4-difluoromethyl benzamides with herbicidal action

Abstract

The invention relates to 4-difluoromethyl benzamides of formula (I) as herbicides. In formula (I) X, R and Ra represent groups such as alkyl, cycloalkyl, chlorine and bromine.

Description

[0001] Herbicidal 4-difluoromethylbenzoic acid amides

[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 2011 / 035874 Al, WO 2012 / 126932 Al, WO 2012 / 028579 Al, WO 2016 / 146561 Al and

[0004] WO 2018 / 202535 A1 describes herbicidally active benzoic acid amides that differ from one another essentially in the nature of the heterocyclic substituent. These benzoic acid amides can be substituted by a variety of different residues in the 2-, 3-, and 4-positions of the phenyl ring. However, the benzoic acid amides known from the above-mentioned documents often exhibit an unfavorable profile with regard to their biological properties, such as herbicidal activity, crop tolerance, and toxicological and ecotoxicological properties.

[0005] The object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the benzoic acid amides according to the invention described below, which bear an alkyl group, a cycloalkyl group, a chlorine atom, or a bromine atom in the 2-position of the phenyl ring, a sulfur-containing radical in the 3-position, a CHF2 group in the 4-position, and an unsubstituted 1,3,4-oxadiazole on the nitrogen atom of the amide group.

[0006] The present invention therefore relates to benzoic acid amides of the formula (I) and their

[0007] Salts where the symbols have the following meanings:

[0008] X means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, chlorine or bromine,

[0009] R means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-Ce)-alkyl or (Ci-Ce)-alkyl-

[0010] O-(Ci-C6)-alkyl. In formula (I) and all subsequent formulas, alkyl radicals with more than two carbon atoms can be straight-chain or branched. Alkyl radicals are, 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. Cycloalkyl is a carbocyclic, saturated ring system with three to six carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0011] The compounds of formula (I) 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 can be obtained from the mixtures obtained during preparation by conventional separation methods, for example by chromatographic separation processes. Stereoisomers can also be selectively prepared by using stereoselective reactions using optically active starting materials and / or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof encompassed by formula (I) but not specifically defined.

[0012] 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 an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula | NPB'B"P'"| +. 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 (Ci-Cr -trialkylsulfonium and (Ci-Cr -trialkylsulfoxonium salts.

[0013] Preferred are benzoic acid amides of the formula (I), where the symbols have the following meanings:

[0014] X is (C1-C4)alkyl or chlorine,

[0015] R means (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C4)-alkyl or (Ci-C j-Alkyl-O-(Ci-C4)-alkyl.

[0016] Particularly preferred are benzoic acid amides of the formula (I), where the symbols have the following meanings: X is methyl, ethyl or chlorine,

[0017] R means methyl or ethyl.

[0018] In all formulas mentioned below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).

[0019] Compounds according to the invention can be prepared, for example, by the methods described in WO 2012 / 126932 A1 or WO 2018 / 202535 A1. The 2-amino-1,3,4-oxadiazoles underlying these amides are commercially available or can be synthesized using common methods known from the literature.

[0020] The benzoic acid chlorides or the corresponding benzoic acids on which the compounds (I) according to the invention are based can be prepared, for example, by the methods given in WO 2018 / 202535 A1.

[0021] The respective reaction mixtures are generally processed using known methods, for example by crystallization, aqueous extractive processing, chromatographic methods or a combination of these methods.

[0022] 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, whereby this 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. Overall, this 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.

[0023] 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 parallelized purification of compounds of formula (I) and their salts or of intermediates obtained during preparation, chromatography apparatus is available, for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

[0024] The equipment listed results in a modular approach in which the individual work steps are automated, but manual operations must be performed between them. This can be circumvented by using partially or fully integrated automation systems, in which the respective automation modules are operated, for example, by robots. Such automation systems can be purchased, for example, from Caliper, Hopkinton, MA 01748, USA.

[0025] The implementation 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).

[0026] 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-assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis, or of a synthesis adapted for the corresponding procedure, are bound to a synthetic resin. Solid-phase-assisted 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-assisted synthesis methods allows for a number of well-known protocols, which 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, CA92064, USA.

[0027] Both in the solid and liquid phases, 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 literature, for example, in "Microwaves in Organic and Medicinal Chemistry" (editors: C.O. Kappe and A. Stadler), Wiley, 2005.

[0028] Preparation according to the processes described here yields compounds of formula (I) and their salts in the form of collections of substances called libraries. The present invention also relates to libraries containing at least two compounds of formula (I) and their salts. The compounds according to the invention exhibit excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds. Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other permanent organs are effectively controlled by the active ingredients.

[0029] The present invention therefore also provides 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. harmful plants 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 mono- and dicotyledonous weed flora which can be controlled by the compounds according to the invention may be mentioned by way of example, without the mention of these compounds being intended to imply a restriction to specific species.

[0030] Monocot 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.

[0031] 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.

[0032] 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, but then stop growing and finally die completely after three to four weeks.

[0033] When the active ingredients are applied to the green parts of the plant using the post-emergence method, 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 in this way weed competition that is harmful to the crops is eliminated very early and sustainably.

[0034] Although the compounds according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crop plants of economically important crops, for example 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, in particular Zea and Triticum, are only insignificantly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate thereof. 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 plantings.

[0035] Furthermore, the compounds according to the invention, depending on their respective chemical structure and the applied rate, exhibit outstanding growth-regulating properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant constituents 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 reduce or completely prevent lodging, for example.

[0036] 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. Transgenic plants are generally characterized by particularly advantageous properties, for example, 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 affect, for example, the harvested crop in terms of quantity, quality, storability, composition, and specific constituents. For example, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known.

[0037] With regard to transgenic crops, the use of the compounds according to the invention is preferred in economically important transgenic crops of crops 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 according to 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.

[0038] Conventional methods for producing new plants with modified properties compared to existing plants include, for example, classical breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described of genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806), transgenic crop plants that are resistant to certain herbicides of the glufosinate type (see, for example,EP-A-0242236, EP-A-242246) or glyphosate (WO 92 / 00377) or sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259). transgenic crops with a modified fatty acid composition (WO 91 / 13972). genetically modified crops with new ingredients or secondary substances, e.g. B. new phytoalexins that cause increased disease resistance (EPA 309862, EPA0464461) genetically modified plants with reduced photorespiration that have higher yields and greater stress tolerance (EPA 0305398).

[0039] 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 properties (“gene stacking”).

[0040] Numerous molecular biological techniques for producing new transgenic plants with modified traits are known in principle; see, for example, BI Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0041] For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to the DNA fragments to connect them together, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones," VCH Weinheim, 2nd ed., 1996.

[0042] 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, or DNA molecules that comprise only 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.

[0043] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of nucleic acid molecules can also occur in the organelles of plant cells.

[0044] 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.

[0045] Transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0046] Preferably, the compounds according to the invention can be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl lisoxazoles 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 which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops.

[0047] The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crops.

[0048] The compounds according to the invention can be applied 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 compositions containing the compounds according to the invention.

[0049] 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, granules for coating, and adsorption, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0050] These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology",

[0051] Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[0052] 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, NY 1963, 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, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0053] Wettable powders are preparations that are evenly dispersible in water. In addition to the active ingredient, they contain a diluent or inert substance and 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. To produce the wettable powders, the herbicidally active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

[0054] 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 calcium 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.

[0055] 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.

[0056] 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, such as those listed above for the other formulation types.

[0057] Emulsions, e.g., oil-in-water emulsions (EW), can be produced using stirrers, colloid mills, and / or static mixers, using aqueous organic solvents and, if appropriate, surfactants, such as those listed above for the other formulation types. Granules can be produced either by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils, to the surface of carriers such as sand, kaolinite, or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired, in a mixture with fertilizers.

[0058] Water-dispersible granules are usually produced by conventional processes such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0059] For the production of disc, fluidized bed, extruder and spray granules see e.g. processes 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.

[0060] For further details on the formulation of pesticides 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.

[0061] 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.

[0062] In wettable powders, for example, the active ingredient concentration is approximately 10 to 90 wt.%, with the remainder (100 wt.%) consisting of conventional formulation ingredients. In emulsifiable concentrates, the active ingredient concentration can be approximately 1 to 90, preferably 5 to 80 wt.%. Dust-like formulations contain

[0063] 1 to 30 wt.% active ingredient, preferably 5 to 20 wt.% active ingredient; sprayable solutions contain approximately 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, for example, the active ingredient content is between 1 and 95 wt.%, preferably between 10 and 80 wt.%.

[0064] In addition, the active ingredient formulations mentioned may contain the usual adhesives,

[0065] Wetting agents, dispersing agents, emulsifying agents, penetrating agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents that affect pH and viscosity.

[0066] On the basis of these formulations, combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, can also be produced, e.g. in the form of a ready-to-use formulation or as a tank mix.

[0067] For application, the commercially available formulations are diluted in the usual way, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances prior to use.

[0068] The required application rate of the compounds of formula (I) varies with external conditions such as temperature, humidity, the type of herbicide used, and others. It can vary within wide limits, e.g., between 0.001 and 1.0 kg / ha or more of active ingredient, but is preferably between 0.005 and 750 g / ha.

[0069] The compounds of formula (I) according to the invention can also be used as a mixture with other herbicides, if required. Combination partners for the compounds of formula (I) in mixture formulations or in tank mixes include, for example, known active ingredients 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 described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual," 14th edition, The British Crop Protection Council and the Royal Society of Chemistry, 2006, and the literature cited therein.

[0070] Known herbicides or plant growth regulators that can be combined with compounds of formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name or code number) and always include all application forms such as acids, salts, esters, and isomers, such as stereoisomers and optical isomers. One and, in some cases, several application forms are mentioned as examples:

[0071] Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-Natrium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-Natrium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3- chlor-6-(4-chlor-2-fluor-3-methylphenyl)-5-fluorpyridin-2-carbonsäure, Aminocyclopyrachlor, Aminocyclopyrachlor-Kalium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid- dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammoniumsulfamate, Anilofos, Asulam, Asulam-Kalium, Asulam-Natrium, Atrazin, Azafenidin, Azimsulfuron, Beflubutamid, (S)-(-)- Beflubutamid, Beflubutamid-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, Chlorambenmethylammonium, Chlor amben-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. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, d.h. ( 1 R,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- l,2-oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-butotyl, Dichlorprop-Dimethylammonium, Dichhlorprop-etexyl, Dichlorpropethylammonium, 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- 1 H-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,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 sodium, Flucetosulfuron, Fluchloraline, Flufenacet, Flufenpyr, Flufenpyr ethyl, Flumetsulam, Flumiclorac, Flumiclorac pentyl, Flumioxazine, Fluometuron, Flurenol, Flurenol butyl, dimethylammonium and methyl, Fluoroglycofen, Fluoroglycofen ethyl, Flupropanate, Flupropanate sodium, Flupyrsulfuron, Flupyrsulfuron methyl, Flupyrsulfuron methyl sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr butometyl, Fluroxypyr meptyl, Flurtamone, Fluthiacet, Fluthiacet methyl, Fomesafen, Fomesafen sodium, Foramsulfuron, Foramsulfuron sodium, fosamine, fosamine ammonium, glufosinate, glufosinate ammonium, glufosinate sodium, E-glufosinate ammonium, E-glufosinate sodium, glufosinate P-sodium, glufosinate P-ammonium, glyphosate, glyphosate ammonium, Glyphosate isopropyl ammonium, glyphosate diammonium, glyphosate dimethyl ammonium, glyphosate potassium, glyphosate sodium, glyphosate sesquinodium and glyphosate trimesium, H-9201, i.e. 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, Haloxif op-Natrium, Hexazinon, HNPC-A8169, i.e. Prop-2-yn-l-yl (2S)- 2- { 3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy Jpropanoat, 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, lodosulfuron, lodosulfuron-Methyl, lodosulfuron-Methyl- Natrium, Ioxynil, loxynil-Eithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043,d.h. 3-({[5-(Difluormethyl)-l-methyl-3- (trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Eactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethyl- ammonium, -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-(l-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC- 310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl-5-benzyloxypyrazol, NC-656, i.e. 3- [(Isopropylsulfonyl)methyl]-N-(5-methyl-l,3,4-oxadiazol-2-yl)-5-(trifluormethyl)[l,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- lH-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. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chlor-4- (trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l-yl)-3,4- dihydro-2H-l,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-l(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-l(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-methyl pyridazine-3(2H)-on, 2-( { 2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexan-l,3-dion, (5 -Hydroxy- 1-methyl- lH-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]- lH-pyrazol-5-yl propan- 1 - sulfonat, 4- { 2-Chlor-3-[(3,5-dimethyl- IH-pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl} - 1 -methyl- lH-pyrazol-5-yl-l,3-dimethyl-lH-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7- fluor- 1 H-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn- 1 -yl 4-amino-3-chlor-5-fluor-6-(7 -fluor- 1 H-indol- 6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat, 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carbonsäure, Benzyl-4-amino- 3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Ethyl-4-amino-3-chlor-5-fluor-6-(7- fluor- 1 H-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7 -fluor- 1 -isobutyryl- 1 H- indol-6-yl)pyridin-2-carboxylat, Methyl 6-(l-acetyl-7-fluor-lH-indol-6-yl)-4-amino-3-chlor-5- fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6- [ 1 -(2,2-dimethylpropanoyl)-7 -fluor- 1 H-indol-6- yl]-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-l-(methoxyacetyl)-lH- indol-6-yl]pyridin-2-carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat, Natrium-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Butyl-4- amino-3-chlor-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridin-2-carboxylat, 4-Hydroxy-l-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-l-methylimidazolidin- 2-on, 4-Hydroxy-l-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2-yl]imidazolidin-2-on, 6-[(2- Hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] - 1 ,5-dimethyl-3-(2-methylphenyl)chinazolin-2,4( 1H,3H)- dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] - 1 -methylchinazolin- 2,4(lH,3H)-dion,2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex- 2-en-l-one, l-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidin- 1 (2H)-yl]phenyl Jmethyliden) amino] oxy Jpropanoat, Methyl (2S)-2- { [(E)-({2-chlor-4- fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(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-l(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-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulflnyl]-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-l(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-l(2H)- yl]phenoxy}cyclopropyl)carbonyl]oxy}essigsäure, 2-(2-Brom-4-chlorbenzyl)-4,4-dimethyl-l,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-l(2H)- yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazol-6a-carboxylat.,

[0072] Abscisinsäure und verwandte Analoga [z.B. (2Z,4E)-5-[6-Ethynyl-l-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-diensäure, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-diensäure, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-diensäure, methyl (2E,4E)-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoat, (2Z,4E)-5-(2-hydroxy-l,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 -ylcarboxylic acid N-methyl- 1-aminocyclopropyl-l -carboxylic acid, 1-aminocyclopropyl- 1 -carboxylic acid amide, 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 LCOs lack the characteristic fatty acid side chain. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(CSHBNOS)^ CAS NO. 1398-61-4] and chitosan molecules [(C5H11NO CAS No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilides,3-(Cycloprop-l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[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, l-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, in some cases also referred to as symbiotic nodulation signals (Nod or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of ß-l,4-linked V-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain,which is condensed at 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, l-(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[l,2-b]furan-2-one and related lactones as described in EP2248421, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture,4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its 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-l-en-l-yl acetate, sodium cycloprop-2-en-l-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.which can be used in combination with the compounds of the 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:,

[0073] SI) Compounds of the formula (SI), where the symbols and indices have the following meanings: nA is a natural number from 0 to 5, preferably 0 to 3;

[0074] RA 1 is halogen, (Ci-C4)alkyl, (C1-C4)alkoxy, nitro or (Ci-C4)haloalkyl;

[0075] 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), mA is 0 or 1 ;

[0076] RA 2 is ORA 3 , SRA 3 or NRA 3 RA 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 to the carbonyl group in (S1) via the N atom 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 ORA 3 , NHRA 4 or N(CH3)2, in particular of the formula ORA 3 ;

[0077] RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;

[0078] RA 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl; RA 5is H, (Ci -Cs)alkyl, (Ci-Cs)haloalkyl, (Ci-C4)alkoxy(Ci -Cs)alkyl, cyano or COORA 9 , where RA 9 is hydrogen, (Ci-Cs)alkyl, (Ci-Cs)haloalkyl, (Ci-C4)alkoxy-(Ci-C4)alkyl, (Ci-C6)hydroxyalkyl, (C3-Ci2)cycloalkyl or tri-(Ci-C4)alkylsilyl;

[0079] RA 6 , Attorney 7 , Attorney 8 are identical or different and are hydrogen, (Ci-Cs)alkyl, (Ci-Cs)haloalkyl, (C3-Ci2)cycloalkyl or substituted or unsubstituted phenyl;

[0080] RA 10 is H, (C3-Ci2)cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (Sl a), preferably compounds such as l-(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 (S 1 - 1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-methyl-pyrazole-3-carboxylate (Sl-2), ethyl l-(2,4-dichlorophenyl)-5-isopropyl-pyrazole-3-carboxylate (Sl-3), ethyl l-(2,4-dichlorophenyl)-5-(l,l-dimethyl-ethyl)pyrazole-3-carboxylate (Sl-4) and related compounds as described in EP-A-333 131 and EP-A-269 806; c) derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as

[0081] 1-(2,4-Dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), l-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (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 l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazole-3-carboxylic acid ethyl ester (Sl-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; e) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e), preferably compounds such as 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) ("Isoxadifen-ethyl") or -n-propyl ester (S1-12) or the

[0082] 5-(4-Fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-13), as described in patent application WO-A-95 / 07897. f) Compounds of the triazolyloxyacetic acid derivative type (Sl f), preferably compounds such as methyl-{[l,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-15) or methyl-{[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-16) or {[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-17) or methyl-{[l-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (S 1 - 18) or {[l-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (S 1-19), as described in patent application W02021105101

[0083] S2) quinoline derivatives of the formula (S2), where the symbols and indices have the following meanings:

[0084] RB 1 is halogen, (Ci-C) alkyl, (C1-C4) alkoxy, nitro or (Ci-C4)haloalkyl; ns is a natural number from 0 to 5, preferably 0 to 3;

[0085] RB 2 is ORB 3 , SRB 3 or NRB 3 RB 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 ;

[0086] RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;

[0087] RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;

[0088] TB is a (Ci or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (Ci-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 (l-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 l-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-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, 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,

[0089] Diallyl (5-chloro-8-quinolinoxy)malonic acid, methyl ethyl (5-chloro-8-quinolinoxy)malonic acid and related compounds as described in EP-A-0 582 198.

[0090] S3) Compounds of formula (S3) where the symbols and indices have the following meanings:

[0091] Rc 1 is (Ci-C4)alkyl, (Ci-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;

[0092] Rc 2 , Rc 3are the same or different hydrogen, (Ci-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (Ci-C4)haloalkyl, (C2-C4)haloalkenyl, (Ci-C4)alkylcarbamoyl-(Ci-C4)alkyl, (C2-C4)alkenylcarbamoyl-(Ci-C4)alkyl, (Ci-C4)alkoxy-(Ci-C4)alkyl, dioxolanyl-(Ci-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together 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-active safeners), such as

[0093] "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-l,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(l,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-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R)-isomer (S3-11).

[0094] S4) N- Acylsulfonamide der Formel (S4) und ihre Salze, worin die Symbole und Indizes folgende Bedeutungen haben:

[0095] XD ist CH oder N;

[0096] RD 1 ist CO-NR D 5 RD 6 oder NHCO-RD 7 ;

[0097] RD 2 ist Halogen, (Ci-C4)-Haloalkyl, (Ci-C4)-Haloalkoxy, Nitro, (C1-C4)- Alkyl, (Ci-C4)-Alkoxy, (Ci- C4)-Alkylsulfonyl, (Ci-C4)-Alkoxycarbonyl oder (Ci-C4)-Alkylcarbonyl;

[0098] RD 3 ist Wasserstoff, (C1-C4) Alkyl, (C2-C4) Alkenyl oder (C2-C4)-Alkinyl;

[0099] RD 4 ist Halogen, Nitro, (C1-C4)- Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Haloalkoxy, (C3-Ce)-Cycloalkyl, Phenyl, (Ci-C4)-Alkoxy, Cyano, (C1-C4)- Alkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci- C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl;

[0100] RD 5is hydrogen, (Ci-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-mentioned seven radicals are substituted by VD substituents from the group halogen, (Ci-Ce) alkoxy, (Ci-Ce)haloalkoxy, (C1-C2) alkylsulfinyl, (C1-C2) alkylsulfonyl, (C3-Ce)cycloalkyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C1-C4) alkyl and (Ci-COhaloalkyl);

[0101] RD 6 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkenyl or (C2-Ce) alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy and (Ci-C4) alkylthio, or

[0102] RD 5 and RD 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical; RD7 is hydrogen, (Ci-C4)alkylamino, di-(Ci-C4)alkylamino, (Ci-Ce)alkyl, (C3-Ce)cycloalkyl, where the last two radicals are substituted by VD substituents from the group halogen, (C1-C4)alkoxy, (Ci-Ce)haloalkoxy and (Ci-COalkylthio and in the case of cyclic radicals also (Ci-C alkyl and (Ci-COhaloalkyl); no is 0, 1 or 2; mo is 1 or 2;

[0103] VD is 0, 1, 2 or 3; preferred compounds are those of the N-acylsulfonamide type, e.g. of the following formula (S4 a ), which are known, for example, from WO-A-97 / 45016 wherein

[0104] RD 7 (Ci-Ce)alkyl, (C3-Ce)cycloalkyl, where the last two radicals are substituted by VD substituents from the

[0105] Group halogen, (C1-C4) alkoxy, (Ci-Ce)haloalkoxy and (Ci-C4)alkylthio and in the case of cyclic

[0106] radicals are also substituted by (C1-C4) alkyl and (Ci-C4)haloalkyl;

[0107] RD 4Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF 3; mo 1 or 2;

[0108] 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, e.g. those in which

[0109] RD 5 = Cyclopropyl and (RD 4 ) = 2-OMe ("Cyprosulfamide", S4-1),

[0110] RD 5 = Cyclopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-2),

[0111] RD 5 = Ethyl and (RD 4 ) = 2-OMe is (S4-3),

[0112] RD 5 = Isopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-4) and

[0113] RD 5 = Isopropyl and (RD 4 ) = 2-OMe (S4-5). as well as compounds of the N-acylsulfamoylphenylurea type of the formula (S4 C ), which are known for example from EP-A-365484, wherein

[0114] RD 8 and RD 9independently of one another hydrogen, (Ci-Cs)alkyl, (C3-Cs)cycloalkyl, (C3-Ce)alkenyl,

[0115] (C3-C6)alkynyl,

[0116] RD 4 Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3mo represents 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

[0117] S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 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.

[0118] S6) Active substances from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.

[0119] 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydroquinoxalin-2-one hydrochloride, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.

[0120] S7) Compounds of formula (S7) as described in WO-A-1998 / 38856 where the symbols and indices have the following meanings: RE 1 , RE 2 are independently halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (Ci-C4)haloalkyl, (Ci-C4)alkylamino, di-(Ci-C4)alkylamino, nitro;

[0121] AE is COORE 3 or COSRE 4

[0122] RE 3 , RE 4 are independently hydrogen, (C1-C4)alkyl, (Ci-Co)alkenyl, (C2-C4)alkynyl, cyanoalkyl, (Ci-C4)haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, nE 1is 0 or 1 nE 2 , nE 3 are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, diphenylmethoxyacetic acid ethyl ester, diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1).

[0123] S8) Compounds of formula (S8) as described in WO-A-98 / 27049

[0124] Wherein

[0125] X F CH or N, nF in the case that XF=N, an integer from 0 to 4 and in the case that XF=CH, an integer from 0 to 5 ,

[0126] RF 1 Halogen, (C1-C4) alkyl, (Ci-C4) haloalkyl, (C1-C4) alkoxy, (Ci-C4) haloalkoxy, nitro, (Ci-C4) alkylthio, (Ci-C4) alkylsulfonyl, (C1-C4) alkoxycarbonyl, optionally substituted. phenyl, optionally substituted phenoxy,

[0127] RF 2 Hydrogen or (C1-C4) alkyl

[0128] RF 3hydrogen, (Ci-Cs) 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

[0129] X F CH, nF is an integer from 0 to 2 ,

[0130] RF 1 Halogen, (C1-C4) alkyl, (Ci-C jHaloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, RF 2 hydrogen or (C1-C4) alkyl,

[0131] RF 3 Hydrogen, (Ci-Cs) 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.

[0132] S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.

[0133] S10) Compounds of the formulas (S10 a ) or (S10 b ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764 wherein

[0134] RG 1 Halogen, (Ci-C4)alkyl, methoxy, nitro, cyano, CF3, OCF3

[0135] YG, ZG independently of each other O or S, nc an integer from 0 to 4, RG 2 (CI-Cie)alkyl, (Ci-Ce)alkenyl, (Cs-Cejcycloalkyl, aryl; benzyl, halobenzyl, RG 3 hydrogen or (Ci-Ce) alkyl.

[0136] Si l) Active substances of the oxyimino compound type (Si l), which are known as seed dressings, such as: B. "Oxabetrinil" ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sl l-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim" (l-(4-chlorophenyl)-2,2,2-trifluoro-l-ethanone-O-(l,3-dioxolan-2-ylmethyl)-oxime) (Sl l-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against metolachlor damage. 512) 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.

[0137] 513) 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, "CF 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-l-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-l,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorus dithioate) (S13-7), "Dietholate" (O,O-diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

[0138] 514) Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crops such as rice, such as

[0139] "Dimepiperate" or "MY-93" (GS-1-methyl-1-phenylethyl-piperidine-l-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)-l-(l-methyl-l-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" (l-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.

[0140] S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008 / 131861 and WG-A-2008 / 131860 where RH 1a (Ci-Ce)haloalkyl radical and

[0141] RH 2 hydrogen or halogen and

[0142] RH 3 , RH 4 independently of one another are hydrogen, (Ci-Cie) alkyl, (C2-C16) alkenyl or (C2-Cie) 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,

[0143] (C 1 -C 4 ) alkylamino, di[(C 1 -C alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloal koxy ] carbonyl, (C 8 -C 12 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C 8 -C 12 ) cycloalkyl, (C 4 -C 12 ) cycloalkenyl, (C 8 -C 12 ) cycloalkyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or Gr-G cycloalkoxy which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C1-C4) alkyl, (Cl-C4) haloalkyl, (C1-C4) alkoxy, (Cl-C4) haloalkoxy, (Cl-C4) alkylthio, (Cl-C4) alkylamino, di[(Cl-C4)alkyl] amino,

[0144] [(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

[0145] RH 3 (Ci-Ct -alkoxy, (C2-C4)alkenyloxy, (C2-Ce)alkynyloxy or (C2-C4)haloalkoxy and RH 4 hydrogen or (Ci-C j-alkyl or

[0146] RH 3 and RH 4 together 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, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy and (Ci-C4) alkylthio.

[0147] S16) Active ingredients 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), l-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl). Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.

[0148] The following examples illustrate the invention.

[0149] A. Chemical Examples

[0150] Synthesis of 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)-N-(l,3,4-oxadiazol-2-yl)benzamide (Example Nos. 1-5)

[0151] Step 1: Synthesis of 3-(Dihydromethyl)-6-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-(methylsulfanyl)aniline

[0152] A total of 40.9 g (1.78 mol) of lithium amide was added portionwise to 15.3 g (50.9 mmol) of 2-[4-(difluoromethyl)-2-methoxy-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole in 380 ml of dry tetrahydrofuran under an argon atmosphere. The reaction mixture was stirred for 19 h at 40-50 °C until the reaction mixture indicated complete conversion. For workup, the contents were carefully poured into ice-water. The mixture was extracted with diethyl ether. The organic phase was washed with water, and after phase separation, the organic phase was dried. The filtrate was thoroughly concentrated, yielding 14.2 g of the desired product.

[0153] Step 2: Synthesis of 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoic acid. 615 ml of 6M hydrochloric acid were added to 3.00 g (10.5 mmol) of 3-(difluoromethyl)-6-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-(methylsulfanyl)aniline, and the reaction mixture was heated under reflux for 6 hours. For workup, the contents were largely concentrated. The resulting suspension was cooled in an ice bath and then filtered. The residue was washed twice with ice water and finally dried, yielding 1.68 g of the desired product.

[0154] Step 3: Synthesis of ethyl 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoate

[0155] To a mixture of 49.0 g (210 mmol) of 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoic acid and 735 ml of ethanol, 75.0 g (630 mmol) of thionyl chloride was slowly added dropwise. The reaction mixture was then heated under reflux for a total of four days. Additional thionyl chloride (48.8 g (410 mmol) in total) was added three times after cooling to room temperature until the reaction was monitored. For workup, the contents were cooled to room temperature and concentrated, and the residue was taken up in ethyl acetate. The mixture was washed twice with saturated aqueous sodium bicarbonate solution and then twice with cold 1M sodium hydroxide solution. After phase separation, the organic phase was dried, and the filtrate was freed from the solvent. The residue yielded 50.5 g of the desired product.

[0156] Step 4: Synthesis of ethyl 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)benzoate

[0157] 38.5 g (287 mmol) of copper(II) chloride were placed in 600 ml of acetonitrile, and the mixture was heated to a temperature of 50–60 °C. A solution of 64.0 g (90 wt% purity; 220 mmol) of ethyl 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoate in 200 ml of acetonitrile and a solution of 27.8 g (90 wt% purity; 242 mmol) of tert-butyl nitrite in 200 ml of acetonitrile were added dropwise simultaneously and separately. After the addition was complete, the contents were stirred for a further 45 minutes at 50–60 °C. The mixture was then cooled to room temperature and concentrated for workup. The residue was dissolved in water and ethyl acetate. Sufficient 6M hydrochloric acid was then added to dissolve all the salts. After phase separation, the aqueous phase was extracted twice with ethyl acetate, then the combined organic phases were dried and the filtrate was freed from the solvent.The residue was purified by chromatography to yield 58.5 g of the desired product with a purity of 95 wt%.

[0158] Step 5: Synthesis of 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)benzoic acid

[0159] 58.5 g (95 wt.% purity; 198 mmol) of ethyl 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)benzoate in 500 ml of methanol were treated with 297 ml (1M, 297 mmol) of sodium hydroxide solution, and the reaction mixture was then stirred at room temperature for 16 h. For workup, the contents were largely freed of methanol using a rotary evaporator. The residue was taken up in water, the mixture was then washed with tert-butyl methyl ether, and the aqueous phase was subsequently acidified with concentrated hydrochloric acid. The mixture was stirred for 15 minutes and then extracted twice with ethyl acetate. The combined organic phases were dried, and the filtrate was freed from solvent. The residue yielded 51.3 g of the desired product.

[0160] Step 6: Synthesis of 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)-N-(l,3,4-oxadiazol-2-yl)benzamide (Example Nos. 1-5)

[0161] A mixture of 700 mg (2.77 mmol) of 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)benzoic acid and 322 mg (95 wt% purity; 3.60 mmol) of l,3,4-oxadiazol-2-amine in 20 ml of pyridine was cooled to 0-5 °C in an ice bath. 527 mg (4.16 mmol) of oxalic acid dichloride were then added portionwise. The reaction mixture was stirred for 1 h at 0-5 °C and then for 16 h at room temperature. For workup, the mixture was concentrated, and the residue was treated with dichloromethane and water. After phase separation, the organic phase was concentrated, and the residue was purified by chromatography, yielding 540 mg of the desired product.

[0162] The examples listed in the table below were prepared analogously to the methods mentioned above or are available analogously to the methods mentioned above. These compounds are particularly preferred. The abbreviations used mean:

[0163] Me = Methyl Et = Ethyl c-Pr = cyclo-propyl

[0164] Table 1: Compounds of formula (I) according to the invention 'H-NMR data:

[0165] The following abbreviations are used for manual evaluation of NMR signals: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), me (multiplet centered)

[0166] Example connection 1-1:

[0167] >H NMR (400 MHz, CDC13) 5 ppm 2.30 (s, 3H) 2.77 (s, 3H) 7.37 (t, 1H) 7.67 (d, 1H) 7.71 (d, 1H) 8.22

[0168] (s, 1H)

[0169] Example connection 1-2:

[0170] >H NMR (400 MHz, CDCh) 5 ppm 1.22 (t, 3H) 2.72 - 2.78 (m, 5H) 7.39 (t, 1H) 7.65 - 7.75 (m, 2H)

[0171] 8.22 (s, 1H)

[0172] Example connection 1-3:

[0173] 'H NMR (600 MHz, CDCh) 5 ppm 1.27 (t, 3H) 2.33 (s, 3H) 3.20 (q, 2H) 7.39 (t, 1H) 7.68 (s, 2H) 8.23

[0174] (s, 1H)

[0175] Example connection 1-4:

[0176] 'H NMR (400 MHz, CDCh) 5 ppm 1.24 (eg, 6H) 2.77 (q, 2H) 3.21 (q, 2H) 7.40 (t, 1H) 7.68 (eg, 2H)

[0177] 8.23 (s, 1H)

[0178] Example connection 1-5:

[0179] >H NMR (400 MHz, CDCh) 5 ppm 2.42 (s, 3H) 7.31 (t, 1H) 7.74 (d, 1H) 7.77 (d, 1H) 8.21 (s, 1H)

[0180] Example connection 1-6:

[0181] >H NMR (400 MHz, CDCh) 5 ppm 1.24 (t, 3H) 2.92 (q, 2H) 7.33 (t, 1H) 7.76 (eg, 2H) 8.21 (s, 1H)

[0182] Example connection 1-7:

[0183] >H NMR (400 MHz, CDCh) 5 ppm 2.42 (s, 3H) 7.33 (t, 1H) 7.65 (d, 1H) 7.78 (d, 1H) 8.20 (s, 1H)

[0184] Example connection 1-8:

[0185] >H NMR (400 MHz, CDCh) 5 ppm 1.25 (t, 3H) 2.92 (q, 2H) 7.34 (t, 1H) 7.65 (d, 1H) 7.78 (d, 1H) 8.21

[0186] (s, 1H)

[0187] Example connection 1-9:

[0188] 'H NMR (400 MHz, CDCh) 5 ppm 2.77 (s, 3H) 2.91 (t, 2H) 3.31 (s, 3H) 3.46 (t, 2H) 7.44 (t, 1H) 7.69

[0189] (me, 2H) 8.23 (s, 1H)

[0190] Beispielverbindung 1-10:

[0191] 'H NMR (600 MHz, CDCh) 5 ppm 0.14 (me, 2H) 0.54 (me, 2H) 0.92 (me, 1H) 2.63 (d, 2H) 2.78 (s, 3H)

[0192] 7.46 (t, 1H) 7.68 (me, 2H) 8.21 (s, 1H) B. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting 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 salts thereof, 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 wetting and dispersing agent and milling in a pin mill. c) A dispersion concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (©Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. approx.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 its salts, 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

[0193] 75 parts by weight of a compound of formula (I) and / or salts thereof,

[0194] 10 parts by weight of calcium ligninsulfonate,

[0195] 5 parts by weight of sodium lauryl sulfate,

[0196] 3 parts by weight of polyvinyl alcohol and

[0197] 7 parts by weight of kaolin, grinding it on a pin mill and granulating the powder in a fluidized bed by spraying water as a granulating liquid. f) Water-dispersible granules are also obtained by

[0198] 25 parts by weight of a compound of formula (I) and / or salts thereof, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium

[0199] 2 parts by weight of sodium oleoylmethyltaurine, 1 part by weight of polyvinyl alcohol,

[0200] 17 parts by weight of calcium carbonate and

[0201] 50 parts by weight of water are homogenized and pre-crushed on a colloid mill, then ground on a bead mill and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle.

[0202] C. Biological examples

[0203] The abbreviations used here mean:

[0204] ABUTH Abutilon theophrasti AMARE Amaranthus retroflexus

[0205] DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli

[0206] LOLRI Lolium rigidum MATIN Matricaria inodora

[0207] PHBPU Pharbitis purpureum SETVI Setaria viridis

[0208] VERPE Veronica persica VIOTR Viola tricolor

[0209] 1. Herbicidal effect against weeds in pre-emergence

[0210] Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown 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 test period of 3 weeks, in comparison to untreated controls (herbicidal efficacy in percent (%): 100% efficacy = plants are dead, 0% efficacy = same as control plants).Numerous of the compounds of the invention tested showed at least 80% effectiveness against a variety of important weeds at an application rate of 80 g or less per hectare.

[0211] Some of the compounds according to the invention exhibit high selectivity and are therefore suitable for pre-emergence control of undesirable weeds in agricultural crops. The data in the following tables show, by way of example, the herbicidal activity of the compounds according to the invention in pre-emergence, with the herbicidal activity expressed as a percentage.

[0212]

[0213] Table 1b: Pre-emergence effect at 80g / ha against ABUTH in %

[0214] Table 2a: Pre-emergence effect at 20g / ha against AMARE in %

[0215]

[0216] Table 3a: Pre-emergence effect at 20g / ha against DIGSA in % Table 3b: Pre-emergence effect at 80g / ha against DIGSA in %

[0217]

[0218] Table 5: Pre-emergence effect at 80g / ha against MATIN in % Table 6a: Pre-emergence effect at 20g / ha against SETVI in %

[0219]

[0220] Table 7: Pre-emergence effect at 80g / ha against VERPE in % Table 8a: Pre-emergence effect at 20g / ha against VIOTR in % Table 8b: Pre-emergence effect at 80g / ha against VIOTR in %

[0221] 2. Herbicidal effect against post-emergence weeds

[0222] Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown in wood fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under favorable growth conditions. Two to three weeks after sowing, the test plants are treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green plant parts as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l / ha, with the addition of 0.2% wetting agent. After approximately three weeks of the test plants in the greenhouse under optimal growth conditions, the effectiveness of the preparations is visually assessed in comparison to untreated controls (herbicidal effectiveness in percent (%): 100% effectiveness = plants are dead, 0% effectiveness = same as control plants).Numerous of the tested compounds of the invention demonstrated at least 80% efficacy against a wide range of major weeds at an application rate of 80 g or less per hectare. Some of the compounds of the invention exhibit high selectivity and are therefore suitable for post-emergence control of undesirable weeds in agricultural crops. The data in the following tables provide examples of the post-emergence herbicidal activity of the compounds of the invention, with the herbicidal activity expressed as a percentage.

[0223] Table 10a: Post-emergence effect at 5g / ha against AMARE in % Table 10b: Post-emergence effect at 20g / ha against AMARE in %

[0224] Table 11: Post-emergence effect at 20g / ha against DIGS A in %

[0225] Table 13: Post-emergence effect at 80g / ha against LOLRI in % Table 14a: Post-emergence effect at 20g / ha against MATIN in %

[0226] Table 15: Post-emergence effect at 20g / ha against PHBPU in % Table 16: Post-emergence effect at 20g / ha against SETVI in % Table 17: Post-emergence effect at 20g / ha against VERPE in %

[0227] Table 18a: Post-emergence effect at 20g / ha against VIOTR in % Table 18b: Post-emergence effect at 80g / ha against VIOTR in % 3. Comparison experiments

[0228] For comparison purposes, the herbicidal activity of compounds according to the invention was tested with the most structurally similar compounds known from WO 2018202535. These data are listed in Table 1 below, with the upper compound in each comparison pair being the compound according to the invention and the lower compound being the compound known from the prior art. Table 19: Comparison with compounds known from WO 2018202535 in pre-emergence.

Claims

Patent claims 1. Benzoic acid amides of formula (I) and their salts where the symbols have the following meanings: X means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, chlorine or bromine, R means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-Ce)-alkyl or (Ci-Ce)-alkyl- O-(Ci-C6)-alkyl.

2. Benzoic acid amides according to claim 1, wherein the symbols have the following meanings: X means (C1-C4)-alkyl or chlorine, R means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C3-Ce)-cycloalkyl-(Ci-C4)-alkyl or (Ci-C4)-alkyl-O-(Ci-C4)-alkyl.

3. Benzoic acid amides according to claim 1 or, wherein the symbols have the following meanings: X means methyl, ethyl or chlorine, R means methyl or ethyl.

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

5. Herbicidal compositions according to claim 4 containing 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 undesirable plants, characterized in that an effective amount of at least one benzoic acid amide according to one of claims 1 to 3 or of herbicidal agents according to claim 4 or 5 is applied to the plants or to the site of undesirable plant growth.

7. Use of benzoic acid amides 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 undesirable plants.

8. Use according to claim 7, characterized in that the benzoic acid amides of the formula (I) used to control undesirable plants in crops.

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

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