Herbicidal compositions

Abstract

The invention relates to herbicidal compositions that contain an N-(1,3,4-oxadiazol-2-yl)arylcarboxylic acid amide and further herbicides

Description

[0001] Herbicidal compositions

[0002] Description

[0003] The present invention relates to agrochemically active herbicidal compositions, processes for their preparation and their use for controlling weeds.

[0004] WO2015 / 059187 A1 discloses herbicidal compositions containing

[0005] N-(l,3,4-oxadiazol-2-yl)arylcarboxylic acid amides. Herbicidal compositions containing 2-chloro-N-(5-methyl-l,3,4-oxadiazol-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide in racemic form are also described therein as Example No. Al-14.

[0006] However, these herbicidal compositions known from WO2015 / 059187 Al often have an unfavorable profile with regard to their biological properties, such as herbicidal activity, compatibility with crops, toxicological and ecotoxicological properties.

[0007] The object of the present invention is to provide alternative herbicidally active compositions. This object is achieved by the herbicidal compositions according to the invention described below, comprising a specific N-(1,3,4-oxadiazol-2-yl)phenylcarboxamide.

[0008] The present invention relates to herbicidal compositions containing

[0009] (A) the compound having the absolute configuration given in formula (1-5) (component A) or its salts, and (B) one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9:

[0010] Bl: Dioxopyritrione, Benquitrione, Tolpyralate, Lancotrione,

[0011] B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-isoxazol-5-carbonyl] amino] tetrahydrofuran-2-carboxylat, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy lat, Dimesulfacet,

[0012] B5: Trifludimoxazin, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen, Bixlozone,

[0013] B6: 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl) pyridin-2-carbonsäure,

[0014] B8: Rimisoxafen,

[0015] B9: Tiafenacil, Flufenoximacil, Ethyl-3-{2-chlor-4-fhror-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl] phenyl} -5-methyl-4,5-dihydro- 1 ,2-oxazol-5-carboxylat.

[0016] In a further embodiment, these herbicidal compositions contain C) one or more safeners (component C) from the group consisting of benoxacor (CI), cloquintocet-mexyl (C2), cyprosulfamide (C3), dichlormid (C4), fenclorim (C5), fenchlorazole (C6), furilazole (C7), isoxadifen-ethyl (C8), mefenpyr-diethyl (C9), 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane of CAS 71526-07-3 (CIO), 2,2,5-trimethyl-3-(dechloroacetyl)-l,3-oxazolidine of CAS 52836-31-4 (CII).

[0017] Components B) and C) are known, for example, from "The Pesticide Manual," 19th edition, The British Crop Protection Council and the 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 WO2018 / 228985 Al. Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5-carbonyl] amino]cyclopent-2-ene-l -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 WO2019 / 145245 Al.

[0018] Preferred as component B are the following herbicides: Bl: Dioxopyritrione, Benquitrione, Tolpyralate,

[0019] B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-isoxazol-5-carbonyl] amino] tetrahydrofuran-2-carboxylat, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy lat,

[0020] B5: Trifludimoxazin, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen, Bixlozone,

[0021] B6: 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl) pyridin-2-carbonsäure,

[0022] B8: Rimisoxafen,

[0023] B9: Tiafenacil, Flufenoximacil, Ethyl-3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl] phenyl} -5-methyl-4,5-dihydro- 1 ,2-oxazol-5-carboxylat.

[0024] Besonders bevorzugt als Komponente B sind die folgenden Herbizide:

[0025] Bl: Dioxopyritrione, Benquitrione, Tolpyralate,

[0026] B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-isoxazol-5-carbonyl] amino] tetrahydrofuran-2-carboxylat, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy lat,

[0027] B5: Trifludimoxazin, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen,

[0028] B6: 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl) pyridin-2-carbonsäure,

[0029] B8: Rimisoxafen,

[0030] B9: Tiafenacil, Flufenoximacil, Ethyl-3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl] phenyl} -5-methyl-4,5-dihydro- 1 ,2-oxazol-5-carboxylat.

[0031] The herbicidal compositions according to the invention can contain additional further components, for example other types of crop protection active ingredients and / or additives and / or formulation aids customary in crop protection, or can be used together with these. The herbicides (A), (B) and optionally the safeners (C) can be applied in a known manner, for example together (for example as a co-formulation or as a tank mix) or in quick succession (splitting), e.g. to the plants, parts of plants, plant seeds or the area on which the plants are growing. It is possible, for example, to apply the individual active ingredients or the herbicide-safener combination in several portions (sequential application), e.g. after pre-emergence applications, followed by post-emergence applications or after early post-emergence applications, followed by mid- or late post-emergence applications.The preferred method is the joint or concurrent application of the active ingredients of the respective combination. It is also possible to use the individual active ingredients or the herbicide-safener combination for seed treatment.

[0032] The application rate of component (A) in the herbicidal compositions according to the invention is usually 0.01 to 200 g ai / ha, preferably 0.02 to 150 g ai / ha, particularly preferably 0.05 to 120 g ai / ha.

[0033] The application rate of component (B) in the herbicidal compositions according to the invention is usually 0.01 to 400 g ai / ha, preferably 0.05 to 300 g ai / ha, particularly preferably 0.1 to 200 g ai / ha.

[0034] When the herbicidal compositions according to the invention are used pre- and post-emergence, a very broad spectrum of weeds is controlled, e.g., annual and perennial monocotyledonous or dicotyledonous weeds, as well as undesirable crops. The herbicidal compositions according to the invention are particularly suitable for use in crops such as cereals, maize, rice, soybeans, rapeseed, sugar beet, cotton, sugar cane, as well as for use in permanent crops, plantations, and on non-cultivated land. They are also very suitable for use in transgenic crops of maize, cereals, sugar beet, rice, cotton, and Glycine max. (e.g.,RR soy or LL soy) and their crosses), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potatoes, leeks, cabbages, carrots, tomatoes, and onions, as well as perennial and plantation crops such as pome and stone fruit, soft fruit, vines, Hevea, bananas, sugar cane, coffee, tea, citrus, nut plantations, lawns, palm crops, and forestry crops. These crops are likewise preferred for the application of the herbicide-safener combinations (A)+(B) according to the invention; particular preference is given to use in cereals (e.g. wheat, barley, rye, oats), rice, maize, millet, sugar beet, sugar cane, sunflowers, rapeseed, and cotton. The herbicide-safener combinations (A)+(B) can also be used in tolerant and non-tolerant mutant crops and tolerant and non-tolerant transgenic crops, preferably of maize, rice, cereals, rapeseed, cotton, sugar beet and soybeans, e.g.those that are resistant to imidazolinone herbicides, atrazine, glufosinate, glyphosate, 2,4 D, dicamba and herbicides from the group of hydroxyphenylpyruvate dioxygenase inhibitors, such as sulcotrione, mesotrione, tembotrione, tefuryltrione, benzobicyclon, bicyclopyrone and ketospiradox.

[0035] For the purposes of the invention, a herbicidally effective amount means an amount of one or more herbicides that is capable of adversely affecting plant growth. For the purposes of the invention, an antidotally effective amount means an amount of one or more safeners that is capable of reducing the phytotoxic effect of plant protection product active ingredients (e.g., herbicides) on crop plants.

[0036] Depending on their properties, the safeners (C) present in the herbicidal compositions according to the invention can also be used to pretreat the seeds of the crop (e.g., for seed dressing), or introduced into the seed furrows before sowing, or applied together with the herbicide before or after plant emergence. Pre-emergence treatment includes both the treatment of the cultivated area (including any water present on the cultivated area, e.g., in rice applications) before sowing and the treatment of the sown but not yet overgrown cultivated areas. Preference is given to joint application with the herbicide. Tank mixes or ready-to-use formulations can be used for this purpose.

[0037] In a preferred embodiment, the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or seedlings are pretreated with the safeners (C), optionally in combination with other agrochemical active ingredients. To pretreat the seed, the active ingredients can be applied to the seed, for example by dressing, or the active ingredients and the seed can be placed in water or other solvents, and the active ingredients can be taken up, for example, by deposition or diffusion in an immersion process or by swelling or pre-germination. To pretreat seedlings, the young plants can be brought into contact with the safeners, optionally in combination with other agrochemical active ingredients, for example by spraying, dipping or watering and then transplanted and optionally aftertreated with the herbicides (A) and (B).

[0038] The seed or seedling treatment can be carried out with the safeners (C) alone or together with other agrochemical active ingredients - such as fungicides, insecticides or agents for plant strengthening, fertilizing or accelerating the swelling and germination processes. After the pretreatment application, the safeners can then be applied again before, after or together with the herbicide of the formula (1-5) (A) and the herbicides (B), possibly also in combination with other known herbicides. By pretreating the seed or seedlings, an improved long-term action of the safeners can be achieved. The present invention thus further provides a method for controlling unwanted plants in plant crops, which is characterized in that the components (A), (B) and optionally (C) of the herbicidal compositions according to the invention are applied to the plants (e.g.harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed (e.g. grains, seeds or vegetative propagating organs such as tubers or shoot parts with buds) or the area on which the plants grow (e.g. the cultivated area), e.g. together or separately. One or more safeners (C) can be applied to the plants, the seed or the area on which the plants grow (e.g. the cultivated area) before, after or simultaneously with the herbicide of the formula (1-5) (A) and the herbicides (B). In a preferred embodiment, the safeners (C) are used for seed treatment.

[0039] Undesirable plants are defined as all plants that grow in places where they are undesirable. These can include harmful plants (e.g., monocotyledonous or dicotyledonous weeds or undesirable crops), including those that are resistant to certain herbicidal active ingredients such as glyphosate, atrazine, glufosinate, or imidazolinone herbicides.

[0040] Monocotyledonous weeds come, for example, from the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Folium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Dicotyledonous weeds come, for example, from the genera Sinapis, Eepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Eindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia.

[0041] The invention also relates to the use of the herbicidal compositions according to the invention for controlling unwanted plant growth, preferably in plant crops.

[0042] The herbicidal compositions according to the invention can be prepared by known processes, e.g. as mixed formulations of the individual components, optionally with other active ingredients, additives and / or customary formulation auxiliaries, which are then applied diluted with water in the usual way, or as so-called tank mixes by joint dilution of the separately formulated or partially separately formulated individual components with water. Likewise possible is the staggered application (split application) of the separately formulated or partially separately formulated individual components. It is also possible to apply the individual components or the herbicidal compositions in several portions (sequential application), e.g. after pre-emergence applications, followed by post-emergence applications or after early post-emergence applications, followed by mid- or late post-emergence applications.The preferred method is to use the active ingredients of the respective combination together or at the same time.

[0043] 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.

[0044] Transgenic plants are generally characterized by particularly advantageous traits, such as resistance to certain pesticides, especially certain herbicides; resistance to plant diseases or pathogens that cause plant diseases, such as certain insects; or microorganisms such as fungi, bacteria, or viruses. Other special traits affect the harvested crop in terms of quantity, quality, storability, composition, and specific ingredients. Transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known. Other special traits may include tolerance or resistance to abiotic stressors, such as heat, cold, drought, salt, and ultraviolet radiation.

[0045] The herbicidal compositions according to the invention are preferably used in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0046] Conventional methods for producing new plants with modified properties compared to existing plants include, for example, classical breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described of genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806), transgenic crop plants that are resistant to certain herbicides of the glufosinate type (see, for example,EP-A-0242236, EP-A-242246) or glyphosate (WO 92 / 00377) or sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259). transgenic crops with a modified fatty acid composition (WO 91 / 13972). genetically modified crops with new ingredients or secondary substances, e.g. B. new phytoalexins that cause increased disease resistance (EPA 309862, EPA0464461) genetically modified plants with reduced photorespiration that have higher yields and greater stress tolerance (EPA 0305398).

[0047] Transgenic crops that produce pharmaceutically or diagnostically important proteins (“molecular pharming”); transgenic crops that are characterized by higher yields or better quality; transgenic crops that are characterized by a combination of, for example, the above-mentioned new traits (“gene stacking”)

[0048] Numerous molecular biological techniques for producing new transgenic plants with modified traits are known in principle; see, for example, BI 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.

[0049] For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to the DNA fragments to connect them together, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, "Genes and Clones," VCH Weinheim, 2nd ed., 1996.

[0050] The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.

[0051] For this purpose, DNA molecules can be used that contain the entire coding sequence of a gene product, including any flanking sequences present, or DNA molecules that contain only parts of the coding sequence. These parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical.

[0052] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to the person 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). Expression of nucleic acid molecules can also occur in the organelles of plant cells.

[0053] The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can, in principle, be plants of any plant species, i.e., both monocotyledonous and dicotyledonous.

[0054] Transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0055] The compositions according to the invention can preferably be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl isoxazoles and analogous active ingredients.

[0056] When the compositions according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops.

[0057] The invention therefore also relates to the use of the compositions according to the invention for controlling harmful plants in transgenic crops. The use of the compositions according to the invention is preferred in economically important transgenic crops of useful and ornamental plants, e.g., cereals (e.g., wheat, barley, rye, oats), millet, rice, cassava, and maize, or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetable crops.

[0058] The invention therefore also relates to the use of the compositions according to the invention for controlling harmful plants in transgenic crops or crops which exhibit tolerance through selective breeding.

[0059] The herbicides (A), (B), and optionally the safeners (C) can be converted together or separately into conventional formulations, e.g., for spraying, pouring, spraying, and seed dressing applications, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic substances impregnated with active ingredients, and microencapsulations in polymeric materials. The formulations may contain the usual excipients and additives.

[0060] These formulations are prepared in a known manner, e.g. by mixing the active ingredients with extenders, i.e. liquid solvents, pressurised liquefied gases and / or solid carriers, optionally using surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-forming agents.

[0061] If water is used as an extender, organic solvents can also be used as co-solvents. The following are essentially suitable liquid solvents: aromatics such as xylene, toluene, alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes, or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffins, e.g., petroleum fractions, mineral and vegetable oils; alcohols such as butanol or glycol and their 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.

[0062] The following can be used as solid carriers: e.g. ammonium salts and natural mineral flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic mineral flours such as highly dispersed silica, aluminum oxide and silicates; the following can be used as solid carriers for granules: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; the following can be used as emulsifying and / or foam-forming agents: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; Possible dispersants include: e.g. lignin sulphate waste liquors and methylcellulose.

[0063] Adhesives such as carboxymethylcellulose, natural and synthetic, powdered, granular, or latex-like polymers such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives may include mineral and vegetable oils.

[0064] Dyes such as inorganic pigments, e.g. iron oxide, titanium oxide, ferrocyanine blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

[0065] The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90% by weight.

[0066] The herbicides (A), (B) and optionally the safeners (C) can be used as such or in their formulations also in admixture with other agrochemical active ingredients for controlling unwanted plant growth, e.g. for weed control or for controlling unwanted crop plants, where ready-made formulations or tank mixes are possible.

[0067] Mixtures with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil improvers are also possible, as are additives and formulation aids commonly used in plant protection.

[0068] The herbicides (A), (B), and optionally the safeners (C) can be applied as such, in the form of their formulations, or in the application forms prepared from them by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes, and granules. Application is typically carried out by, for example, watering, spraying, or spreading.

[0069] The active ingredients can be applied to the plants, plant parts, seeds, or the cultivated area (arable soil), preferably to the seeds or green plants and plant parts, and if necessary, also to the arable soil. One possible application is the joint application of the active ingredients in the form of tank mixes, in which the optimally formulated concentrated formulations of the individual active ingredients are mixed together with water in the tank, and the resulting spray mixture is applied.

[0070] A joint formulation of the inventive combination of active ingredients (A), (B), and optionally (C) has the advantage of easier application because the amounts of the components can already be adjusted in the optimal ratio to one another. Furthermore, the excipients in the formulation can be optimally coordinated.

[0071] For application, the commercially available formulations are diluted in the usual way, e.g., with water for wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances prior to use.

[0072] Biological examples:

[0073] The abbreviations used for the pests mean:

[0074] ABUTH: Abutilon theophrasti BRAPP: Brachiaria platyphylla

[0075] CYPIR: Cyperus iria EMEAU: Emex australis

[0076] EPHHL: Euphorbia heterophylla ERIBO: Erigeron bonariensis

[0077] PHBPU: Pharbitis purpurea POLCO: Polygonum convolvulus

[0078] SETVI: Setaria viridis SOLNI: Solanum nigrum

[0079] SORHA: Sorghum halepense XANST: Xanthium strumarium

[0080] Herbicidal activity against post-emergence weeds

[0081] Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown in wood fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under favorable growth conditions. Two to three weeks after sowing, the test plants are treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green plant parts as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l / ha, with the addition of 0.2% wetting agent. After approximately three weeks of the test plants in the greenhouse under optimal growth conditions, the effectiveness of the preparations is visually assessed in comparison to untreated controls (herbicidal effectiveness in percent (%): 100% effectiveness = plants are dead, 0% effectiveness = same as control plants).Numerous compounds of the invention demonstrated very good activity against a wide range of important weeds. The following tables show examples of the postemergence herbicidal activity of the compounds of the invention, with the herbicidal activity expressed as a percentage.

[0082] In the following tables, the abbreviations mean the following:

[0083] E: means the expected synergism value according to Colby formula.

[0084] A SYN: means the difference between the actual and the expected synergism

[0085] Value.

[0086] DAT: means days after treatment. 1-5 denotes the chiral (S-configured) compound of the formula:

[0087] Pl: means methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl] amino] tetrahydrofuran-2-carboxylate.

[0088] P2: bedeutet Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5-carbonyl] amino] cyclopent-2-ene- 1 -carboxylat.

[0089] P3: bedeutet 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl) pyridin-2-carbonsäure.

[0090] P4: bedeutet Ethyl-3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl] phenyl} -5-methyl-4,5-dihydro- 1 ,2-oxazol-5-carboxylat.

Claims

Patent claims 1. Herbicidal compositions containing (A) the compound having the absolute configuration given in formula (1-5) (component A) or its salts, as well as (B) one or more herbicides (component B) selected from groups B1, B2, B5, B6, B8 and B9: Bl: Dioxopyritrione, Benquitrione, Tolpyralate, Lancotrione, B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl] amino] tetrahydrofuran-2-carboxylate, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy late, dimesulfacet, B5: Trifludimoxazine, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen, Bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimisoxafen, 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.

2. Herbicidal compositions according to claim 1, containing one or more herbicides (component B) selected from the groups B1, B2, B5, B6, B8 and B9: Bl: Dioxopyritrione, Benquitrione, Tolpyralate, B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl] amino] tetrahydrofuran-2-carboxylate, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy lat, B5: Trifludimoxazine, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen, Bixlozone, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimisoxafen, 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.

3. Herbicidal compositions according to claim 1 or 2, containing one or more herbicides (component B) selected from the groups B1, B2, B5, B6, B8 and B9: Bl: Dioxopyritrione, Benquitrione, Tolpyralate, B2: Methyl-(2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl] amino] tetrahydrofuran-2-carboxylate, Methyl-(lS,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] cyclopent-2-ene-l -carboxy lat, B5: Trifludimoxazine, Tetflupyrolimet, Fenpyrazone, Florpyrauxifen, B6: 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylic acid, B8: Rimisoxafen, B9: Tiafenacil, flufenoximacil, ethyl 3-{2-chloro-4-fhror-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. Herbicidal compositions according to one of claims 1 to 3, additionally containing as component C one or more safeners from the group consisting of benoxacor, cloquintocet-mexyl, cyprosulfamide, dichlormid, fenclorim, fenchlorazole, furilazole, isoxadifen-ethyl, mefenpyr- diethyl, 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane, 2,2,5-trimethyl-3-(dechloroacetyl)-l,3-oxazolidine.

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

6. Process according to claim 5, characterized in that the plants come from the group consisting of sugar cane, maize, wheat, rye, barley, oats, rice, sorghum, cotton and soy.

7. A method according to claim 5 or 6, characterized in that the plants are genetically modified.

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