Weeding composition

Abstract

The present invention relates to herbicidal compositions comprising N-(1, 3, 4-oxadiazol-2-yl) aryl carboxylic acid amides and other herbicides.

Description

[0001] The present invention relates to an agrochemically active herbicidal composition, a process for its preparation and its use for controlling harmful plants.

[0002] WO2015 / 059187A1 discloses a herbicide composition comprising N-(1,3,4-oxadiazole-2-yl)arylcarboxamide. It also describes a herbicide composition comprising a racemic form of 2-chloro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, such as Example No. A1-14.

[0003] However, the herbicidal compositions known from WO 2015 / 059187 A1 generally have disadvantageous properties with regard to their biological properties (eg herbicidal action, crop plant tolerance, toxicological and ecotoxicological properties).

[0004] An object of the present invention is to provide an alternative herbicidally active composition. This object is achieved by the herbicidal composition of the present invention described below, which comprises a specific N-(1,3,4-oxadiazol-2-yl)arylcarboxamide.

[0005] The present invention provides a herbicidal composition comprising

[0006] (A) a compound having an absolute configuration represented by formula (I-5) (component A) or a salt thereof

[0007]

[0008] and

[0009] (B) one or more herbicides (component B) selected from Groups B1, B2, B5, B6, B8 and B9:

[0010] B1: dioxopyritrione, benquitrione, tolpyralate, lancotrione,

[0011] B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester, dimesulfacet,

[0012] B5: trifludimoxazin, tetflupyrolimet, fenpyrazone, florpyrauxifen, bixlozone,

[0013] B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid,

[0014] B8: rimisoxafen,

[0015] B9: tiafenacil, flufenoximacil, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

[0016] In another embodiment, these herbicidal compositions comprise (C) one or more safeners (component C) selected from

[0017] benoxacor (C1), cloquintocet-mexyl (C2), cyprosulfamide (C3), dichlormid (C4), fenclorim (C5), fenchlorazole (C6), furilazole (C7), isoxadifen-ethyl (C8), mefenpyr-diethyl (C9), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane of CAS 71526-07-3 (C10), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine of CAS 52836-31-4 (C11).

[0018] Component B) and component C) are known, for example, from "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, and from the website http: / / www.alanwood.net / pesticides / . Methyl (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate is known, for example, from WO 2018 / 228985 A1. Methyl (1S,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate and ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate are known, for example, from WO 2019 / 145245 A1.

[0019] Preferred component B are the following herbicides:

[0020] B1: dioxopyritrione, quinclorac, tolpyralate,

[0021] B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester,

[0022] B5: trifluoxetine, tetrafluthrin, fenpyrazone, clofopyralid, diclofenac,

[0023] B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid,

[0024] B8: rimisoxafen,

[0025] B9: fluazifop-butyl, fluazifop-butyl, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

[0026] Particularly preferred components B are the following herbicides:

[0027] B1: dioxopyritrione, quinclorac, tolpyralate,

[0028] B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester,

[0029] B5: trifluoxetine, tetraflupyralid, fenpyrazone, clofopyralid,

[0030] B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid,

[0031] B8: rimisoxafen,

[0032] B9: fluazifop-butyl, fluazifop-butyl, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

[0033] The herbicidal compositions according to the invention may comprise or be used together with further components, for example other types of active crop protection ingredients and / or additives and / or formulation auxiliaries customary in crop protection.

[0034] The herbicides (A), (B) and any safeners (C) can be applied in a known manner, for example, together (for example as a combined formulation or as a tank mix) or in a short-term continuous manner at different times (separately), applied to, for example, plants, plant parts, plant seeds or areas where plants grow. For example, a single active ingredient or herbicide-safener combination can be applied several times (sequentially), for example by pre-emergence application followed by post-emergence application, or by early post-emergence application followed by mid-term or late post-emergence application. Preferably, the active ingredients in the corresponding combination are applied in combination or immediately in succession. It is also possible to use a single active ingredient or herbicide-safener combination for seed treatment.

[0035] The application rate of component (A) in the herbicidal composition of the present invention is generally 0.01 to 200 g ai / ha, preferably 0.02 to 150 g ai / ha, more preferably 0.05 to 120 g ai / ha. The application rate of component (B) in the herbicidal composition of the present invention is generally 0.01 to 400 g ai / ha, preferably 0.05 to 300 g ai / ha, more preferably 0.1 to 200 g ai / ha.

[0036] When applying the herbicidal compositions according to the invention, a very broad spectrum of harmful plants is controlled before and after emergence, for example annual and perennial monocotyledonous or dicotyledonous weeds and unwanted crop plants. The herbicidal compositions according to the invention are particularly suitable for use in crops such as cereals, corn, rice, soybeans, rapeseed, sugar beet, cotton, sugar cane, and also for use in perennial crops, plantations and uncultivated land. They are also very suitable for use in transgenic crops of maize, corn, sugar beet, rice, cotton and soybean (Glycine max.) (e.g. RR soybean or LL soybean and their hybrids), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from different plant groups, such as potato, leek, cabbage, carrot, tomato, onion, and perennial and plantation crops, such as pome and stone fruits, soft fruit, grapes (wine), Hevea, banana, sugar cane, coffee, tea, citrus, nut plantations, lawns, palm crops and forest crops. These crops are also preferred for the use of the herbicide-safener combinations (A) + (B) according to the invention, with particular preference for use in cereals (e.g. wheat, barley, rye, oats), rice, maize, millet / sorghum, sugar beet, sugar cane, sunflower, rape and cotton. The herbicide-safener combinations (A) + (B) can also be used in tolerant and intolerant mutant crops and tolerant and intolerant transgenic crops, preferably those of the following plants: corn, rice, corn, rapeseed, cotton, sugar beet and soybean, for example those that are resistant to the following: imidazolinone herbicides, atrazine, glufosinate, glyphosate, 2,4D, dicamba and herbicides of the class of hydroxyphenylpyruvate dioxygenase inhibitors, for example sulcotrione, mesotrione, tembotrione, benzobicyclon, bicyclopyrone and ketospiradox.

[0037] "Herbicide active amount" in the sense of the present invention is an amount of one or more herbicides suitable for adversely affecting plant growth. "Antitoxic active amount" in the sense of the present invention refers to an amount of one or more safeners suitable for reducing the phytotoxic effects of the active compounds (e.g. herbicides) of the crop protection composition on crop plants.

[0038] According to its properties, the safener (C) present in the herbicidal composition of the present invention can also be used for the pretreatment of crop plant seeds (e.g., for seed dressing) or introduced into the sowing furrow before sowing, or used together with a herbicide before or after plant emergence. Pre-emergence treatment includes the treatment of the cultivation area (including any water present in the cultivation area, such as in the case of application to rice) before sowing, and the treatment of the cultivation area that has been sown but not yet covered by the growing plants. It is preferably applied together with a herbicide. For this purpose, a tank mix or a ready-made formulation can be used.

[0039] In a preferred embodiment, seeds (e.g., grains, seeds or vegetative propagation organs such as tubers or shoots with buds) or seedlings are pretreated with a safener (C), optionally in combination with other active agrochemical ingredients. For seed pretreatment, the active compound can be applied to the seed, for example, by seed dressing, or the active compound and the seed can be added to water or other solvents, and the active compound can be absorbed, for example, by adsorption or diffusion during immersion, or by swelling or pregermination. For seedling pretreatment, the young plants can be contacted with the safener (optionally in combination with other active agrochemical ingredients), for example, by spraying, dipping or watering, and then transplanted and optionally post-treated with herbicides (A) and (B).

[0040] Seeds or seedlings can be treated with safener (C) alone or together with other active agrochemical ingredients, such as fungicides, insecticides or plant enhancers, fertilizers or bulking and germination promoters. After the pretreatment application, the safener can be applied again before, after or together with the herbicide (A) of formula (I-5) and the herbicide (B), or in combination with other known herbicides. Pretreatment of seeds or seedlings can improve the long-term efficacy of the safener.

[0041] The present invention therefore also provides a method for controlling unwanted plants in plant crops, characterized in that the components (A), (B) and optionally (C) of the herbicidal composition according to the invention are applied, for example together or separately, to plants (e.g. harmful plants, for example monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g. cereals, seeds or vegetative propagation organs such as tubers or shoots with buds) or to the area where the plants grow (e.g. the cultivation area). One or more safeners (C) can be applied to the plants, seeds or the area where the plants grow (e.g. the cultivation area) before, after or simultaneously with the herbicides (A) of the general formula (I-5) and the herbicides (B). In a preferred embodiment, the safener (C) is used for seed treatment.

[0042] Unwanted plants are understood to mean all plants that grow in a location where they are not wanted. These may be, for example, harmful plants (for example monocotyledonous or dicotyledonous weeds or unwanted crop plants), including, for example, those that are resistant to certain active herbicidal compounds (such as glyphosate, atrazine, glufosinate or imidazolinone herbicides).

[0043] Monocotyledonous weeds from, for example, the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron , Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, and Apera. Dicotyledonous weeds are, for example, from the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Thistle, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia.

[0044] The invention further provides for the use of the herbicidal compositions according to the invention for controlling unwanted vegetation, preferably in plant crops.

[0045] The herbicidal composition of the present invention can be prepared by known methods, for example, in the form of mixed preparations of each component optionally with other active ingredients, additives and / or conventional formulation adjuvants, then they are diluted with water in a conventional manner to apply, or by diluting each component prepared separately or partially separately with water together and applying as a bucket mixture. It is also possible to apply (separately apply) each component prepared separately or partially separately at different times. It is also possible to apply a separate component or herbicidal composition (sequential application) in multiple portions, for example, by applying before seedlings and then applying after seedlings, or by applying after seedlings in the early stage and then applying after seedlings in the middle or late stage. It is preferred to apply the active ingredient in the corresponding combination jointly or immediately continuously.

[0046] The herbicidal compositions of the present invention can also be used for controlling harmful plants in crops of genetically modified plants which are known or yet to be developed.

[0047] In general, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides, particularly certain herbicides, resistance to plant diseases or plant disease pathogens (e.g., certain insects or microorganisms such as fungi, bacteria or viruses). Other specific characteristics relate to, for example, the quantity, quality, storage, composition and specific ingredients of harvested material. For example, transgenic plants with elevated starch content or altered starch quality are known, or those with different fatty acid compositions in harvested material. Other specific characteristics can be tolerance or resistance to abiotic stress factors, such as heat, low temperature, drought, salinity and ultraviolet radiation.

[0048] The herbicidal compositions according to the invention are preferably used in transgenic crops of economically important useful and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet / sorghum, rice, cassava and corn, or crops, such as sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0049] Conventional methods for producing new plants with improved properties compared to existing plants include, for example, traditional breeding methods and the generation of mutants. Alternatively, new plants with improved properties can be produced by recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following situations have been described:

[0050] - genetic modification of crop plants with the aim of modifying the starch synthesized in the plants (e.g. WO 92 / 11376, WO 92 / 14827, WO 91 / 19806),

[0051] - transgenic crop plants resistant to specific herbicides of the glufosinate group (see, for example, EP-A-0242236, EP-A-242246) or the glyphosate group (WO 92 / 00377) or the sulfonylurea group (EP-A-0257993, US-A-5013659),

[0052] - transgenic crop plants, such as cotton, that produce Bacillus thuringiensis toxins (Bt toxins) that render the plants resistant to specific pests (EP-A-0142924, EP-A-0193259),

[0053] - transgenic crop plants with altered fatty acid composition (WO 91 / 13972),

[0054] - Genetically modified crop plants with new components or secondary metabolites that provide enhanced disease resistance (e.g. novel phytoalexins) (EPA 309862, EPA 0464461),

[0055] - Genetically modified plants with reduced photorespiration, which have higher yield and greater stress tolerance (EPA 0305398),

[0056] - transgenic crop plants producing pharmaceutically or diagnostically important proteins ("molecular pharming"),

[0057] - genetically modified crop plants characterized by higher yield or better quality,

[0058] - Transgenic crop plants characterized by, for example, a combination of novel traits mentioned above ("gene stacking").

[0059] Many molecular biology techniques which can be used to produce novel transgenic plants with modified properties are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.), Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, "Trends in Plant Science" 1 (1996) 423-431).

[0060] For such genetic manipulations, nucleic acid molecules that allow mutations or sequence changes by recombinant DNA sequences can be introduced into plasmids. By means of standard methods, for example, base exchange, removal of partial sequences, or addition of natural or synthetic sequences can be performed. In order to connect DNA fragments to each other, adapters or linkers can be added to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

[0061] For example, the production of plant cells having a gene product with reduced activity can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving co-suppression, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above gene product.

[0062] For this purpose, DNA molecules containing the complete coding sequence of the gene product (including any flanking sequences that may be present) can be used, as well as DNA molecules containing only parts of the coding sequence, in which case these parts of the coding sequence must be long enough to have an antisense effect in the cell. DNA sequences that are highly homologous to the coding sequence of the gene product, but not completely identical to them, can also be used.

[0063] When expressing nucleic acid molecules in plants, the synthesized protein can be located in any desired compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be connected to a DNA sequence that ensures localization in a specific compartment, for example. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in organelles of plant cells.

[0064] The transgenic plant cells can be regenerated by known techniques to give rise to whole plants.In principle, the transgenic plants can be plants of any desired plant species, ie not only monocotyledons but also dicotyledons.

[0065] In this way, transgenic plants can be obtained which have altered properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

[0066] Preferably, the composition of the present invention can be used in transgenic crops that are resistant to growth regulators such as dicamba, or to herbicides that inhibit essential plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides selected from sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active ingredients.

[0067] When the composition of the present invention is used in transgenic crops, not only the effects on harmful plants observed in other crops will appear, but also often there will be effects specific to the application in a specific transgenic crop, such as a change or especially a broadening of the spectrum of weeds that can be controlled, a change in the application rate that can be used for application, preferably good combination with herbicides that are resistant to transgenic crops, and an effect on the growth and yield of transgenic crop plants.

[0068] The present invention therefore also provides the use of the compositions according to the invention for controlling harmful plants in transgenic crop plants.

[0069] Preference is given to the use of the compositions according to the invention in transgenic crops of economically important useful and ornamental plants, such as cereals (e.g. wheat, barley, rye, oats), millet / sorghum, rice, cassava and maize, or the crops sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable crops.

[0070] The present invention therefore also provides for the use of the compositions according to the invention for controlling harmful plants in transgenic crop plants or in crop plants made tolerant by selective breeding.

[0071] The herbicides (A), (B) and any safeners (C) can be converted together or separately into conventional formulations for application, for example, by spraying, watering, sprinkling and seed dressing, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic substances impregnated with the active ingredient, microcapsules in polymeric substances. The formulations may contain conventional adjuvants and additives.

[0072] These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam formers.

[0073] When the extender used is water, it is also possible to use, for example, an organic solvent as a cosolvent. Useful liquid solvents are primarily: aromatic compounds (e.g. xylene, toluene or alkylnaphthalene), chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g. chlorobenzene, vinyl chloride or methylene chloride), aliphatic hydrocarbons (e.g. cyclohexane) or paraffins (e.g. mineral oil fractions, mineral oils and vegetable oils), alcohols (e.g. butanol or ethylene glycol) and their ethers and esters, ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (e.g. dimethylformamide or dimethyl sulfoxide), and water.

[0074] Useful solid carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth), and ground synthetic minerals (e.g., finely divided silica, alumina and silicates); useful solid carriers for granules include, for example, crushed and classified natural rocks (e.g., calcite, marble, pumice, sepiolite, dolomite) and synthetic particles of inorganic and organic powders, and particles of organic materials (e.g., sawdust, coconut shells, corn cobs and tobacco stalks); useful emulsifiers and / or foam formers include, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (e.g., alkylaryl polyglycol ethers), alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; useful dispersants include, for example, lignin sulfite waste liquor and methylcellulose.

[0075] In the preparation, viscosity increasing agents such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids (such as cephalin and lecithin) and synthetic phospholipids can be used. Other additives can be mineral oils and vegetable oils.

[0076] Colorants such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue, and organic colorants, such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc, can be used.

[0077] The formulations generally comprise from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of active compound.

[0078] The herbicides (A), (B) and any safeners (C) - as such or in the form of their formulations - can also be used in the form of a mixture with other active agrochemical ingredients for controlling unwanted vegetation, for example for controlling weeds or for controlling unwanted crop plants, for example, ready formulations or tank mixes are possible.

[0079] A mixture with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible and may also contain the additives and formulation auxiliaries customary in crop protection.

[0080] The herbicides (A), (B) and any safeners (C) can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution (e.g. ready-to-use solutions, suspensions, emulsions, powders, pastes and granules). Application is usually accomplished by, for example, watering, spraying, atomizing, broadcasting.

[0081] The active compound can be applied to plants, plant parts, seeds or cultivated areas (farmland), preferably to seeds or green plants and plant parts, and optionally also to farmland. One possible use is the joint application of the active ingredients in the form of a tank mix, wherein the optimally formulated concentrates of the individual active ingredients are mixed together in a bucket with water and the spray liquor obtained is applied.

[0082] The combined formulation of the composition of the herbicides (A), (B) and optionally (C) according to the invention has the advantage of being easier to apply, since the amounts of the components are already in an optimal ratio. In addition, the adjuvants in the formulation can be optimized with respect to one another.

[0083] For application, commercially available formulations are diluted, if appropriate, in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Formulations in the form of dusts, granules for soil application or granules for dispersion and sprayable solutions are usually not diluted further with other inert substances before application.

[0084] Biological Examples:

[0085] Abbreviations used for noxious plants:

[0086] ABUTH:Abutilon theophrasti

[0087] BRAPP: Brachiaria platyphylla

[0088] CYPIR: Cyperus iria

[0089] EMEAU: Emex australis

[0090] EPHHL: Euphorbia heterophylla

[0091] ERIBO:Erigeron bonariensis

[0092] PHBPU: Pharbitis purpurea

[0093] POLCO: Polygonum convolvulus

[0094] SETVI: Setaria viridis

[0095] SOLNI: Solanum nigrum

[0096] SORHA: Sorghum halepense

[0097] XANST: Xanthium strumarium

[0098] Post-emergence herbicidal effect on harmful plants

[0099] Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam in wood fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. The test plants are treated 2 to 3 weeks after sowing at the one-leaf stage. The compounds according to the invention (formulated in the form of wettable powders (WP) or emulsifiable concentrates (EC)) are then sprayed on the green parts of the plants in the form of aqueous suspensions or emulsions with the addition of 0.2% of a wetting agent, with a water application rate corresponding to 600 to 800 l / ha. After the test plants have been placed in a greenhouse under optimal growth conditions for about 3 weeks, the effect of the preparations is visually assessed compared with the untreated control group (herbicidal effect in percentage (%): 100% activity = plant has died, 0% activity = same as control plant). Many compounds according to the invention show very good effects on a variety of important harmful plants. The following table shows the post-emergence herbicidal effect of the compounds according to the invention in an exemplary manner, the herbicidal activity being expressed in percentage.

[0100] In the following table, the abbreviations have the following meanings:

[0101] E: represents the expected synergistic effect value according to Colby's formula.

[0102] ΔSYN: represents the difference between the actual synergy value and the expected synergy value.

[0103] DAT: indicates days after treatment.

[0104] I-5 represents a chiral (s-configuration) compound of the following formula:

[0105]

[0106] P1: represents (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester.

[0107] P2: represents methyl (1S,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate.

[0108] P3: represents 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid.

[0109] P4: represents ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

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Claims

1. A herbicidal composition comprising (A) a compound having an absolute configuration represented by formula (I-5) (component A) or a salt thereof and (B) one or more herbicides (component B) selected from Groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrione, quinclorac, tolpyralate, lancotrione, B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester, dimesulfacet, B5: trifluoxetine, tetrafluthrin, fenpyrazone, clofopyralid, diclofenac, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: fluazifop-butyl, fluazifop-butyl, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

2. The herbicidal composition according to claim 1, comprising one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrione, quinclorac, tolpyralate, B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester, B5: trifluoxetine, tetrafluthrin, fenpyrazone, clofopyralid, diclofenac, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: fluazifop-butyl, fluazifop-butyl, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

3. The herbicidal composition according to claim 1 or 2, comprising one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrione, quinclorac, tolpyralate, B2: (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester, (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester, B5: trifluoxetine, tetraflupyralid, fenpyrazone, clofopyralid, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: fluazifop-butyl, fluazifop-butyl, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

4. The herbicidal composition according to any one of claims 1 to 3, further comprising as component C one or more safeners selected from the group consisting of fenthiocarb, cloquintocet-mexyl, cyproconazole, dichloropropene, fenthiocarb, fenthiocarb, fenthiopyrad, isoxadiazole, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine.

5. A method for controlling harmful plants in crops, characterized in that: A herbicidally active amount of the herbicidal composition according to one or more of claims 1 to 4 is applied to the harmful plants, plants, plant seeds or the area where the plants grow.

6. The method according to claim 5, characterized in that The plant is selected from the group consisting of sugarcane, corn, wheat, rye, barley, oats, rice, sorghum, cotton and soybean.

7. The method according to claim 5 or 6, characterized in that: The plants have been genetically modified.

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