Use of isoxazolinecarboxamide as pre-emergent herbicide in dicotyledonous crops

Abstract

The invention relates to the field of crop protection, more specifically to the use of methyl (2R*,4R*)-4- [[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I) and / or a salt thereof for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants.

Description

[0001] Use of isoxazolinecarboxamide as pre-emergent herbicide in dicotyledonous crops

[0002] The invention relates to the field of crop protection, more specifically to the use of methyl (2R*,4R*)-4- [[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2 -carboxylate (I) and / or a salt thereof for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants.

[0003] Compounds from the structural class of substituted isoxazolinecarboxamides are known from WO2018 / 228985 and WO2019 / 145245 as herbicides useful for weed control against a broad range of weeds in bum-down applications. It is also known to combine such herbicidal active ingredients with other herbicides for weed control, see e. g. WO 2020 / 114932.

[0004] For the purpose of weed control in dicotyledonous crops, the herbicide used must exhibit a selective action against the weeds without significantly damaging the crops, which emerge at the same spatial location as the weeds. However, many herbicides used in weed control management do not show the required level of selectivity. Some herbicides need to be applied in combination with a safener to achieve a sufficient level of selectivity. For example, it is known from WO 2021 / 245004 that substituted isoxazolinecarboxamides can be used as pre-emergent herbicides for monocotyledonous crops if they are applied in combination with a safener. Other agrochemicals do not control the weed plants sufficiently or do not control some weed species at all.

[0005] Accordingly, there is a need for novel and alternative methods to efficiently protect dicotyledonous crops against weeds without diminishing crop quality.

[0006] It is therefore an object of the present invention to provide improved control of undesired vegetation in dicotyledonous crop plants such as sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower, carrots, lactuca (lettuce), edamame, chicory, caraway, salsify, endivie artichoke, chamomile, coneflower and cotton.

[0007] This object has been achieved by the use of methyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H- isoxazole-5-carbonyl]amino]tetrahydrofuran-2 -carboxylate (I), which exists in the form of two stereoisomers: methyl (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]-amino]- tetrahydrofuran-2-carboxylate of formula (la) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl- 4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (lb), and / or a salt thereof for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants:

[0008] Surprisingly, it has been found that the isoxazolinecarboxamide of formula (I) exhibits high herbicidal activity against a broad spectrum of monocotyledon and dicotyledon weeds and has hardly any phytotoxic effect on dicotyledonous crops if applied prior to the emergence of the dicotyledonous crops. Co-application of a safener is not necessary to achieve a high level of selectivity. This particularly applies when mixtures of the compound of formula (I) with surfactants, such as methylated seed oil, are applied and application rates of 300 g active ingredient per hectare or less of compound (I) are used.

[0009] Another object of the invention is the use of a composition comprising methyl(2R*,4R*)-4-[[(5S)-3-(3,5- difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I) and / or a salt thereof for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants.

[0010] According to the invention, the compound of the formula (I) shows an excellent and desirable effect in terms of weed control in dicotyledonous crops without, or without substantial, injury to the crop and its quality in pre-emergence treatments, i.e. when applied prior to the emergence of the dicotyledonous crop.

[0011] The treatment can take place shortly before sowing or planting or thereafter but prior to the emergence of the dicotyledonous crop plants. The soil may already have undesired vegetation. Application onto bare soil with the broadleaf crop seeds underneath is however preferred. The term “seeds” as used herein also includes the planting of plant parts or tubers in case of e.g. potatoes. The compound (I) used according to the invention can be used to combat both already emerged and newly emerging weeds.

[0012] Preferably, the compound of formula (I) and / or salt thereof is applied after sowing or planting and prior to the emergence of the dicotyledonous crop plants, i.e., on the day of sowing or planting or up to a BBCH stage 09 of the crop plant, more preferably up to BBCH stage of 08 of the crop plant, onto the soil of the area under cultivation. More preferably, the compound of formula (I) and / or salt thereof is applied to a moist and firm seed bed of the dicotyledonous crop plants right after planting or sowing of the crop plants.

[0013] The treatment can be applied once or repeatedly. Suitable dicotyledonous crop plants are sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower, carrots, lactuca (lettuce), edamame, chicory, caraway, salsify, endivie artichoke, chamomile, coneflower and cotton.

[0014] Preferably, the dicotyledonous crop plants are selected from the group consisting of sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower, sesame, canola and cotton. Especially preferred dicotyledonous crops are sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea and chickpea.

[0015] The crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non- protectable by plant breeders’ rights.

[0016] Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

[0017] The compound of formula (I) and / or salt thereof used according to the invention can be advantageously used to treat transgenic plants, plant cultivars or plant parts that received genetic material which imparts advantageous and / or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention may be combined with one or more recombinant traits or transgenic event(s) or a combination thereof. For the purposes of this application, a transgenic event is created by the insertion of a specific recombinant DNA molecule into a specific position (locus) within the chromosome of the plant genome. The insertion creates a novel DNA sequence referred to as an “event” and is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to / flanking both ends of the inserted DNA. Such trait(s) or transgenic event(s) include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, in which the trait is measured with respect to a plant lacking such trait or transgenic event. Concrete examples of such advantageous and / or useful properties (traits) are better plant growth, vigor, stress tolerance, standability, lodging resistance, nutrient uptake, plant nutrition, and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and / or a higher nutritional value of the harvested products, better storage life and / or processability of the harvested products, and increased resistance against animal and microbial pests, such as against insects, arachnids, nematodes, mites, slugs and snails.

[0018] As used herein, the term "undesired vegetation" (also referred to as "weeds") is understood to include any vegetation growing at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired dicotyledonous crop. Weeds, in the broadest sense, are plants considered undesirable in a particular location.

[0019] Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the use of the compound of the formula (I) according to the invention are as follows, though the enumeration is not intended to impose a restriction to particular species.

[0020] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0021] Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0022] According to the invention, the compound of the formula (I) can be used as such or in form of a agrochemically acceptable salt. Agrochemically acceptable salts include acid addition salts of suitable inorganic or organic acids, for example mineral acids such as hydrogen chloride, hydrogen bromide, sulfuric acid, phosphoric acid and nitric acid, 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.

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

[0024] According to the invention, in order to control undesired vegetation, a herbicidally effective amount of the compound of the formula (I) and / or salt thereof is applied to the cultivation site for the dicotyledonous crop plants, preferably to the whole area under cultivation. As used herein, the term "effective amount" denotes an amount, which is sufficient for controlling the undesired vegetation and which does not result in a substantial damage to the dicotyledonous crop plants. The application rates for the herbicidal compound of formula (I) or salts thereof can vary within a broad range and generally depend on the type of treatment, such as, for example spraying or spreading, weather conditions, timing of the year, time of application, on the particular dicotyledonous crop, and on whether the compound of formula (I) is combined with other herbicides. Suitable applications rates for the compound of formula (I) for selective control of harmful vegetation in dicotyledonous crops are within the range of from 10 to 500 g a.i. / ha, preferably within the range of from 10 to 350 g a.i. / ha and most preferably within the range of from 25 to 200 g a.i. / ha.

[0025] If the dicotyledonous crop is soybean, the compound of formula (I) and / or a salt thereof is preferably applied at an application rate within the range of from 25 to 150 g a.i. / ha.

[0026] The compound of formula (I) can be applied using a composition comprising the compound of formula (I) and / or a salt thereof. The composition is preferably applied to the whole area under cultivation by spraying or drenching liquid (sprayable) formulations or dissolvable or dispersing formulations. Spray and drench application with water volumes from 50 to 10000 liter per hectare can be applied with all common application equipment like large motor driven professional spray equipment, knapsack sprayer, hose end applicators, RTU pump sprayers, arerosol cans, ULV applicators or watering cans.

[0027] The application can be done as broadcast application covering the entire cultivated and planted or seeded area, as well as only sections, bands, strips or spots within the cultivated area. The application can be targeted to specific areas, based upon camera recognition of already emerged weeds, surrounding already emerged crop plants in case of uneven crop emergence, based on georeferenced weed maps generated from monitoring emerged weeds or weed infestations recorded from previous seasons based on weed recognition, yield decrease or previous crop growth.

[0028] The applied dose rate can be kept constant or adjusted according to weed infestation in terms of density and species composition, topography and soil type.

[0029] Furthermore, the composition can be applied by spreading or granular (active ingredient on inert or active ingredient on fertilizer) formulations. It is also possible to water in the product after applications with additional irrigations for all application methods.

[0030] In one embodiment, the composition comprising the compound of formula (I) or salt thereof is applied to the area under cultivation as a sprayable liquid formulation. In another embodiment, the composition is applied to the area under cultivation as a granular formulation. Suitable granules include inert and fertilizer granules. The active ingredient may be dispersed throughout, impregnated into, or coated on the surface of the granules.

[0031] The herbicidal action of the compound of formula (I) used according to the invention can be enhanced by using surfactants, preferably selected from the groups of vegetable oil -based surfactants. The term vegetable oil -based surfactant is to be understood as meaning oils of oleaginous plant species, such as soybean oil, rapeseed oil, com oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular soybean oil or rapeseed oil, and also their transesterification products, for example alkyl esters, such as rapeseed oil methyl ester, rapeseed oil ethyl ester, such as Stefes Mero®, or methylated soybean oil, such as Destiny® HC.

[0032] The vegetable oil-based surfactants are preferably esters of C10-C22-, preferably C12-C20-, fatty acids. The Cw-C22-fatty acid esters are, for example, esters of unsaturated or saturated Cio-C22-fatty acids having, in particular, an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular Cis-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

[0033] Examples of Cio-C22-fatty acid esters are esters which are obtained by reacting glycerol or glycol with the Cio-C22-fatty acids present, for example, in oils of oleaginous plant species, or Cio-C22-fatty acid Ci-C2o-alkyl esters which can be obtained, for example, by transesterification of the glycerol or glycol Cio-C22-fatty acid esters mentioned above with Ci-C20-alcohols (for example methanol, ethanol, propanol or butanol). The transesterification can be carried out by known methods as described, for example, in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.

[0034] Preferred Cio-C22-fatty acid Ci-C2o-alkyl esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2- ethylhexyl esters and dodecyl esters. Preferred glycol and glycerol Cio-C22-fatty acid esters are the uniform or mixed glycol esters and glycerol esters of Cio-C22-fatty acids, in particular fatty acids having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular Cis-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

[0035] In the herbicidal mixtures / compositions according to the invention, the vegetable oil based surfactants can be present, for example, in the form of commercially available vegetable oil-based surfactants, in particular those based on soybean oil, such as Destiny® HC (Winfield United, main ingredient: methylated soybean oil), orthose based on rapeseed oil, such as Hasten® (Victorian Chemical Company, Australia, hereinbelow referred to as Hasten, main ingredient: rapeseed oil ethyl ester), Actirob®B (Novance, France, hereinbelow referred to as ActirobB, main ingredient: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany, hereinbelow referred to as Rako-Binol, main ingredient: rapeseed oil), Renol® (Stefes, Germany, hereinbelow referred to as Renol, vegetable oil ingredient: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinbelow referred to as Mero, main ingredient: rapeseed oil methyl ester).

[0036] Methylated seed oils, such as methylated soybean oil or rapeseed oil methyl ester, are particularly preferred. Methylated seed oils are produced by esterification of vegetable-based oils with methanol. The methylation process increases the hydrophilic / lipophilic balance (HLB) of the seed oil. The HLB describes the ability of a surfactant to associate with hydrophilic and lipophilic compounds. Suitable methylated seed oils preferably have a HLB value of at least 12. Suitable applications rates for surfactants are within the range of from 0.1 to 10 L / ha, preferably within the range of from 0.2 to 5 L / ha and most preferably within the range of from 0.5 to 3.0 L / ha.

[0037] Another object of the invention is therefore the use of a composition comprising (i) the compound of formula (I) and / or a salt thereof and (ii) a surfactant, preferably selected from the groups of vegetable oil-based surfactants as described above, for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants. Preference is given to compositions comprising the compound of formula (I) and / or salt thereof and a surfactant based on methylated seed oil.

[0038] The compound of formula (I) and the compositions used according to the invention can be formulated in various ways, according to the biological and / or physicochemical parameters required. Examples of general formulation options are: wettable powders (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), dispersions, oil dispersions (OD), suspoemulsions (SE), dusts (DP), seed-dressing products, granules for soil application or spreading (GR) or water-dispersible granules (WG), ultra-low volume formulations, microcapsule dispersions or wax dispersions.

[0039] The individual types of formulation are known in principle and are described, for example, in: "Manual on Development and Use of FAO and WHO Specifications for Pesticides", FAO and WHO, Rome, Italy, 2002; Winnacker-Ktichler, "Chemische Technologic" [Chemical Engineering], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker N.Y. 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

[0040] The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, 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. 1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schbnfeldt, "Grenzflachenaktive Athylenoxidaddukte [Interface-active ethylene oxide adducts]", Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker Ktichler, "Chemische Technologic [Chemical Engineering]", Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

[0041] Wettable powders (sprayable powders) are products which are uniformly dispersible in water and which, besides the active compounds and in addition to one or more diluents or inert substances, also comprise ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, propylene oxide / ethylene oxide copolymers, alkanesulfonates or alkylbenzenesulfonates or alkylnaphthalenesulfonates, sodium lignosulfonate, sodium 2,2’- dinaphthylmethane-6,6’ -disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. Emulsifiable concentrates are prepared by dissolving the active compounds in an organic solvent or solvent mixture, for example butanol, cyclohexanone, dimethylformamide, acetophenone, xylene or other higher- boiling aromatics or hydrocarbons with addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

[0042] Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0043] Suspension concentrates are water-based suspensions of active compounds. They may be prepared, for example, by wet grinding by means of commercially available bead mills and optional addition of further surfactants as have, for example, already been listed above for the other formulation types. In addition to the suspended active compound or active compounds, other active compounds may also be present in the formulation in dissolved form.

[0044] Oil dispersions are oil-based suspensions of active compounds, where oil is to be understood as meaning any organic liquid, for example vegetable oils, aromatic or aliphatic solvents, or fatty acid alkyl esters. They can be prepared, for example, by wet grinding by means of commercially available bead mills and, if appropriate, addition of further surfactants (wetting agents, dispersants) as have already been mentioned, for example, above in the case of the other formulation types. In addition to the suspended active compound or active compounds, other active compounds may also be present in the formulation in dissolved form.

[0045] Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers from mixtures of water and water-immiscible organic solvents and, if appropriate, further surfactants as have already been mentioned, for example, above in the case of the other formulation types. Here, the active compounds are present in dissolved form.

[0046] Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active compound concentrates to the surface of carriers such as sand, kaolinites, chalk or granulated inert material with the aid of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers. Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw Hill, New York 1973, p. 8-57. For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0047] Agrochemical formulations generally comprise from 0.1 to 99% by weight, in particular from 2 to 95% by weight, of active compounds of the herbicide components, the following concentrations being customary, depending on the type of formulation: In wettable powders, the active compound concentration is, for example, about 10 to 95% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In the case of emulsifiable concentrates, the active compound concentration can be, for example, from 5 to 80% by weight. In most cases, formulations in the form of dusts comprise from 5 to 20% by weight of active compound, sprayable solutions comprise about 0.2 to 25% by weight of active compound. In the case of granules such as dispersible granules, the active compound content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries and fillers are used. In water-dispersible granules, the content is generally between 10 and 90% by weight.

[0048] In addition, the active compound formulations mentioned optionally comprise the respective customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colourants and carriers, antifoams, evaporation inhibitors and pH- or viscosity-modifying agents.

[0049] For application, the formulation containing the compound of formula (I) is, 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 granules for scattering and sprayable formulations are not normally diluted further with other inert substances prior to application.

[0050] General formulation examples a) A dust is obtained by mixing 10 parts by weight of an active compound / active compound mixture and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill. b) A wettable powder which is readily 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 inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant, and grinding the mixture in a pinned-disc mill. c) A suspension concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 5 parts by weight of tristyrylphenol polyglycol 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 below 5 microns. d) An oil dispersion which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approx. 255 to 277°C), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. e) An emulsifiable concentrate is obtained from 15 parts by weight of an active compound / active compound mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. f) Water-dispersible granules are obtained by mixing

[0051] 75 parts by weight of an active compound / active compound mixture,

[0052] 10 parts by weight of calcium lignosulfonate,

[0053] 5 parts by weight of sodium lauryl sulfate,

[0054] 3 parts by weight of polyvinyl alcohol and

[0055] 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. g) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

[0056] 25 parts by weight of an active compound / active compound mixture,

[0057] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate

[0058] 2 parts by weight of sodium oleoylmethyltaurate,

[0059] 1 part by weight of polyvinyl alcohol,

[0060] 17 parts by weight of calcium carbonate and

[0061] 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.

[0062] It is also possible to use the compound of formula (I) in combination with other active ingredients or nutrients, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, or with combinations or compositions comprising thereof.

[0063] According to the invention, the expression “combination” stands for the various combinations of compound (I) and the other active ingredient or nutrient, for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other within a reasonably short period, such as a few hours or days. Preferably, the order of applying the active compounds is not essential for working the present invention.

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

[0065] Another object of the invention is therefore the use of a composition comprising (i) methyl(2R*,4R*)-4- [[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2 -carboxylate (I) and / or a salt thereof and (ii) at least one further herbicide for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants.

[0066] As used in this application and unless otherwise indicated the term “herbicide” refers to a compound that is produced, sold, or used in a field in order to kill or otherwise inhibit the growth of undesired plants such as, but not limited to, deleterious or annoying weeds, undesired broadleaf plants, grasses, and sedges; and can be used for crop protection, edifice protection or turf protection. The term “herbicide” includes the end-use herbicidal product. This composition can be a pure compound, a solution of chemical compounds, a mixture of chemical compounds, an emulsion, a suspension, a solid-liquid mixture, or a liquid-liquid mixture. The term “herbicide” also refers to the product that passes through the commercial channels from the manufacturer to the ultimate end user who can either apply the herbicide to the affected field as sold or mix it with other excipients.

[0067] Examples of herbicides which could be used in combination with the compound of formula (I) are: acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, 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, amitrole, ammoniumsulfamate, anilofos, asulam, asulam- potassium, asulam-sodium, atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium, benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, bentazone-sodium, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozon, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamin, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac -ammonium, chlorfenac-sodium, chlorfenprop, chlorfenpropmethyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, i.e. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2- methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, i.e. (lR,2S,4S)-4-isopropyl-l- methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid- methyl, clopyralid-olamin, clopyralid-potassium, clopyralid-tripomin, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (as well as ammonium, butotyl, butyl, cholin, dimethylammonium, diethylammonium, diolamine, doboxyl, dodecylammonium, etexyl, ethyl, 2- ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salts thereof), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon- sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl- pyrazolate (DTP), dicamba and its salts (e.g. dicamba-biproamine, dicamba-N,N-bis(3- aminopropyl)methylamine, dicamba-butotyl, dicamba-cholin, dicamba-diglycolamine, dicamba- dimethylammonium, dicamba-diethanolamine, dicamba-diethylammonium, dicamba-isopropyl- ammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamin, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2- oxazolidin-3 -one, 2-(2,5 -dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3 -one, dichlorprop, dichlorprop- butotyl, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop- isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, 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, dinoterb, dinoterb- acetate, diphenamid, diquat, diquat dibromide, diquat dichloride, dithiopyr, diuron, DNOC, DNOC- ammonium, DNOC-potassium, DNOC-sodium, endothal, endothal-diammonium, endothal-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-lH-tetrazol-l- yl]phenyl]ethansulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-lH-benzimidazol-4- yl] - 1 -methyl-6-(trifluoromethyl)pyrimidine-2,4( lH,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop- ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop- P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, 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, 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, i.e. O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P -methyl, haloxyfop-sodium, hexazinone, HNPC-A8169, i.e. Prop-2-yn-l-yl (2S)-2-{3-[(5- tert-butylpyridin-2-yl)oxy]phenoxy}propanoat, HW-02, i.e. l-(dimethoxyphosphoryl)ethyl (2,4- dichlorophenoxy)acetate, hydantocidin, icafolin, icafolin-methyl, imazamethabenz, imazamethabenz- methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr- isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin-methyl, imazethapyr, imazethapyr- ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, ioxynil-octanoate, -potassium and -sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3- ({ [5-(difluoromethyl)- 1 -methyl-3 -(trifluoromethyl)- lH-pyrazol-4-yl]methyl } sulfonyl)-5 ,5 -dimethyl -4,5 - dihydro- 1,2-oxazole, ketospiradox, ketospiradox-potassium, lactofen, lenacil, linuron, MCPA, MCPA- butotyl, -butyl, -dimethylammonium, -diolamin, -2-ethylhexyl, -ethyl, -isobutyl, -isooctyl, -isopropyl, - isopropylammonium, -methyl, -olamin, -potassium, -sodium and trolamin, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamin, mecoprop-etexyl, mecoprop-ethadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, mecoprop-trolamin, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2- ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamin, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, 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, monosulfuron-methyl, MT-5950, i.e. N-[3-chloro-4-(l-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, paraquat dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, phenmedipham-ethyl, picloram, picloram- dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamin, picloram- potassium, picloram-triethylammonium, picloram-tripromin, picloram-trolamin, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyraquinat, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac, pyriminobac- methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinclorac -dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop- ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, i.e. l-{2-chloro-3-[(3- cyclopropyl-5-hydroxy-l-methyl-lH-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e. 1 -ethoxy-3 -methyl- l-oxobut-3-en-2-yl

[0068] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2 -nitrobenzoate, SYP-300, i.e. l-[7-fluoro-3-oxo-4-(prop-2-yn- l-yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4, 5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid) and its salts,, e.g. TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-cholin, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron- methyl, tritosulfuron, urea 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-dihydropyrimidin- 1 (2H)-yl)phenyl)-5 -methyl -4,5 -dihydroisoxazol-5 -carboxylate, ethyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-l(2H)- yl)phenyl)-5-methyl-4,5 -dihydroisoxazol-5 -carboxylate, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4- trifluoromethyl-3,6-dihydropyrimidin-l(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-dihydropyrimidin- l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazol-5-yl]phenyl-5- chloropyrimidin-2-ylether, 2-(3 ,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] -

[0069] 6-methylpyridazin-3 (2 / / )-onc. 2-( {2-[(2-methoxyethoxy)methyl] -6-methylpyridin-3 -yl } carbonyl)cyclo- hexane-1, 3-dione, (5-hydroxy-l-methyl-lH-pyrazol-4-yl)(3,3,4-trimethyl-l,l-dioxido-2,3-dihydro-l- benzothiophen-5-yl)methanone, l-methyl-4-[(3,3,4-trimethyl-l,l-dioxido-2,3-dihydro-l-benzothiophen- 5-yl)carbonyl]-lH-pyrazol-5-yl propan- 1 -sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-lH-pyrazol-l- yl)methyl] -4-(methylsulfonyl)benzoyl } - 1 -methyl- lH-pyrazol-5 -yl- 1 ,3 -dimethyl- lH-pyrazol-4- carboxylate; cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2 -carboxylate, prop-2 -yn-l-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2 -carboxylate, methyl 4- amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, benzyl-4-amino-3-chloro-5- fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro- lH-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-l-isobutyryl-lH- indol-6-yl)pyridine-2-carboxylate, methyl 6-(l-acetyl-7-fluoro-lH-indol-6-yl)-4-amino-3-chloro-5- fluoropyridine-2-carboxylate, methyl-4-amino-3-chloro-6-[l-(2,2-dimethylpropanoyl)-7-fluoro-lH- indol-6-yl]-5-fluoropyridine-2 -carboxylate, methyl-4-amino-3-chloro-5-fluoro-6-[7-fluoro-l-

[0070] (methoxyacetyl)-lH-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7- fluoro-lH-indol-6-yl)pyridine-2 -carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6- yl)pyridine-2 -carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro- lH-indol-6-yl)pyridine-2- carboxylate, 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidin-2-one, 3-(5-tert- butyl-l,2-oxazol-3-yl)-4-hydroxy-l-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridine- 2-yl] -4-hydroxy- 1 -methylimidazolidin-2-one, 4-hydroxy- 1 -methoxy-5 -methyl-3- [4-(trifluoromethyl)- pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-l,5-dimethyl-3-(2- methylphenyl)quinazoline-2,4(lH,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l- en-l-yl)carbonyl]-l-methylquinazoline-2,4(lH,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-

[0071] (morpholin-4-ylmethyl)benzoyl] -3 -hydroxy cyclohex-2-en- 1 -one, 1 -(2-carboxyethyl)-4-(pyrimidin-2- yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoracetate), l-(2- carboxyethyl)-4-(pyridazin-3-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoracetate), 4-(pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoracetate), 4-(pyridazin-3-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoracetate), l-(2-carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l- ium salt (with suitable anions such as chloride, acetate or trifluoracetate), l-(2-carboxyethyl)-4-(l,3,4- thiadiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoracetate), 2- fluoro-N-(5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfmyl]-4-(trifluoromethyl)benzamide, 2- ethoxy-2-oxoethyl-l-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro- pyrimidin- 1 (2H)-yl]phenoxy } cyclopropanecarboxy lie acid, 2-methoxy-2 -oxoethyl- 1 -{2-chloro-4-fluoro- 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropane- carboxylic acid, {[(l-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro- pyrimidin-l(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4- dimethyl-l,2-oxazolidin-3-one, methyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)- 3 ,6-dihydropyrimidin- 1 (2H)-yl]phenyl } -3 a, 4, 5 ,6-tetrahydro-6aH-cyclopenta[d] [1,2] oxazol-6a- carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro- pyrimidin- 1 (2H)-yl]phenyl } -3a, 4, 5 ,6-tetrahydro-6aH-cyclopenta[d] [ 1 ,2] oxazol-6a-carboxylate .

[0072] Preferred herbicides which could be used in combination with the compound of formula (I) are selected from the group consisting of acetochlor, aclonifen, ametryn, amitrole, bentazone, chlorimuron, chlorimuron-ethyl, clomazone, cloransulam, cloransulam-methyl, dimenthenamid, diflufenican, flufenacet, flumioxazin, fluometuron, fluridone, fomesafen, fomesafen-sodium, foramsulfuron, glyphosate, glyphosate, glyphosate- ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium, glyphosate-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, mesotrione, metribuzin, metolachlor, norflurazon, oryzalin, oxadiargyl, oxadiazon, oxaziclomefon, oxyfluorfen, pendimethalin, phenmedipham, propyzamide, prosulfocarb, pyraflufen, pyraflufen-ethyl, pyrasulfotole rimsulfuron, saflufenacil, simazine, sulfentrazone, S-metolachlor.

[0073] The herbicides mentioned herein are known, for example, from "The Pesticide Manual", 16th edition 2012.

[0074] The compound of formula (I) can be used in combination with further active ingredients selected from the group comprising insecticides, acaricides, nematicides, fungicides, safeners, fertilizers and / or growth regulators and combinations or compositions comprising thereof.

[0075] Examples of suitable plant growth regulators are:

[0076] Abscisic acid and related analogs [e.g. (2Z,4E)-5-[6-Ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en- l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en- 1 -yl)penta-2,4-dienoic acid, (2E,4E)-5-( 1 -hydroxy-2, 6, 6-trimethyl-4-oxocyclohex-2-en- l-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5 -(1 -hydroxy-2, 6, 6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-l,3-dimethyl-5- oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzolar, acibenzolar-S-methyl, S- adenosylhomocysteine, allantoin, 2-Aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (Isopropylidene)-aminooxyacetic acid-2-(methoxy)-2-oxoethylester, (Isopropylidene)- aminooxyacetic acid-2-(hexyloxy)-2-oxoethylester, (Cyclohexylidene)-aminooxyacetic acid-2- (isopropyloxy)-2-oxoethylester], 1 -aminocycloprop- 1-yl carboxylic acid and derivatives thereof, e.g. disclosed in DE3335514, EP30287, DE2906507 or US5123951, 5 -aminolevulinic acid, ancymidol, 6- benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canaline, catechin and catechines (e.g. (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromen-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the pendant fatty acid chain that is characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc residues but have side chain decorations that make them different from chitin molecules [ (CSHBNO A- CAS No. 1398-61-4] and chitosan molecules [(CsHnNO^n, CAS No. 9012-76-4]), chitinous compounds, chlormequat chloride, cloprop, cyclanilide, 3 -(Cycloprop- l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclo- hexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, Jasmonic acid or derivatives thereof (e.g. jasmonic acid methyl ester, jasmonic acid ethyl ester), lipo-chitooligosaccharides (LCO, sometimes referred to as symbiotic nodulation (Nod) signals (or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of P-l,4-linked / V-acetyl-D-glucosamine (“GlcNAc”) residues with an N-linked fatty acyl chain condensed at the non-reducing end. As understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, in the length and degree of saturation of the fatty acyl chain and in the substitutions of reducing and non-reducing sugar residues), linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1- methylcyclopropene, 3 -methylcyclopropene, 1 -ethylcyclopropene, 1-n-propylcyclopropene, 1- cyclopropenylmethanol, methoxyvinylglycin (MVG), 3’-methyl abscisic acid, l-(4-methylphenyl)-N-(2- oxo-l-propyl-l,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-Methyl-5-oxo-2,5-dihydrofuran- 2-yl]oxy}methylen)-3,3a,4,8b-tetrahydro-2H-indeno[l,2-b]furan-2-one and related lactones as outlined in EP2248421, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate- mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its related salts (e.g. sodium-4-phenylbutanoate, potassium-4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, putrescine, prohydrojasmon, rhizobitoxin, salicylic acid, salicylic acid methyl ester, sarcosine, sodium cycloprop- 1-en-l-yl acetate, sodium cycloprop-2-en-l-yl acetate, sodium-3-(cycloprop-2-en-l-yl)propanoate, sodium-3 -(cycloprop- 1-en-l-yl) propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac- ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, 2-chloro-N-(3 -methoxy phenyl )-9H-purin-6-amine .

[0077] Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the compound of formula (I) towards the undesired vegetation. The safener can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application of the dicotyledonous crop plant. The safener and the compound of formula (I) can be applied either simultaneously or sequentially.

[0078] Preferably, however, the compound of formula (I) and / or salt thereof is applied in absence of any safener.

[0079] The compound of the formula (I) may be used in combination with one or more suitable nutrient(s) and / or fertilizer(s), such as organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), macrominerals (e.g., phosphorous, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), vitamins, (e.g., vitamin A, vitamin B complex (i.e., vitamin Bi, vitamin B2, vitamin Bs, vitamin B5, vitamin Be, vitamin B7, vitamin Bs, vitamin B ,. vitamin B12, choline) vitamin C, vitamin

[0080] D, vitamin E, vitamin K.), and / or carotenoids (a-carotene, P-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), and combinations thereof. In an aspect, the compound and the composition of the invention may be combined with macro- and micronutrients of plants or microbes, including phosphorous, boron, chlorine, copper, iron, manganese, molybdenum and / or zinc. According to some embodiments, the compound and the composition of the invention may be combined with one or more beneficial micronutrients. Non-limiting examples of micronutrients for use in compositions described herein may include vitamins, (e.g., vitamin A, vitamin B complex (i.e., vitamin Bl, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B 12, choline) vitamin C, vitamin D, vitamin

[0081] E, vitamin K, carotenoids (a-carotene, P-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), macrominerals (e.g., phosphorous, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), and combinations thereof (BAYFOLAN secure, BAYFOLAN complete, BAYFOLAN energy, BAYFOLAN power, Aglukon GmbH, Germany). In a particular aspect, compositions may comprise phosphorous, boron, chlorine, copper, iron, manganese, molybdenum, and / or zinc, and combinations thereof. For compositions comprising phosphorous, it is envisioned that any suitable source of phosphorous may be used. For example, phosphorus may be derived from a rock phosphate source, such as monoammonium phosphate, diammonium phosphate, monocalcium phosphate, super phosphate, triple super phosphate, and / or ammonium polyphosphate, an organic phosphorous source, or a phosphorous source capable of solubilization by one or more microorganisms (e.g., Penicillium bilaiae).

[0082] Combinations of the compound of formula (I) with other active compounds can be applied jointly in the form of tank mixes, where the optimally formulated concentrated formulations of the individual active compounds are, together, mixed in a tank with water, and the spray liquor obtained is applied. This has the advantage that the combination of active compounds can be applied more easily since the quantities of the components are already adjusted to the correct ratio to one another. Moreover, the auxiliaries in the formulation can be optimized to one another.

[0083] The present invention also relates to a method for control of undesired vegetation at a cultivation site for dicotyledonous crop plants comprising the step of applying a herbicidally effective amount of methyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbo-nyl]amino]tetrahydrofuran-2- carboxylate (I), which exists in the form of two stereoisomers: methyl (2R,4R)-4-[[(5S)-3-(3,5- difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]-amino]tetra-hydrofuran-2-carboxylate of formula (la) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetra- hydrofuran-2 -carboxylate of formula (lb), and / or a salt thereof prior to emergence of the dicotyledonous crop plants to the cultivation site:

[0084] The information, preferred ranges and preferred embodiments given above for the use according to the invention also apply to the method according to the invention.

[0085] In particular, the following is particularly preferred for the use according to the invention and the method according to the invention: the dicotyledonous crop plants are selected from the group consisting of sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower and cotton, the compound of formula (I) and / or salt thereof is applied at an application rate within the range of from 10 to 350 g a.i. / ha, more preferably 25 to 200 g a.i. / ha, the compound of formula (I) and / or salt thereof is applied after sowing or planting and prior to emergence of the dicotyledonous crop plants onto the soil of the area under cultivation, the compound of formula (I) and / or salt thereof is applied in form of a composition comprising the compound of formula (I) and / or salt thereof and a surfactant selected from the groups of vegetable oil-based surfactants, preferably methylated seed oil.

[0086] If the dicotyledonous crop is soybean, the compound of formula (I) and / or salt thereof is preferably applied at an application rate within the range of from 25 to 150 g a.i. / ha in form of a composition comprising the compound of formula (I) and / or salt thereof and a vegetable oil-based surfactant, preferably methylated seed oil, after sowing or planting and prior to emergence of the dicotyledonous crop plants onto the soil of the area under cultivation. Examples

[0087] The selectivity of the compound of formula (I) in controlling a broad spectrum of weeds in dicotyledonous crops through an application prior to the emergence of the dicotyledonous crop plants was determined in replicated field trials and compared with that of commercially available herbicides.

[0088] The compound of formula (I) was used in form of a suspension concentrate (200 g / L) containing a mixture of the stereoisomers (la) and (lb), prepared according to the method described in WO2018 / 228985.

[0089] For the comparative tests, the following commercially available formulations were used:

[0090] Metribuzin: suspension concentrate (600 g / L or 480 g / L)

[0091] Aclonifen: suspension concentrate (600 g / L)

[0092] Clomazone: microcapsule suspension (360 g / L)

[0093] Flufenacet + Metribuzin: waterdispersible granulate (containing 240 g / kg flufenacet) + waterdispersible granulate (containing 175 g / kg metribuzin)

[0094] Pyroxasulfone: water-dispersible granules (850 g / kg)

[0095] Dimethenamid-P : emulsion concentrate (720 g / L)

[0096] S-Metolachlor: emulsion concentrate (960 g / L)

[0097] Pendimethalin: microcapsule suspension (455 g / L)

[0098] Sulfentrazone: suspension concentrate (480 g / L)

[0099] 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)

[0100] Example 1 : Peanut (arachis hypogaea)

[0101] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on peanuts, a field trial was conducted in the southern US in the spring under typical conditions for peanut cultivation. The field was prepared for crop planting according to farmers practice. The peanut seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after peanut planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 187 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Destiny® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of peanuts per plot. The spray was calibrated to an application rate of 187 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design. 20 days after application (= 21 days after planting), the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants.

[0102] Over a period of from 13 to 63 days after application (13-63 DAA), the maximum damage to the developed peanut plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants.

[0103] The results are summarized in Table 1 below.

[0104] Table 1: g a.i. / ha: gram of active ingredient per hectare

[0105] ARHHY : Arachis hypogaeci (peanut)

[0106] AMAPA: Amaranthus palmeri

[0107] CONSS: Convolvulus spp. ECHCG: Echinocloa crus galli

[0108] BRAPP: Brachicirici platyphylla

[0109] ABUTH: Abutilon theophrasti

[0110] MOLVE: Mollugo verticillata

[0111] RCHSC: Richardici scabrci MSO: methylated seed oil

[0112] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment

[0113] Example 2: Common bean (phaseolus vulgaris), Flax (linum usitatissimum), Lentil (lens culinaris}

[0114] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on beans, lentil and flax, a field trial was conducted in the northern US in the spring under typical conditions. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 187 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Destiny® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 187 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design.

[0115] 35 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants.

[0116] Over a period of from 14 to 35 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants.

[0117] The results are summarized in Table 2 below.

[0118] Table 2: g a.i. / ha: gram of active ingredient per hectare

[0119] PHSVX. phaseolus vulgaris (common bean)

[0120] LIUUT: linum usitatissimum (flax)

[0121] LENCU: lens culinaris (lentil)

[0122] KCHSC: bassia scoparia

[0123] AMATA: amaranthus rudis

[0124] SETVI: setaria viridis

[0125] PANRA: urochloa ramosa

[0126] LOLMU: lolium multiflorum

[0127] MSO: methylated seed oil

[0128] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment

[0129] Example 3: Lentil (lens culinaris), 2 varieties of pea (pisum sativum)

[0130] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on lentil and pea varities, a field trial was conducted in the northern US in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 187 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Destiny® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 187 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design.

[0131] Over a period of from 27 to 53 days after application, the maximum damage to the developing crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described in examples 1 and 2.

[0132] The results are summarized in Table 3 below.

[0133] Table 3: g a.i. / ha: gram of active ingredient per hectare

[0134] LENCU. lens culinaris (lentil)

[0135] PIBSA (I): Pisum sativum subsp. Arvense, variety “Bluemoon” (pea)

[0136] PIBSA (II): Pisum sativum subsp. Arvense, variety “Majestic” (pea)

[0137] MSO: methylated seed oil

[0138] Example 4: Two varieties of sunflower (Helianthus annus)

[0139] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on sunflower, a field trial was conducted in the northern US in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 187 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Destiny® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 187 L / ha spray slurry.

[0140] Each treatment was replicated three times within the field trial in a completely randomized block design.

[0141] 38 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead weed plants.

[0142] Over a period of from 14 to 38 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants. The results are summarized in Table 4 below.

[0143] Table 4: g a.i. / ha: gram of active ingredient per hectare

[0144] HELAN (I): Helianthus annus, variety P64ME01 (common sunflower)

[0145] HELAN (II): Helianthus annus, variety B8H307CL (common sunflower) AMAPA: Amaranthus palmeri

[0146] MSO: methylated seed oil

[0147] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment

[0148] Example 5: Potato (Solanum tuberosum)

[0149] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on potato, a field trial was conducted in northern Germany in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The tubers were planted in rows and hilled as in commercial fields after initial ground preparation using commercial tractor pulled planting equipment. The hilled ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 300 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Stefes Mero® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed air powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 300 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design.

[0150] 60 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants.

[0151] Over a period of from 14 to 60 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described for the weed plants.

[0152] The results are summarized in Table 5 below.

[0153] Table 5: g a.i. / ha: gram of active ingredient per hectare

[0154] SOLTU: Solcinum tuberosum “Pelikan” (potatoe)

[0155] MATCH: Matricaria chamomilla

[0156] CHEAL: Chenopodium album

[0157] POLLA: Persicaria lapathifolia

[0158] ECHCG: Echinochloa crus-galli

[0159] POLCO: Fallopia convolvulus

[0160] MSO: methylated seed oil

[0161] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment

[0162] Example 6: Laba bean (vicia faba}, sunflower (helianthus annus)

[0163] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on faba bean and sunflower, a field trial was conducted in southern Germany in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 300 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Stefes Mero® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 300 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design. 49 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants.

[0164] Over a period of from 18 to 49 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants.

[0165] The results are summarized in Table 6 below.

[0166] Table 6: g a.i. / ha: gram of active ingredient per hectare

[0167] VICFX: Vicia faba “Fanfare” (faba bean)

[0168] HELAN: Helianthus annuus “Peredovick” (sunflower)

[0169] STEME: Stellaria media

[0170] GASPA: Galinsoga parviflora

[0171] MATCH: Matricaria chamomilla

[0172] POATR: Poa trivialis

[0173] MSO: methylated seed oil

[0174] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment Example 7: Chickpea (cicer arietinuni}. sunflower (helianthus annus), common bean (yhaseolus vulgaris)

[0175] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on chickpea, sunflower and common bean, a field trial was conducted in Canada in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 180 L / ha. Aside from the herbicide, the spray slurry contained 1.75 L / ha methylated seed oil (Destiny® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 180 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design.

[0176] 42 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants.

[0177] Over a period of from 13 to 42 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants.

[0178] The results are summarized in Table 7 below.

[0179] Table 7: g a.i. / ha: gram of active ingredient per hectare

[0180] CIEAR: Cicer arietinum “CDC frontier” (chickpea)

[0181] HELAN: Helianthus annuus “Peredovick” (sunflower)

[0182] PHSVX: Phaseolus vulgaris “Nautica” (common bean)

[0183] AMARE: Amaranthus retroflexus

[0184] SETVI: Setaria viridis

[0185] CHEAL: Chenopodium album

[0186] MSO: methylated seed oil

[0187] % ground coverage: coverage (in percent) of the area by the particular weed without herbicide treatment

[0188] Example 8: Soybean (glycine max “BMX POTENCIA RR”)

[0189] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide on soybean, a field trial was conducted in Southern Germany in the spring under typical conditions. The field was prepared for crop planting according to farmers practice. The crop seeds were planted in rows as in commercial fields after initial ground preparation using commercial tractor pulled seeding equipment. The ground was allowed to settle after planting before the application of the test treatments was carried out 1 day after crop planting onto damp and bare soil. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 200 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Stefes Mero® HC) in the treatments as indicated in the table below. The application of the different treatments was done with a compressed CO2 powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 200 L / ha spray slurry. Each treatment was replicated three times within the field trial in a completely randomized block design.

[0190] 42 days after application, the herbicidal effect on the developed weed plants was visually evaluated as percent (%) herbicidal effect compared to normal developed and untreated weed plants grown on untreated soil. The rating scale reached from 0 % damage indicating weed plants showing the same growth habit and size compared to untreated plants, until 100 % damage or completely controlled plants, meaning no visible emergence or dead plants. Over a period of from 14 to 42 days after application, the maximum damage to the developed crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described above for the weed plants.

[0191] The results are summarized in Table 8 below.

[0192] Table 8:

[0193] 1:>: the dose refers to glyphosate acid g a.i. / ha: gram of active ingredient per hectare MSO: methylated seed oil

[0194] The results summarized in Tables 1 to 8 show that the compound of formula (I) exhibits good pre-emergence herbicidal activity against a broad spectrum of weeds at application rates of 300 g and less of active ingredient per hectare and has hardly any phytotoxic effect on dicotyledonous crops at application rates of up to 200 g a.i. / ha (flax, lentil, faba bean, common bean, soybean) or even up to 300 g a.i. / ha (sunflower, peanut, potatoe, pea, chickpea). This particularly applies when tank mixes of the compound of formula (I) and methylated seed oil were applied.

[0195] Example 9: Influence of crop growth stage on crop selectivity using the example of potato (solanum tuberosum

[0196] To assess the selectivity of the compound of formula (I) when used as pre-emergence herbicide and limitations in terms of crop growth stages, a field trial was conducted in northern Germany in the spring under typical conditions. The trial was conducted in potatoes. The field was prepared for crop planting according to farmers practice. The tubers were planted in rows and hilled as in commercial fields after initial ground preparation using commercial tractor pulled planting equipment. The hilled ground was allowed to settle after planting before the application of the test treatments was carried out. To asses the window of safe application in crops as a preemergence treatment, 5 applications timings at different developmental stages of the potatoes were scheduled. Applications were carried out at BBCH growth stage 01, 03, 05, 08 and 10, respectively, of the potatoes. The growth stage of the potatoes at the specific application timing was checked in an adjacent plot at time of each application. The untreated plot was kept weed free manually. The treatments were prepared as mentioned in the table below by adding the respective dose rate of herbicide into the spray slurry at a water volume of 300 L / ha. Aside from the herbicide, the spray slurry contained 1.5 L / ha methylated seed oil (Stefes Mero® HC). The application of the different treatments was done with a compressed air powered research backpack sprayer with a handheld spray boom equipped with 02 flatfan nozzles covering 4 rows of each of the crops per plot. The spray was calibrated to an application rate of 300 L / ha spray slurry. Each treatment was replicated 4 times within the field trial in a completely randomized block design.

[0197] At 14, 28 and 42 days after crop emergence the maximum damage to the developing crop plants was assessed visually and determined as percent (%) maximum phytotoxic effect compared to untreated control plants following the same rating scale as described for the weed plants.

[0198] At 149 days after planting the potatoes were harvested and yield per treatment within the trial was determined as kg tubers / plot and compared to the yield of the untreated plot. Non marketable potatoes were not considered for the yield. The measured yield in kg / plot as well as the relative yield compared to untreated is provided in the table below (table 9).

[0199] Table 9: g a.i. / ha: gram of active ingredient per hectare

[0200] SOLTU: Solanum tuberosum “Bintje” (potatoe)

[0201] MSO: methylated seed oil included in all treatments at 1.5 L / ha

[0202] DAA: days after application

Claims

Claims1. Use ofmethyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbo-nyl]amino]- tetrahydrofuran-2 -carboxylate (I), which exists in the form of two stereoisomers: methyl (2R,4R)-4-[[(5S)- 3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2 -carboxylate of formula (la) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetra- hydrofuran-2 -carboxylate of formula (lb), and / or a salt thereof for control of undesired vegetation at a cultivation site for dicotyledonous crop plants through an application prior to the emergence of the dicotyledonous crop plants:

2. The use according to claim 1, wherein the dicotyledonous crop plants are selected from the group consisting of sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower and cotton.

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

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

5. The use according to any of the precedings claims, wherein the compound of formula (I) and / or a salt thereof is applied after sowing or planting and prior to emergence of the dicotyledonous crop plants.

6. The use according to claim 5, wherein the compound of formula (I) and / or a salt thereof is applied to a moist and firm seed bed of dicotyledonous crop plants.

7. The use according to any of the precedings claims, wherein the dicotyledonous crop plant is soybean and wherein the compound of formula (I) and / or a salt thereof is applied at an application rate within the range of from 25 to 150 g a.i. / ha.

8. The use according to any of the precedings claims, wherein a composition comprising the compound of formula (I) and / or a salt thereof and a surfactant selected from the groups of vegetable oil-based surfactants is applied.

9. Use of the compound of formula (I) and / or salt thereof according to any of the precedings claims in absence of safener.

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

11. The use according to claim 10, wherein the compound of formula (I) and / or salt thereof is combined with at least one further herbicide selected from the group consisting of acetochlor, aclonifen, ametryn, amitrole, bentazone, chlorimuron, chlorimuron-ethyl, clomazone, cloransulam, cloransulam-methyl, dimenthenamid, diflufenican, flufenacet, flumioxazin, fluometuron, fluridone, fomesafen, fomesafen- sodium, foramsulfuron, glyphosate, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium, glyphosate-trimesium, glufosinate, glufosinate-ammonium, glufosinate-sodium, U-glufosinate-ammonium, U-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil- sodium, isoxaflutole, mesotrione, metribuzin, metolachlor, norflurazon, oryzalin, oxadiargyl, oxadiazon, oxaziclomefon, oxyfluorfen, pendimethalin, phenmedipham, propyzamide, prosulfocarb, pyraflufen, pyraflufen-ethyl, pyrasulfotole rimsulfuron, saflufenacil, simazine, sulfentrazone, S-metolachlor.

12. The use according to claim 10 or 11, wherein a composition comprising the compound of formula (I) and / or salt thereof and the further herbicide is applied.

13. A method for control of undesired vegetation at a cultivation site for dicotyledonous crop plants comprising the step of applying a herbicidally effective amount of methyl (2R*,4R*)-4-[[(5S)-3-(3,5- difluorophenyl)-5-vinyl-4H-isoxazole-5-carbo-nyl]amino]tetrahydrofuran-2-carboxylate (I), which exists in the form of two stereoisomers: methyl (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5- carbonyl]-amino]tetra-hydrofuran-2-carboxylate of formula (la) and methyl (2S,4S)-4-[[(5S)-3-(3,5- difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (lb), and / or a salt thereof prior to emergence of the dicotyledonous crop plants to the cultivation site:

14. The method according to claim 13 , wherein the dicotyledonous crop plants are selected from the group consisting of sunflower, flax, peanut, potatoe, lentil, soybean, common bean, faba bean, pea, chickpea, safflower and cotton.

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