Herbicidal composition

Abstract

The present invention relates to herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)arylcarboxylic acid amides and a further herbicide.

Description

[Technical Field]

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

[0002] WO 2015 / 059187 discloses herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)arylcarboxamides.

[0003] It also describes a herbicidal composition containing the racemic form of 2-chloro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide as Example No. A1-14.

[0004] However, the herbicidal compositions known from WO 2015 / 059187 often have an unfavourable profile in terms of biological properties such as herbicidal action, resistance by crop plants, toxicological and ecotoxicological properties. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2015 / 059187 Brochure Summary of the Invention [Problem to be solved by the invention]

[0006] The object of the present invention is to provide an alternative herbicidally active composition, which is achieved by the herbicidal composition of the present invention, which comprises the specific N-(1,3,4-oxadiazol-2-yl)arylcarboxamides described below. [Means for solving the problem]

[0007] The present invention provides (A) A compound (component A) having the absolute configuration specified by formula (I-5) or a salt thereof [ka]

[0008] and (B) one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: Dioxopyritrone, benquitrione, tolpiralate, lancotrione, B2: methyl (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, dimesulfacet, B5: Trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimixoxafen, B9: Thiafenacil, 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 The present invention provides a herbicide composition comprising:

[0009] In further embodiments, these herbicidal compositions include: (C) Contains one or more safeners (ingredient C) selected from the group consisting of 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 (C10) of CAS 71526-07-3, and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (C11) of CAS 52836-31-4.

[0010] Components B) and C) are known for example from the Pesticides Manual, 15th Edition, British Crop Protection Council and Royal Society 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.

[0011] Preferred component B are the following herbicides: B1: Dioxopyritrone, Benquitrione, Torpiralate, B2: methyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, B5: Trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimixoxafen, B9: Thiafenacil, 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.

[0012] Particularly preferred components B are the following herbicides: B1: Dioxopyritrone, Benquitrione, Torpiralate, B2: methyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, B5: Trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimixoxafen, B9: Thiafenacil, 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.

[0013] The herbicidal compositions according to the invention may comprise or be used together with additional further ingredients, for example other types of active crop protection ingredients and / or additives and / or formulation adjuvants customary in crop protection.

[0014] Herbicides (A), (B) and optional safener (C) can be applied in a known manner, for example, together (for example, as a co-formulation or as a tank mix), or at different times, in short succession (split), for example, to plants, plant parts, plant seeds, or plant growing areas.For example, individual active ingredients or herbicide-safener combinations can be applied in several parts (sequential application), for example, by pre-emergence application, followed by post-emergence application, or by early post-emergence application, followed by intermediate or late application.Preference is given to the combined application or immediate successive application of the active ingredients in each combination.It is also possible to use individual active ingredients or herbicide-safener combinations for seed treatment.

[0015] The application rate of component (A) in the herbicidal composition according to the present invention is typically 0.01 to 200 g ai / ha, preferably 0.02 to 150 g ai / ha, more preferably 0.05 to 120 g ai / ha.

[0016] The application rate of component (B) in the herbicidal composition according to the present invention is typically 0.01 to 400 g ai / ha, preferably 0.05 to 300 g ai / ha, more preferably 0.1 to 200 g ai / ha.

[0017] When the herbicidal composition according to the present invention is applied, a very wide spectrum of harmful plants, such as annual and perennial monocotyledonous or dicotyledonous weeds and undesirable crop plants, is controlled pre- and post-emergence. The herbicidal composition according to the present invention is particularly suitable for use in crops such as cereals, corn, rice, soybeans, rapeseed, sugar beet, cotton, sugarcane, and the like, as well as in perennial crops, plantations, and uncultivated land. They are also highly suitable for use in transgenic crops of corn, cereals, 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 plants from various plant groups, such as potato, leek, cabbage, carrot, tomato, onion, and also perennial and plantation crops such as pome and stone fruits, soft fruits, vines, rubber trees, bananas, sugarcane, coffee, tea, citrus fruits, nut plantations, turf, palm crops, and forest crops. These crops are also preferred for the use of the herbicide-safener combinations (A)+(B) of the invention, with use in cereals (e.g., wheat, barley, rye, oats), rice, corn, millet / sorghum, sugar beet, sugarcane, sunflower, rapeseed, and cotton being particularly preferred. The herbicide-safener combinations (A)+(B) can also be used in resistant and non-resistant mutant crops and resistant and non-resistant transgenic crops, preferably maize, rice, cereals, rapeseed, cotton, sugar beet and soybean, which are tolerant to, for example, imidazolinone herbicides, atrazine, glufosinate, glyphosate, 2,4D, dicamba, and herbicides from the group of inhibitors of hydroxyphenylpyruvate dioxygenase, such as sulcotrione, mesotrione, tembotrione, tefuryltrione, benzobicyclon, bicyclopyrone and ketospiradox.

[0018] A "herbicidally active amount" in the sense of the present invention is an amount of one or more herbicides suitable for adversely affecting plant growth. An "antidote-active amount" in the sense of the present invention means an amount of one or more safeners suitable for reducing the phytotoxic effect of the active compounds of the crop protection composition (e.g., herbicides) on crop plants.

[0019] According to their properties, the safener (C) present in the herbicidal composition of the present invention can also be used for pre-treatment of crop plant seeds (for example, for seed dressing), or can be introduced into the seed furrow before sowing, or can be used together with herbicides before or after plant emergence. Pre-emergence treatment includes both treatment of the cultivated area before sowing (for example, in the case of application to rice, including any water present in the cultivated area), and treatment of the cultivated area where seeds have been sown but have not yet been covered by growing plants. It is preferable to apply it together with herbicides. For this purpose, tank mixes or ready-to-use formulations can be used.

[0020] In a preferred embodiment, seeds (e.g., grains, seeds, or vegetative propagation organs such as tubers or sprouts) or seedlings are pretreated with the safener (C), optionally in combination with other active pesticide ingredients.For seed pretreatment, the active compound can be applied to the seeds, for example, by dusting, or the active compound and the seeds can be added to water or other solvents, and the active compound can be taken up by, for example, adsorption or diffusion in a soaking process, or by swelling or pre-germination.For seedling pretreatment, young plants can be contacted with the safener, for example, by spraying, soaking, or irrigation, optionally in combination with other active pesticide ingredients, and then transplanted and optionally post-treated with herbicides (A) and (B).

[0021] The seeds or seedlings can be treated with the safener (C) alone or together with other active pesticide ingredients (e.g., fungicides, insecticides, or plant strengthening agents, fertilizers, or swelling and germination promoters). After pre-treatment application, the safener can be applied again before, after, or together with the herbicide (A) of formula (I-5) and the herbicide (B), optionally in combination with other known herbicides. Pre-treatment of seeds or seedlings can achieve improved long-term effectiveness of the safener.

[0022] Therefore, the present invention further provides a method for controlling undesirable plants in plant crops, characterized in that components (A), (B), and optionally (C) of the herbicidal composition according to the present invention are applied, for example, together or separately, to plants (e.g., harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable crop plants), seeds (e.g., grains, seeds, or vegetative propagation organs, such as tubers or sprout-bearing emergent parts), or areas where plants grow (e.g., areas under cultivation). One or more safeners (C) can be applied to plant seeds or areas where plants grow (e.g., areas under cultivation) before, after, or together with the herbicide (A) of general formula (I-5) and herbicide (B). In a preferred embodiment, the safener (C) is used in seed treatment.

[0023] Unwanted plants are understood to mean all plants that grow in undesirable locations. These may be, for example, harmful plants (for example, monocotyledonous or dicotyledonous weeds or undesirable crop plants), including those that are resistant to certain active herbicidal compounds, such as glyphosate, atrazine, glufosinate, or imidazolinone herbicides.

[0024] Monocotyledonous weeds include, for example, Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, and Agrobacterium. They belong to the genera opyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, and Aper.Dicotyledonous weeds include, for example, Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, These plants belong to the genera Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, and Euphorbia.

[0025] The present invention also provides the use of a herbicidal composition according to the invention for controlling undesired vegetation, preferably in plant crops.

[0026] The herbicidal composition according to the present invention can be prepared by known methods, for example, as a mixed formulation of individual components, optionally with further active ingredients, additives and / or conventional formulation auxiliaries, and then applied in a conventional manner by diluting with water, or as a tank mix by co-diluting the separately formulated or partially separately formulated individual components with water.Similarly, the separately formulated or partially separately formulated individual components can be applied at different times (split application).Individual components or herbicidal compositions can also be applied in multiple portions (sequential application), for example, by pre-emergence application, followed by post-emergence application, or early post-emergence application, followed by mid- or late application.The combined application or immediate successive application of the active ingredients in each combination is preferred.

[0027] The herbicidal compositions according to the invention can also be used to control harmful plants in crops of known or yet to be developed genetically modified plants.

[0028] Generally, transgenic plants are characterized by certain advantageous properties, such as resistance to certain pesticides, especially certain herbicides, or resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria, or viruses. Other specific properties relate to, for example, the quantity, quality, storability, composition, and specific components of the harvested material. For example, transgenic plants are known that have a high starch content or altered starch quality, or that have a different fatty acid composition in the harvested material. Other specific properties can be, for example, resistance or tolerance to abiotic stress factors, such as heat, low temperature, drought, salinity, and UV radiation.

[0029] The use of the herbicidal compositions according to the invention in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oat, millet / sorghum, rice, cassava and maize, or crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables, is preferred.

[0030] Conventional methods for producing new plants with modified properties compared to existing plants include, for example, conventional cultivation methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example: - genetic modification of crop plants in order to modify the starch synthesized in the plants (for example WO 92 / 11376, WO 92 / 14827, WO 91 / 19806), - transgenic crop plants which are resistant to certain herbicides of the glufosinate type (see, for example, EP-A-0242236, EP-A-242246) or glyphosate type (WO 92 / 00377) or sulfonylurea type (EP-A-0257993, US-A-5013659), - transgenic crop plants, such as cotton, which have the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259), - transgenic crop plants with modified fatty acid composition (WO 91 / 13972), - genetically modified crop plants with novel components or secondary metabolites, such as novel phytoalexins that confer increased resistance to diseases (EPA309862, EPA0464461); - Genetically modified plants with reduced photorespiration that have higher yields and greater stress tolerance (EPA0305398); - transgenic crop plants producing proteins of pharmaceutical or diagnostic importance ("molecular farming"); - Transgenic crop plants characterized by high yield or quality - For example, transgenic crop plants characterized by combinations of the above novel traits ("gene stacking"). There were descriptions of several cases.

[0031] A large number of molecular biological techniques are known in principle that can be used to produce new transgenic plants with modified properties; 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.

[0032] For such genetic manipulation, nucleic acid molecules that allow for recombination mutagenesis or sequence change of DNA sequence can be introduced into a plasmid.Using standard methods, for example, base exchange can be performed, part of the sequence can be removed, or natural or synthetic sequence can be added.In order to link DNA fragments to each other, adapters or linkers can be added to the fragments; for example, see 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.

[0033] For example, the generation of plant cells with reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA to achieve a co-suppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above-mentioned gene product.

[0034] For this purpose, it is possible to use DNA molecules that contain the entire coding sequence of the gene product, including any flanking sequences that may be present, as well as DNA molecules that contain only a portion of the coding sequence, in which case these portions must be long enough to have an antisense effect in cells. It is also possible to use DNA sequences that are highly homologous to the coding sequence of the gene product, but not completely identical to it.

[0035] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of plant cells.However, to achieve localization in a specific compartment, it is possible to link the coding region to a DNA sequence that ensures localization in a specific compartment, for example.Such 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.

[0036] Transgenic plant cells can be regenerated by known techniques to give rise to whole plants. In principle, the transgenic plants can be of any desired plant species, i.e., dicotyledonous as well as monocotyledonous plants.

[0037] The result is a transgenic plant with altered properties due to the overexpression, suppression or inhibition of a homologous (= natural) gene or gene sequence, or the expression of a heterologous (= foreign) gene or gene sequence.

[0038] Preferably, the compositions according to the invention can be used in transgenic crops that are tolerant to growth regulators, such as dicamba, or herbicides that inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active ingredients.

[0039] When the compositions according to the invention are used in transgenic crops, not only do they produce the effects against harmful plants observed in other crops, but they also frequently produce effects specific to the application in the particular transgenic crop, such as a modified or specifically expanded spectrum of weeds that can be controlled, modified application rates that can be used for application, preferably good compatibility with herbicides to which the transgenic crop is resistant, and effects on the growth and yield of the transgenic crop plants.

[0040] The present invention therefore also provides the use of a composition according to the invention for the control of harmful plants in transgenic crop plants.

[0041] The use of the compositions according to the invention in economically important transgenic crops of useful and ornamental plants, such as cereals (e.g. wheat, barley, rye, oats), millet / sorghum, rice, cassava and maize, or sugar beet, cotton, soybean, oilseed rape, potato, tomato, pea and other plant crops, is preferred.

[0042] The present invention therefore also provides the use of a composition according to the invention for the control of harmful plants in transgenic crop plants or crop plants which have resistance due to selective breeding.

[0043] The herbicides (A), (B) and optional safener (C) can be converted, together or separately, into conventional formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic materials, microencapsulated in polymeric materials, for application by spraying, watering, dusting and seed dressing. The formulations can contain conventional auxiliaries and additives.

[0044] These formulations are prepared in a known manner, for example by mixing the active compound with an extender, i.e., a liquid solvent, a liquefied gas under pressure, and / or a solid carrier, optionally with the use of surfactants, i.e., emulsifiers and / or dispersants, and / or foaming agents.

[0045] When the extender used is water, for example, organic solvent can also be used as auxiliary solvent.Useful liquid solvents are essentially the following: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils and vegetable oils, alcohols, such as butanol or glycol and its ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water.

[0046] Useful solid carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina, and silicates; useful solid carriers for granules include, for example, ground and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic powders, as well as granules of organic materials such as sawdust, coconut shells, corn cobs, and tobacco stalks; useful emulsifiers and / or foaming agents 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 dispersing agents include, for example, lignosulfite waste liquor and methylcellulose.

[0047] Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, as well as synthetic phospholipids, can be used in the formulation. Further additives may be mineral oils and vegetable oils.

[0048] As colorants it is possible to use inorganic pigments, such as iron oxide, titanium oxide and Prussian blue, as well as 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.

[0049] The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the active compound.

[0050] As such, or in their formulations, the herbicides (A), (B) and optional safener (C) can also be used as final formulations or tank mixes to control undesirable vegetation, for example to control weeds, or as mixtures with other active pesticide ingredients to control undesirable crop plants.

[0051] Mixtures with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, bird antifeedants, plant nutrients and soil conditioners, as well as with additives and formulation auxiliaries customary in crop protection, are also possible.

[0052] The herbicides (A), (B) and optional safener (C) can be used as they are, in the form of their formulations, or in use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Application is typically achieved, for example, by watering, dusting, spraying or broadcasting.

[0053] Active compound can be applied to plants, plant parts, seeds or the area under cultivation (agricultural land), preferably applied to seeds or green plants and plant parts, and optionally also applied to agricultural land.One possible use is the combined application of active ingredient in the form of tank mix, where the optimally formulated concentrated preparation of each active ingredient is mixed with water in tank together, and the spray solution obtained is applied.

[0054] The combination of herbicides (A), (B) and optionally (C) according to the invention has the advantage that it is easier to apply, since the amounts of the components are already in the optimal ratio. Furthermore, the adjuvants in the formulation can be optimized with respect to one another.

[0055] For application, the commercial formulations are diluted, if appropriate, in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-form preparations, granules for soil application or granules for broadcasting and sprayable solutions are usually not further diluted with other inert substances before application. [Example]

[0056] Biological Examples: The abbreviations used for harmful plants have the following meanings: ABUTH:Abutilon theophrasti BRAPP: Brachiaria platyphylla CYPIR: Cyperus iria EMEAU: Emex australis EPHHL: Euphorbia heterophylla ERIBO: Erigeron bonariensis PHBPU: Morning glory (Pharbitis purpurea) POLCO: Bindweed (Polygonum convolvulus) SETVI: Green foxtail (Setaria viridis) SOLNI: Nightshade (Solanum nigrum) SORHA: Sorghum (Sorghum halepense) XANST: Cocklebur (Xanthium strumarium) Post-emergence herbicidal activity against harmful plants Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam soil in wood fiber pots, covered with soil, and cultivated in a greenhouse under favorable growing conditions. Two to three weeks after sowing, the test plants are treated at the one-leaf stage. Compounds of the present invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of aqueous suspensions or emulsions, with the addition of 0.2% wetting agent, at a water application rate equivalent to 600-800 l / ha. After the test plants are left in the greenhouse for approximately three weeks under optimal growing conditions, the activity of the preparations is visually assessed in comparison with untreated controls (herbicidal activity in percent (%): 100% activity = plant death, 0% activity = similar to control plants). Many compounds of the present invention have shown very good activity against a number of important harmful plants. The following table shows, in an exemplary format, the postemergence herbicidal activity of compounds of the present invention, with herbicidal activity stated in percent.

[0057] In the table below, the abbreviations have the following meanings:

[0058] E denotes the expected synergy value according to Colby's formula.

[0059] Δ SYN refers to the difference between actual and expected synergy.

[0060] DAT means days after treatment.

[0061] I-5 refers to a chiral (S-configuration) compound of the formula: [ka]

[0062] P1 means methyl (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate.

[0063] P2 means methyl (1S,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate.

[0064] P3 means 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid.

[0065] P4 means 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. [Table 1] [Table 2] [Table 3] [Table 4] [Table 5] [Table 6] [Table 7] [Table 8] [Table 9] [Table 10] [Table 11]

Table 12

Table 13

Table 14

Table 15

Table 30

Table 50

Table 91

Table 95

Table 99

Table 100

Claims

1. (A) A compound (component A) having the absolute configuration specified by formula (I-5) or a salt thereof 【Chemical 1】 and (B) one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrone, benquitrione, tolpiralate, lancotrione, B2: methyl (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, dimesulfazate, B5: trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: thiafenacil, 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 1. A herbicide composition comprising:

2. One or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrone, benquitrione, tolpiralate, B2: methyl (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, B5: trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: thiafenacil, 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 2. The herbicidal composition of claim 1, comprising:

3. One or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: B1: dioxopyritrone, benquitrione, tolpiralate, B2: methyl (2R*, 4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate, methyl (1S, 4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]cyclopent-2-ene-1-carboxylate, B5: trifludimoxazine, tetofurpirolimet, fenpyrazone, florpiruxifen, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, B8: rimisoxafen, B9: thiafenacil, 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 3. The herbicidal composition according to claim 1 or 2, comprising:

4. 4. The herbicidal composition according to claim 1, further comprising, as component C, one or more safeners selected from the group consisting of benoxacor, cloquintocet-mexyl, cyprosulfamide, dichlormid, fenclorim, fenchlorazole, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane, and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine.

5. 10. A method for controlling harmful plants in crops, comprising applying a herbicidally active amount of the herbicidal composition according to claim 1 to the harmful plants, plants, plant seeds or areas where the plants are growing.

6. 6. The method according to claim 5, characterized in that the plants are from the group of sugarcane, corn, wheat, rye, barley, oat, rice, sorghum, cotton and soybean.

7. 7. The method according to claim 5 or 6, characterized in that the plant is genetically modified.

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