) BRAPP: Brachiaria platyphylla ABUTH: Abutilon theophrasti MOLVE: Plant Mollugo verticillata. RCHSC: Richardia scabra MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 2: Common bean (Phaseolus vulgaris) and flax (Linum) usitatissimum), lentils (small lentils (lens culinaris)) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for common bean, lentil, and flax, a field trial was conducted in the northern United States under typical conditions in the spring. Land was initially prepared using a commercial tractor-pulled seeding device, after which crop seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatments were applied to moist, bare soil one day after planting. The treatments, as described in the table below, were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 187 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Destiny® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. Spraying was calibrated to an application rate of 187 L / ha of spray slurry. Each treatment was repeated three times in a completely randomized block design field trial.

[0087] Thirty-five days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of plants).

[0088] During the period of 14 to 35 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds mentioned above.

[0089] The results are summarized in Table 2 below.

[0090] Table 2: g ai / ha: grams of active ingredient per hectare PHSVX : Common bean (phaseolus vulgaris) LIUUT: Flax (linum usitatissimum) LENCU: Lentil (lens culinaris) (Lentinula) KCHSC: Kochia scoparia AMATA: Western Amaranth (Amaranthis rudis) SETVI: Setaria viridis ) PANRA: Urochloa ramosa LOLMU: Multiflorum ryegrass MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 3: Lentils (Lens culinaris) and two pea varieties (Pisum sativum) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for lentil and pea varieties, a field trial was conducted in the northern United States under typical conditions in the spring. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using commercial tractor-pulled seeding equipment, after which crop seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting. The treatments were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 187 L / ha, as shown in the table below. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Destiny® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 187 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0091] During the period of 27 to 53 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxic effect (%) relative to untreated control plants, according to the same rating criteria as in Examples 1 and 2.

[0092] The results are summarized in Table 3 below.

[0093] Table 3: g ai / ha: grams of active ingredient per hectare LENCU: Lentil (lens culinaris) (Lentinula) PIBSA (I): Early-maturing pod peas ( Pisum sativum subsp. Arvense ) ， The variety "Bluemoon" (pea) PIBSA (II): Early-maturing pod peas ( Pisum sativum subsp. Arvense ) ， The variety "Majestic" (pea) MSO: Methylated seed oil Example 4: Two sunflower varieties ( Helianthus annus ) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for sunflower, a field trial was conducted in the northern United States under typical conditions during the spring. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using commercial tractor-pulled seeding equipment, after which crop seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting. As described in the table below, the treatment was prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 187 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Destiny® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 187 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0094] Thirty-eight days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of weeds).

[0095] During the period from 14 to 38 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds mentioned above.

[0096] The results are summarized in Table 4 below.

[0097] Table 4: g ai / ha: grams of active ingredient per hectare HELAN (I): Sunflower (Helianthus annus), variety P64ME01 (common sunflower) HELAN (II): Sunflower (Helianthus annus), variety B8H307CL (common sunflower) AMAPA: Long-awned amaranth (Amaranthus palmeri) MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 5: Potato (Solanum tuberosum) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for potatoes, a field trial was conducted in northern Germany in spring under typical conditions. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using a commercial tractor-pulled planting device, after which tubers were planted in rows and mounded with soil as in commercial fields. The mounded soil was allowed to settle after planting, and the test treatment was applied to the moist, bare soil one day after planting. As shown in the table below, the treatments were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 300 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Stefes Mero® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed air-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 300 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0098] Sixty days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of plants).

[0099] During the period from 14 to 60 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds.

[0100] The results are summarized in Table 5 below.

[0101] Table 5: g ai / ha: grams of active ingredient per hectare SOLTU: Potato (Solanum tuberosum) "Pelikan" (potato) MATCH: Matricaria chamomilla CHEAL: Chenopodium album POLLA: Persicaria lapathifolia ECHCG: Barnyard grass (Echinochloa crus-galli) POLCO: Fallopia convolvulus MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 6: Broad beans (Vicia faba) and sunflowers (Helianthus annus) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for broad beans and sunflowers, field trials were conducted in spring in southern Germany under typical conditions. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using commercial tractor-pulled seeding equipment, followed by planting crop seeds in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting. The treatments, as shown in the table below, were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 300 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Stefes Mero® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 300 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0102] Forty-nine days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of plants).

[0103] During the period of 18 to 49 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds mentioned above.

[0104] The results are summarized in Table 6 below.

[0105] Table 6: g ai / ha: grams of active ingredient per hectare VICFX: Vicia faba "Fanfare" (broad bean) HELAN: Sunflower (Helianthus annuus) "Peredovick" (Sunflower) STEME: Stellaria media GASPA: Galinsoga parviflora MATCH: Matricaria chamomilla POATR: Kentucky bluegrass (Poa trivialis) MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 7: Chickpeas (Cicera arietinum) and sunflowers (Helianthus) annus), green bean (phaseolus vulgaris) To evaluate the selectivity of compound (I) as a pre-emergence herbicide for chickpeas, sunflowers, and common beans, a field trial was conducted in Canada under typical conditions in the spring. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using a commercial tractor-pulled seeding device, after which crop seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting. As shown in the table below, the treatments were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 180 L / ha. In addition to the herbicide, the spray slurry also contained 1.75 L / ha of methylated seed oil (Destiny® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 180 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0106] Forty-two days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of plants).

[0107] During the period from 13 to 42 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds mentioned above.

[0108] The results are summarized in Table 7 below.

[0109] Table 7: g ai / ha: grams of active ingredient per hectare CIEAR: Chickpea (Cicer arietinum) "CDC frontier" (chickpea) HELAN: Sunflower (Helianthus annuus) "Peredovick" (Sunflower) PHSVX: Nautica (bean) (Phaseolus vulgaris) AMARE: Amaranthus retroflexus SETVI: Setaria viridis CHEAL: Chenopodium album MSO: Methylated seed oil % Ground Cover: The percentage of a specific weed covering the area without herbicide treatment. Example 8: Soybeans (soybeans ( glycine max "BMX POTÊNCIA RR") To evaluate the selectivity of compound (I) as a pre-emergence herbicide for soybean, a field trial was conducted in spring in southern Germany under typical conditions. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using a commercial tractor-pulled seeding device, after which crop seeds were planted in rows as in commercial fields. After planting, the soil was allowed to settle, and the test treatment was applied to moist, bare soil one day after planting. The treatments, as shown in the table below, were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 200 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Stefes Mero® HC) in the treatment, as shown in the table below. Different treatments were applied using a compressed CO2-powered research backpack sprayer with a handheld spray bar equipped with an O2 flat fan nozzle, covering four rows of each crop per plot. The spray was calibrated to an application rate of 200 L / ha of spray slurry. Each treatment was repeated three times in a field trial with a completely randomized block design.

[0110] Forty-two days after application, the weed control effect on the formed weeds was visually evaluated as a percentage (%) compared to the normally formed and untreated weeds growing on untreated soil. The rating criteria ranged from 0% damage (indicating that the weeds exhibited the same growth habits and size as the untreated plants) to 100% damage or complete control of plants (meaning no visible emergence or death of plants).

[0111] During the period from 14 to 42 days after application, the maximum damage to the resulting crop plants was visually evaluated and determined as the percentage of maximum phytotoxicity effect (%) compared to the untreated control plants, according to the same rating criteria as for the weeds mentioned above.

[0112] The results are summarized in Table 8 below.

[0113] Table 8: 1) This dosage refers to glyphosate. g ai / ha: grams of active ingredient per hectare MSO: Methylated seed oil The results summarized in Tables 1 to 8 indicate that compounds of formula (I) exhibit good pre-emergence herbicidal activity against broad-spectrum weeds at application rates of 300 g / ha or less of the active ingredient, and show virtually no phytotoxicity to dicotyledonous crops at application rates up to 200 g ai / ha (flax, lentils, broad beans, kidney beans, soybeans) or even up to 300 g ai / ha (sunflower, peanuts, potatoes, peas, chickpeas). This is particularly applicable when applying tank mixtures of compounds of formula (I) and methylated seed oils.

[0114] Example 9: The effect of crop growth stage on crop selectivity, using potatoes as an example. solanum tuberosum For example, To evaluate the selectivity and crop growth stage limitations of compound (I) as a pre-emergence herbicide, a field trial was conducted in northern Germany under typical conditions in the spring. Potatoes were used in the trial. Fields were prepared for crop planting according to farmer practices. Land was initially prepared using a commercial tractor-pulled planting device, after which tubers were planted in rows and mounded with soil as in commercial fields. The mounded soil was allowed to settle after planting, followed by application of the test treatment. To assess the safe application window as a pre-emergence herbicide, five applications were scheduled at different developmental stages of the potato. Applications were made at BBCH growth stages 01, 03, 05, 08, and 10. At each application, the potato growth stage at the specific application time was checked in adjacent plots. Untreated plots were manually kept weed-free.

[0115] As described in the table below, the treatment agents were prepared by adding the corresponding dosage rate of the herbicide to a spray slurry with a water volume of 300 L / ha. In addition to the herbicide, the spray slurry also contained 1.5 L / ha of methylated seed oil (Stefes Mero® HC). Different treatment agents were applied using a compressed air research backpack sprayer with a handheld spray boom equipped with an O2 flat fan nozzle, covering four rows of each crop in each plot. The spray was calibrated to an application rate of 300 L / ha of spray slurry. Each treatment was repeated four times in a completely randomized block design field trial.

[0116] At 14, 28, and 42 days after crop emergence, the maximum damage to the resulting crop plants was visually assessed and determined as the percentage of maximum phytotoxicity effect (%) relative to the untreated control plants, according to the same rating criteria as for the weeds.

[0117] Potatoes were harvested 149 days after planting, and the yield of each treatment in the experiment was determined as kg tubers / plot and compared with the yield of untreated plots. The yield of potatoes that were not marketable was not considered. The measured yields in kg / plot and the relative yields compared to untreated plots are provided in the table below (Table 9).

[0118] Table 9: g ai / ha: grams of active ingredient per hectare SOLTU: Potato (Solanum tuberosum) "Bintje" (potato) MSO: Methylated seed oil is included in all treatments at 1.5 L / ha. DAA: Number of days after administration.

Claims

1. (2R 4R Methyl tetrahydrofuran-2-carboxylate (I) and / or its salts are used for the prevention of unwanted vegetation at the planting site of dicotyledonous crops by application before emergence of dicotyledonous crops. Formula (I) exists in two stereoisomers: (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isooxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ia) and (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isooxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ib). 。 2. The use according to claim 1, wherein the dicotyledonous crop plant is selected from sunflower, flax, peanut, potato, lentil, soybean, kidney bean, broad bean, pea, chickpea, safflower and cotton.

3. The use according to claim 1 or 2, wherein the compound of formula (I) and / or its salt is applied at an application rate in the range of 10 to 350 g ai / ha.

4. The use according to claim 1 or 2, wherein the compound of formula (I) and / or its salt is applied at an application rate in the range of 25 to 200 g ai / ha.

5. The use according to any one of the preceding claims, wherein the compound of formula (I) and / or its salt is applied after sowing or planting and before the emergence of dicotyledonous crop plants.

6. The use according to claim 5, wherein the compound of formula (I) and / or its salt is applied to a moist and firm seedbed for dicotyledonous crops.

7. The use according to any one of the preceding claims, wherein the dicotyledonous crop is soybean, and wherein the compound of formula (I) and / or its salt is applied at an application rate in the range of 25 to 150 g ai / ha.

8. The use according to any one of the preceding claims, wherein the application comprises a composition including a compound of formula (I) and / or a salt thereof, and a composition selected from vegetable oil-based surfactants.

9. Use of the compound of formula (I) according to any one of the preceding claims and / or its salt in the absence of a safener.

10. Use of a compound of formula (I) according to any one of the preceding claims and / or a salt thereof in combination with at least one other herbicide.

11. The use according to claim 10, wherein the compound of formula (I) and / or its salt is combined with at least one other herbicide selected from: acetochlor, aclofen, ametryn, amitrol, bentazone, chlorimuron, chlorimuron-ethyl, clonazon, cloransulam, cloransulam-methyl, dimethylphenidate. enthenamid, diflufenican, flufenacet, flumioxazin, fluometuron, fluridone, fomesafen, fomesafen-sodium, foramsulfuron, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium glyphosate diammonium, glyphosate dimethylammonium, glyphosate potassium, glyphosate sodium, glyphosate sesquisodium, glyphosate trimethylsulfonium, glufosinate, and glufosinate ammonium are all glyphosate diammonium, glyphosate potassium, glyphosate sodium, glyphosate sesquisodium, glyphosate trimethylsulfonium, glufosinate, and glufosinate ammonium are also mentioned. ), glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoatePotassium and sodium iodide, isoxaflutole, mesotrione, metribuzin, metolachlor, norflurazon, oryzalin, oxadiargyl, oxadiazon, oxaziclomefon, oxyfluorfen, pendimethalin Pendimethalin, phenmedipham, propyzamide, prosulfocarb, pyraflufen, pyraflufen-ethyl, pyrasulfotole, rimsulfuron, saflufenacil, simazine, sulfentrazone, S-metolachlor.

12. The use according to claim 10 or 11, wherein the application comprises a composition containing a compound of formula (I) and / or its salt and the other herbicide.

13. A method for controlling unwanted vegetation at a planting site of dicotyledonous crops, the method comprising applying a herbicide-effective amount (2R) before the dicotyledonous crops emerge. 4R Methyl tetrahydrofuran-2-carboxylate (I) and / or its salts are brought to the planting site, wherein formula (I) exists in two stereoisomers: methyl tetrahydrofuran-2-carboxylate of formula (Ia) as (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate and methyl tetrahydrofuran-2-carboxylate of formula (Ib) as (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate: 。 14. The method according to claim 13, wherein the dicotyledonous crop plant is selected from sunflower, flax, peanut, potato, lentil, soybean, kidney bean, broad bean, pea, chickpea, safflower and cotton.

15. The method according to claim 13 or 14, wherein the compound of formula (I) and / or its salt is applied to the soil of the planting area after sowing or planting and before the emergence of dicotyledonous crop plants.

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