Substituted aryl carboxamides

Abstract

The invention relates to aryl carboxamides of formula (I) as herbicides. In formula (I), X, Y, Z and Rx are groups such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

[0001] Substituted arylcarboxamides

[0002] The invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and grass weeds in crops.

[0003] WO 2020 / 148175 and the documents cited therein describe herbicidally active benzoylamides. These benzoylamides can be substituted in the 3-position of the phenyl ring by a variety of different residues. However, the benzoylamides known from these documents do not always exhibit sufficient herbicidal activity and / or tolerance to crop plants.

[0004] The object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the arylcarboxamides according to the invention described below, which bear a sulfur-containing radical linked via a methylene group in the 3-position of the phenyl ring and a haloalkoxy radical in the 4-position.

[0005] The present invention thus relates to arylcarboxamides of the formula (I) and their salts where the symbols and indices have the following meanings:

[0006] R x means (Ci-C6)-alkyl,

[0007] X is halogen or (Ci-Ce)-alkyl,

[0008] Y means halogen-(Ci-C6)-alkoxy,

[0009] Z means (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or (Ci-Ce)-alkyl-

[0010] O-(Ci-C6)-alkyl, and n is 0, 1 or 2.

[0011] In formula (I) and all subsequent formulas, alkyl radicals with more than two carbon atoms can be straight-chain or branched. Alkyl radicals denote, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Analogously, alkenyl denotes, for example, allyl, l-methylprop-2-en-l-yl, 2-methyl-prop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methyl-but-3-en-l-yl and l-methyl-but-2-en-l-yl. Alkynyl denotes, for example, propargyl, but-2-yn-l-yl, but-3-yn-l-yl, l-methyl-but-3-yn-l-yl. The multiple bond can be located in any position of the unsaturated residue. Cycloalkyl means a carbocyclic, saturated ring system with three to six carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Halogen-substituted alkyl means straight-chain or branched alkyl groups, where the hydrogen atoms in these groups may be partially or completely replaced by halogen atoms, e.g.,C1-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro,2-difluoroethyl, 2,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. Halogen stands for fluorine, chlorine, bromine or iodine. The compounds of the general formula (I) or (II) can exist as stereoisomers depending on the nature and linkage of the substituents. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers also occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods, for example, chromatographic separation techniques.Stereoisomers can also be selectively prepared by employing stereoselective reactions using optically active starting materials and / or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof encompassed by the general formula (I) or (II) but not specifically defined. The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine, or pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate.These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR´R´´R´´´]. +, wherein R to R''' each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts. The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids such as HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g. carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Preferred compounds are those of the general formula (I), where the symbols and indices have the following meanings: R Xmeans (C1-C3)-alkyl, X means halogen or (C1-C3)-alkyl, Y means OCF3 or OCHF2, OCF2Me, Z means (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or (C1-C3)-alkyl-O-(C1-C3)-alkyl, and n means 0, 1 or 2. Particular preference is given to compounds of the general formula (I) where the symbols and indices have the following meanings: R X means Me or Et, X means chlorine, bromine, Me or Et, Y means OCF3, OCHF2 or OCF2Me, Z means Me, Et, c-Pr, CH2-c-Pr or (CH2)2OMe, and n means 0, 1 or 2. The abbreviations used in the present application mean: Me: Methyl Et: Ethyl Ph: Phenyl Pr: Propyl c-Pr: Cyclopropyl i-Pr: Isopropyl Compounds of the formula (II) are novel and are very suitable as intermediates for the preparation of the compounds of the formula (I) according to the invention. The present invention thus further relates to compounds of the formula (II), where the symbols and indices have the following meanings: L means halogen or R 2 O, R 2denotes hydrogen or (C1-C6)-alkyl, and n denotes 0, 1 or 2. Preferred compounds (II) are those in which L denotes chlorine, methoxy or hydroxy, X denotes chlorine, bromine, methyl or ethyl, Y denotes OCF3, OCHF2 or OCF2Me, Z denotes methyl, ethyl, c-propyl, CH2-c-propyl or (CH2)2OMe, and n denotes 0, 1 or 2. In all formulas mentioned below, the substituents and symbols, unless defined otherwise, have the same meaning as described under formula (I). Compounds according to the invention of the general formula (Ia), where n denotes 0, can be prepared, for example, by reacting the compounds according to the invention of the general formula (IIb: compounds II, where L = hydroxy) with substituted aminotetrazoles (as also described, for example, in WO2012 / 028579). N r'iIIi The compounds of the general formula (Ib) according to the invention with n = 1 or 2 can be prepared from compounds of the general formula (Ia) according to the invention by reaction with an oxidizing agent. The synthesis of the compounds of the general formulas (IIa) and (IIb) can be carried out, for example, according to the following scheme and methods known to the person skilled in the art: Collections of compounds of formula (I) and / or their salts, which can be synthesized by the above-mentioned reactions, can also be prepared in a parallelized manner, which can be done manually, partially automated, or fully automated. For example, it is possible to automate the reaction procedure, the workup, or the purification of the products or intermediates. This generally refers to a procedure such as that described, for example, by D. Tiebes in Combinatorial Chemistry – Synthesis, Analysis, Screening (editor Günther Jung), Wiley Publishers 1999, pages 1 to 34. A range of commercially available devices can be used for parallelized reaction execution and workup, for example, Calpyso reaction blocks (Caylpso reaction blocks) from Barnstead International, Dubuque, Iowa 52004-0797.USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallel purification of compounds of formula (I) and their salts or intermediates arising during their preparation, chromatography equipment is available, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. The listed equipment results in a modular approach in which the individual work steps are automated, but manual operations must be performed between the work steps. This can be circumvented by the use of partially or fully integrated automation systems.where the respective automation modules are operated, for example, by robots. Such automation systems can be purchased, for example, from Caliper, Hopkinton, MA 01748, USA. The execution of individual or multiple synthesis steps can be supported by the use of polymer-supported reagents / scavenger resins. A number of experimental protocols are described in the literature, for example, in ChemFiles, Vol. 4, No. 1.Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich). In addition to the methods described here, the preparation of compounds of formula (I) and their salts can be carried out entirely or partially by solid-phase-supported methods. For this purpose, individual intermediates or all intermediates of the synthesis, or of a synthesis adapted for the respective procedure, are bound to a synthetic resin. Solid-phase-supported synthesis methods are adequately described in the specialist literature, e.g., Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998, and Combinatorial Chemistry – Synthesis, Analysis, Screening (editor Günther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods allows for a number of well-known protocols.which in turn can be carried out manually or automatically. The reactions can be carried out, for example, using IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA. Both in the solid and liquid phase, the implementation of individual or multiple synthesis steps can be supported by the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (editors C.O. Kappe and A. Stadler), Wiley Publishers, 2005. Preparation according to the processes described here yields compounds of formula (I) and their salts in the form of substance collections, called libraries. The present invention also relates to libraries,which contain at least two compounds of the formula (I) and salts thereof. The compounds according to the invention exhibit excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous annual weeds. Even difficult-to-control perennial weeds which sprout from rhizomes, rootstocks or other permanent organs are well controlled by the active ingredients. The present invention therefore also relates to a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, in which one or more compounds according to the invention are applied to the plants (e.g. weeds such as mono- or dicotyledonous weeds or undesirable crop plants), the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the area on which the plants grow (e.g. the cultivated area).The compounds according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence, or post-emergence methods. Some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned as examples, without implying a restriction to specific species. Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum. Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens,Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium. If the compounds according to the invention are applied to the soil surface before germination, either the emergence of weed seedlings is completely prevented or the weeds grow to the cotyledon stage,However, they then cease growth and finally die completely after three to four weeks. When the active ingredients are applied post-emergence to the green parts of the plant, growth stops after treatment and the weeds remain in the growth stage present at the time of application or die completely after a certain time, so that weed competition that is harmful to the crop plants is eliminated very early and sustainably. Although the compounds according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, are only slightly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate. For these reasons, the present compounds are very suitable for the selective control of unwanted plant growth in plant crops such as agricultural crops or ornamental plants. Furthermore, the compounds according to the invention, depending on their respective chemical structure and the application rate,They exhibit outstanding growth-regulating properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant components and facilitate harvesting, for example, by inducing desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as it can, for example, reduce or completely prevent lodging. Due to their herbicidal and plant growth-regulating properties, the active ingredients can also be used to control weeds in crops of plants modified genetically or through conventional mutagenesis. The transgenic plants are generally characterized by particularly advantageous properties,for example, through resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition and special ingredients. For example, transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known. With regard to transgenic crops, the use of the compounds according to the invention is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, cassava, tomatoes,Peas and other vegetables. The compounds of the invention can preferably be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant. Conventional approaches to producing new plants that have modified properties compared to previously 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 methods (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described: - 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 which are resistant to certain herbicides of the glufosinate type (cf. e.g. EP-A-0242236,EP-A-242246) or glyphosate (WO 92 / 00377) or sulfonylureas (EP-A-0257993, US-A-5013659), - transgenic crop plants, 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 crop plants with a modified fatty acid composition (WO 91 / 13972). - genetically modified crop plants 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 exhibit higher yields and greater stress tolerance (EPA 0305398). - 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"). Numerous molecular biological techniques with which new transgenic plants with modified traits can be produced are known in principle, see, for example, B. 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). For such genetic manipulations, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base exchanges can be performed, for example.Partial sequences can be removed or natural or synthetic sequences can be added. Adapters or linkers can be attached to the 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 "Gene and Clones," VCH Weinheim, 2nd ed. 1996. The production of plant cells with reduced activity of a gene product can be achieved, for example, by expressing 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 aforementioned gene product. For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules thatwhich only comprise parts of the coding sequence, whereby 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. 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). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells. 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 plants. Thus, transgenic plants are obtainable which have altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences. The compounds according to the invention can preferably be used in transgenic cultures which are resistant to growth factors, such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, e.g. B. inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), respectively against herbicides from the group of sulfonylureas,glyphosate, glufosinate or benzoyl isoxazole and analogous active ingredients. When the active ingredients according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur that are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum that can be controlled, modified application rates that can be used for 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. The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling weeds in transgenic crops. The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions,Dusts or granules in the usual preparations. The invention therefore also relates to herbicidal and plant growth regulating agents containing the compounds according to the invention. The compounds according to the invention can be formulated in various ways, depending on the biological and / or chemical-physical parameters specified. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed dressings, granules for broadcast and soil application, granules (GR) in the form of microgranules, spray granules, coating granules, and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules, and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology," Volume 7, C. Hanser Verlag, Munich, 4th ed. 1986; Wade van Valkenburg, "Pesticide Formulations," Marcel Dekker, NY, 1973; and K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd., London. The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schönfeldt,"Surface-active ethylene oxide adducts", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986. Wettable powders are preparations that are uniformly dispersible in water and contain, in addition to the active ingredient and a diluent or inert substance, ionic and / or non-ionic surfactants (wetting agents, dispersants), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyltaurine. For the production of the wettable powders, the herbicidal active ingredients are, for example, milled in conventional equipment such as hammer mills,The mixtures are finely ground in blower mills and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries. Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acid, such as Ca-dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers,Sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, as already listed above for the other formulation types. Emulsions, e.g. oil-in-water emulsions (EW), can be produced, for example, using stirrers, colloid mills and / or static mixers using aqueous organic solvents and, if necessary, surfactants, as already listed above for the other formulation types. Granules can be obtained either by spraying the active ingredient onto adsorptive,They can be produced from granulated inert material or by applying active ingredient concentrates to the surface of carrier materials such as sand, kaolinite, or granulated inert material using adhesives, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired, mixed with fertilizers. Water-dispersible granules are generally produced using conventional processes such as spray drying, fluidized-bed granulation, disc granulation, mixing with high-speed mixers, and extrusion without solid inert material. For the production of disc, fluidized bed, extruder and spray granules see e.g. procedures in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill,New York 1973, pp. 8-57. For further details on the formulation of plant protection products, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of conventional formulation ingredients. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dust-like formulations contain 1 to 30 wt.% active ingredient, preferably 5 to 20 wt.% active ingredient, sprayable solutions contain about 0.05 to 80,preferably 2 to 50 wt.% active ingredient. In water-dispersible granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In water-dispersible granules, the active ingredient content is, for example, between 1 and 95 wt.%, preferably between 10 and 80 wt.%. In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents, and solvents, fillers, carriers, and dyes, defoamers, evaporation inhibitors, and agents that affect pH and viscosity. These formulations can also be used to produce combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers, and / or growth regulators.e.g. in the form of a ready-to-use formulation or as a tank mix. For application, the formulations available in commercial form are diluted, if necessary, in the usual way, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Dust-like preparations, soil or broadcast granules and sprayable solutions are not normally diluted with other inert substances before use. The required application rate of the compounds of formula (I) varies with external conditions such as temperature, humidity and the type of herbicide used, among others. It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha. The compounds of the formula (I) according to the invention can also be used as a mixture with other herbicides, if required. Combination partners for the compounds of the formula (I) in mixture formulations or in tank mixes which can be used are, for example, known active ingredients which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or which act as plant growth regulators, as they are known, for example, from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein. Known herbicides or plant growth regulators that can be combined with compounds of formula (I) includeFor example, the following active ingredients are to be mentioned (the compounds are designated either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. One and sometimes several application forms are mentioned as examples: Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsulfuron, Beflubutamid, (S)-(-)-Beflubutamide, Beflubutamide-M,Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulid, Bentazon, Bentazon-Natrium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Natium, Bipyrazone, Bispyribac, Bispyribac-Natium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-Natrium, Bromobutid, Bromofenoxim, Bromoxynil, Bromoxynilbutyrat, Bromoxynil-Kalium, Bromoxynil-heptanoat und Bromoxynil-octanoat, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylat, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazon, Carfentrazon-Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamin, Chlroamben-methyl, Chloramben-methylammonium, Chloramben-Natium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-Natium, Chlorfenprop, Chlorfenprop- methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal,Chlorthal-dimethyl, Chlorthal-monomethyl, Cinidon, Cinidon-ethyl, Cinmethylin, exo-(+)-Cinmethylin, d.h. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2- methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, d.h. (1R,2S,4S)-4-isopropyl-1- methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop-propargyl, Clomazon, Clomeprop, Clopyralid, Clopyralid- methyl, Clopyralid-olamin, Clopyralid-Kalium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloat, Cyclopyranil, Cyclopyrimorat, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazin, 2,4-D (sowie die Ammonium, Butotyl, Butyl, Cholin, Diethylammonium, Dimethylammonium, Diolamin, Doboxyl, Dodecylammonium, Etexyl, Ethyl, 2- Ethylhexyl, Heptylammonium, Isobutyl, Isooctyl, Isopropyl, Isopropylammonium, Lithium, Meptyl, Methyl, Kalium, Tetradecylammonium, Triethylammonium, Triisopropanolammonium,Tripromin and Trolamin Salze davon), 2,4-DB, 2,4-DB-butyl, 2,4-DB-Dimethylammonium, 2,4-DB-isooctyl, 2,4-DB- Kalium und 2,4-DB-Natrium, Daimuron (Dymron), Dalapon, Dalapon-Calcium, Dalapon-Magnesium, Dalapon-Natium, Dazomet, Dazomet-Natrium, n-Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl-pyrazolat (DTP), Dicamba und seine Salze (z.B. Dicamba-biproamin, Dicamba-N,N-Bis(3- aminopropyl)methylamin, Dicamba-butotyl, Dicamba-cholin, Dicamba-Diglycolamin, Dicamba- Dimethylammonium, Dicamba-Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba- isopropylammonium, Dicamba-methyl, Dicamba-monoethanolamin, Dicamba-olamin, Dicamba-Kalium, Dicamba-Natium, Dicamba-Triethanolamin), Dichlobenil, 2-(2,4-Dichlorbenzyl)-4,4-dimethyl-1,2- oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, Dichlorprop, Dichlorprop- butotyl, Dichlorprop-Dimethylammonium, Dichhlorprop-etexyl, Dichlorprop-ethylammonium, Dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-Kalium,Dichlorprop-Natrium, Dichlorprop-P, Dichlorprop-P-Dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-Kalium, Dichlorprop-Natrium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat- metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-Natrium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamid, Diquat, Diquat-Dibromid, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-Ammonium, DNOC-Kalium, DNOC-Natrium, Endothal, Endothal- Diammonium, Endothal-Dikalium, Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen- Ethyl, Ethoxysulfuron, Etobenzanid, F-5231, d.h. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5- oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F-7967,i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H- benzimidazol-4-yl]-1-methyl-6-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamid, Flamprop, Flamprop-Isoproyl, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Florasulam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop- Methyl, Fluazifop-P, Fluazifop-P-Butyl, Flucarbazone, Flucarbazone-Natrium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-Ethyl, Flumetsulam, Flumiclorac, Flumiclorac-Pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-Butyl, -Dimethylammonium und -Methyl, Fluoroglycofen, Fluoroglycofen-Ethyl, Flupropanat, Flupropanat-Natrium, Flupyrsulfuron, Flupyrsulfuron-Methyl, Flupyrsulfuron-Methyl-Natrium, Fluridon, Flurochloridon, Fluroxypyr, Fluroxypyr-Butometyl, Fluroxypyr-Meptyl, Flurtamon, Fluthiacet, Fluthiacet-Methyl, Fomesafen,Fomesafen-Natrium, Foramsulfuron, Foramsulfuron-Natrium, Fosamine, Fosamine-Ammonium, Glufosinat, Glufosinat- Ammonium, Glufosinat-Natrium, L-Glufosinat-Ammonium, L-Glufosinat-Natrium, Glufosinat-P- Natrium, Glufosinat-P-Ammonium, Glyphosat, Glyphosat-Ammonium, Glyphosat-Isopropylammonium, Glyphosat-Diammonium, Glyphosat-Dimethylammonium, Glyphosat-Kalium, Glyphosat-Natrium, Glyphosat-Sesquinatrium und Glyphosat-Trimesium, H-9201, d.h. O-(2,4-Dimethyl-6-nitrophenyl)-O- ethyl-isopropylphosphoramidothioat, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop-Methyl, Haloxyfop-P-Methyl, Haloxifop-Natrium, Hexazinon, HNPC-A8169, i.e. Prop-2-yn- 1-yl (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoat, HW-02, d.h. 1- (Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat, Hydantocidin, Imazamethabenz, Imazamethabenz-Methyl, Imazamox, Imazamox-Ammonium, Imazapic,Imazapic-Ammonium, Imazapyr, Imazapyr-Isopropylammonium, Imazaquin, Imazaquin-Ammonium, Imazaquin-Methyl, Imazethapyr, Imazethapyr-Ammonium, Imazosulfuron, Indanofan, Indaziflam, Iodosulfuron, Iodosulfuron-Methyl, Iodosulfuron-Methyl-Natrium, Ioxynil, Ioxynil-Lithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043, d.h. 3-({[5-(Difluormethyl)-1-methyl- 3-(trifluormethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -Diolamin, -2-Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, -Isopropylammonium, -Methyl, Olamin, - Kalium, –Natrium und -Trolamin, MCPB, MCPB-Methyl, -Ethyl und -Natrium, Mecoprop, Mecoprop- Butotyl, Mecoprop- dimethylammonium, Mecoprop-Diolamin, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop-Isoctyl, Mecoprop-Methyl, Mecoprop-Kalium, Mecoprop-Natrium, und Mecoprop-Trolamin,Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl und -Kalium, Mefenacet, Mefluidid, Mefluidid-Diolamin, Mefluidid-Kalium, Mesosulfuron, Mesosulfuron-Methyl, Mesosulfuron- Natrium, Mesotrion, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanat, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT-5950, d.h. N-[3-Chlor-4-(1-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC-310, i.e.4-(2,4-Dichlorbenzoyl)-1-methyl-5- benzyloxypyrazol, NC-656, i.e. 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5- (trifluormethyl)[1,2,4]triazolo-[4,3-a]pyridin-8-carboxamid, Neburon, Nicosulfuron, Nonansäure (Pelargonsäure), Norflurazon, Ölsäure (Fettsäuren), Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron,Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat-dichlorid, Paraquat- Dimethylsulfat, Pebulat, Pendimethalin, Penoxsulam, Pentachlorphenol, Pentoxazon, Pethoxamid, Petroleumöl, Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram- Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Kalium, Picloram- Triethylammonium, Picloram-Tripromin, Picloram-Trolamin, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan,Pyrithiobac, Pyrithiobac- Natrium, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop- P-Tefuryl, QYM201, i.e.1-{2-Chlor-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6- (trifluormethyl)phe-nyl}piperidin-2-on, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP- 249, d.h. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. 1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2- thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trichloressigsäure) und seine Salze, z.B. TCA-ammonium, TCA-Calcium, TCA-Ethyl, TCA-Magnesium, TCA-Natrium, Tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumeton, Terbuthylazine, Terbutryn,Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazon-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralat, Topramezon, Tralkoxydim, Triafamon, Tri-allat, Triasulfuron, Triaziflam, Tribenuron, Tribenuron-Methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Cholin, Triclopyr- Ethyl, Triclopyr-Triethylammonium, Trietazine, Trifloxysulfuron, Trifloxysulfuron-Natrium, Trifludimoxazin, Trifluralin, Triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Harnstoffsulfat, Vernolat, XDE-848, ZJ-0862, d.h.3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3- (2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5- methyl-4,5-dihydroisoxazole-5-carbonsäureethylester, Ethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo- 4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat, 3-Chlor-2-[3- (difluormethyl)isoxazolyl-5-yl]phenyl-5-chlorpyrimidin-2-ylether, 2-(3,4-Dimethoxyphenyl)-4-[(2- hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-on, 2-({2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexan-1,3-dion, (5-Hydroxy-1-methyl-1H- pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanon, 1-Methyl-4- [(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propan-1- sulfonat, 4-{2-Chlor-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl- 1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7- fluor-1H-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn-1-yl 4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6- yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat, 4-Amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carbonsäure, Benzyl-4-amino-3-chlor-5- fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat,Ethyl-4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol- 6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-1-isobutyryl-1H-indol-6-yl)pyridin- 2-carboxylat, Methyl 6-(1-acetyl-7-fluor-1H-indol-6-yl)-4-amino-3-chlor-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6-[1-(2,2-dimethylpropanoyl)-7-fluor-1H-indol-6-yl]-5-fluorpyridin-2- carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-1-(methoxyacetyl)-1H-indol-6-yl]pyridin-2- carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat, Natrium-4- amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat, Butyl-4-amino-3-chlor-5-fluoro-6- (7-fluoro-1H-indol-6-yl)pyridin-2-carboxylat, 4-Hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2- yl]imidazolidin-2-on, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-on, 3-[5-Chlor- 4-(trifluormethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-on,4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin-2,4(1H,3H)-dione, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidine-2- yl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1- ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3- thiazol-2-yl)pyridazin-1-iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), 1- (2-Carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-1-ium salz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), Methyl (2R)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, Methyl (2S)- 2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)- yl]phenyl}methyliden)amino]oxy}propanoat, Methyl (2R / S)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, (E)- 2-(Trifluormethyl)benzaldehyd-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxim, 2-Fluor-N- (5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluormethyl)benzamid, (2R)-2-[(4-Amino- 3,5-dichlor-6-fluor-2-pyridyl)oxy]propancarbonsäure,2-Ethoxy-2-oxoethyl-1-{2-chlor-4-fluor-5-[3- methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropancarboxylat, 2- Methoxy-2-oxoethyl-1-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin- 1(2H)-yl]phenoxy}cyclopropancarboxylat, {[(1-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}essigsäure, 2-(2- Brom-4-chlorbenzyl)-4,4-dimethyl-1,2-oxazolidin-3-on, Methyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH- cyclopenta[d][1,2]oxazol-6a-carboxylat, Ethyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH- cyclopenta[d][1,2]oxazol-6a-carboxylat. Abscisinsäure und verwandte Analoga [z.B. (2Z,4E)-5-[6-Ethynyl-1-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-diensäure, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-diensäure, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-diensäure, methyl (2E,4E)-5-(1-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoat, (2Z,4E)-5-(2-hydroxy-1,3- dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-diensäure], Acibenzolar, Acibenzolar-S- methyl, S-Adenosylhomocystein, Allantoin, 2-Aminoethoxyvinylglycin (AVG), Aminooxyessigsäure and verwandte Ester [z.B. (Isopropyliden)-aminooxyessigsäure-2-(methoxy)-2-oxoethylester, (Isopropyliden)- aminooxyessigsäure-2-(hexyloxy)-2-oxoethylester, (Cyclohexyliden)-aminooxyessigsäure-2- (isopropyloxy)-2-oxoethylester], 1-Aminocycloprop-1-ylcarbonsäure N-Methyl-1-aminocyclopropyl-1- carbonsäure, 1-Aminocyclopropyl-1-carbonsäureamid,substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canalin, catechin and catechins (e.g. (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from Chitin molecules [(C8H13NO5)n, CAS No.1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid,1-[2-(4-Cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-Cyclopropenylmethanol, Daminozide, Dazomet, Dazomet sodium, n-Decanol, Dikegulac, Dikegulac sodium, Endothal, Endothal-di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), Ethephon, 1-Ethylcyclopropene, Flumetralin, Flurenol, Flurenol-butyl, Flurenol-methyl, Flurprimidol, Forchlorfenuron, Gibberellic acid, Inabenfid, Indole-3-acetic acid (IAA), 4-Indol-3-ylbutyric acid, Isoprothiolane, Probenazole, Jasmonic acid, jasmonic acid esters or other derivatives (e.g. jasmonic acid methyl ester, jasmonic acid ethyl ester), Lipochitooligosaccharides (LCO, Sometimes referred to as symbiotic nodulation signals (Nod or Nod factors) or Myc factors, they consist of an oligosaccharide backbone of β-l,4-linked N-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end. As can be seen from the literature,LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-Methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones as described in EP2248421, 2-(1-Naphthyl)acetamide, 1-Naphthylacetic acid, 2-Naphthyloxyacetic acid, Nitrophenolate mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, Paclobutrazol,4-Phenylbutyric acid and its salts (e.g. sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid and salicyclic acid methyl ester, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine. Although the compounds of formula (I) according to the invention generally exhibit good selectivity towards crop plants, it may be useful to combine them with known safeners. Safeners which, in combination with the compounds of formula (I) according to the invention and optionally in combination with other active ingredients such as insecticides,Acaricides, herbicides, fungicides as listed above, are preferably selected from the group consisting of: S1) Compounds of formula (S1), where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3; RA 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; N WA is an unsubstituted or substituted divalent heterocyclic radical from the group of saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (WA 1 ) to (WA 5 ), m A is 0 or 1; R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N atom to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (C1-C4)alkyl, (C1-C4)alkoxy or optionally substituted phenyl, preferably a radical of the formula OR A 3 , NHR A 4 or N(CH3)2, in particular of the formula OR A 3 ; R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms; R A 4 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl; R A 5 is H, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy(C1-C8)alkyl, cyano or COOR A 9 , where R A 9Hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C6)hydroxyalkyl, (C3-C 12 )cycloalkyl or tri-(C1-C4)alkylsilyl; R A 6 , R A 7 , R A 8 are identical or different hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C3- C 12 )Cycloalkyl or substituted or unsubstituted phenyl; R A 10 is H, (C3-C 12 )Cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S1 a), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid ethyl ester (S1-1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methyl-pyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-pyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; d) compounds of the triazolecarboxylic acid type (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), ie 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620; e) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91 / 08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or -n-propyl ester (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A-95 / 07897. f) Compounds of the triazolyloxyacetic acid derivative type (S1 f), preferably compounds such as methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-15) or methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-17) or methyl {[1-(4-chloro-2-fluorophenyl)-5- (2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-19), as described in patent application WO2021105101 S2) Quinoline derivatives of the formula (S2), where the symbols and indices have the following meanings: RB 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; nB is a natural number from 0 to 5, preferably 0 to 3; RB 2 is ORB 3 , SRB 3 or NRB 3RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C1-C4)alkyl, (C1-C4)alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or N(CH3)2, in particular of the formula ORB 3 ; R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms; R B 4 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl; T Bis a (C1 or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4)alkyl radicals or by [(C1-C3)-alkoxy]carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid type (S2 a), preferably (5-chloro-8-quinolinoxy)acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetic acid allyl ester (S2-7), (5-chloro-8- quinolinoxy)acetic acid 2-(2-propylidene-iminoxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366, and (5-chloro-8-quinolinoxy)acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium,or phosphonium salts as described in WO-A-2002 / 34048; b) compounds of the type (5-chloro-8-quinolinoxy)malonic acid (S2, b ), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester, (5-chloro-8-quinolinoxy)malonic acid diallyl ester, (5-chloro-8-quinolinoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582198. S3) Compounds of the formula (S3) O where the symbols and indices have the following meanings: RC 1 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl; RC 2 , RC 3sind gleich oder verschieden Wasserstoff, (C1-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C1-C4)Haloalkyl, (C2-C4)Haloalkenyl, (C1-C4)Alkylcarbamoyl-(C1-C4)alkyl, (C2- C4)Alkenylcarbamoyl-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Dioxolanyl-(C1-C4)alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder RC 2 und RC 3together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: active ingredients of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-acting safeners), such as: B. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane) from Nitrokemia orMonsanto (S3-7), "TI-35" (1-Dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, "Furilazole" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R)-isomer (S3-11). S4) N-Acylsulfonamides of the formula (S4) and their salts, R. 3 where the symbols and indices have the following meanings: X D is CH or N; RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ; RD 2 is halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; RD 3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; RD 4is halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)alkoxycarbonyl or (C1-C4)alkylcarbonyl; RD 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing vD heteroatoms from the group nitrogen, oxygen and sulfur, where the last seven radicals are replaced by v D Substituents from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C2)alkylsulfinyl, (C1-C2)alkylsulfonyl, (C3-C6)cycloalkyl, (C1-C4)alkoxycarbonyl, (C1-C4)alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (C1-C4)alkyl and (C1-C4)haloalkyl; R D 6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, where the last three radicals are represented by v Dradicals from the group halogen, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkylthio, or R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical; R D 7 is hydrogen, (C1-C4)alkylamino, di-(C1-C4)alkylamino, (C1-C6)alkyl, (C3-C6)cycloalkyl, where the last two radicals are replaced by v D Substituents from the group consisting of halogen, (C1-C4)alkoxy, (C1-C6)haloalkoxy and (C1-C4)alkylthio and, in the case of cyclic radicals, also (C1-C4)alkyl and (C1-C4)haloalkyl; n D is 0, 1 or 2; m D is 1 or 2; v D is 0, 1, 2 or 3; of these, preference is given to compounds of the N-acylsulfonamide type, e.g. of the following formula (S4 a ), which are known, for example, from WO-A-97 / 45016 OOO 4 where RD 7(C1-C6)alkyl, (C3-C6)cycloalkyl, where the last two radicals are substituted by vD substituents from the group halogen, (C1-C4)alkoxy, (C1-C6)haloalkoxy and (C1-C4)alkylthio and, in the case of cyclic radicals, also (C1-C4)alkyl and (C1-C4)haloalkyl; RD 4 Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3; mD is 1 or 2; vD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4 b ), which are known, for example, from WO-A-99 / 16744, 5 e.g. those where R D 5 = Cyclopropyl and (R D 4 ) = 2-OMe is ("Cyprosulfamide", S4-1), RD 5 = Cyclopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-2), RD 5 = Ethyl and (RD 4 ) = 2-OMe is (S4-3), RD 5 = Isopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-4) and RD 5 = Isopropyl and (RD 4 ) = 2-OMe (S4-5). as well as compounds of the N-acylsulfamoylphenylurea type of the formula (S4c ), which are known for example from EP-A-365484, 8 where RD 8 and RD 9 independently of one another hydrogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, RD 4Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3 mD means 1 or 2; for example 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea. S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001. S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630. S7) Compounds of formula (S7), as described in WO-A-1998 / 38856 - A. where the symbols and indices have the following meanings: RE 1 , RE 2 are independently halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)alkylamino, di-(C1-C4)alkylamino, nitro; A E is COOR E 3 or COSR E 4 R E 3 , R E 4 are independently hydrogen, (C1-C4)alkyl, (C2-C6)alkenyl, (C2-C4)alkynyl, cyanoalkyl, (C1-C4)haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n E 1 is 0 or 1 nE2 , nE 3 are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1). S8) Compounds of the formula (S8), as described in WO-A-98 / 27049 R 2 ( RF 1 )nF Wherein X F CH or N, n F in case X F =N is an integer from 0 to 4 and in case X F =CH is an integer from 0 to 5 , R F 1 Halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, nitro, (C1-C4)alkylthio, (C1-C4)alkylsulfonyl, (C1-C4)alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy, R F 2 Hydrogen or (C1-C4)alkyl R F 3hydrogen, (C1-C8)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, preferably compounds wherein XF is CH, nF is an integer from 0 to 2, R F 1 Halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, RF 2 hydrogen or (C1-C4)alkyl, RF 3Hydrogen, (C1-C8)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or salts thereof. S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020. S10) Compounds of the formulas (S10 a ) or (S10 b ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764 O where R G 1 Halogen, (C1-C4)alkyl, methoxy, nitro, cyano, CF3, OCF3Y G , Z G independently O or S, n G an integer from 0 to 4, R G2 (C1-C 16 )Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, R G 3hydrogen or (C1-C6)alkyl. S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressings, such as B. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor damage. S12) Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in sown rice, "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphodithioate) (S13-7), "Dietholate" (O,O-diethyl O-phenylphosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9). S14) Active ingredients that, in addition to herbicidal activity against harmful plants, also have a safener effect on crops such as rice, such as"Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), known as a safener for rice against damage from the herbicide molinate, "Daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a safener for rice against damage from the herbicide imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a safener for rice against damage from some herbicides, "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai (CAS Reg. No. 54091-06-4), which is known as a safener against the damage of some herbicides in rice. S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008 / 131861 and WO-A-2008 / 131860 O. where R H 1 a (C1-C6)haloalkyl radical and RH 2 hydrogen or halogen and R H 3 , R H 4 independently of each other hydrogen, (C1-C 16 )Alkyl, (C2-C 16 )alkenyl or (C2-C 16)Alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, or (C3-C6)cycloalkyl, (C4-C6)cycloalkenyl, (C3-C6)cycloalkyl, which is on one side of the ring fused to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)cycloalkenyl fused to a 4 to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring, each of the last-mentioned 4 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy,(C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or R, H 3 (C1-C4)alkoxy, (C2-C4)alkenyloxy, (C2-C6)alkynyloxy or (C2-C4)haloalkoxy and R H 4 hydrogen or (C1-C4)-alkyl or R H 3 and R H 4together with the directly bonded N atom forms a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio. S16) Active substances which are primarily used as herbicides but also have a safener effect on crops, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid, and metcamifen. The following examples illustrate the invention. A. Chemical Examples Synthesis of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (1): Step 1: Preparation of 1-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4): 20.35 ml (145.2 mmol) of diisopropylamine were initially charged to 250 ml of tetrahydrofuran under argon and stirred at -60°C. o C, 79.4 ml (127.1 mmol) of n-butyllithium (1.6 M solution in hexane) were added dropwise and the solution stirred for 1 h. Then, the mixture was briefly cooled to -40 o C and then at -60 oC, a solution of 25 g (90.8 mmol) of 1-bromo-2-chloro-4-(trifluoromethoxy)benzene (3) in 60 ml of tetrahydrofuran was added dropwise. The solution was stirred for 1 h. Then, 11.5 ml (181.5 mmol) of iodomethane were added dropwise, and stirring was continued for another 1 h. The still-cold reaction solution was mixed with 800 ml of water and adjusted to pH 1 with concentrated hydrochloric acid. After extraction with ethyl acetate, the organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→80 / 20). This gave 25.00 g (95%) of 1-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4). 1H-NMR (400 MHz, DMSO-d6): δ = 7.79 (d, 1H); 7.35 (d, 1H); 2.39 (s, 3H). Step 2: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5): 18.91 g (65.33 mmol) of 1-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4) was dissolved in 150 mL of dimethylformamide, and 11.7 g (130.65 mmol) of copper(I) cyanide was added at room temperature. The resulting reaction mixture was heated to reflux for 12 h. It was then poured into 1 l of cold water and treated with ethyl acetate. After vigorous stirring for 10 min, the mixture was filtered and the phases were separated. The organic phase was dried and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). This yielded 11.83 g (77%) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5). 1H-NMR (400 MHz, DMSO-d6): δ = 8.01 (d, 1H); 7.60 (br d, 1H); 2.37 (s, 3H). Step 3: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6): 10.92 g (46.35 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5) was dissolved in a solution of 17.73 g (443 mmol) of sodium hydroxide in 180 ml of water and heated to reflux for 6 h. The mixture was then left to stand overnight at room temperature. The mixture was then washed with dichloromethane, and the aqueous phase was adjusted to pH 1 with 2M hydrochloric acid. The mixture was then extracted with ethyl acetate, and the organic phase was separated, dried, and evaporated. 11.07 g (94%) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6) were obtained. 1H-NMR (400 MHz, DMSO-d6): δ = 13.59 (br s, 1H); 7.72 (d, 1H); 7.45 (br d, 1H); 2.35 (s, 3H). Step 4: Preparation of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7): 22.08 g (86.73 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6) were initially dissolved in 400 ml of dichloromethane and 3 ml of dimethylformamide. 11.58 ml (13.09 mmol) of oxalyl chloride were slowly added at room temperature. The mixture was then stirred for 1 h at room temperature. 20 ml (1734.5 mmol) of methanol were added dropwise, followed by stirring for 3 h at room temperature, and the solution was evaporated to dryness. The residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). This yielded 21.26 g (91%) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7). 1H-NMR (400 MHz, DMSO-d6): δ = 7.75 (d, 1H); 7.49 (br d, 1H); 3.88 (s, 3H); 2.36 (s, 3H). Step 5: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (1): 10.42 g (38.79 mmol) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7) was dissolved in 100 g of chlorobenzene, and 13.81 g (77.58 mmol) of N-bromosuccinimide and 0.64 g (3.88 mmol) of AIBN were added. The reaction mixture was stirred for 8 h at 120 °C. o C. It was then evaporated, and the residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). This gave 13.25 g (98%) of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (1). 1H-NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.57 (br d, 1H); 4.75 (s, 2H); 3.89 (s, 3H). Synthesis of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (2): Step 1: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (9): To a solution of 19.93 g of potassium hydroxide in 75 ml of acetonitrile and 75 ml of water at 0 o C 10 g (47.35 mmol) of commercially available methyl 2-chloro-4-hydroxy-3-methylbenzoate (8) were added in portions. Then, 17.52 ml (94.71 mmol) of diethyl [bromo(difluoro)methyl]phosphonate were added, and the mixture was stirred for 1 h at 0 o C. After addition of ethyl acetate, the organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→85 / 15). This yielded 9.80 g (82%) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (9). 1H-NMR (400 MHz, DMSO-d6): δ = 7.71 (d, 1H); 7.33 (t, 1H); 7.27 (d, 1H); 3.86 (s, 3H); 2.31 (s, 3H). Step 2: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (2): 20.65 g (82.39 mmol) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (9) was dissolved in 200 g of chlorobenzene, and 29.33 g (164.79 mmol) of N-bromosuccinimide and 1.35 g (8.24 mmol) of AIBN were added. The reaction mixture was stirred for 8 h at 120 °C. o C. It was then evaporated, and the residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). This gave 26.47 g (97%) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (2). 1H NMR (400 MHz, DMSO-d6): δ = 7.89 (d, 1H); 7.48 (t, 1H); 7.36 (d, 1H); 4.73 (s, 2H); 3.88 (s, 3H). Examples for the preparation of the compounds (II) and (I) according to the invention: Preparation of methyl 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoate (1-31), (R,S)-2-chloro-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-32) and 2-chloro-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-33): Step 1: Preparation of methyl 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoate (3-31): 3.00 g (8.63 mmol) Methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (1) was initially dissolved in 100 ml of dimethylformamide and 0.67 g (8.63 mmol) of sodium thiomethylate was added at room temperature. The mixture was stirred at room temperature for 5 h and then evaporated. The residue was dissolved in 2M hydrochloric acid and extracted with dichloromethane.The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→50 / 50). This yielded 2.15 g (79%) of methyl 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoate (3-31). Step 2: Preparation of 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoic acid (4-31): 2.15 g (6.83 mmol) of methyl 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoate (3-31) were initially dissolved in 100 ml of methanol, and 6.83 ml (13.66 mmol) of 2M sodium hydroxide solution were added at room temperature. The reaction mixture was stirred at room temperature for 12 h and then evaporated. The residue was taken up with water, and the aqueous phase was adjusted to pH 1 with 2M hydrochloric acid. The organic phase was separated, dried, and evaporated. This yielded 1.93 g (94%) of 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoic acid (4-31).Step 3: Preparation of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31): 600 mg (2 mmol) of 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoic acid (4-31) and 302.7 mg (3 mmol) of 5-amino-1-methyl-1H-tetrazole were initially charged in 10 ml of pyridine, and 0.27 ml (3 mmol) of oxalyl chloride was added dropwise at room temperature. The reaction solution was stirred for 12 h at room temperature. After adding 30 ml of saturated aqueous sodium bicarbonate solution, the mixture was stirred for a further 30 min, followed by extraction with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, C18, gradient: acetonitrile / water (+0.05% trifluoroacetic acid) 10 / 90→100 / 0). This yielded 200 mg (25%) of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31).Step 4: Preparation of (R,S)-2-chloro-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-32): 68 mg (0.17 mmol) of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31) were placed in 3 ml of glacial acetic acid and treated at room temperature with 0.016 ml (0.17 mmol) of a 25% aqueous hydrogen peroxide solution and stirred at 60. oC for 4 h. After evaporation of the mixture, the residue was taken up in water and extracted with ethyl acetate. The organic phase was separated, dried, and evaporated. This gave 60 mg (80%) of (R,S)-2-chloro-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-32). Step 5: Preparation of 2-chloro-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-33). 68 mg (0.17 mmol) of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31) were placed in 3 ml of glacial acetic acid and treated at room temperature with 0.047 ml (0.53 mmol) of a 25% aqueous hydrogen peroxide solution and a catalytic amount of sodium tungstate. The mixture was then stirred for 4 h at 60 °C. oC. After evaporation of the mixture, the residue was taken up in water and extracted with ethyl acetate. The organic phase was separated, dried, and evaporated. This gave 68 mg (88%) of 2-chloro-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-33). The examples listed in the following tables were prepared analogously to the methods mentioned above or are obtainable analogously to the methods mentioned above. These compounds are very particularly preferred. The examples listed in the following tables were prepared analogously to the methods mentioned above or are obtainable analogously to the methods mentioned above. These compounds are very particularly preferred. The abbreviations used mean: Me = Methyl Et = Ethyl c-Pr = cyclopropyl Table 1: Compounds of the formula (I) according to the invention, wherein R xrepresents a methyl group and the other substituents have the meanings given below. N

[0012] Table 2: Compounds of formula (I) according to the invention, wherein R x represents an ethyl group and the other substituents have the meanings given below. N Table 3: Compounds of formula (II) according to the invention, wherein L is methoxy and the other substituents have the meanings given below,

[0013] Table 4: Compounds of the formula (II) according to the invention, wherein L is hydroxy and the other substituents have the meanings given below, OX

[0014] Table 5: Compounds of formula (II) according to the invention, wherein L is chlorine and the other substituents have the meanings given below

[0015] For further characterization, NMR data are disclosed below for numerous compounds of formula (I) and (II) according to the invention mentioned in the tables above: Example No. 1-31: 1 H NMR (400 MHz, DMSO-d6): δ = 11.88 (br s, 1H); 7.81 (d, 1H); 7.58 (d, 1H); 4.01 (s, 3H); 3.93 (2H); 2.12 (s, 3H); Example no. 1-32: 1 H NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 7.88 (d, 1H); 7.62 (d, 1H); 4.39 (d, 1H); 4.34 (d, 1H); 4.01 (s, 3H); 2.75 (s, 3H); Example no. 1-33: 1 H NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.82 (s, 2H); 4.01 (s, 3H); 3.17 (s, 3H); Example no. 1-91: 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 7.74 (d, 1H); 7.41 (t, 1H); 7.36 (d, 1H); 4.00 (s, 3H); 3.89 (s, 2H); 2.10 (s, 3H); Beispiel-Nr. 1-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 7.82 (d, 1H); 7.40 (d, 1H); 7.35 (t, 1H); 4.33 (m, 2H); 4.00 (s, 3H); 2.71 (s, 3H); Beispiel-Nr. 1-93: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.87 (br s, 1H); 7.87 (d, 1H); 7.41 (d, 1H); 7.36 (t, 1H); 4.76 (s, 2H); 4.00 (s, 3H); 3.12 (s, 3H); Beispiel-Nr.2-31: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.78 (br s, 1); 7.80 (d, 1H); 7.58 (d, 1H); 4.37 (q, 2H); 3.93 (s, 2H); 2.12 (s, 3H); 1.47 (t, 3H); Beispiel-Nr. 2-32: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.88 (d, 1H); 7.62 (d, 1H); 4.36 (m, 4H); 2.75 (s, 3H); 1.47 (t, 3H); Beispiel-Nr. 2-33: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.83 (s, 2H); 4.37 (q, 2H); 3.17 (s, 3H); 1.48 (t, 3H); Beispiel-Nr. 2-91: 1H-NMR (400 MHz, DMSO-d6): δ = 11.71 (br s, 1H); 7.73 (d, 1H); 7.41 (t, 1H); 7.36 (d, 1H); 4.38 (d, 1H); 4.34 (d, 1H); 3.89 (2H); 2.11 (s, 3H); 1.47 (t, 3H); Beispiel-Nr. 2-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 7.82 (d, 1H); 7.40 (d, 1H); 7.35 (t, 1H); 4.34 (m, 4H); 2.71 (s, 3H); 1.47 (t, 3H); Beispiel-Nr. 2-93: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.77 (br s, 1H); 7.86 (d, 1H); 7.41 (d, 1H); 7.36 (d, 1H); 4.76 (s, 2H); 4.36 (q, 2H); 3.12 (s, 3H); 1.48 (t, 3H); Beispiel-Nr.3-31: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.82 (d, 1H); 7.52 (br d, 1H); 3.90 (s, 2H); 3.88 (s, 3H); 2.09 (s, 3H); Beispiel-Nr. 3-33: 1 H-NMR (400 MHz, CDCl3): δ = 7.91 (d, 1H); 7.35 (br d, 1H); 4.71 (d, 2H); 3.96 (s, 3H); 2.96 (s, 3H); Beispiel-Nr. 3-91: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.78 (d, 1H); 7.40 (t, 1H); 7.30 (d, 1H); 3.87 (s, 2H); 3.86 (s, 3H); 2.08 (s, 3H); Beispiel-Nr.4-31: 1H-NMR (400 MHz, DMSO-d6): δ = 13.68 (br s, 1H); 3.78 (d, 1H); 7.48 (br d, 1H); 3.90 (d, 2H); 2.09 (s, 3H); Beispiel-Nr.4-33: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.74 (br s, 1H); 7.91 (d, 1H); 7.53 (br d, 1H); 4.80 (s, 2H); 3.14 (s, 3H); Beispiel-Nr. 4-91: 1H-NMR (400 MHz, DMSO-d6): δ = 13.47 (br s, 1H); 7.75 (d, 1H); 7.38 (t, 1H); 7.27 (br d, 1H); 3.87 (s, 2H); 2.08 (s, 3H). B. Formulation examples a) A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or its salts and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as a wetting and dispersing agent, and grinding the mixture in a pin mill. c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and / or its salts with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of-parts of paraffinic mineral oil (boiling range, for example, approximately 255 to over 277°C) and ground in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent, and 10 parts by weight of ethoxylated nonylphenol as emulsifier. e) Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of formula (I) and / or salts thereof, 10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, grinding on a pin mill and granulating the powder in a fluidized bed by spraying on water as a granulation liquid. f) Water-dispersible granules are also obtained by mixing 25 parts by weight of a compound of formula (I) and / or salts thereof, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of-parts of oleoylmethyltaurine sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water are homogenized and pre-crushed on a colloid mill, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower by means of a single-component nozzle. C. Biological examples The abbreviations used for the weeds mean: ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AVEFA Avena fatua AMARE Amaranthus retroflexus CYPES Cyperus esculentus DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli HORMU Hordeum murinum KCHSC Kochia scoparia LOLMU Lolium multiflorum LOLRI Lolium rigidum MATIN Matricaria inodora PHBPU Pharbitis purpurea POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor 1. Herbicidal action against weeds in pre-emergence Seeds of monocotyledonous or dicotyledonous weeds orCrops are placed in wood fiber pots in sandy loam soil and covered with soil. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the covering soil 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 treatment, the pots are placed in a greenhouse and maintained under favorable growth conditions for the test plants. Visual assessment of damage to the test plants is carried out after a trial period of 3 weeks, in comparison to untreated controls (herbicidal activity in percent (%): 100% activity = plants died, 0% activity = same as control plants). Numerous compounds of the invention demonstrated very good activity against a wide range of important weeds.The following tables show, by way of example, the post-emergence herbicidal activity of the compounds according to the invention, with the herbicidal activity being given in percent. Table C-8: Pre-emergence effect at 80g / ha against ALOMY in % Table C-9: Pre-emergence effect at 20g / ha against AMARE in % Table C-10: Pre-emergence effect at 80g / ha against AMARE in % Table C-17: Pre-emergence effect at 80g / ha against MATIN in % Table C-18: Pre-emergence effect at 80g / ha against PHBPU in % Table C-19: Pre-emergence effect at 20g / ha against POLCO in % Table C-20: Pre-emergence effect at 80g / ha against POLCO in % Table C-27: Pre-emergence effect at 20g / ha against KCHSC in % Table C-28: Pre-emergence effect at 80g / ha against KCHSC in % 2. Post-emergence herbicidal activity against weeds: 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 parts of the plants 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 the test plants have been in the greenhouse for approximately three weeks under optimal growth conditions, the effectiveness of the preparations is visually assessed in comparison to untreated controls (herbicidal activity in percent (%): 100% activity = plants are dead, 0% activity = 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. Table C-29: Postemergence activity at 20 e / ha of ZEAMX in %. Table C-35: Post-emergence effect at 80g / ha against ALOMY in % Table C-36: Post-emergence effect at 20g / ha against AMARE in % Table C-37: Post-emergence effect at 80g / ha against AMARE in % Table C-44: Post-emergence effect at 80g / ha against PHBPU in % Table C-45: Post-emergence effect at 80g / ha against POLCO in % Table C-46: Post-emergence effect at 20g / ha against SETVI in % I Table C-47: Post-emergence effect at 80g / ha against SETVI in % I Table C-48: Post-emergence effect at 20 / ha een VERPE in % Table C-53: Post-emergence effect at 80g / ha against KCHSC in % Comparative experiments In the following experiments, the herbicidal activity of numerous compounds according to the invention and the structurally closest compounds known from WO2020 / 148175 was compared under the above-mentioned pre-emergence and post-emergence conditions. The example numbers listed in the tables.refer to the compounds according to the invention of the present application; The respective comparison compounds are disclosed in the above-mentioned document but not specifically named (compounds V-1 to V-6) and are designated by their IUPAC name below: V-1: 2-chloro-4-methoxy-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide V-2: (R,S)-2-chloro-4-methoxy-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide V-3: 2-chloro-4-methoxy-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide V-4: 2-chloro-N-(1-ethyl-1H-tetrazol-5-yl)-4-methoxy-3-[(methylsulfanyl)methyl]benzamide V-5: (R,S)-2-chloro-N-(1-ethyl-1H-tetrazol-5-yl)-4-methoxy-3-[(methylsulfinyl)methyl]benzamide V-6: 2-chloro-N-(1-ethyl-1H-tetrazol-5-yl)-4-methoxy-3-[(methylsulfonyl)methyl]benzamide Herbicidal action in pre-emergence: efg = inventive compound of the present application.

[0016] Post-emergence herbicidal activity: erf.gem. = according to the invention, compound of the present application

Claims

Claims:

1. Arylcarboxamides of the formula (I) or their salts N where the symbols and indices have the following meanings: R X means (C1-C6)-alkyl, X means halogen or (C1-C6)-alkyl, Y means halogen-(C1-C6)-alkoxy, Z means (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or (C1-C6)-alkyl-O-(C1-C6)-alkyl, and n means 0, 1 or 2.

2. Arylcarboxamides according to claim 1, wherein the symbols have the following meanings: R X means (C1-C3)-alkyl, X means halogen or (C1-C3)-alkyl, Y means OCF3, or OCHF2 or OCF2Me, Z means (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or (C1-C3)-alkyl-O-(C1-C3)-alkyl, and n means 0, 1 or 2.

3. Arylcarboxamides according to claim 1 or, where the symbols have the following meanings: R Xmeans Me or Et, X means chlorine, bromine, Me or Et, Y means OCF3, OCHF2 or OCF2Me, Z means Me, Et, c-Pr, CH2-c-Pr or (CH2)2OMe, and n is 0, 1, or 2.

4. Herbicidal compositions comprising at least one arylcarboxamide according to any one of claims 1 to 3 in a mixture with formulation auxiliaries.

5. Herbicidal compositions according to claim 4 comprising at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

6. A method for controlling unwanted plants, which comprises applying an effective amount of at least one arylcarboxamide according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 to the plants or to the site of unwanted plant growth.

7. Use of arylcarboxamides of the formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 for controlling unwanted plants. 8.Use according to claim 7, characterized in that the arylcarboxamides of the formula (I) are used to control undesirable plants in crops of useful plants.

9. Use according to claim 8, characterized in that the useful plants are transgenic useful plants.

10. Compounds of the formula (II), O X. where the symbols and indices have the following meanings: L means halogen or R 2 O, X means halogen or (C 1 -C 6 )-alkyl, Y is halogen-(C 1 -C 6 )-alkoxy, Z means (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-Cycloalkyl-(C 1 -C 6 )-alkyl or (C 1 -C 6 )- Alkyl-O-(C 1 -C 6 )-alkyl, R 2 means hydrogen or (C 1 -C 6 )-alkyl, and n is 0, 1 or 2.

11. Compounds of formula (II) according to claim 10, wherein L is chlorine, methoxy or hydroxy, X is chlorine, bromine, methyl or ethyl, Y is OCF3, OCHF2 or OCF2Me, Z is methyl, ethyl, c-propyl, CH2-c-propyl or (CH2)2OMe, and n is 0, 1 or 2.

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